Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 26, 1996 - Issue 10
56
Views
63
CrossRef citations to date
0
Altmetric
Original Article

Molecular modelling of CYP3A4 from an alignment with CYP102: Identification of key interactions between putative active site residues and CYP3A-specific chemicals

, , &
Pages 1067-1086 | Received 12 Apr 1996, Published online: 27 Aug 2009

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (10)

Dong Dong, Baojian Wu, Diana Chow & Ming Hu. (2012) Substrate selectivity of drug-metabolizing cytochrome P450s predicted from crystal structures and in silico modeling. Drug Metabolism Reviews 44:2, pages 192-208.
Read now
Nitish Kumar Mishra. (2011) Computational modeling of P450s for toxicity prediction. Expert Opinion on Drug Metabolism & Toxicology 7:10, pages 1211-1231.
Read now
C. Emoto, H. Nishida, H. Hirai & K. Iwasaki. (2007) CYP3A4 and CYP3A5 catalyse the conversion of the -methyl-D-aspartate (NMDA) antagonist CJ-036878 to two novel dimers. Xenobiotica 37:12, pages 1408-1420.
Read now
David F.V. Lewis, Brian G. Lake & Maurice Dickins. (2006) Quantitative structure–activity relationships (QSARs) in CYP3A4 inhibitors: The importance of lipophilic character and hydrogen bonding. Journal of Enzyme Inhibition and Medicinal Chemistry 21:2, pages 127-132.
Read now
Sean Ekins, Sergey Andreyev, Andy Ryabov, Eugene Kirillov, Eugene A Rakhmatulin, Andrej Bugrim & Tatiana Nikolskaya. (2005) Computational prediction of human drug metabolism. Expert Opinion on Drug Metabolism & Toxicology 1:2, pages 303-324.
Read now
David F. V. Lewis, Sandeep Modi & Maurice Dickins. (2002) Structure–activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metabolism Reviews 34:1-2, pages 69-82.
Read now
David F. V. Lewis. (2002) Molecular modeling of human cytochrome P450–substrate interactions. Drug Metabolism Reviews 34:1-2, pages 55-67.
Read now
D. F. V. Lewis, C. Ioannides & D. V. Parke. (1998) An Improved and Updated Version of the Compact Procedure for the Evaluation of P450-Mediated Chemical Activation. Drug Metabolism Reviews 30:4, pages 709-737.
Read now

Articles from other publishers (53)

Lyubov S. Klyushova, Maria L. Perepechaeva & Alevtina Y. Grishanova. (2022) The Role of CYP3A in Health and Disease. Biomedicines 10:11, pages 2686.
Crossref
Usman Ali Ashfaq, Farah Shahid & Samman Munir. 2022. Biochemistry of Drug Metabolizing Enzymes. Biochemistry of Drug Metabolizing Enzymes 29 72 .
Ngoc Nguyen, Ngoc Cao, Thi Nguyen, Thien-Kim Le, Gun Cha, Soo-Keun Choi, Jae-Gu Pan, Soo-Jin Yeom, Hyung-Sik Kang & Chul-Ho Yun. (2020) Regioselective Hydroxylation of Phloretin, a Bioactive Compound from Apples, by Human Cytochrome P450 Enzymes. Pharmaceuticals 13:11, pages 330.
Crossref
Seung Heon Lee, Sukmo Kang, Mi Sook Dong, Jung-Duck Park, Jinseo Park, Sangkee Rhee & Doug-Young Ryu. (2015) Characterization of the Ala62Pro polymorphic variant of human cytochrome P450 1A1 using recombinant protein expression. Toxicology and Applied Pharmacology 285:3, pages 159-169.
Crossref
M. Ramesh & Prasad V. Bharatam. (2011) CYP isoform specificity toward drug metabolism: analysis using common feature hypothesis. Journal of Molecular Modeling 18:2, pages 709-720.
Crossref
Ka-Wing Cheng, Chi-Chun Wong, Mingfu Wang, Qing-Yu He & Feng Chen. (2009) Identification and characterization of molecular targets of natural products by mass spectrometry. Mass Spectrometry Reviews, pages n/a-n/a.
Crossref
Jihoon Jung, Nam Doo Kim, Su Yeon Kim, Inhee Choi, Kwang-Hwi Cho, Won Seok Oh, Doo Nam Kim & Kyoung Tai No. (2008) Regioselectivity Prediction of CYP1A2-Mediated Phase I Metabolism. Journal of Chemical Information and Modeling 48:5, pages 1074-1080.
Crossref
Anja KrickStefan KehrausClarissa GerhäuserKarin KlimoMartin NiegerArmin MaierHeinz-Herbert FiebigIuliana AtodireseiGerhard RaabeJörg FleischhauerGabriele M. König. (2007) Potential Cancer Chemopreventive in Vitro Activities of Monomeric Xanthone Derivatives from the Marine Algicolous Fungus Monodictys putredinis . Journal of Natural Products 70:3, pages 353-360.
Crossref
Nick Plant. (2007) The human cytochrome P450 sub-family: Transcriptional regulation, inter-individual variation and interaction networks. Biochimica et Biophysica Acta (BBA) - General Subjects 1770:3, pages 478-488.
Crossref
Michal Otyepka, Josef Skopalík, Eva Anzenbacherová & Pavel Anzenbacher. (2007) What common structural features and variations of mammalian P450s are known to date?. Biochimica et Biophysica Acta (BBA) - General Subjects 1770:3, pages 376-389.
Crossref
Larry J. Jolivette & Sean Ekins. 2007. 131 176 .
Miia Turpeinen, Laura E. Korhonen, Ari Tolonen, Jouko Uusitalo, Risto Juvonen, Hannu Raunio & Olavi Pelkonen. (2006) Cytochrome P450 (CYP) inhibition screening: Comparison of three tests. European Journal of Pharmaceutical Sciences 29:2, pages 130-138.
Crossref
Ya-Chi Chen, S. Karl. Gotzkowsky, Anne N. Nafziger, Robert W. Kulawy, Mario L. Rocci, Joseph S. Bertino & Angela D. M. Kashuba. (2006) Poor correlation between 6β-hydroxycortisol:cortisol molar ratios and midazolam clearance as measure of hepatic CYP3A activity. British Journal of Clinical Pharmacology 62:2, pages 187-195.
Crossref
P. Crivori & I. Poggesi. (2006) Computational approaches for predicting CYP-related metabolism properties in the screening of new drugs. European Journal of Medicinal Chemistry 41:7, pages 795-808.
Crossref
Peter Hlavica. (2006) Functional interaction of nitrogenous organic bases with cytochrome P450: A critical assessment and update of substrate features and predicted key active-site elements steering the access, binding, and orientation of amines. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 1764:4, pages 645-670.
Crossref
Bo Wen, Catalin E. Doneanu, Jed N. Lampe, Arthur G. Roberts, William M. Atkins & Sidney D. Nelson. (2005) Probing the CYP3A4 active site by cysteine scanning mutagenesis and photoaffinity labeling. Archives of Biochemistry and Biophysics 444:2, pages 100-111.
Crossref
Xia Fang & Chen Xiao-yin. (2005) Effect of intestinal cytochrome P450 3A on phytochemical presystemic metabolism. Chinese Journal of Integrative Medicine 11:3, pages 232-236.
Crossref
Michael Murray. 2005. Modern Biopharmaceuticals. Modern Biopharmaceuticals 1603 1636 .
Chris de Graaf, Nico P. E. Vermeulen & K. Anton Feenstra. (2005) Cytochrome P450 in Silico:  An Integrative Modeling Approach. Journal of Medicinal Chemistry 48:8, pages 2725-2755.
Crossref
Ann-Charlotte Egnell, J. Brian Houston & C. Scott Boyer. (2005) Predictive Models of CYP3A4 Heteroactivation: In Vitro-in Vivo Scaling and Pharmacophore Modeling. Journal of Pharmacology and Experimental Therapeutics 312:3, pages 926-937.
Crossref
Carol A. Kemp, Jean-Didier Maréchal & Michael J. Sutcliffe. (2005) Progress in cytochrome P450 active site modeling. Archives of Biochemistry and Biophysics 433:2, pages 361-368.
Crossref
Pamela A. WilliamsJose CosmeDijana Matak VinkovićAlison WardHayley C. AngovePhilip J. DayClemens VonrheinIan J. TickleHarren Jhoti. (2004) Crystal Structures of Human Cytochrome P450 3A4 Bound to Metyrapone and Progesterone. Science 305:5684, pages 683-686.
Crossref
David F. V. Lewis. (2003) Quantitative structure–activity relationships (QSARs) within the cytochrome P450 system: QSARs describing substrate binding, inhibition and induction of P450s. InflammoPharmacology 11:1, pages 43-73.
Crossref
Costas Ioannides. (2003) Drug–phytochemical interactions. InflammoPharmacology 11:1, pages 7-42.
Crossref
David F.V. Lewis. (2002) Modelling human cytochromes P450 involved in drug metabolism from the CYP2C5 crystallographic template. Journal of Inorganic Biochemistry 91:4, pages 502-514.
Crossref
Darko Butina, Matthew D Segall & Katrina Frankcombe. (2002) Predicting ADME properties in silico: methods and models. Drug Discovery Today 7:11, pages S83-S88.
Crossref
Thierry Cresteil, Bernard Monsarrat, Joelle Dubois, Michelle Sonnier, Paul Alvinerie & Françoise Gueritte. (2002) Regioselective Metabolism of Taxoids by Human CYP3A4 and 2C8: Structure-Activity Relationship. Drug Metabolism and Disposition 30:4, pages 438-445.
Crossref
Stewart B Kirton, Carol A Baxter & Michael J Sutcliffe. (2002) Comparative modelling of cytochromes P450. Advanced Drug Delivery Reviews 54:3, pages 385-406.
Crossref
Marcel J. de Groot & Sean Ekins. (2002) Pharmacophore modeling of cytochromes P450. Advanced Drug Delivery Reviews 54:3, pages 367-383.
Crossref
Hossein Hamzeiy, Nasser Vahdati-Mashhadian, Helen J. Edwards & Peter S. Goldfarb. (2002) Mutation analysis of the human CYP3A4 gene 5′ regulatory region: population screening using non-radioactive SSCP. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis 500:1-2, pages 103-110.
Crossref
D. F. V. Lewis. 2002. Pharmacokinetic Challenges in Drug Discovery. Pharmacokinetic Challenges in Drug Discovery 235 248 .
Peter Hlavica & David F. V. Lewis. (2008) Allosteric phenomena in cytochrome P450‐catalyzed monooxygenations. European Journal of Biochemistry 268:18, pages 4817-4832.
Crossref
David Lewis. 2001. Guide to Cytochromes P450. Guide to Cytochromes P450 164 210 .
Regina Eiselt, Tammy Domanski, Arne Zibat, Romy Mueller, Elena Presecan-Siedel, Elisabeth Hustert, Ulrich Zanger, Jurgen Brockmoller, Hans-Peter Klenk, Urs Meyer, Kishore Khan, You-Ai He, James Halpert & Leszek Wojnowski. (2001) Pharmacogenetics 11:5, pages 447-458.
Crossref
David F?V Lewis. (2001) COMPACT: a structural approach to the modelling of cytochromes P450 and their interactions with xenobiotics. Journal of Chemical Technology & Biotechnology 76:3, pages 237-244.
Crossref
Caroline S Miles, Tobias W.B Ost, Michael A Noble, Andrew W Munro & Stephen K Chapman. (2000) Protein engineering of cytochromes P-450. Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology 1543:2, pages 383-407.
Crossref
D.F.V. Lewis, C. Ioannides, D.V. Parke & R. Schulte-Hermann. (2000) Quantitative structure–activity relationships in a series of endogenous and synthetic steroids exhibiting induction of CYP3A activity and hepatomegaly associated with increased DNA synthesis. The Journal of Steroid Biochemistry and Molecular Biology 74:4, pages 179-185.
Crossref
David F.V. Lewis. (2000) On the recognition of mammalian microsomal cytochrome P450 substrates and their characteristics. Biochemical Pharmacology 60:3, pages 293-306.
Crossref
Eva Anzenbacherová, Nicole Bec, Pavel Anzenbacher, Jiří Hudeček, Pavel Souček, Christiane Jung, Andrew W. Munro & Reinhard Lange. (2001) Flexibility and stability of the structure of cytochromes P450 3A4 and BM‐3. European Journal of Biochemistry 267:10, pages 2916-2920.
Crossref
David F.V. Lewis. (2000) Structural characteristics of human P450s involved in drug metabolism: QSARs and lipophilicity profiles. Toxicology 144:1-3, pages 197-203.
Crossref
Fabienne Roussel, Kishore K. Khan & James R. Halpert. (2000) The Importance of SRS-1 Residues in Catalytic Specificity of Human Cytochrome P450 3A4. Archives of Biochemistry and Biophysics 374:2, pages 269-278.
Crossref
D.F.V. Lewis. (2000) Modelling Human Cytochromes P450 for Evaluating Drug Metabolism: An Update. Drug Metabolism and Drug Interactions 16:4.
Crossref
Lucie Bořek-Dohalská, Petr Hodek & Marie Stiborová. (2000) New Selective Inhibitors of Cytochrome P450 2B4 and an Activator of Cytochrome P450 3A6 in Rabbit Liver Microsomes. Collection of Czechoslovak Chemical Communications 65:1, pages 122-132.
Crossref
David F.V. Lewis, Brian G. Lake, Stephen G. George, Maurice Dickins, Peter J. Eddershaw, Michael H. Tarbit, Alan P. Beresford, Peter S. Goldfarb & F.Peter Guengerich. (1999) Molecular modelling of CYP1 family enzymes CYP1A1, CYP1A2, CYP1A6 and CYP1B1 based on sequence homology with CYP102. Toxicology 139:1-2, pages 53-79.
Crossref
Andrea L Crampton, Glenn D Baxter & Stephen C Barker. (1999) A new family of cytochrome P450 genes (CYP41) from the cattle tick, Boophilus microplus. Insect Biochemistry and Molecular Biology 29:9, pages 829-834.
Crossref
David F.V. Lewis. (1999) Homology modelling of human cytochromes P450 involved in xenobiotic metabolism and rationalization of substrate selectivity. Experimental and Toxicologic Pathology 51:4-5, pages 369-374.
Crossref
D.F.V. Lewis, P.J. Eddershaw, M. Dickins, M.H. Tarbit & P.S. Goldfarb. (1998) Structural determinants of cytochrome P450 substrate specificity, binding affinity and catalytic rate. Chemico-Biological Interactions 115:3, pages 175-199.
Crossref
D.F.V. Lewis, E. Watson & B.G. Lake. (1998) Evolution of the cytochrome P450 superfamily: sequence alignments and pharmacogenetics. Mutation Research/Reviews in Mutation Research 410:3, pages 245-270.
Crossref
K. E. ThummelG. R. Wilkinson. (1998) IN VITRO AND IN VIVO DRUG INTERACTIONS INVOLVING HUMAN CYP3A. Annual Review of Pharmacology and Toxicology 38:1, pages 389-430.
Crossref
David F.V. Lewis & Brian G. Lake. (1998) Molecular modelling and quantitative structure-activity relationship studies on the interaction of omeprazole with cytochrome P450 isozymes. Toxicology 125:1, pages 31-44.
Crossref
Tomas Cvrk & Henry W. Strobel. (1998) Photoaffinity Labeling of Cytochrome P4501A1 with Azidocumene: Identification of Cumene Hydroperoxide Binding Region. Archives of Biochemistry and Biophysics 349:1, pages 95-104.
Crossref
Dennis A. Smith, Mark J. Ackland & Barry C. Jones. (1997) Properties of cytochrome P450 isoenzymes and their substrates Part 1: active site characteristics. Drug Discovery Today 2:10, pages 406-414.
Crossref
E.S. Tomlinson, D.F.V. Lewis, J.L. Maggs, H.K. Kroemer, B.K. Park & D.J. Back. (1997) In vitro metabolism of dexamethasone (DEX) in human liver and kidney: The involvement of CYP3a4 and CYP17 (17,20 LYASE) and molecular modelling studies. Biochemical Pharmacology 54:5, pages 605-611.
Crossref

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.