Search results for "ANTHRACENE"
showing 10 items of 171 documents
Regiospecific oxidation of polycyclic aromatic dihydrodiols by rat liver dihydrodiol dehydrogenase
1991
Rat liver dihydrodiol dehydrogenase (DDH, E.C. 1.3.1.20) has recently been shown to oxidize the highly carcinogenic benz[a]anthracene-3,4- dihydrodiol in an NADP(+)-dependent reaction to its corresponding catechol. The present study is a systematic investigation of the substrate specificity of the purified enzyme towards synthetic trans-dihydrodiol metabolites of phenanthrene, benz[a]anthracene, chrysene, dibenz[a, h]anthracene and benzo[a]pyrene. DDH exhibited a remarkable regiospecificity of enzymatic catalysis with regard to the site of the dihydrodiol moiety of the parent hydrocarbon. M-region- and, with lower efficiency, bay-region dihydrodiols were found to be good substrates of the e…
erbB expression changes in ethanol and 7,12- dimethylbenz (a)anthracene-induced oral carcinogenesis.
2012
The authors (Garcia Carrancá A, Zentero Galindo E, Jiménez Farfán MD and Hernandez Guerrero JC) express that one of the figures of the original article (Jacinto-Alemán LF, García-Carrancá A, LeybaHuerta ER, Zenteno-Galindo E, Jiménez-Farfán MD, Hernández-Guerrero JC. erbB expression changes in ethanol and 7,12- dimethylbenz (a)anthracene-induced oral carcinogenesis. Med Oral Patol Oral Cir Bucal. 2013 Mar 1;18(2):e325-31.) corresponding to Western blots have not been found and the voluntary alteration of this figure is evident. The coauthors Alejandro García Carranca, Edgar Zenteno Galindo, Maria Dolores Jiménez Farfán and Juan Carlos Hernández Guerrero have made the decision to take back w…
Bisdihydrodiols, rather than dihydrodiol oxides, are the principal microsomal metabolites of tumorigenic trans-3,4-dihydroxy-3,4-dihydrodibenz[a,h]an…
1994
Several studies on metabolism and biological activity of tumorigenic dibenz[a,h]anthracene (DBA) and its derivatives have led to the conclusion that the M-region dihydrodiol, trans-3,4-dihydroxy-3,4-dihydro-DBA (DBA-3,4-dihydrodiol), is the precursor of the ultimate mutagenic and tumorigenic metabolite of DBA with the presumed structure of a bay-region dihydrodiol oxide. Incubations of DBA-3,4-dihydrodiol (50 microM) with the microsomal hepatic fraction of Sprague-Dawley rats pretreated with Aroclor 1254 yielded more than 13 metabolites upon separation by HPLC. anti-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydro-DBA [0.27 nmol/(nmol of P450.15 min)] could be identified for the first time by UV …
Electrochemistry and Spectroelectrochemistry of Bismanganese Porphyrin-Corrole Dyads
2011
A series of homobimetallic manganese cofacial porphyrin-corrole dyads were synthesized and investigated as to their electrochemistry, spectroelectrochemistry, and ligand binding properties in nonaqueous media. Four dyads were investigated, each of which contained a Mn(III) corrole linked in a face-to-face arrangement with a Mn(III) porphyrin. The main difference between compounds in the series is the type of spacer, 9,9-dimethylxanthene, anthracene, dibenzofuran, or diphenylether, which determines the distance and interaction between the metallomacrocycles. Each redox process of the porphyrin-corrole dyads was assigned on the basis of spectroscopic and electrochemical data and by comparison…
Diacetylene Linked Anthracene Oligomers Synthesized by One-Shot Homocoupling of Trimethylsilyl on Cu(111)
2018
On-surface chemical reaction has become a very powerful technique to conjugate small precursor molecules and several reactions have been proposed with the aim to fabricate functional nanostructures on surfaces. Here we present an unforeseen adsorption mode of 9,10-bis-((trimethylsilyl)ethynyl)anthracene on a Cu(111)surface and the resulting one-shot desilylative homocoupling of of the adsorbate by annealing at 400 K. With a combination of high-resolution atomic force microscopy and density functional theory calculations, we found that the triple bonds and silicon atoms of the monomer chemically interact with the copper surface. After the oligomerization, we discovered that the anthracene un…
Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals
2016
The consequence of unpaired electrons in organic molecules has fascinated and confounded chemists for over a century. The study of open-shell molecules has been rekindled in recent years as new synthetic methods, improved spectroscopic techniques and powerful computational tools have been brought to bear on this field. Nonetheless, it is the intrinsic instability of the biradical species that limits the practicality of this research. Here we report the synthesis and characterization of a molecule based on the diindeno[b,i]anthracene framework that exhibits pronounced open-shell character yet possesses remarkable stability. The synthetic route is rapid, efficient and possible on the gram sca…
Glutathione Conjugation of Bay- and Fjord-Region Diol Epoxides of Polycyclic Aromatic Hydrocarbons by Glutathione Transferases M1-1 and P1-1
1997
Metabolism of polycyclic aromatic hydrocarbons in mammalian cells results in the formation of vicinal diol epoxides considered as ultimate carcinogens if the oxirane ring is located in a bay- or fjord-region of the parent compound. In the present study, individual stereoisomers of the bay-region diol epoxides of chrysene, dibenz[a,h]anthracene, and benzo[a]pyrene as well as of the fjord-region diol epoxides of benzo[c]phenanthrene, benzo[c]chrysene, and benzo[g]-chrysene have been incubated with GSH in the presence of human glutathione transferases GSTM1-1 (a mu-class enzyme) and GSTP1-1 (a pi-class enzyme). As previously shown with GSTA1-1 (an alpha-class enzyme) both M1-1 and P1-1 demonst…
Fluorescent substituted amidines of benzanthrone: synthesis, spectroscopy and quantum chemical calculations.
2012
Abstract Several new substituted amidine derivatives of benzanthrone were synthesized by a condensation reaction from 3-aminobenzo[de]anthracen-7-one and appropriate aromatic and aliphatic amides. The obtained derivatives have a bright yellow or orange fluorescence in organic solvents and in solid state. The novel benzanthrone derivatives were characterized by TLC analysis, 1H NMR, IR, MS, UV/vis, and fluorescence spectroscopy. The solvent effect on photophysical behaviors of these dyes was investigated, and the results showed that the Stoke’s shift increased, whereas quantum yield decreased with the growth of the solvent polarity. The structure of some dyes was confirmed by the X-ray singl…
A Dendrimer Chiroptical Switch Based on the Reversible Intramolecular Photoreaction of Anthracene and Benzene Rings
2010
A series of Fréchet-type dendrimers with 9-benzyloxymethylanthracene cores were synthesized and characterized. The chiral source for the dendrimers was an (S)-2-methyl-1-butoxy group in the 3-position of the benzene ring. Irradiation at 366 nm of a dilute benzene solution led to the formation of two diastereomers (1:1) through a quantitative intramolecular [4pi+4pi] cycloaddition between the central anthracene ring and the neighboring benzene ring. The process can be reversed with 254 nm UV light or heat. The benzene rings in the dendrons work as a light-harvesting system. The optical rotation values measured for the reversible process showed fatigue resistance. Thus, a promising new type o…
Oxidative C-N fusion of pyridinyl-substituted porphyrins.
2018
International audience; The mild (electro) chemical oxidation of pyridin-2-ylthio-meso substituted Ni(II) porphyrins affords C-N fused cationic and dicationic pyridinium-based derivatives. These porphyrins are fully characterized and the molecular structure of one of them was confirmed by X-ray crystallography. A mechanism for the intramolecular oxidative C-N coupling is proposed based on theoretical calculations and cyclic voltammetry analyses.