Search results for "Apoptosi"

showing 10 items of 1846 documents

Cytotoxicity of Artesunic Acid Homo- and Heterodimer Molecules toward Sensitive and Multidrug-Resistant CCRF-CEM Leukemia Cells

2010

A novel approach to circumvent multidrug resistance is hybridization of natural products in dimers. We analyzed homodimers of two artesunic acid molecules and heterohybrids of artesunic acid and betulin in human CCRF-CEM and multidrug-resistant P-glycoprotein-overexpressing CEM/ADR5000 leukemia cells. Multidrug-resistant cells were not cross-resistant to the novel compounds. Collateral sensitivity was observed for artesunic acid homodimer. Artesunic acid and artesunic acid homodimer induced G0/G1 cell cycle arrest, apoptosis, and formation of reactive oxygen species.

Spectrometry Mass Electrospray IonizationMagnetic Resonance SpectroscopyCell SurvivalApoptosischemistry.chemical_compoundCell Line TumorDrug DiscoverymedicineHumansCytotoxicitychemistry.chemical_classificationReactive oxygen speciesFormazansLeukemiaBetulinCell CycleSuccinatesCell cycleFlow Cytometrymedicine.diseaseArtemisininsTriterpenesMultiple drug resistanceLeukemiachemistryBiochemistryDrug Resistance NeoplasmCell cultureApoptosisMolecular MedicineReactive Oxygen SpeciesJournal of Medicinal Chemistry
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4,5,6,7-Tetrahydro-isoxazolo-[4,5-c]-pyridines as a new class of cytotoxic Hsp90 inhibitors.

2014

Hsp90 is considered an interesting therapeutic target for anticancer drug development. Here we describe a new class of 4,5,6,7-tetrahydro-isoxazolo-[4,5-c]-pyridine compounds. A small library of derivatives has been synthesized and investigated. Some reported compounds show interesting properties combining both notable binding to Hsp90 and potent cell growth inhibitory activity. N-5 substitution with a 2,4 resorcinol carboxamide appears crucial for activity. Moreover, a derivative bearing a hydroxamic acid residue bound to C-3 amide portion was found to inhibit both Hsp90 and HDAC6.

Spectrometry Mass Electrospray IonizationMagnetic Resonance Spectroscopymedicine.drug_classStereochemistryPyridinesCarboxamideApoptosisResorcinolAnti-cancer drugschemistry.chemical_compoundResidue (chemistry)AmideDrug DiscoveryHeat shock protein 90 Anti-cancer drugs 4567-Tetrahydro-isoxazolo-[45-c]- pyridinesmedicineCytotoxic T cellHumansHeat shock protein 90HSP90 Heat-Shock ProteinsPharmacologyHydroxamic acidChemistryCell growthOrganic ChemistryGeneral MedicineNuclear magnetic resonance spectroscopy4 5 6 7-Tetrahydro-isoxazolo-[4 5-c]-pyridinesFlow CytometrySettore CHIM/08 - Chimica Farmaceuticahsp90Settore BIO/14 - Farmacologia4 5 6 7-Tetrahydro-isoxazolo-[4 5-c]-pyridines; Anti-cancer drugs; Heat shock protein 90;K562 CellsCell DivisionEuropean journal of medicinal chemistry
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Synthesis of platinum complexes with 2-(5-perfluoroalkyl-1,2,4-oxadiazol-3yl)-pyridine and 2-(3-perfluoroalkyl-1-methyl-1,2,4-triazole-5yl)-pyridine …

2016

Five new mononuclear Pt(II) complexes with 5-perfluoroalkyl-1,2,4-oxadiazolyl-pyridine and 3-perfluoroalkyl-1,2,4-triazolyl-pyridine ligands are reported. The ligands 2-(5-perfluoroheptyl-1,2,4-oxadiazole-3yl)-pyridine (pfhop), 2-(5-perfluoropropyl)-1,2,4-oxadiazole-3yl)-pyridine (pfpop), 2-(3-perfluoroheptyl-1-methyl-1,2,4-triazole-5yl)-pyridine (pfhtp), 2-(3-perfluoropropyl-1-methyl-1,2,4-triazole-5yl)-pyridine (pfptp) and their complexes [PtCl2(pfhop)(2)]center dot 1.5 DMSO (2a), [PtCl2(pfpop)(2)]center dot 1.5 DMSO (3a), [PtCl2(pfhtp)(2)]center dot 1.5 DMSO (4a), PtCl2(pfhtp) (4b), [PtCl2(PfPtP)(2)]center dot 1.5 DMSO (5a) have been synthesized and structurally characterized. The comple…

Spectrophotometry InfraredStereochemistryPyridinesProton Magnetic Resonance SpectroscopyTriazoleOxadiazoleAntineoplastic AgentsApoptosisPlatinum Compounds010402 general chemistryLigands01 natural sciencesBiochemistryInorganic Chemistrychemistry.chemical_compoundSettore BIO/10 - BiochimicaCell Line TumorEthidiumPyridineMoleculeHumansFluorescent DyesPlatinum complexes oxadiazole antitumor activity010405 organic chemistryLigandAcridine orange124-TriazoleSettore CHIM/06 - Chimica OrganicaAcridine Orange0104 chemical scienceschemistrySettore CHIM/03 - Chimica Generale E InorganicaEthidium bromideJournal of inorganic biochemistry
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CO-releasing binuclear rhodium complexes as inhibitors of nitric oxide generation in stimulated macrophages.

2013

Nontoxic CO-releasing dirhodium complexes act as inhibitors of NO in stimulated macrophage cells, suggesting that novel antiinflammatory treatments could involve the use of these types of binuclear complexes.

StereochemistryAnti-Inflammatory Agentschemistry.chemical_elementApoptosisNitric OxideModels BiologicalNitric oxideRhodiumCell LineInorganic Chemistrychemistry.chemical_compoundQUIMICA ORGANICACoordination ComplexesQUIMICA ANALITICAMacrophageMoleculeAnimalsHumansRhodiumPhysical and Theoretical ChemistryCarbon monoxideCarbon MonoxideMacrophagesRegulatorQUIMICA INORGANICAMoleculesHeme oxygenaseHeme oxygenaseCormschemistrySmooth muscle cellsCell cultureApoptosisBiological AssayCarbon monoxideInorganic chemistry
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Synthesis, chemical characterization and biological activity of new histone acetylation/deacetylation specific inhibitors: a novel and potential appr…

2013

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 …

StereochemistryCell SurvivalAntineoplastic AgentsBiochemistryInorganic ChemistryHistonesHistone H3Organotin CompoundsCytotoxic T cellHumansViability assayCells CulturedMOSSBAUER SPECTROSCOPYOrganoTin(IV)biologyX-RAY DIFFRACTIONChemistryMössbauer spectroscopyValproic AcidESI-MSBiological activityAcetylationHep G2 CellsLigand (biochemistry)NMRHistoneBiochemistryApoptosisAcetylationSettore CHIM/03 - Chimica Generale E Inorganicabiology.proteinX-ray spectroscopy
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Antiproliferative agents that interfere with the cell cycle at the G(1)-->S transition: further development and characterization of a small library o…

2008

In this continuation of our research on derivatives containing the stilbene privileged structure or that are derived from it, we report the results of further studies carried out on the previously initiated collection of compounds. We used a parallel synthetic approach to rapidly obtain small sets of compounds and started the annotation of the library in progress by calculating some physicochemical properties to be eventually correlated with biological activities. A pharmacophore for the antiproliferative activity was also built to summarize the features of the library. We evaluated the antiproliferative and pro-apoptotic activities of all compounds as well as the cell-cycle effects of some…

StereochemistryCellular differentiationAntineoplastic AgentsApoptosisHL-60 CellsBiochemistryS PhaseSmall Molecule Librarieschemistry.chemical_compoundInhibitory Concentration 50Biological profileCell Line TumorDrug DiscoveryStilbenespharmacophoresHumansGeneral Pharmacology Toxicology and PharmaceuticsPhosphorylationPharmacologyChemistryOrganic ChemistryG1 PhaseRetinoblastomaSmall Molecule LibrariesG1/S transitionCell DifferentiationCell cycleFlow CytometryCombinatorial chemistryantitumor agentAntiproliferative AgentsMolecular MedicineTriolcell cyclePharmacophoreC-C couplingK562 Cells
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Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G0−G1 Phase and Induces Differentiation in Leukemia Cells

2006

To further explore the SAR of resveratrol-related trans-stilbene derivatives, here we describe the synthesis of (a) a series of 3,5-dimethoxy analogues in which a variety of substituents were introduced at positions 2', 3', 4', and 5' of the stilbene scaffold and (b) a second group of derivatives (2-phenylnaphthalenes and terphenyls) that incorporate a phenyl ring as a bioisosteric replacement of the stilbene alkenyl bridge. We thoroughly characterized all of the new compounds with respect to their apoptosis-inducing activity and their effects on the cell cycle. One of the new derivatives, 13g, behaved differently from the others, as it was able to block the cell cycle in the G(0)-G(1) phas…

StereochemistryCellular differentiationFusion Proteins bcr-ablAntineoplastic AgentsApoptosis.ResveratrolResting Phase Cell CycleChemical synthesisStructure-Activity Relationshipchemistry.chemical_compoundLeukemia Promyelocytic AcuteCell Line TumorTerphenyl CompoundsTerphenylStilbenesDrug DiscoveryHumansStructure–activity relationshipATP Binding Cassette Transporter Subfamily B Member 1G1 PhaseCell DifferentiationCell cycleIn vitrochemistryDrug Resistance NeoplasmResveratrolCell cultureMolecular MedicineDrug Screening Assays AntitumorJournal of Medicinal Chemistry
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11H‑Pyrido[3′,2′:4,5]pyrrolo[3,2‑c]cinnoline and Pyrido[3′,2′:4,5]pyrrolo[1,2‑c][1,2,3]benzotriazine: Two New Ring Systems with Antitumor Activity

2014

Derivatives of new ring systems 11H-pyrido[3',2':4,5]pyrrolo[3,2-c]cinnoline and pyrido[3',2':4,5]pyrrolo[1,2-c][1,2,3]benzotriazine have been prepared from the key intermediates 2-(1H-pyrrolo[2,3-b]pyridin-2-yl)anilines in excellent yields (94-99%) and screened by the National Cancer Institute (Bethesda, MD) on about 60 human tumor cell lines derived from nine cancer cell types. The tested compounds exhibited antiproliferative activity against all the human cell lines, showing comparable MG_MID (mean graph midpoint) values in the range of 0.74-1.15 μM. A particular efficacy was observed against the leukemia subpanel (GI50 = 0.73-0.0090 μM). Flow cytometric analysis of the cell cycle demons…

StereochemistryCinnolines; triazinesChemistry PharmaceuticalAntineoplastic AgentsApoptosisHeterocyclic Compounds 2-RingHeterocyclic Compounds 4 or More Ringschemistry.chemical_compoundJurkat CellsCell Line TumorNeoplasmsDrug DiscoverytriazinesHumansCinnolineCell Proliferationchemistry.chemical_classificationReactive oxygen speciesCell DeathChemistryCell growthCell CycleCell MembraneTemperatureDepolarizationCell cycleCaspase InhibitorsMitochondriaEnzyme ActivationCell cultureApoptosisCaspasesCinnolines triazinesCancer cellMolecular MedicineLysosomesReactive Oxygen SpeciesCinnolines
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Synthesis and biological evaluation of 4-nitro-substituted 1, 3-diaryltriazenes as a novel class of potent antitumor agents

2011

Abstract We describe the synthesis and biological activity of a new class of 1,3-diaryltriazenes, namely 4-nitro-substituted 1,3-diaryltriazenes. Structure–activity relationship analysis reveals that 1,3-diaryltriazenes can be modified from inactive to highly cytotoxic compounds by the introduction of two nitro groups at the para positions of benzene rings and two additional electron-withdrawing groups (bromo, chloro, trifluoromethyl or fluoro substituents) at their ortho position. In order to increase the solubility of the modified compounds, we introduced various acyl groups to their triazene nitrogen. The results of LC-MS/MS analysis showed that N -acyltriazenes can be considered as prod…

StereochemistryNitro compoundAntineoplastic AgentsApoptosis1 ; 3-diaryltriazenes ; synthesis ; cytotoxicity ; ROS induction ; apoptosisChemical synthesisNitrophenolschemistry.chemical_compoundStructure-Activity RelationshipCell Line TumorDrug DiscoveryCytotoxic T cellHumansProdrugsTriazeneCell ProliferationPharmacologychemistry.chemical_classificationChemistryOrganic ChemistryBiological activityGeneral MedicineDNA NeoplasmProdrugEndoplasmic Reticulum StressIn vitroDrug Resistance NeoplasmNitroCisplatinTriazenesReactive Oxygen Species
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New complex polycyclic compounds: Synthesis, antiproliferative activity and mechanism of action

2020

Abstract Polycyclic or O-glycoconiugate polycyclic compounds 1a-g were previously tested for their in vitro antiproliferative activity. In this series of compounds, activity increases as log P decreases. Specifically, compounds 1d and 1g showed lower log P values together with the best antiproliferative profiles. With the aim of extending our understanding of the structure–activity relationship (SAR) of this class of compounds, we prepared new polycyclic derivatives 2a-c, which bear on each of the two phenyl rings hydrophilic substituents (OH, SO2NH2 or NHCOCH3). These substituents are able to form hydrogen bonds and to decrease the partition coefficient value as compared with compound 1d. …

StereochemistryO-glycoconjugate polycyclic compoundsApoptosisAntiproliferative activityCrystallography X-Ray01 natural sciencesBiochemistryStructure-Activity RelationshipBreast cancer cell lineCell Line TumorDrug DiscoverymedicineAutophagyMDA-MB231 breast cancer cellsHumansPolycyclic CompoundsCytotoxicityMolecular BiologyCell Proliferation010405 organic chemistryHydrogen bondChemistryOrganic ChemistryHydrogen BondingIn vitro0104 chemical sciencesPartition coefficient010404 medicinal & biomolecular chemistryMechanism of actionApoptosisPyrazolo[34-b]pyrazolo[3′4′:23]azepino[45-f]azocinemedicine.symptom
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