QSAR of Cytochrome P450

References

• Backes W. L., Hogaboom M., Canady W. J. The true hydrophobicity of microsomal cytochrome P‐450 in the rat. J. Biol. Chem. 1982; 257: 4063–4070, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Bessems J. G.M., Te Hoppele J. M., van Dijk P. A., van Stee L. L.P., Commandeur J. N.M., Vermeulen M. P.E. Rat liver microsomal P450‐dependent oxidation of 3,/5‐disubstituted analogues of paracetamol. Xenobiotica 1996; 26: 647–666, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Blake R. C., II, Coon M. J. On the mechanism of action of cytochrome P‐450. J. Biol. Chem. 1980; 255: 4100–4111, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Blake R. C., Coon M. Y. On the mechanism of action of cytochrome P‐450. J. Biol. Chem. 1981; 256: 12127–12133, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Ceñas N., Anusevicius Z., Bironaite D., Bachmanova G. I., Archakov A. I., Ollinger K. The electron transfer reactions of NADPH: cytochrome P450 reductase with nonphysiological oxidants. Arch. Biochem. Biophys. 1994; 315: 400–406, [CSA]
   PubMed Web of Science ®Google Scholar
• Chan F. C.Y., Potter G. A., Barrie S. E., Haynes B. P., Rowland M. G., Houghton J., Jarman M. 3‐ and 4‐ pyridylalkyl adamantane carboxylates: inhibitors of human cytochrome P450 (17a‐hydroxylase/C17, 20)‐lyase. Potential nonsteroidal agents for the treatment of prostatic cancer. J. Med. Chem. 1996; 39: 3319–3323, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Chubben N. H.P., Peelen S., Borst J.‐W., Vervoort J., Veeger C., Rietjens I. M.C.M. Molecular orbital‐based quantitative structure‐activity relationship for the P450‐catalyzed 4‐hydroxylation of halogenated anilines. Chem. Res. Toxicol. 1994; 7: 590–598, [CSA]
   PubMed Web of Science ®Google Scholar
• Chubben N. H.P., Veroot J., Boersma M. G. The effect of varying halogen substituent patterns on the cytochrome P‐450 catalyzed dehalogenation of 4‐halogenated anilines to 4‐aminophenol metabolites. Biochem. Pharmacol. 1995; 49: 1235–1248, [CSA]
   PubMed Web of Science ®Google Scholar
• Conway C. C., Jiao D., Chung F.‐L. Inhibition of rat liver cytochrome P450 isozymes by isothiocyanates and their conjugates: A structure‐activity relationship study. Carcinogenesis 1996; 17: 2423–2427
   PubMed Web of Science ®Google Scholar
• Deller S., Turner M. K. The effect of n‐alcohols on the activity of cytochrome P450‐BM3. Jubilee Research Event. Nottinghom Inst. Chemical Engineers. 1997
   Google Scholar
• Dickings M., Elcombe C. R., Moloney J., Netter K. J., Bridges J. W. Further studies on the dissociation of the isosafriole metabolite‐cytochrome P‐450 complex. Biochem. Pharmacol. 1979; 28: 231–238
   PubMed Web of Science ®Google Scholar
• Dinnocenzo J. P., Karki S. B., Jones J. P. On isotopic effects for the cytochrome P‐450 oxidative of substituted N,N–dimethylanilines. J. Am. Chem. Soc. 1993; 115: 7111–7116
   Web of Science ®Google Scholar
• Ferrari S., Leemann T., Dayer P. The role of lipophilicity in the inhibition of polymorphic cytochrome P450 11D6 oxidation of β‐blocking agents in vitro. Life Sci. 1991; 48: 2259–2265, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Garg R., Kurup A., Mekapati S. B., Hansch C. Searching for allosteric effects via QSAR. Part II. Bioorg. Med. Chem. 2003; 11: 621–628, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Guengerich F. P., Willard R. J., Shea J. P., Richards L. E., MacDonald T. L. Mechanism‐based inactivation of cytochrome P‐450 by heteroatom‐substituted cyclopropanes and formation of ring‐opened products. J. Am. Chem. Soc. 1984; 106: 6446–6447
   Web of Science ®Google Scholar
• Ha‐Duong N. T., Dijols S., Marq‐Soares C., Minoletti C., Dansette P. M., Mansuy D. Synthesis of sulfaphenazole derivatives and their use as inhibitors and tools for comparing the active sites of human liver cytochrome P450 of the 2C subfamily. J. Med. Chem. 2001; 44: 3622–3631, [CSA]
   PubMed Web of Science ®Google Scholar
• Hansch C., Leo A. Exploring QSAR. Fundamentals and Applications in Chemistry and Biology. American Chemical Society, Washington, DC 1996
   Google Scholar
• Hansch C., Zhang L. Quantitative structure‐activity relationships of cytochrome P‐450. Drug Metab. Rev. 1993; 25: 1–48, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Hansch C., Sinclair J. F., Sinclair P. R. Induction of cytochrome P450 by barbiturates in chick embryo hepatocytes: a quantitative structure analysis. Quant. Struct.‐Act. Relat. 1990; 9: 223–226
   Web of Science ®Google Scholar
• Hansch C., Steinmetz W. E., Leo A. J., Mekapati S. B., Kurup A., Hoekman D. On the role of polarizability in chemical‐biological interactions. J. Chem. Inf. Comput. Sci. 2003; 43: 120–125, [PUBMED], [INFOTRIEVE], [CSA]
   PubMedGoogle Scholar
• Ichikawa Y., Yamano T. The role of the hydrophobic bonding in P450 and the effect of organic compounds on the conversion of P‐450 to P‐420. Biochem. Biophys. Acta 1967; 518–525, [CSA]
   PubMed Web of Science ®Google Scholar
• Fu X.‐C., Jiang H. D., Liu Z.‐Q. Quantitative structure‐activity relationship for p‐amino‐diphenyl ether compounds to interact with cytochrome P450. Chim. Biochem. J. 1994; 10: 11–15, [CSA]
   Google Scholar
• Kim S., Ko H., Park J. E., Jung S., Lee S. K., Chum Y.‐J. Design, synthesis, and discovery of novel trans‐stilbene analogues as potent and selective human P450 1B1 inhibitors. J. Med. Chem. 2002; 45: 160–164, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Komives E. A., Ortiz de Montellano P. R. Mechanism of oxidation of π bonds by cytochrome P‐450. J. Biol. Chem. 1987; 262: 9793–9802, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Krainev A. G., Weiner L. M., Alferyev I. S., Slynko N. M. Bifunctional compound study of the active‐center location of cytochrome P‐450 in a microsomal membrane (“float” molecules method). Biochem. Biophys. Acta 1985; 818: 96–104, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• LaBella F. S., Chen Q.‐M., Stein C. D., Queen G. The site of general anesthesia and cytochrome P450 oxygenases: similarities defined by straight chain and cyclic alcohols. Br. J. Pharm. 1997; 120: 1158–1164, [CSA]
   PubMed Web of Science ®Google Scholar
• Lewis D. F.V., Dickens P. J. Quantitative structure‐activity relationships (QSARs) within a series of inhibitors for mammalian cytochrome P450 (CYPs). J. Enzyme Inhib. 2001; 16: 321–330, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Lewis D. F.V., Ioannides C., Park D. V. A quantitative structure‐activity relationship study on a series of 10 para‐substituted toluenes binding to cytochrome P‐450 2B4 and their hydroxylation rates. Biochem. Pharmacol. 1995; 50: 619–625, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Lewis D. F.V. Quantitative structure‐activity relationships in a series of alcohols exhibiting inhibition of cytochrome P‐450‐mediated aniline hydroxylation. Chem.‐Biol. Interact. 1987; 62: 271–280, [CSA]
   PubMed Web of Science ®Google Scholar
• Lewis D. F.V. On the recognition of mammalian microsomal cytochrome P‐450 substrates and their characteristics. Biochem. Pharmacol. 2000; 60: 293–306, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Lewis D. F.V., Modi S., Dickins M. Quantitative structure‐activity relationships (QSARs) within substrates of human cytochrome P450 involved in drug metabolism. Drug Metab. Dispos. 2001; 18: 221–242
   Google Scholar
• Lindeke B., Paulsen‐Sorman U., Hallström G., Khuthier A.‐H., Cho A. K., Kammerer R. C. Cytochrome P‐455nm complex formation in the metabolism of phenylalkylamines. Drug Metab. Dispos. 1982; 10: 700–705, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• MacDonald T. L., Gutheim W. G., Martin R. B., Gungerich F. P. Oxidation of substituted N,N–dimethylanilines by cytochrome P‐450: estimation of the effective oxidation‐reduction potential of cytochrome P‐450. Biochemistry 1989; 28: 2071–2077, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Morgan E. T., Koop D. R., Coon M. J. Catalytic activity of cytochrome P‐450 isozyme 3A isolated from liver microsomes of ethanol‐treated rabbits. J. Biol. Chem. 1982; 257: 13951–13957, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Murray M. Inhibition of hepatic drug metabolism by penothiazine tranquilizers: quantitative structure‐activity relationships and selective inhibition of cytochrome P‐450 isoform‐specific activities. Chem. Res. Toxicol. 1989; 2: 240–246, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Nambo T. The steric and electrostatic effect of 4‐substituent of N,N–dimethylaniline on the affinity to P‐450 of rabbit. Quant. Struct.‐Act. Relat. 1998; 17: 465–467
   Web of Science ®Google Scholar
• Peng H. ‐M., Raner G. M., Vaz A. D.N., Coon M. J. Oxidative cleavage of esters and amides by cytochrome P450. Arch. Biochem. Biophys. 1995; 318: 333–339, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Poso A., Gynther J., Juvonen R. Comparative molecular field analysis of cytochrome P450 2A5 and 2A6 inhibitors. J. Comput. Aided Mol. Des. 2001; 15: 195–202, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Sargent N. S.E., Upshall D. G., Bridges J. W. The relationship between binding to cytochrome P‐450 and metabolism of n‐alkyl carbanates in isolated rat hepatocytes. Biochem. Pharmacol. 1982; 31: 1209–1313
   Web of Science ®Google Scholar
• Scott J. G., Foroozesh M., Hopkins N. E., Alefantis T. G., Alworth W. L. Inhibition of cytochrome P450 6D1 by alkynylarenes, methylenedioxyarenes and other substituted aromatics. Pestic. Biochem. Physiol. 2000; 67: 6371
   Web of Science ®Google Scholar
• Shusterman A. J., Johnson A. S. The role of hydrophobicity and electronic factors in regulating alcohol inhibition of cytochrome P‐450‐mediated aniline hydroxylation. Chem.‐Biol. Interact. 1990; 74: 63–77
   PubMed Web of Science ®Google Scholar
• Sinclair J., Cornell N. W., Zaitlin L., Hansch C. Induction of cytochrome P‐450 by alcohols and 4‐substituted pyrazoles. Biochem. Pharmacol. 1986; 35: 707–710, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Vaz A. D.N., Coon M. J. On the mechanism of action of cytochrome P450: evaluation of hydrogen abstraction in oxygen‐dependent alcohol oxidation. Biochemistry 1994; 33: 6442–6449, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Venhorst J., Onderwater R. C.A., Meerman J. H.M., Commandeur J. N.M., Vermeulen N. P.E. Influence of N‐substitution of 7‐methoxy‐4‐(aminomethyl)‐coumarin on cytochrome P450 metabolism and selectivity. Drug Metab. Dispos. 2000; 28: 1524–1532, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Venhorst J., Ter Laak A. M., Commandeur J. N.M., Funae Y., Hiroi T., Vermeulen N. P.E. Homology modeling of rate and human cytochrome P450 2D (CYP2D)1 isoforms and computational rationalization of experimental ligand‐binding specificities. J. Med. Chem. 2003; 46: 74–86, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Virginia M., Mason R. P. Correlation of kinetic parameters of nitroreductase enzymes with redox properties of nitroaromatic compounds. J. Biol. Chem. 1989; 264: 12379–12384
   PubMed Web of Science ®Google Scholar
• Wachall B. G., Hector M., Zhuange Y., Hartman R. W. Imidazole substituted biphenyls: a new class of highly potent and in vivo active inhibitors of P450 17 as potential therapeutics for treatment of prostate cancer. Bioorg. Med. Chem. 1999; 7: 1913–1924, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Wang Y., Olson M. J., Baker M. T. Interaction of fluoroethane chlorofluorocarbon (CFC) substitutes with microsomal cytochrome p450. Biochem. Pharmacol. 1993; 46: 87–94, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Watanabe Y., Iyanagi T., Oae S. Kinetic study on enzymic 5‐oxygenation promoted by a reconstituted system with purified cytochrome P‐450. Tetra. Lett. 1980; 21: 3685–3688
   Web of Science ®Google Scholar
• Watanabe Y., Iyanagi T., Ore S. One electron transfer mechanism in the enzymatic oxydation of sulfoxide to sulfone promoted by a reconstituted system with purified cytochrome P‐450. Tetra. Lett. 1982a; 23: 533–536
   Web of Science ®Google Scholar
• Watanabe Y., Oae S., Iyanagi T. Mechanisms of enzymatic S–oxygenation of thioanisole derivatives and O–demethylation of anisole derivatives promoted by both microsomes and a reconstituted system with purified cytochrome P‐450. Bull. Chem. Soc. Jpn. 1982b; 55: 188–195
   Web of Science ®Google Scholar
• White R. E., McCarthy M. B. Active site mechanics of liver microsomal cytochrome P‐450. Arch. Biochem. Biophys. 1986; 246: 19–32, [PUBMED], [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Zhuang Y., Wachall B. G., Hartman R. W. Novel Imidazolyl and Triazolyl Substituted Biphenyl Compounds: Synthesis and Evaluation as Nonsteroidal Inhibitors of Human 17α Hydroxylase‐C17, 20‐Lyase (P450 17)
   Google Scholar