Benzo pyrene derivative

Coman et al. [82] used a new modeling of the chromatographic separation process of some polar (hydroxy benzo[a]pyrene derivatives) and nonpolar (benzo[a]pyrene, dibenz[a,/ ]anthracene, and chrysene) polycyclic aromatic compounds in the form of third-degree functions. For the selection of the optimum composition of the benzene-acetone-water mobile phase used in the separation of eight polycyclic aromatic compounds on RP-TLC layers, some computer programs in the GW-BASIC language were written. 

Benzylic-type cations derived from PAHs have been studied under superacid conditions, where, not surprisingly, they are relatively stable.Lifetimes in water of diastereomeric forms of the benzo[a]pyrene derivative (100) have been deter-... 

Deshpande SS, Maru GB. 1995. Effects of curcumin on the formation of benzo[a]pyrene derived DNA adducts in vitro. Cancer Lett 1 71-80. 

Reed GA. Sulfite-dependent mutagenicity of benzo [a] pyrene derivatives. Carcinogenesis 1987 8(8) 1145-8. 

Colpa et al. (1963) calculated p/ (S )-values for a series of aromatic hydrocarbons, but could not detect fluorescence changes in the regions of acidity indicated by the Forster cycle, although fluorescence spectra attributed to proton complexes of 3,4-benzo-pyrene and 1,2-benzanthracene were observed in some solutions containing only the neutral molecule in the ground state. Flurry and co-workers (1963, 1966, 1967) have carried out theoretical and Forster cycle calculation on the excited state basicities of poly-methylbenzenes and Kuz min et al. (1967) have also calculated p/sT(S1)- and p7 (T )-values for polycyclic aromatic hydrocarbons increases in base strength of from 7 to 30 powers of ten were derived for Sj. 

Fang, A. H., Smith, W. A., Vouros, R, and Gupta, R. C. (2001). Identification and characterization of a novel benzo[ij]pyrene-derived DNA adduct. Biochem Biophys Res Commun 281, 383-389. 

Other examples of generating free radicals utilized in our laboratory are the consecutive two-photon ionization of the aromatic pyrene residue in the benzo[a] pyrene derivative 7,8,9,10-tetrahydroxytetrahydrobenzo[a]pyrene (B[a]PT) or the covalent adducts derived from the reactions of racemic anti-r7,t8-dihydroxy-t9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (B[a]PDE) with the N2-exocyclic amino groups of guanine or adenine bases in DNA [43-47]. The selective excitation of the pyrenyl residue of B[a]PT by intense 355-nm nanosecond laser pulses yields free radical products by a two-photon mechanism ... 

Ruan, Q., Gelhaus, S.L., Penning, T.M., Harvey, R.G., and Blair, I.A. (2007) Aldo-keto reductase- and cytochrome P450-dependent formation of benzo[a] pyrene-derived DNA adducts in human bronchoalveolar cells. Chem. Res. 

Cai, Y., Patel, D.J., Geacintov, N.E., and Broyde, S. (2007) Dynamics of a benzo[a]pyrene-derived guanine DNA lesion in TGT and CGC sequence contexts enhanced mobility in TGT explains conformational heterogeneity, flexible bending, and greater susceptibility to nucleotide excision repair. 

Benzo[a]pyrene-Derived DNA Lesions as a Useful Model... 

Levin W, Wood AW, Wislocki PG, Chang RL, Kapitulnik J, Mah HD, Yagi H, Jerina DM, Conney AH (1978) Mutagenicity and carcinogenicity of benzo[a]pyrene and benzo[a]pyrene derivatives. In Gelboin H V, TS o POP (eds) Polycyclic hydrocarbons and cancer, Vol 1. Environment, chemistry and metabolism. Academic Press, New York, pp 189-202 Liimatainen A, Hanninen O (1982) Occurrence of cytochrome P-450 in the earthworm Lumbricus terrestris. In Hietanen E, Laitinen M, Hanninen O (eds) Biochemistry, biophysics and environmental implications. Elsevier Biomedical, pp 255-258... 

D. M. Jerina, P. E. Lehr, H. Yagi, O. Hernandez, P. Dansette, P. G. Wislocki, G. Wislocki, A. W. Wood, R. I. Chang, W. Levin, and A. H. Conney, Mutagenicity of benzo(a)-pyrene derivatives and the description of a quantum mechanical model which predicts the phase of carbonium ion formation from diol epoxides, in In-Vitro Activation in Mutagenesis Testing, F. J. De-Seres, J. R. Bond, and R. M. Philpot (Eds.), Elsevier, Amsterdam, 1976. 

Banasiewicz, M., Nelson, G., Swank, A., Grubor, N., Ross, J., Nesnow, S., Kofeler, H., Small, G. J. Jankowiak, R. (2004). Identification and quantization of benzo(o)pyrene-derived DNA adducts formed at low adduction level in mice lung tissue. Analitical... 

Benzo(b)fIuoranthrene la 39, 85 Benzo(k)fluoranthrene la 39, 86 Benzo(ghi)perylene la 39,85 Benzophenone derivatives lb 282 Benzo(a)pyrene la 39,85,103 p-Benzoquinone derivatives la 72 Benzothiazoles lb 237 Benzoyl chloride la 70 Benzoylecgonine lb 32,34,35 3,4-Benzpyrene la 60 Benzthiazide lb 188 Benztriazole, 2-(2-hydroxy-5-methyl-phe-nyl)- la 282... 

Methods for the synthesis of the biologically active dihydrodiol and diol epoxide metabolites of both carcinogenic and noncarcinogenic polycyclic aromatic hydrocarbons are reviewed. Four general synthetic routes to the trans-dihydrodiol precursors of the bay region anti and syn diol epoxide derivatives have been developed. Syntheses of the oxidized metabolites of the following hydrocarbons via these methods are described benzo(a)pyrene, benz(a)anthracene, benzo-(e)pyrene, dibenz(a,h)anthracene, triphenylene, phen-anthrene, anthracene, chrysene, benzo(c)phenanthrene, dibenzo(a,i)pyrene, dibenzo(a,h)pyrene, 7-methyl-benz(a)anthracene, 7,12-dimethylbenz(a)anthracene, 3-methylcholanthrene, 5-methylchrysene, fluoranthene, benzo(b)fluoranthene, benzo(j)fluoranthene, benzo(k)-fluoranthene, and dibenzo(a,e)fluoranthene. 

The diol epoxide derivative of benzo(a)pyrene, trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene also known as (+) -73,8a-dihydroxy-9ot,10a-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene,was the first diol epoxide to be synthesized. Interest in this compound was stimulated by the report by Borgen et al. (8) that a metabolite of benzo(a)pyrene, tentatively identified as the trans-7,8-diol ( 1) became covalently bound to DNA in the presence of rat liver micro-somes. Sims et al. ( ) suggested that the active metabolite was a diol epoxide derivative of unspecified stereo chemistry. 

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