CYTOCHROME P450 Biochemistry, Biophysics and Molecular Biology
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8th International Conference Lisbon, Portugal 24-28 October 1993 CYTOCHROME P450 Biochemistry, Biophysics and Molecular Biology Edited by: Gulbenkian Institute of Science JohnLibbey ra JEUROTEXT CONTENTS V Preface VII Committee VIII Acknowledgements IX Foreword EVOLUTION AND PHYLOGENETIC DIVERSITY OF P450 GENES 3 Evolutionary argument for a connection between drug metabolism and signal transaction. D.W. NEBERT, R. FEYEREISEN 15 Hierarchical clustering and proposed classification of the P450 superfamily using consensus sequences. A.I. ARCHAKOV, K.N. DEGTYARENKO 23 Function and diversity of plant cytochrome P450. F. DURST, I. BENVENISTE, J.-P. SALAUN, D. WERCK 31 Insect cytochrome P450: functions, regulation and diversify. R. FEYEREISEN, J.F. ANDERSEN, F.A. CARINO, M.B. COHEN, J.F. KOENER, S. REPECKO, J.A SCOTT, M.J. SNYDER 37 The role of conserved 5'-flanking (Barbie Box) DNA sequences and barbi- turate-responsive DNA-binding proteins in the mechanism of induction by barbiturates of P450 cytochromes in Bacillus megaterium and other proka- ryotic and eukaryotic organisms. A.J. FULCO, J.-S. HE, Q. LIANG 43 Nitric oxide synfhase: mechanisms and relationship to cytochrome P450. K.A. WHITE, R.A. PUFAHL, N.M. OLKEN, J.M. HEVEL, M.K. RICHARDS, M.A. MARLETTA XI II CONTROL MECHANISMS I—-I IN THE BIOGENESIS OF CYTOCHROME P450'S 51 Growth hormone regulation of liver sexual differentiation. J.A. GUSTAFSSON, P. TOLLET, A. MODE 59 Mechanisms of liver-specific expression of the CYP2D5 gene. Y.-H. LEE, F.J. GONZALEZ 67 Expression and function of Ad4BP, a steroidogenic cell-specific transcrip- tion factor. K.-l. MOROHASHI, S.-l. HONDA, M. NOMURA, K. TAKAYAMA, M. HARA, T. OMURA 75 DNA-binding regulatory factors and inducible expression of the P4501A1 gene. K. SOGAWA, N. MATSUSHITA, M. EMA, Y. FUJII-KURIYAMA 81 Induction of brain P450 by solvents and pharmaceuticals. M. WARNER, M. STROMSTEDT, A. WYSS, S. YOSHIDA, J.A. GUSTAFSSON 89 Hormonal influence on developmental changes in hepatic P450 in rat liver. Y. YAMAZOE, N. MURAYAMA, M. SHIMADA, K. NAGATA, H. ISHIKAWA, H. HASHIMOTO, K. NAKAYAMA, K. SOGAWA, Y. FUJII-KURIYAMA, R. KATO 97 Mechanisms of enhancement and inhibition of cytochrome P450 catalytic activities. F.P. GUENGERICH, B.-R. KIM, E.M.J. GILLAM, T. SHIMADA 103 Role of individual human liver P450s and other enzymes in anti-cancer drug metabolism: drug activation and drug resistance mechanisms. T.K.H. CHANG, G. CHEN, D.J. WAXMAN 109 Comparative analysis of cytochrome P450 3A expression in cultures of rat, rabbit and human hepatocytes. P.S. GUZELIAN 115 Receptor-dependent coregulation of CYP4A genes and peroxisome prolife- ration. G.G. GIBSON 121 Phenobarbital induction of P450 cytochromes in rat liver: genetic and endocrine control of a common regulatory mechanism. M. LARSEN, F. IKEGWUONU, P. BRAKE, C. JEFCOATE XII 125 Structural and functional characteristics of CYP3A genes related to the development-dependent phenotypic expression and induction by Dexame- thasone. M.C. LECHNER, M.M. TELHADA, V. RIBEIRO, T.M. PEREIRA, MJ. GAMA 129 Expression of xenobiotic-metabolizing cytochrome P450 forms in human adult and fetal liver. J. HAKKOLA, M. PASANEN, R. PURKUNEN, S. SAARIKOSKI, O. PELKONEN, J. MAENPAA, A. RANE, H. RAUNIO 133 Transcriptional regulation of CYP2B1 /B2 gene in rat liver. G. PADMANABAN, C. NIRODI, L PRABHU, N. RAM, S. SULTANA 137 Identification of DNA sequences involved in basal and phenobarbital indu- ced transcription of a CYP2B2 gene. A. SHERVINGTON, I.R. PHILLIPS, E.A. SHEPHARD 141 Tissue-specific expression of cytochrome P450arom gene by alternative use of multiple exons 1 and promoters, and a switching of tissue-specific exons 1. N. HARADA, S.-l. HONDA, Y. TAKAGI in CYTOCHROME P450 III I IN CANCER AND IN IMMUNOTOXYCOLOGY 147 Importance of individual enzymes in the control of ultimate carcinogens. F. OESCH, B. OESCH-BARTLOMOWICZ, H. GLATT, K.-L PLATT, M. ARAND 155 Genetic polymorphism of P450 and human cancer. K. KAWAJIRI, J. WATANABE, S.-l. HAYASHI 163 Polymorphisms of cytochrome P450 CYP2D6 as risk factor in carcinogene- sis. U.A. MEYER 173 CYP1A1 -dependent benzo[a]pyrene metabolism activates genes regulated by the human immunodeficiency virus 1 long terminal repeat DNA sequences. A. PUGA, Y. YAO 183 Cytochrome P450 2B4 antigenic determinants revealed by pepscan. E.F. KOLESANOVA, S.A. KOZIN, A.I. ARCHAKOV XIII 189 Specificity of covalent binding and autoantibodies in drug-induced immu- noallergic hepatotoxicity. S. LECOEUR, D. CHALLINE, J.C. GAUTIER, F. BALLET, P. BEAUNE 193 Metabolic activation of the thiophene ring as a primary event in immuno- allergic hepatitis to tienilic acid. P.M. DANSETTE, M.P. LOPEZ-GARCIA, C. AMAR, C. PONS, P. VALADON, E. BONIERBALE, PH. BEAUNE, J.C. HOMBERG, D. MANSUY 197 Anti-cytochrome P450 antibodies in patients with aromatic anticonvulsant- induced hypersensitivity reactions. J.S. LEEDER, V.A. COOK, R.J. RILEY 201 Presence of cytochrome P450 on human hepatocyte plasma membrane. Recognition by several autoantibodies. J. LOEPER, V. DESCATOIRE, M. MAURICE, P. BEAUNE, G. FELDMANN, F.P. GUENGERICH, D. PESSAYRE 205 Activation of promutagens by rat CYP P450 expressing V79 cells. A.S. RODRIGUES, I. DUARTE SILVA, M.J. MONTEIRO, H. CARIA, A. LAIRES, T. CHAVECA, J. RUEFF 209 P450 and azole tolerance in fungi. S.L KELLY, D.C. LAMB, B.C. BALDWIN, D.E. KELLY 213 Cytochrome P4502E1-dependent metabolism as a biomarker for genetic susceptibility to chemically-induced cancers: a pilot study. S.L. CAMPLEMAN, S.J. TAMAKI, B.-A. HOENER, M.T. SMITH 217 Comparison of the principal drug-metabolizing enzyme systems in human tumors and corresponding peritumoral tissues: importance for sensitivity and/or resistance to anticancer drugs. G.G. CHABOT, L. MASSAAD, C. TOUSSAINT, N. ALBIN, O. PARISE, V. RIBRAG, F. JANOT, A. GOUYETTE BIOTECHNOLOGY AND NOVEL P450 FUNCTIONS. FROM IV BASIC P450 RESEARCH TO APPLICATIONS IN DRUG DESIGN 225 Molecular engineering steroid hydroxylase activity of mammalian P450s. M. NEGISHI, M. IWASAKI, T. SUEYOSHI, T.A DARDEN, L.G. PEDERSEN 233 Co-expression of mammalian, plant or yeast P450s and P450 reductases in Saccharomyces cerevisiae as cloning and bioconversion tools. D. POMPON, G. TRUAN, A. BELLAMINE, M. KAZMAIER, P. URBAN XIV 241 Expression in E. coli of enzymatically active fusion proteins containing cyto- chrome P450 and cytochrome P450 reductase. C.W. FISHER, M.S. SHET, P.L HOLMANS, R.W. ESTABROOK 249 The role of P450s in insect-plant interactions. H. PRAPAIPONG, C.-F. HUNG, M.R. BERENBAUM, M.A. SCHULER 257 From basic cytochrome P450 research to applications in drug develop- ment. A.Y.H. LU i 1 BIOSYNTHESIS AND MEMBRANE TOPOLOGY OF MICROSOMAL P450. 1 V 1 FUNCTIONAL IMPLICATIONS OF P450 STRUCTURE 265 Biosynthesis and membrane topology of microsoma! cyiochrome P450. M. SAKAGUCHI, K. MIHARA, T. OMURA 271 Structure and function in P450s: are bacterial P450s good models for eukaryotic P450s? J.A. PETERSON, J.DEISENHOFER, C. HASEMANN, K.G. RAVICHAN- DRAN, S.S. BODDUPALLI, S. GRAHAM-LORENCE 279 Structural and functional mapping of P450 proteins inferred from multiple sequence alignment. O. GOTOH 285 Role of the NH2-ferminal region of microsomal P450s in catalysis and membrane binding. S.J. PERNECKY, V.S. FUJITA, L.L BESTERVELT, M.J. COON 293 Structure-function analysis of eukaryotic P450s expressed in E. col!. I.A. PIKULEVA, CM. JENKINS, M.R. WATERMAN 299 Proton and electron transfer mechanism in dioxygen activation by cyto- chrome P450cam. H. SHIMADA, R. MAKINO, M. UNNO, T. HORIUCHI, Y. ISHIMURA 307 High level expression of integral membrane proteins induces proliferation of the endoplasmic reticulum. R. MENZEL, E. KARGEL, C. WOLFF, F VOGEL, W.-H. SCHUNK 311 Membrane topology and complex formation of cytochrome P450SCC in proteoliposomes studied by delayed fluorescence depolarization. D. SCHWARZ, A. CHERNOGOLOV, V. KROGER, S. USANOV, A. STIER XV 315 Core glycosylafion of cytochrome P450(arom): evidence for localization of N-terminus of microsomal cytochrome P450 in the lumen. O. SHIMOZAWA, M. SAKAGUCHI, H. OGAWA, N. HARADA, K. MIHARA, T. OMURA 319 Systematic analysis of N-terminal transmembrane segments of microsomal P450s. K.N. DEGTYARENKO, A.I. ARCHAKOV 323 Membrane topology of P450c21. L.-C. HSU, B.-C. CHUNG 327 Study of the membrane topology and functional importance of the central region of cytochrome P450scc (CYP11A1) molecule by selective chemical modification of Cys264. A. CHERNOGOLOV; S. USANOV, R. KRAFT, D. SCHWARZ DETERMINANTS OF COMPONENT INTERACTIONS IN P450 VI SYSTEMS. ELECTRON TRANSFER AND OXYGEN ACTIVATION 333 The importance of one-electron transfers in the mechanism of cytochrome P450. R.E. WHITE 341 Studies of the interactions of microsomal cytochrome P450 reductase with cytochromes P450. H.W STROBEL, S. SHEN 349 On the nature of the NADPH-cytochrome P450 reductase-cytochrome P450 electron transfer complex. A.I. VOZNESENSKY, J.B. SCHENKMAN 357 Electron pathways in adrenal mitochondrial cytochrome P450 systems: relative rates of leakage and hydroxylation. R. RAPOPORT, M. RAIKHINSTEIN, D. SKLAN, I. HANUKOGLU 365 Reaction mechanism of P450 dependent steroidogenesis: regulation of catalytic activity of bovine adrenal P450 (11 (3) S. TAKEMORI, S. KOMINAM1, S.I. 1KUSHIRO, T. YAMAZAKI, D. HARADA 373 Electron transfer associated dioxygen activation in P450 systems S.G. SUGAR, J. AIKENS, N. GERBER, M. MCLEAN, K. SUSLICK, D. BENSON XVI 379 Conformational control of interprotein electron transfer. F. MILLETT, B. DURHAM, A. WILLIE, S. HAHM, L. GEREN, R. LIU, P. STAYTON, M. McLEAN, M. MILLER, S. SUGAR, G. PEILAK, J. KRAUT 387 Studies on electron transfer pathways in cytochrome P450 systems. R. BERNHARDT, V. BECKERT, H. UHLMANN, S.G. SUGAR 395 Electron transfer and protein-protein interactions in soluble reconstituted liver monooxygenase systems. G.I. BACHMANOVA, I.P. KANAEVA, I.F. SEVRUKOVA, O.V. NIKITYUK, N.V. STEPANOVA, TV. KNUSHKO, Y.M. KOEN, A.I. ARCHAKOV 403 Thermodynamic and kinetic studies of the process of camphor entry into cytochrome P450cam.