Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 32, 2002 - Issue 12
32
Views
8
CrossRef citations to date
0
Altmetric
Research Article

Quantitative structure-activity relationship (QSAR) and three-dimensional QSAR analysis of a series of xanthates as inhibitors and inactivators of cytochrome P450 2B1

, &
Pages 1063-1077 | Published online: 22 Sep 2008

References

  • BURKE, M. D., THOMPSON, S., ELCOMBE, C. R., HALPERT, J., HAAPARANTA, T. and MAYER, R. T., 1985, Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P450. Biochemical Pharmacology, 34, 3337–3345.
  • CHANG, Y. T., STIFFELMAN, O. B. and LOEW, G. H., 1996, Computer modeling of 3D structures of cytochrome P450s. Biochimie, 78, 771–779.
  • DAI, R., PINCUS, M. R. and FRIEDMAN, F. K., 1998, Molecular modeling of cytochrome P450 2B1: mode of membrane insertion and substrate specificity. journal of Protein Chemistry, 17, 121–129.
  • ELDIRDIRI, N., 1992, Uptake and metabolic effects of some halogenoalkanes. PhD thesis, University of Surrey, Guildford.
  • FANG, X., KOBAYASHI, Y. and HALPERT, J. R., 1997, Stoichiometry of 7-ethoxycoumarin metabolism by cytochrome P450 2B1 wild-type and five active-site mutants. FEBS Letters, 416: 77–80.
  • GAO, H. and HANSCH, C., 1996, QSAR of P450 oxidation: on the value of comparing keat and Km with lec„t1Km. Drug Metabolism Reviews, 28, 513–526.
  • HALPERT, J. R. and HE, Y. A., 1993, Engineering of cytochrome P450 2B1 specificity. Conversion of an androgen 16 beta-hydroxylase to a 15 alpha-hydroxylase. Journal of Biological Chemistry, 268, 4453–4457.
  • HE, Y. A., BALFOUR, C. A., KEDZIE, K. M. and HALPERT, J. R., 1992, Role of residue 478 as a determinant of the substrate specificity of cytochrome P450 2B1. Biochemistry, 31, 9220–9226.
  • HE, Y. A., Luo, Z., KLEKOTKA, P. A., BURNETT, V. L. and HALPERT, J. R., 1994, Structural determinants of cytochrome P450 2B1 specificity: evidence for five substrate recognition sites. Biochemistry, 33, 4419–4424.
  • HE, Y. Q., HE, Y. A. and HALPERT, J. R., 1995, Escherichia coli expression of site-directed mutants of cytochrome P450 2B1 from six substrate recognition sites: substrate specificity and inhibitor selectivity studies. Chemical Research and Toxicology, 8, 574–579.
  • JEFCOATE, C. R., GAYLOR, J. L. and CALABRESE, R. L., 1969, Ligand interactions with cytochrome P450. I. Binding of primary amines. Biochemistry, 8, 3455–3463.
  • KENT, U. M., YANEV, S. and HOLLENBERG, P., 1999, Mechanism-based inactivation of cytochromes P450 2B1 and P450 2B6 by n-propylxanthate. Chemical Research and Toxicology, 12, 317–322.
  • KOBAYASHI, Y., FANG, X., SZKLARZ, G. D. and HALPERT, J. R., 1998, Probing the active site of cytochrome P450 2B1: metabolism of 7-alkoxycoumarins by the wild type and five site-directed mutants. Biochemistry, 37, 6679–6688.
  • LEWIS, D. F. V., IOANNIDES, C. and PARKE, D. V., 1987, Structural requirements for substrates of cytochromes P450 and P-448. Chemico -BiologicalInteractions, 64, 39–60.
  • LEWIS, D. F. V., IOANNIDES, C. and PARKE, D. V., 1995a, A quantitative structure—activity relationship study on a series of 10 para-substitute d toluenes binding to cytochrome P4502B4 (CYP2B4), and their hydroxylation rates. Biochemical Pharmacology, 50, 619–625.
  • LEWIS, D. F. V. and LAKE, B. G., 1997, Molecular modelling of mammalian CYP2B isoforms and their interactions with substrates, inhibitors and redox partners. Xenobiotica, 27, 443–478.
  • LEWIS, D. F. V., LAKE, B. G. and PARKE, D. V., 1995b, Molecular orbital-generated QSARs in an homologous series of alkoxyresorufins and studies of their interactive docking with cytochromes P450. Xenobiotica, 25, 1355–1369.
  • LUO, Z., HE, Y. A. and HALPERT, J. R., 1994, Role of residues 363 and 206 in conversion of cytochrome P450 2B1 from a steroid 16-hydroxylase to a 15 alpha-hydroxylase. Archives of Biochemistry and Biophysics, 309, 52–57.
  • MURRAY, M., 1989, Inhibition of hepatic drug metabolism by phenothiazine tranquillizers: quantitative structure—activity relationships and selective inhibition of cytochrome P450 isoform-specific activities. Chemical Research and Toxicology, 2, 240–246.
  • NELSON, D. R., KOYMANS, L., KAMATAKI, T., STEGEMAN, J. J., FEYEREISEN, R., WAXMAN, D. J., WATERMAN, M. R., GOTOH, O., COON, M. J., ESTABROOK, R. W., GUNSALUS, I. C. and NEBERT, D. W., 1996, P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature,. Pharmacogenetics, 6, 1–42.
  • ROFFEY, S. J., 1993, Structure—activity relationships in the metabolism of a series of tertiary amines by cytochrome P450. PhD thesis, University of Surrey, Guildford.
  • ROSSI, M., MARKOVITZ, S. and CALLAHAN, T., 1987, Defining the active site of cytochrome P450: the crystal and molecular structure of an inhibitor, SKF-525A. Carcinogenesis, 8, 881–887.
  • SZKLARZ, G. D., HE, Y. A. and HALPERT, J. R., 1995, Site-directed mutagenesis as a tool for molecular modeling of cytochrome P450 2B1. Biochemistry, 34, 14312–14322.
  • SZYMULA, M., KOZIOL, A. E. and SZCZYPA, J., 1996, Effect of xanthates chain length on decrease of xanthates concentration in solutions in contact with copper sulphides. International Journal of Mineral Processing, 46, 123–135.
  • WALEY, S. G., 1980, Kinetics of suicide substrates. Biochemical Journal, 185, 771–773.
  • WALLER, S. C., HE, Y. A., HARLOW, G. R., HE, Y. Q., MASH, E. A. and HALPERT, J. R., 1999, 2,2',3,3',6,6'-hexachlorobiphenyl hydroxylation by active site mutants of cytochrome P450 2B1 and 2B11. Chemical Research in Toxicology, 12, 690–699.
  • YANEV, S., FRANK, H., REMMER, H. and STOYTCHEV, T., 1985, Xanthogenates as 'suicide' substrates of cyt P450. In L. Vereczkey and K. Magyar (eds), Cytochrome P450 Biochemistry, Biophysics and Induction (Budapest: Akademia Kiado), pp. 87-90.
  • YANEV, S., KENT, U. M., PANDOVA, B. and HOLLENBERG, P., 1999, Selective mechanism-based inactivation of cytochromes P450 2B1 and P450 2B6 by a series of xanthates. Drug Metabolism and Disposition, 27, 600–604.
  • YANEV, S., KENT, U. M., ROBERTS, E. S., BALLOU, D. P. and HOLLENBERG, P. F., 2000, Mechanistic studies of cytochrome P450 2B1 inactivation by xanthates. Archives of Biochemistry and Biophysics, 378, 157–166.
  • ZAHRADNIK, R., 1960, Reaktionskinetik und eigenschaften von stoffen in homologen reihen nichtaromatischer verbundungen. V. Zerzatzung in sauerem milieu und spektraleigenschaften der alkylxanthogensauren. Zeitschrift fur Physikalische Chemie, 213, 318–337.
  • ZAHRADNIK, R., HVATIL, M., VOSTAL, I. and TEISINGER, I., 1962, Toxicology of alcohols and potassium salts of alkylxanthogenic acids. Farmakologia I Toksikologia, 25, 618–622. [in Russian]

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.