Bortezomib potentiates the antitumor effect of tributyltin(IV) ferulate in colon cancer cells exacerbating ER stress and promoting apoptosis

Organotin(IV) complexes represent promising drugs in medicinal chemistry for their potential use in cancer therapy. We recently reported synthesis and characterization of a new organotin(IV) complex of ferulic acid (FA), tributyltin(IV) ferulate (TBT-F), showing its antitumor action in colon cancer cells. Here we provide evidence that the efficacy of this compound is strongly potentiated by the proteasome inhibitor bortezomib (BTZ). While low concentrations of tributyltin(IV) ferulate alone promoted autophagy without reducing cell viability, combination of the two compounds markedly affected colon cancer cell viability, cell morphology and exasperated endoplasmic reticulum (ER) stress, as r…

Organometallic complexes with biological molecules

Novel triorganotin(IV) complexes of two beta-lactamic antibiotics, 6-[D-(-)-beta-amino-p-hydroxyphenyl-acetamido]penicillin (=amoxicillin) and 6-[D-(-)-alpha-aminobenzyl]penicillin (=ampicillin), have been synthesized and investigated both in solid and solution states. The complexes corresponded to the general formula R(3)Sn(IV)antib*H(2)O (R=Me, n-Bu, Ph; antib=amox=amoxicillinate or amp=ampicillinate). Structural investigations about configuration in the solid state have been carried out by interpreting experimental IR and 119Sn Mossbauer data. In particular, IR results suggested polymeric structures both for R(3)Sn(IV)amox.H(2)O and R(3)Sn(IV)amp*H(2)O. Moreover, both antibiotics appear …

Diorganotin(IV) and triorganotin(IV) complexes of meso-tetra(4-sulfonatophenyl) porphine induce apoptosis in A375 human melanoma cells

The cytotoxic effect of several diorganotin(IV) and triorganotin(IV)-meso-tetra(4-sulfonatophenyl)porphine derivatives was tested and only the (Bu(2)Sn)(2)TPPS and the (Bu(3)Sn)(4)TPPS showed cytotoxicity on A375 human melanoma cells. To examine the pathway of (Bu(2)Sn)(2)TPPS or (Bu(3)Sn)(4)TPPS induced A375 cell death, DNA fragmentation analysis, Annexin V binding and PI uptake as well as caspases activation analysis by Western blot were carried out. A375 cells treated exhibited several typical characteristics of apoptosis. Both the (Bu(2)Sn)(2)TPPS and the (Bu(3)Sn)(4)TPPS compounds activate caspase-8 and caspase-9 leading to caspase-3 activation. Thus, we propose that these two porphiri…

Preparation and structural studies on dibutyltin(IV) complexes with pyridine mono- and dicarboxylic acids

Abstract A number of organotin(IV) complexes with pyridine mono- and dicarboxylic acids (containing ligating –COOH group(s) and aromatic {N} atoms) were prepared in the solid state. The bonding sites of the ligands were determined by means of FT-IR spectroscopic measurements. It was found that in most cases the –COO− groups form bridges between two central {Sn} atoms, thereby leading to polymeric (oligomeric) complexes. On this basis, the experimental 119Sn Mossbauer spectroscopic data were treated with partial quadrupole splitting approximations. The calculations predicted the existence of complexes with octahedral (oh) and trigonal-bipyramidal (tbp) structures, but the formation of comple…

Syntesis, characterization and electrochemistry of Ru(III) complexes with several aminoacid ligands

Organotin IV-Quinilone Antibiotic Derivatives: Solid State Investigations

Structural characterization of triorganotin(IV) complexes with sodium fusidate and DFT calculations

Abstract Three new complexes of the steroid sodium fusidate (sodium 2-[(1 S ,2 S ,5 R ,6 S ,7 S ,10 S ,11 S ,13 S , 14 Z ,15 R ,17 R )-13-(acetyloxy)-5,17-dihydroxy-2,6,10,11-tetramethyl tetracyclo[8.7.0.0 2,7 .0 11,15 ] heptadecan-14-ylidene]-6-methylhept-5-enoate = (NaFusidate, Na FA )]), with triorganotin(IV) moieties have been prepared and investigated by conventional techniques as FTIR, Mossbauer, ESI-MS and NMR spectroscopy. The isolated compounds showed stoichiometries organotin(IV)/fusidate 1/1, R 3 Sn(IV) FA (R = Me, FA1 ; Bu, FA2 ; Ph, FA3 ). The ligand coordination sites were determined by FTIR spectroscopic measurements. In the complexes, the carboxylate group of the fusidate li…

Equilibria involved in the diorganotin(IV) and triorganotin(IV) phosphomycin interaction in aqueous solution

Four new diorganotin(IV), (R = Me, Bu), and triorganotin(IV), (R = Me, Ph), derivatives of the phosphomycin disodium salt antibiotic[(1R,2S)-1,2-epoxypropylphosphonate]Na2 have been synthesized and their solid state configuration studied by X-ray crystallography, FT-IR, Mossbauer, UV–Vis spectroscopies. The X-ray diffraction investigation, performed on the bis[trimethyltin(IV)]- phosphomycin, showed that the coordination geometry at all the Sn atoms is trigonal bipyramidal. The structure of the complex forms an unusual polymeric zig-zag planar network. The FT-IR and the 119Sn Mo¨ssbauer studies supported the formation of trigonal bipyramidal (Tbp) molecular structures, both in the diorganot…

Lead(II) ions adsorption onto amyloid particulates: An in depth study

The production of new cost-effective biocompatible sorbent sustainable materials, with natural origins, able to remove heavy metals from water resources is nowadays highly desirable in order to reduce pollution and increase clean water availability. In this context, self-assembled protein materials with amyloid structures seem to have a great potential as natural platform for a broader development of highly-tunable structures. In this work we show how protein particulates, a generic form of protein aggregates, with spherical micro sized shape can be used as adsorbents of Pb2+ ions from aqueous solution. The effect of pH, ionic medium, ionic strength and temperature of the metal ion solution…

Synthesis, structure and electrochemistry of ruthenium(III) complexes whith potential biological activity

3D MICROSIZED PROTEIN AMYLOID PARTICULATES AS EFFECTIVE BIOADSORBERS FOR Pb2+ IONS

The production of new cost-effective biocompatible sorbent sustainable materials, with natural origins, able to remove heavy metals from water resources is nowadays highly desirable in order to reduce pollution and increase clean water availability. In this context, self-assembled protein materials with highly ordered amyloid structures, stabilised by H-bonds, seems to have a great potential as natural platform for a broader development of highly-tunable structures. By suitably varying solution conditions it is possible to tune aggregate size, surface area and morphologies as well as their physicochemical (hydrophobicity, hydrophilicity, swelling/deswelling properties) and mechanical proper…

Organometallic Complexes with Biological Molecules: VIII. Synthesis, Solid State andin vivo Investigation of Triorganotin(IV) Derivatives ofL-Homocysteic Acid

Several new triorganotin(IV) derivatives of L-homocysteic acid (L-HCAH) with formula R3Sn(L-HCA) (R=Me, nBu, Ph) have been synthesized. Their solid-state configurations were determined by IR and Mossbauer spectroscopy. The tin(IV) atom is five-coordinated in all the complexes, with the L-homocysteic acid behaving as a monoanionic bidentate ligand coordinating the tin(IV) atom through a chelating or bridging carboxylate group. The sulfonate (SO3−) and NH3+ groups of L-homocysteic acid maintain their free acid configuration and hence do not participate to the coordination of the tin(IV) atom. Coordination hypotheses have been checked through the correlation between the Mossbauer parameter iso…

Mössbauer Spectroscopy and Organotin Polymers

Mössbauer spectroscopy allows the structural analysis of certain metal atoms situated in complex structures. Briefly, Mössbauer spectroscopy is a resonant absorption spectroscopy that is observed best in isotopes having long lived, low-lying excited nuclear energy states. The largest recoil-free resonant cross-section is found for 57Fe. Currently, Mössbauer spectroscopy is being used on Mars to identify iron compounds that are present in the Martian landscape. There are over 20,000 entries in SciFinder for Mössbauer spectroscopy, of which the two largest entries are for iron and tin containing compounds. There are only about 100 entries for organotin compounds, with only a handful related t…

Organometallic complexes with biological molecules: XII. Solid-state and solution studies on dialkyltin(IV)- and trialkyltin(IV)-thiaminepyrophosphate derivatives

Dialkyltin(IV) and trialkyltin(IV) derivatives of the coenzyme thiaminepyrophosphate (H2TPP) have been synthesized with general formula R2Sn(HTPP)2·nH2O (Alk = Me, n = 2; Alk = Bu, n = 4) and R3SnHTPP·nH2O (R=Me, n = 2; R = Bu, n = 1), respectively. The solid-state structure of the complexes has been investigated through infrared and Mossbauer spectroscopy. The infrared data suggest the involvement of only phosphate oxygen atoms in the coordination of both dialkyl- and trialkyl-tin(IV) moieties, with phosphate anions behaving as monoanionic bidentate bridging or chelating groups, with the tin(IV) involved in six- and five-fold coordination geometries, respectively, in R2Sn(HTPP)2·nH2O (R = …

Infrared Absorption Spectroscopy

Infrared (IR) absorption spectroscopy is one of the most important analytical techniques available to study different kinds of samples including solids, semisolids, biological materials, films, liquids, solutions, and gases. IR spectroscopy not only uses the so-called infrared absorption, but also other techniques such as the attenuated total reflection method, diffuse reflectance method, reflection-absorption method, photoacoustic spectroscopy, and emission spectroscopy. IR spectroscopy is a technique based on the vibrations of the atoms of a molecule. An infrared spectrum is obtained by passing infrared radiation through a sample and determining what fraction of the incident radiation is …

New Ruthenium complexes with antitumoral activity

Effects of two organotin(IV)(sulfonato phenyl)porphynates on the MAPKs and on the growth of A375 human melanoma cells

Previously we showed apoptotic induction in A375 human melanoma cells using two complexes of the meso-tetra(4-sulfonatophenyl)porphinate (TPPS), (Bu 2 Sn) 2 TPPS and (Bu 3 Sn) 4 TPPS. To understand how these compounds activate apoptosis in melanoma cells we studied MAPKs and the (Bu 2 Sn) 2 TPPS and (Bu 3 Sn) 4 TPPS cellular uptake. Western blotting experiments showed activated protein kinases ERK 1/2, JNK and p38 in 10 μM (Bu 2 Sn) 2 TPPS- and 1 μM (Bu 3 Sn) 4 TPPS-treated melanoma cells, which suggests that the three MAP kinases are involved in the apoptotic death of A375-treated cells. By taking advantage of the porphyrin fluorescence, we found a fast concentration of (Bu 2 Sn) 2 TPPS an…

Synthesis, Structural characterization and Exafs investigations of new ruthenium(III) complexes.

Two new complexs of Ru(III) with glucosaminic acid and 1-Methyluracil, [RuCl2(Glun-N,O)2]H (I), (Glun-= glucosaminate); [RuCl4(1-MeU-N3)(DMSO)]H2.H2O (II), (1-MeU-= 1-Methyluracilate) were prepared from the same Ru(III) precursors, RuCl3•3H2O and [(DMSO)2H][trans-RuCl4(DMSO)2]. The characterization of the complexes have been carried out by elemental analysis, FT-IR, ES-MS, NMR and EXAFS.

119Sn NMR Ccomputational study of Dimethyltin(IV) - D-ribonic Acid and Dimethyltin(IV) - N-Acetylneuraminic acid complexes

"Dna binding of organotin(IV) complexes of meso-tetra (4 sulfonatophenyl) porphine showing cellular activity"

Our research group has reported about the synthesis of alkynyl-substituted metallophthalocyanines of symmetric and unsymmetric nature. In this study, a novel phthalocyanine precursor bearing pyridin-3-ylethynyl groups and its tetrasubstituted metallo- phthalocyanines at peripheral positions were reported.

Organometallic complexes with biological molecules. XI. Solid state and in vivo investigations of some diorganotin(IV)-chloramphenicol and cycloserine derivatives

Abstract Diorganotin(IV) derivatives of chloramphenicol, {=D-(-)threo-2,2-dichloro-N-[ β -hydroxy- α -(hydroxymethyl)- β -(4-nitrophenyl)ethyl]acetamide (=Hchloramph)}, and D-cycloserine, {=(R)-4-amino-3-isoxazolidone [=Hcyclos]} have been prepared. The stoichiometries of the obtained compounds were R 2 SnClantib and R 2 Snantib 2 (antib −1 =chloramph −1 , R=methyl and phenyl; antib −1 =cyclos −1 , R=methyl). The solid state configuration of the complexes was investigated by I.R. and Mossbauer spectroscopy, from which structural hypotheses were inferred. In particular, the experimental data suggested monomer structures both for R 2 Sn(IV)Clchloramph and R 2 Sn(IV)chloramph 2 , in which chlo…

INCORPORATION OF METAL-PORPHYRIN DERIVATIVES IN TITANIA NANOSTRUCTURED 3D NETWORKS: THIN FILM PROPERTIES AND APPLICATIONS

Organotin(IV) derivatives of fatty acids: Solid state and solution phase investigations

How organotin(IV)(sulfonatophenyl) porphynate may activate the apoptotic pathways in melanoma cells?

Interference of tri-n-butyltin(IV)chloride (TBTCl) on the vascular plant cells

Supramolecular Assemblies Based on Complexes of Nonionic Amphiphilic Cyclodextrins and a meso-Tetra(4- sulfonatophenyl)porphine Tributyltin(IV) Derivative: Potential Nanotherapeutics against Melanoma

Amphiphilic cyclodextrin (ACyD) provides water-soluble and adaptable nanovectors by modulating the balance between the hydrophobic and hydrophilic chains at both CyD sides. This work aimed to design nanoassemblies based on nonionic and hydrophilic ACyD (SC6OH) for the delivery of a poor-water-soluble organotin(IV)-porphyrin derivative [(Bu3Sn)4TPPS] to melanoma cancer cells. To characterize the porphyrin derivatives under simulated physiological conditions, a speciation was performed using complementary techniques. In aqueous solution (≤ 20 μM), (Bu3Sn)4TPPS primarily exists as a monomer (2 in Figure 1), as suggested by the low static anisotropy (ρ ≈ 0.02) with a negligible formation of por…

Bu2Sn(N-acetyl-L-cysteinate) antitumor activity on HepG2 cells

Diorganotin(IV) N-acetyl-L-cysteinate complexes: synthesis, solid state, solution phase, DFT and biological investigations.

Diorganotin(IV) complexes of N-acetyl-L-cysteine (H(2)NAC; (R)-2-acetamido-3-sulfanylpropanoic acid) have been synthesized and their solid and solution-phase structural configurations investigated by FTIR, Mössbauer, (1)H, (13)C and (119)Sn NMR spectroscopy. FTIR results suggested that in R(2)Sn(IV)NAC (R = Me, Bu, Ph) complexes NAC(2-) behaves as dianionic tridentate ligand coordinating the tin(IV) atom, through ester-type carboxylate, acetate carbonyl oxygen atom and the deprotonated thiolate group. From (119)Sn Mössbauer spectroscopy it could be inferred that the tin atom is pentacoordinated, with equatorial R(2)Sn(IV) trigonal bipyramidal configuration. In DMSO-d(6) solution, NMR spectr…

Organometallic complexes with biological molecules. XVIII. Alkyltin(IV) cephalexinate complexes: synthesis, solid state and solution phase investigations

Abstract Dialkyltin(IV) and trialkyltin(IV) complexes of the deacetoxycephalo-sporin-antibiotic cephalexin [7-( d -2-amino-2-phenylacetamido)-3-methyl-3-cephem-4-carboxylic acid] (Hceph) have been synthesized and investigated both in solid and solution phase. Analytical and thermogravimetric data supported the general formula Alk 2 SnOHceph · H 2 O and Alk 3 Snceph · H 2 O (Alk=Me, n -Bu), while structural information has been gained by FT-IR, 119 Sn Mossbauer and 1 H, 13 C, 119 Sn NMR data. In particular, IR results suggested polymeric structures both for Alk 2 SnOHceph · H 2 O and Alk 3 Snceph · H 2 O. Moreover, cephalexin appears to behave as monoanionic tridentate ligand coordinating th…

Solid State Analysis of Metal-Containing Polymers Employing Mossbauer Spectroscopy, Solid State NMR and F EI TOF MALDI MS

Polymers in general and metal-containing polymers in particular are often sparingly soluble or insoluble, in contrast to small molecules. Thus, special significance is attached to characterization techniques that can be applied to the materials as solids. Here, three techniques are discussed that give structural information gained from the solid material. Mossbauer spectroscopy is a powerful technique that may give information on the structure about the metal-containing moiety for about 44 different nuclei. Its use in describing the structure of the product obtained from organotin dichlorides and the unsymmetrical ciprofloxacin is presented along with the reaction implications of the result…

Fabrication and Characterisation of Titania Photonic Nanostructures

In this work, we report about the preparation and morphological characterization of photonic nanopatterned titania films (~ 200 nm).

Apoptosis and cell growth arrest in A375 human melanoma cells by diorganotin(IV) and triorganotin(IV) complexes of [meso-Tetra(4-sulfonatophenyl)porphine] manganese(III)chloride

In previous studies we have demonstrated that two derivatives of meso-Tetra(4-sulfonatophenyl)porphine (TPPS), (Bu2Sn)2TPPS and (Bu3Sn)4TPPS, cause apoptotic death of A375 melanoma cells and, at lower concentrations, arrest of cell proliferation. In the present study, we examined if the manganese metal inside the porphyrin cavity could improve the efficacy of this class of compounds. Thus, [meso- Tetra(4-sulfonatophenyl)porphine]Mn(III)Cl (=MnTPPS) derivatives, namely (Me2Sn)2MnTPPS, (Bu2Sn)2MnTPPS, (Me3Sn)4MnTPPS and (Bu3Sn)4MnTPPS, were tested on the A375 human melanoma cell line. A cytotoxicity assay showed that (Bu2Sn)2MnTPPS and (Bu3Sn)4MnTPPS were highly cytotoxic by inducing apoptosi…

Synthesis, structural investigations on organotin(IV) chlorin-e6 complexes, their effect on sea urchin embryonic development and induced apoptosis

Four new organotin(IV) chlorin derivatives, [chlorin=chlorin-e(6)=21H,23H-porphine-2-propanoic acid, 18-carboxy-20-(carboxymethyl)-8-ethenyl-13-ethyl-2,3-di-hydro-3,7,12,17-tetramethyl-(2S-trans)-], with formula (R(2)Sn)(3)(chlorin)(2).2H(2)O (R=Me, n-Bu) and (R(3)Sn)(3)chlorin.2H(2)O (R=Me, Ph) have been synthesized. The solid state and solution phase structures have been investigated by FT-IR, (119)Sn Mössbauer, (1)H and (13)C NMR spectroscopy. In the solid state, (R(2)Sn)(3)(chlorin)(2).2H(2)O complexes contain six coordinated Sn(IV), in a skew trapezoidal environment by forming trans-R(2)SnO(4) polymeric units. As far as (R(3)Sn)(3)chlorin.2H(2)O complexes are concerned, Sn(IV) is five …

Organotin(IV) and simple fatty acids: preliminary assessments

Our group has a long researching tradition in the field of organotin(IV) complexes, usually proposed and tested as potential anti-tumor drugs. The leitmotif has usually been the modulation of the intrinsic toxicity/cytotoxicity of the organometallic moiety and a modulation of the toxic effect by means of biologically related molecules (synthetic or natural). Such a modulation is usually achieved by two (often overlapping) routes: dampen the damaging effects of the metal core, and serving as a carrier for specific tissue districts. Since a too tight binding on the organotin moiety is not always desirable – a too much stable complex could be a non-active one – carboxylates have always played …

Organotin(IV)(sulfonatophenyl)porphynate effects on survival and apoptotic signalling pathways in melanoma cells

Effects of sublethal levels of tributyltin chloride on a new toxicity test organism,Liza saliens (osteichthyes, mugilidae): a histological study

The histopathological effects of 10−7 and 10−9M tributyltin(IV)chloride,TBTCl, solutions on different Liza saliens organs have been studied by light microscope. The fish were sacrificed after 3–4 h incubation in 10−7M TBTCl solution or after 15 days incubation in 10−9M solution. The observed histopathological changes were dose- and time-dependent. The 10−7M TBTCl concentration resulted in major damage to the gill epithelium, indicating that TBTCl primarily interfered with the respiration, osmoregulation, acid balance and nitrogenous waste excretion processes. After incubation in 10−9M TBTCl solution the fish lived 20 or more days, but many of the organs were altered. Thymus atrophy, reduced…

Structural investigations on diorgano- and triorganotin(IV) derivatives of [meso-tetra(4-sulfonatophenyl)porphine]metal chlorides.

Abstract Several new complexes of organotin(IV) moieties with MCln[meso-tetra(4-sulfonatophenyl)porphine], (R2Sn)2MCln[meso-tetra(4-sulfonatophenyl)-porphinate]s and (R3Sn)4MCln [meso-tetra(4-sulfonatophenyl)porphinate]s, [M = Fe(III), Mn(III): n = 1, R = Me, n-Bu; Ph; M = Sn(IV): n = 2, R = Me, n-Bu] have been synthesized and their solid state configuration investigated by infrared (IR) and Mossbauer spectroscopy, and by 1H and 13C NMR in D2O. The electron density on the metal ion coordinated inside the porphyrin ring is not influenced by the organotin(IV) moieties bonded to the oxygen atoms of the side chain sulfonatophenyl groups, as it has been inferred on the basis of Mossbauer spectro…

Ciprofloxacin Polymers Derived from Diallyltin and Divinyltin Dihalides

The initial synthesis of condensation polymers from newly available divinyltin dichloride and diallyltin dichloride and ciprofloxacin is accomplished employing a modified interfacial polycondensation process. The polymeric (DP are about 2,000) products are rapidly (less than 15 seconds) formed in good yield. Infrared spectroscopy shows the formation of Sn-O and Sn-N bonds as predicted from the proposed structure. F-MALDI MS also shows ion fragments containing organotin in the predicted isotopic abundances as well as ion fragments containing both organotin and ciprofloxacin. The polymers exhibit low toxicity towards healthy WI-38 cells with variable toxicities towards a variety of cancer cel…

Lipid and fatty acid variations inCiona intestinalis ovary after tri-n-butyltin(IV)chloride exposure

Reduction of total lipids (TL) content and significant variations of triglyceride (TG) and phospholipid (PL) fractions were observed as a consequence of exposure of Ciona intestinalis ovaries to tributyltin chloride (TBTCL) solutions. In particular, an evident TG decrease and a PL increase were observed, which probably provoked an increment in membrane fluidity, because of the high concentration of long chain fatty acids and, as a consequence, PL. This could be a cell adaptive standing mechanism towards the pollutants, as observed in Saccharomyces cerevisiae. Also the increase in the content of the polyunsaturated fatty acids (PUFA), important in the synthesis of compounds such as prostagla…

Synthesis, characterization and in vitro antimicrobial activity of triorganotin(IV)fusidate complexes

Synthesis, structural investigations on organotin(IV) chlorin-e6 complexes, their effect on sea urchin embryonic development and induced apoptotic changes

Semitransparent Design of Planar n-i-p Perovskite Solar Cells using a Cost-Effective, Perovskite-Compatible DMD Structure as the Top Electrode

In recent years, a significant emphasis has been placed on developing multi-functional solar cells that integrate new features such as color and transparency, thereby opening up the possibility of unconventional photovoltaic (PV) applications, including building-integrated PV (BIPV) systems, tandem solar cells, and wearable electronics. In particular, the integration of semitransparent (ST) solar cells into buildings as power-generating windows, facades or other aesthetic architectural elements constitutes one of the most intriguing perspectives [1]. Since silicon-based panels are generally opaque and unaesthetic, there has been a growing research interest in emerging thin-film solar cells …

Luminescence Efficiency of Si/SiO 2 Nanoparticles Produced by Laser Ablation

Photoluminescence properties of Si(core)/SiO 2 (shell) nanoparticles produced by pulsed laser ablation in aqueous solution are investigated with the purpose to highlight the microscopic processes that govern the emission brightness and stability. Time resolved spectra evidence that these systems emit a µs decaying band centered around 1.95 eV, that is associated with the radiative recombination of quantum-confined excitons generated in the Si nanocrystalline core. Both the quantum efficiency and the stability of this emission are strongly dependent on the pH level of the solution, that is changed after the laser ablation is performed. They enhance in acid environment because of the H + pass…

Enhancing the luminescence efficiency of silicon-nanocrystals by interaction with H+ions

The emission of silicon nanocrystals (Si-NCs), synthesized by pulsed laser ablation in water, was investigated on varying the pH of the solution. These samples emit μs decaying orange photoluminescence (PL) associated with radiative recombination of quantum-confined excitons. Time-resolved spectra reveal that both the PL intensity and the lifetime increase by a factor of ∼20 when the pH decreases from 10 to 1 thus indicating that the emission quantum efficiency increases by inhibiting nonradiative decay rates. Infrared (IR) absorption and electron paramagnetic resonance (EPR) experiments allow addressing the origin of defects on which the excitons nonradiatively recombine. The linear correl…

Nonprecious Copper‐Based Transparent Top Electrode via Seed Layer–Assisted Thermal Evaporation for High‐Performance Semitransparent n‐i‐p Perovskite Solar Cells

Semitransparent perovskite solar cells (ST‐PSCs) are highly attractive for applications in building‐integrated photovoltaics as well as in multijunction tandem devices. To fabricate high‐performance ST‐PSCs, suitable transparent top electrodes are strongly needed. Dielectric/metal/dielectric (DMD) multilayer structures have been shown to be promising candidates, though generally based on high‐value metals such as gold or silver, the latter causing also stability issues by reacting with perovskite. Here, a novel DMD transparent electrode based on nonprecious, less‐reactive copper is developed via thermal evaporation and used as a top anode in the fabrication of high‐performance semitranspare…

Dibuthyltin(IV) Complexes with Caffeic acid: Apoptotic Effect on human cancer cells

Organometallic complexes with biological molecules. X: dialkyltin(IV) and trialkyltin(IV) orotates: spectroscopic andin vivo investigations

Several novel diorgano- and triorgano-tin(IV) derivatives of orotic acid, (2,6-dihydroxypyrimidine-4-carboxylic acid; H 3 or) have been synthesized. In the diorganotin(IV) derivatives, the orotic acid behaved either as a monoanionic or as a dianionic ligand, yielding R 2 Sn(H 2 or) 2 and R 2 SnHor (R = Me, Bu) species, respectively, while in the triorganotin(IV) orotates only monodeprotonation of the orotic acid occurred, giving R 3 SnH 2 or (R = Me, Bu) derivatives. Structural hypotheses are proposed and discussed for the solid state based on Mossbauer and IR spectroscopic data, and for solution on 1 H and 1 C NMR results. Finally, investigations have been carried out in vivo, showing the …

Effects of tributyltin(IV) chloride on the gametes and fertilization ofAscidia malaca (Ascidiacea: Tunicata)

Ascidia malaca gametes before fertilization incubated in 10-5 or 10-7 M solutions of tributyltin(IV) chloride, TBTCl, for 3 h appear highly damaged under transmission electron microscopy observation. Also, the fertilization process is affected by the compound: the damaged spermatozoa are present in the vitelline coat and the egg does not cleave. An increase of microbodies, structurally similar to peroxisomes, have been detected in the egg peripheral cytoplasm, probably in relation to their role in alleviating damage to some cellular components. The results have shown that the reproduction of ascidians under unfavourable environmental conditions is prevented. Copyright © 2003 John Wiley &amp…

TPPS derivatives induce apoptosis on A375 human melanoma cells

Effects of sublethal levels of tributyltin chloride on a new toxicity test organism, Liza saliens (Osteichthyes, Mugilidae)

The histopathological effects of 10−7 and 10−9 M tributyltin(IV)chloride,TBTCl, solutions on different Liza saliens organs have been studied by light microscope. The fish were sacrificed after 3–4 h incubation in 10−7 M TBTCl solution or after 15 days incubation in 10−9 M solution. The observed histopathological changes were dose- and time-dependent. The 10−7 M TBTCl concentration resulted in major damage to the gill epithelium, indicating that TBTCl primarily interferedwith the respiration, osmoregulation, acid balance and nitrogenous waste excretion processes. After incubation in 10−9 M TBTCl solution the fish lived 20 or more days, but many of the organs were altered. Thymus atrophy, red…

Effects of organotin(IV)(metal-sulfonatophenyl)porphinates on the growth of A375 human melanoma cells

Carbocysteine degradation catalyzed by organotin(IV) compounds.

Toxic Effects of Organometallic Compounds towards Marine Biota

Organometallic derivatives are compounds containing a direct σ or π carbon metal linkage. Furthermore, the concept of the metallic atom must be extended to all the elements that are less negative than the carbon atom. As a consequence, taking into account all elements that are less negative than carbon and the number of existing organic compounds, it is possible to synthesize millions of organometallic derivatives. Several of these are extensively used in organic syntheses; others may find application in agriculture and in many other fields as pesticides, fire retardants, wood preservatives, antifouling agents, etc. In general, the organic derivatives of the metals are more toxic than the p…

Oxidative stress induced by the novel compound tributyltin(iv) ferulate promotes ER stress and autophagy in colon cancer cells

Novel metallic and organometallic based antiproliferative complexes: Integrated methodologies of evaluation

Potential use of organotin(IV)-tripetide complexes as stopper in tumor cells growth.

Synthesis and structural investigations on R2Sn(IV)-D-aldonic acid complexes (R = methyl; butyl). Their effect on a new toxicity test organism,Liza saliens(Osteichthyes, Mugilidae): a histological study

Eight R2Sn(IV)-D-aldonate complexes [(R = Me, Bu; D-aldonate = D-galactonate2− (Galn), D-Gluconate2− (Glun), D-Gulonate2− (Guln), D-Ribonate2− (Ribn)], five of which are new derivatives, have been synthesized and structurally characterized both in solid and solution state by IR, 119Sn Mossbauer and 1H, 13C, 119Sn NMR spectroscopies, showing that ligands act as dianonic chelating agents. In solution phase, NMR data suggest that the bidentate chelation is attained by the O1 carboxylate and the vicinal O2 alkoxide atoms, which can be dynamically extended to a third binding site (O4) competing with O2. In Me2Sn(IV)-D-gluconate complex the occurrence of a self-association process leading to a di…

ORGANOTIN(IV)-PORPHINATE FOR PHOTOVOLTAIC BULK HETEROJUNCTIONS

Due to the versatility and variability of their molecular structures, optical spectra, electrical properties, and supramolecular organization potential, porphyrins related compounds have been widely studied in organic solar cells [1,2]. Indeed, these applications are a natural function for these compounds, and they have been extensively investigated in a variety of formats including single molecules, macromolecular and supramolecular structures. In this work, poly(hexylthiophene) (P3HT) and organotin(IV)-[meso-tetra(4-carboxyphenyl) porphinate] have been employed for engineering planar and bulk heterojunctions by layer by layer deposition. Improving the overall efficiencies of photovoltaic …

ATTIVITÀ CITOTOSSICA DEI COMPLESSI DIORGANOSTAGNO(IV)-N-ACETILCISTEINA SU CELLULE DI MELANOMA A-375.

Effects of tributyltin(IV) chloride on fertilization ofStyela plicata(Ascidiacea: Tunicata): II. Scanning and transmission electron microscopy studies

The morphological aspects of Styela plicata fertilization after treatment with tributyltin(IV) chloride are described by means of scanning and transmission electron microscopy investigations. Alterations have been shown both on female and male gametes; spermatozoa, all the egg envelopes and the mitochondria of the egg cortical cytoplasm are modified in relation to incubation time. As a consequence, the damage to gametes blocks sperm–egg interaction and fertilization does not occur. Copyright © 2003 John Wiley & Sons, Ltd.

Structural investigations on diorganotin and triorganotin(IV) phosphomycin derivatives.

Abstract Four new diorganotin(IV), (R = Me, Bu), and triorganotin(IV), (R = Me, Ph), derivatives of the phosphomycin disodium salt antibiotic[(1R,2S)-1,2-epoxypropylphosphonate]Na2 have been synthesized and their solid state configuration studied by X-ray crystallography, FT-IR, Mossbauer, UV–Vis spectroscopies. The X-ray diffraction investigation, performed on the bis[trimethyltin(IV)]phosphomycin, showed that the coordination geometry at all the Sn atoms is trigonal bipyramidal. The structure of the complex forms an unusual polymeric zig-zag planar network. The FT-IR and the 119Sn Mossbauer studies supported the formation of trigonal bipyramidal (Tbp) molecular structures, both in the dio…

Preparation and structural studies on diorganotin(IV) complexes of N-nitroso-N-phenylhydroxylaminates

Abstract Diorganotin(IV)-complexes of the N -nitroso- N -phenylhydroxylaminates (hereinafter cupf), Et 2 Sn(cupf) 2 ( 1 ), Bu 2 Sn(cupf) 2 ( 2 ), {[Bu 2 Sn(cupf)] 2 O} 2 ( 3 ), t -Bu 2 Sn(cupf) 2 ( 4 ) and Oc 2 Sn(cupf) 2 ( 5 , 6 ) were prepared and characterised by FT-IR and Mossbauer spectroscopic measurements. The binding modes of the ligand were identified by FT-IR spectroscopy, and it was found that the ligand is coordinated in chelating or bridging mode to the organotin(IV) center. The 119 Sn Mossbauer and FT-IR studies support the formation of trans -O h ( 1 – 6 ) structures. The X-ray diffraction analysis of 4 revealed that the tin centre is in a skew-trapezoidal geometry defined by…

Equilibrium, Structural and Biological Activity Studies on [Organotin(IV)]n+ Complexes

Organotin(IV) compounds are characterized by the presence of at least one covalent C–Sn bond. The compounds contain tetravalent {Sn} centers and are classified as mono-, di-, tri-, and tetraorganotin(IV), depending on the number of alkyl (R) or aryl (Ar) moieties bound. The anions are usually Cl, F, O2, OH,–COO, or –S. It seems that the nature of the anionic group has only secondary importance in biological activity. The rapid rise in the industrial (catalyst in PVC and foam production), agricultural (fungicides and acaricides), and biological applications (wood, stone, and glass preservatives) of organotin(IV) compounds during the last few decades has led to their accumulation in the envir…

Organotin(IV) complexes with epigenetic modulator ligands: New promising candidates in cancer therapy

Organotin(IV) compounds have found their place among a class of non-platinum chemotherapeutic metallo-pharmaceuticals exhibiting good antitumor activity. The cytotoxicity induced by the different kinds of organotins has been related to several mechanism. In this review we report our last decade research activity concerning the synthesis and chemical characterization of new organotin(IV) derivatives containing epigenetic modulator ligand by using, FT-IR, Mössbauer spectroscopy, 119Sn{1H} cross polarization magic angle spinning, electrospray ionization mass spectroscopy, UV–Vis, 1H, 13C{1H} and 119Sn{1H} NMR spectroscopy and density functional theory calculations. The first aim of the biologi…

Electrochemotherapy for "in vivo" experimental trial of new promising anti-melanoma therapy

Interference of tributyltin(IV)chloride on the vascular plant cells

In the recent past years, interest in the environmental impact of organotin(IV) compounds has risen markedly. Considering that most data in the scientific literature refers to the animal kingdom and not to higher plants cells, we tested the effects of organotin compounds on vascular plant cells, by studying the interaction of tributyltin chloride (TBTCl) with Allium cepa, Solanun tuberosum and Solanum melongena, vascular plants that are directly involved in the human food chain. The TBTCl effects on mitotic metaphase plates, on pollen grains and on both microtubers and adult tuber parenchymatic cells were investigated and the concentrations of TBTCl inside the treated parenchymatic cells we…

Nanoassemblies of Amphiphilic Cyclodextrin and Tributyltin(IV)Complexes of meso-Tetra (4-sulfonatophenyl)porphine: Spectroscopy, Release and Cytotoxicity on Human Melanoma Cells

Dibutyltin(IV) and Tributyltin(IV) Derivatives of meso-Tetra(4 sulfonatophenyl)porphine Inhibit the Growth and the Migration of Human Melanoma Cells.

Melanoma is the most aggressive and deadly form of skin cancer, which is largely due to its propensity to metastasize. Therefore, with the aim to inhibit the growth and the metastatic dissemination of melanoma cells and to provide a novel treatment option, we studied the effects of the melanoma treatment with two organotin(IV) complexes of the meso-tetra(4-sulfonato-phenyl)porphine, namely (Bu2Sn)2TPPS and (Bu3Sn)4TPPS. In particular, we showed that nanomolar concentrations of (Bu2Sn)2TPPS and (Bu3Sn)4TPPS are sufficient to inhibit melanoma cell growth, to increase the expression of the full-length poly (ADP-ribose) polymerase (PARP-1), to induce the cell cycle arrest respectively at G2/M a…

Organometallic Complexes with Biological Molecules, VI. Diorganotin(IV) and Triorganotin(IV) Ampicillin and Methicillin Derivatives: Spectroscopic Investigations in the Solid State

Derivatives of D(-)-α-aminobenzylpenicillin (ampicillin) and of 2,6-dimethoxyphenylpenicillin (methicillin) with diorgano- and triorgano-tin(IV) moieties have been synthesized. The stoichiometries of the compounds obtained were of the type R 2 SnCIL.H 2 O, R 3 SnCILNa.H 2 O [L=ampicillin or methicillin monoanion; R=Me, Bu, Ph] and R 2 Snampic 2 . 2H 2 O (ampic=ampicillin; R=Me, Bu, Ph). For R 2 SnCIL.H 2 O and R 3 SnCILNa.-H 2 O, infrared (IR) data suggest five-coordination around the tin(IV) atom; in R 2 Snampic 2 .2H 2 O six-coordination is most likely to occur. Thermogravimetric (TG) analysis excludes any involvement in the coordination of tin(IV) by water molecules, in any of the compou…

Synthesis, chemical characterization, computational studies and biological activity of new DNA methyltransferases (DNMTs) specific inhibitor. Epigenetic regulation as a new and potential approach to cancer therapy.

This work deals with the synthesis, the chemical characterization of dibutyltin(IV) complex of caffeic acid (Bu2Sn(IV)HCAF, caf1) and its cytotoxic action on tumor cells. The coordination environment at the tin center was investigated by FTIR, (119)Sn{(1)H} cross polarization magic angle spinning, electrospray ionization mass spectroscopy in the solid state and UV-vis, fluorescence and (1)H, (13)C and (119)Sn NMR spectroscopy in solution phases. Density functional theory study confirmed the proposed structures in solution phase and indicated the most probably stable conformation. The effects on viability of breast cancer MDA-MB231, colorectal cancer HCT116, hepatocellular carcinoma HepG2 an…

Synthesis, Structural Analysis, Fiber Formation and Preliminary Anticancer Characterization of the Organotin Polyether from Dibutyltin Dichloride and 2,5-Dimethyl-3-hexyne-2,5-diol

The organotin polyether derived from reaction of dibutyltin dichloride and 2,5-dimethyl-3-hexyne-2,5-diol was rapidly synthesized employing classical interfacial polymerization in 65% yield and a chain length of 360 units. IR results are consistent with the polyether structure. Bands characteristic of the formation of the Sn-O are present and bands characteristic of the Sn-Cl are absent. F MALDI MS results in the low mass range gives ion fragment clusters to five units. Isotopic abundance matches for tin are consistent with its presence in these ion fragment clusters. In the high mass range ion fragment clusters to greater than 300 units are found. The products offer outstanding inhibition …

Synthesis, chemical characterization, computational studies and biological activity of organotin(IV) compounds interacting with enzymes involoved in epigenetic regulation. New and potential methodologies for studying molecular interactions

Our studies deal with the synthesis, the chemical characterization of organotin(IV) complexes of molecules, as caffeic acid, interacting with enzymes involved in epigenetic regulation.

Diorganotin(IV) and triorganotin(IV complexes of meso tetra (4 sulfonatophenyl) porphine: do they bind DNA?

It was observed that organometallic porphyrin systems, where the Sn(IV) residue is in side chains, coordinated via sulphonatophenyl groups of porphyrin, show interesting and peculiar in vitro activity, in agreement with the anti-tumour activity of organotin complexes.

Organometallic complexes with biological molecules. XIV. Biological activity of dialkyl and trialkyltin(IV) [meso-tetra(4-carboxy- phenyl)porphinate] derivatives

Molecules. XIV. Biological Activity of Dialkyl and Trialkyltin(IV) [Meso-tetra(4-carboxyphenyl)porphinate] Derivatives C. Mansueto, E. Puccia, F. Maggio, R. Di Stefano, T. Fiore, C. Pellerito, F. Triolo and L. Pellerito* Dipartimento di Biologia Animale, Universita di Palermo, Via Archirafi 18, 90123 Palermo, Italy Dipartimento di Chimica Inorganica, Universita di Palermo, Viale delle Scienze, Parco d’Orleans, 90128 Palermo, Italy

Studi strutturali e indagini biologiche di nuovi complessi di rutenio(III) con 1- tioglucosio e 1-metiluracile

Organometallic Complexes with Biological Molecules: VII. Dialkyl- and Trialkyl-tin (IV)[meso-tetra(4-carboxyphenyl)porphinate] Derivatives: Solid-state, Solution-phase Structural Aspects andIn Vivo Effects

The synthesis, the structural features and the in vivo biological activity of diorganotin(IV) and triorganotin(IV) derivatives of [meso-tetra(4-carboxyphenyl)porphine] (H 4 TPPC) are reported. Derivatives with general formula (R 2 Sn) 2 TPPC and (R 3 Sn) 4 TPPC (R=Me, Bu, and Ph) were obtained, and the main information extracted from the infrared and Mossbauer spectral data, in the solid state, was in favor of the occurrence of five-coordinated tin(IV) atoms, in a polymeric trigonal-bipyramidal configuration, attained through two differently coordinated, estertype and chelating respectively, carboxylate anions in [R 2 Sn] 2 TPPC, while in [Alk 3 Sn] 4 TPPC five-coordination of the tin(IV) a…

Diorganotin(IV) complexes with aldonic acids. Synthesis and structural study in solid state and in solution phase and biological activity

Computational study of dimethyl- and trimethyl-tin(IV) complexes of porphyrin derivatives

The molecular geometry, energetics and electronic charge distribution of diorgano- and triorgano-tin(IV) complexes of [protoporphyrin-IX] and [meso-tetra(4-carboxyphenyl)porphine] derivatives were determined at semi-empirical and ab initio levels. To study the molecular details of the complexes, simpler molecule models were calculated by the ab initio pseudo-potential method. The molecular properties of these complexes are essentially independent of the presence of the peripheral tin atoms. Agreement was always found among the results of the different computational approaches, as well as between the theoretical and the experimental findings on the molecular geometry of the hypothesized comp…

Organotin(IV)derivatives neurotoxicity and their modulation by Baclofen

Several new diorganotin(IV) and triorganotin(IV) complexes with 4-amino-3- (4-chloro phenyl)]-butanoic acid ( = Baclofen) have been synthesized and their structure investigated both in the solid state and in solution phase through spectroscopic methods (FT-IR, Mössbauer, 1H and 13C NMR). According to experimental analytical data, the stoichiometry of the complexes has been proposed as R2SnBac2 and R3SnBac, respectively for diorganotin(IV) and triorganotin(IV) baclofen complexes. (Baclofen = HBac; R = Me, Bu, Ph).

Porphyrin tributyltin(IV) complexes for a novel approach in the tratment of human melanoma

Melanoma is the most deadly form of skin cancer, largely refractory to existing therapies. The study of porphyrin derivatives as potential anti-tumor drugs has been an interesting field of investigation in the last years. Recently, a photo-independent cytotoxic effect of (Bu3Sn)4TPPS in the blocking melanoma cell proliferation an inducing a morphology cell change was investigated.[1] Amphiphilic CD (ACyD) provides more water soluble and adaptable nanovectors through modulation of the balance between hydrophobic and hydrophilic chains at both CD sides. ACyD can be conveniently tailored by covalently appending fluorescent label or receptor-targeting glycosyl- groups and can encapsulate conven…

Synthesis and characterization of some new ruthenium complexes with ligands of biological interest

Organometallic complexes with biological molecules: XIII. Organotin(IV)[meso-tetra (4-carboxyphenyl)porphinate]s and the cell cycle: a flow-cytometric approach

The cytotoxic derivatives diorganotin(IV) and triorganotin(IV) [meso-tetra(4-carboxyphenyl)porphinates, with stoichiometries [R2Sn]2TPPC and [R3Sn]4TPPC [R = Me, Bu, Ph; TPPC4−­= meso-tetra(4-carboxyphenyl)porphinate4−], namely bis[dimethyltin(IV)], bis[dibutyltin(IV)], bis[diphenyltin(IV)], tetra[trimethyltin(IV)], tetra[tributyltin(IV)] and tetra[triphenyltin(IV)] [meso-tetra(4-carboxyphenyl)porphinate]s, have been used to investigate their effects on the cultured human kidney cell cycle in order to understand further the origin of cell-growth inhibition induced by the above-mentioned chemicals. The cell-cycle-dependent DNA content distribution of cultured cells exposed to these compounds…

Tributyltin(Iv) butyrate: A novel epigenetic modifier with er stress-and apoptosis-inducing properties in colon cancer cells

Organotin(IV) compounds are a class of non-platinum metallo-conjugates exhibiting antitumor activity. The effects of different organotin types has been related to several mechanisms, including their ability to modify acetylation protein status and to promote apoptosis. Here, we focus on triorganotin(IV) complexes of butyric acid, a well-known HDAC inhibitor with antitumor properties. The conjugated compounds were synthesized and characterised by FTIR spectroscopy, multi-nuclear (1H, 13C and 119Sn) NMR, and mass spectrometry (ESI-MS). In the triorganotin(IV) complexes, an anionic monodentate butyrate ligand was observed, which coordinated the tin atom on a tetra-coordinated, monomeric enviro…

Organometallic complexes with biological molecules. IX. Diorgano- and triorgano-tin(IV)[meso-tetra (4-sulfonatophenyl)porphinate] derivatives: solid-state and solution-phase structural aspects andin vivo effects

Diorgano- and triorgano-tin(IV) derivatives of meso-tetra(4-sulfonatophenyl)porphine (H4TPPS) with general formula (R2Sn)2TPPS and (R3Sn)4TPPS (TPPS4−=[meso-tetra(4-sulfonatophenyl)porphinate]4−, R=Me, Bu, Ph) have been obtained and their solid-state configuration inferred on the basis of IR and Mossbauer spectroscopy, while solution-phase studies have been carried out by 1H and 13C NMR in DMSO-d6, together with determination of the in vivo cytotoxicity of the new derivatives towards embryonic development of Ciona intestinalis. In particular, octahedral and trigonal-bipyramidal eq-R3Sn polymeric configurations are proposed, in the solid state, respectively for (R2Sn)2TPPS and (R3Sn)4TPPS co…

Equilibrium and spectroscopic studies of diethyltin(iv) complexes formed with hydroxymono- and di-carboxylic acids and their thioanalogues

The complex formation of diethyltin(IV) cation with glycolic (GA), lactic (LA), succinic (SA), malic (MA), tartaric (TA), mercaptoacetic (MAA), 2-mercaptopropionic (MPA), mercaptosuccinic (MSA) and dimercaptosuccinic acid (DMSA) has been investigated by potentiometric, spectrophotometric, 1H NMR and Mossbauer spectroscopic methods. The mercaptocarboxylic acids yielded much more stable complexes than the corresponding hydroxy acids. Below pH 3, the carboxylate and the still protonated hydroxyl group of hydroxy acids are co-ordinated to the metal ion, while in the case of their thio analogues, {COO−, S−} co-ordinated species are dominant. With increasing pH, the metal promoted deprotonation o…

Synthesis, chemical characterization and biological activity of new histone acetylation/deacetylation specific inhibitors: a novel and potential approach to cancer therapy

Three new triorganotin(IV) complexes of valproic acid (vp1, Me3Sn-valproate; vp2, Bu3Sn-valproate; vp3, Ph3Sn-valproate) have been synthesized and investigated by spectroscopic and biological methods. An anionic, monodentate valproate ligand was observed, ester-like coordinating the tin atom on a tetra-coordinated, monomeric environment. The structures, though, can distort towards a penta-coordination, as a consequence of a long range O center dot center dot center dot Sn interaction. Crystallographic and NMR findings confirm this situation both in solid state and solution. Biological finding evidenced a clear cytotoxic action of the complexes in hepatocellular carcinoma cell cultures: one …

Synthesis, structural investigation and biological activity of new diorganotin(IV) N-acetylcysteine Complexes.

Boosting the Performance of One-Step Solution-Processed Perovskite Solar Cells Using a Natural Monoterpene Alcohol as a Green Solvent Additive

The perovskite film is the core of a perovskite solar cell (PSC), and its quality is crucial for the performance of such devices. The morphology, crystallinity, and surface coverage of the perovskite layer greatly affect the power conversion efficiency (PCE), hysteresis, and long-term stability of PSCs. The incorporation of appropriate solvent additives in the perovskite precursor solution is an effective strategy to control the film morphology and reduce the defects and grain boundaries. However, the commonly used solvent additives are environmentally harmful and highly toxic. In this work, α-terpineol (a nontoxic, eco-friendly, and low-cost monoterpene alcohol) is employed for the first t…

Studies on DNA interaction of organotin(IV) complexes of meso-tetra(4-sulfonatophenyl)porphine that show cellular activity.

PubMedID: 27393277 The interaction of the diorgano- and triorganotin(IV) derivatives of meso-tetra-(4-sulfonatophenyl)porphine (Me2Sn)2TPPS, (Bu2Sn)2TPPS, (Me3Sn)4TPPS and (Bu3Sn)4TPPS to natural DNA was analysed (together with free meso-tetra-(4-sulfonatophenyl)porphine (TPPS4 -) for comparison purposes). Particular attention was paid to (Bu3Sn)4TPPS, a species that shows significant cellular action. Preliminary tests were done on the solution properties of the organotin(IV) compounds (pKA and possible self-aggregation). Spectrophotometric and spectrofluorometric experiments showed that all the investigated organotin(IV) derivatives strongly interact with DNA, the binding energy depending …

Corrigendum: Organometallic complexes with biological molecules: VII. Diorgano- and triorgano-tin(IV)[meso-tetra(4-carboxyphenyl)porphinate] derivatives: solid-state, solution-phase structural aspects andin vivo effects

Organometallic complexes with biological molecules. XV. Effects of tributyltin(IV)chloride on enzyme activity, Ca2+, and biomolecule and synthesis inCiona intestinalis (Urochordata) ovary

Considerable attention has been given in recent years to the possibility that xenobiotics in the environment may affect reproduction in animals. In this study, the relative impact of tributyltin(IV) (TBT) chloride, one of the most toxic environmental pollutants, was investigated using Ciona intestinalis ovary as a model system. The pleiotropic effects of TBT exposure are concentration dependent and include a decrease of ATP levels, lipid content and nucleic acid content and synthesis. In contrast, a marked increase in calcium (Ca2+) and glucose content is observed. Furthermore, TBT alters enzymatic activity, inhibiting creatine kinase and stimulating alkaline phosphatase and cholinesterase …

Synthesis, Characterization and in vitro antimicrobial activity of dialkyltin(IV)bis(fusidate) complexes.

The complexation of one steroid antibiotic of the fusidane family, sodium fusidate [sodium 2-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12, 13,15,16-dodeca hydro-1H-cyclopenta[a]phenanthren-7-ylidene)-6-methyl-hept-5-enoate = (Nafus)], by dialkyltin(IV) has been studied by conventional technique as FT-IR, Mössbauer and NMR spectroscopies. Analytical data supported the general formula Alk2Sn(IV)fus2 (Alk = Me, Bu). Infrared spectral data of the complexes imply the presence of both uni- and bidentate, ester-type and bridging carboxylate group, respectively. On the basis of FT-IR and 119Sn Mössbauer spectroscopy, in both Me2Sn(IV)fus2 and Bu2Sn(IV)fus2, trigonal bipyram…

Abnormal Expression of the major Histocompatibility Complex Class II (MHC Class II) Molecules in melanoma and cytotoxic effect of meso-tetra-(4-sulfonatophenyl)porphynate (=TPPS) derivatives.

Tributyltin(IV) ferulate, a novel synthetic ferulic acid derivative, induces autophagic cell death in colon cancer cells: From chemical synthesis to biochemical effects

Ferulic acid (FA) is a natural phenolic phytochemical that has low toxicity and exhibits therapeutic effects against various diseases, behaving as an antioxidant. FA also displays modest antitumor properties that have been reported at relatively high concentrations. With the aim of improving the anti-tumor efficacy of FA, we synthesized the novel compound tributyltin(IV) ferulate (TBT-F). The coordination environment at the tin center was investigated spectroscopically. Following synthesis, chemical characterization and computational analysis, we evaluated TBT-F effects in colon cancer cells. The results showed that TBT-F, at nanomolar range concentrations, was capable of reducing the viabi…

ROS-Dependent ER Stress and Autophagy Mediate the Anti-Tumor Effects of Tributyltin (IV) Ferulate in Colon Cancer Cells

Organotin compounds represent potential cancer therapeutics due to their pro-apoptotic action. We recently synthesized the novel organotin ferulic acid derivative tributyltin (IV) ferulate (TBT-F) and demonstrated that it displays anti-tumor properties in colon cancer cells related with autophagic cell death. The purpose of the present study was to elucidate the mechanism of TBT-F action in colon cancer cells. We specifically show that TBT-F-dependent autophagy is determined by a rapid generation of reactive oxygen species (ROS) and correlated with endoplasmic reticulum (ER) stress. TBT-F evoked nuclear factor erythroid-2 related factor 2 (Nrf2)-mediated antioxidant response and Nrf2 silenc…

New histone acetylation/deacetylation specific inhibitors: a novel and potential approach to cancer therapy

The acetylation status of histones is regulated in eukaryotes by two kinds of enzymes, histone acetyltransferases (HATs) and histone deacetylases (HDACs), which are responsible for acetylation and deacetylation of lysines residues in N-terminal tails of histone.[1] Thus acetylation, together with phosphorylation and methylation of N-terminal tail of histones, are involved in regulating fundamental processes, such as proliferation and cell death.[2-3] Sodium butyrate, which belongs together with valproic acid to the class of short chain fatty acids, was the first HDAC inhibitor (HDACI) to be identified.[1] Organotin compounds have various influences on physical function including the hormone…

Organometallic Complexes with Biological Molecules. Structural investigation of cis-diammineplatinum(II)-Porphyrin derivatives.

CCDC 830010: Experimental Crystal Structure Determination

Related Article: Ornella Pellerito, Cristina Prinzivalli, Elisabetta Foresti, Piera Sabatino, Michele Abbate, Girolamo Casella, Tiziana Fiore, Michelangelo Scopelliti, Claudia Pellerito, Michela Giuliano, Giulia Grasso, Lorenzo Pellerito|2013|J.Inorg.Biochem.|125|16|doi:10.1016/j.jinorgbio.2013.04.008