Identification of inhibitors of the nicotine metabolising CYP2A6 enzyme—an in silico approach

[1]  O Pelkonen,et al.  New potent and selective cytochrome P450 2B6 (CYP2B6) inhibitors based on three‐dimensional quantitative structure‐activity relationship (3D‐QSAR) analysis , 2007, British journal of pharmacology.

[2]  Xiaodong Zhang,et al.  Synthetic inhibitors of cytochrome P-450 2A6: inhibitory activity, difference spectra, mechanism of inhibition, and protein cocrystallization. , 2006, Journal of medicinal chemistry.

[3]  O. Pelkonen,et al.  Cytochrome P450 (CYP) inhibition screening: comparison of three tests. , 2006, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[4]  C. Jepson,et al.  Impact of CYP2A6 genotype on pretreatment smoking behaviour and nicotine levels from and usage of nicotine replacement therapy , 2006, Molecular Psychiatry.

[5]  Antti Poso,et al.  3D-QSAR studies on cannabinoid CB1 receptor agonists: G-protein activation as biological data. , 2006, Journal of medicinal chemistry.

[6]  C David Stout,et al.  Structures of human microsomal cytochrome P450 2A6 complexed with coumarin and methoxsalen , 2005, Nature Structural &Molecular Biology.

[7]  Antti Poso,et al.  Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. , 2005, Journal of medicinal chemistry.

[8]  Chris de Graaf,et al.  Cytochrome p450 in silico: an integrative modeling approach. , 2005, Journal of medicinal chemistry.

[9]  Stahl Gr,et al.  Development of models for cytochrome P450 2A5 as well as two of its mutants. , 2005 .

[10]  Neal L. Benowitz,et al.  Metabolism and Disposition Kinetics of Nicotine , 2005, Pharmacological Reviews.

[11]  R. Tyndale,et al.  Implications of CYP2A6 Genetic Variation for Smoking Behaviors and Nicotine Dependence , 2005, Clinical pharmacology and therapeutics.

[12]  Antti Poso,et al.  Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme. , 2005, Journal of medicinal chemistry.

[13]  Xiaodong Zhang,et al.  5-substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6. , 2005, Journal of medicinal chemistry.

[14]  R. Tyndale,et al.  Ethnic variation in CYP2A6 and association of genetically slow nicotine metabolism and smoking in adult Caucasians. , 2004, Pharmacogenetics.

[15]  Peter C. Fox,et al.  Statistical variation in progressive scrambling , 2004, J. Comput. Aided Mol. Des..

[16]  Anu J. Tervo,et al.  A structure-activity relationship study of catechol-O-methyltransferase inhibitors combining molecular docking and 3D QSAR methods , 2003, J. Comput. Aided Mol. Des..

[17]  Richard D. Taylor,et al.  Improved protein–ligand docking using GOLD , 2003, Proteins.

[18]  Douglas M. Hawkins,et al.  Assessing Model Fit by Cross-Validation , 2003, J. Chem. Inf. Comput. Sci..

[19]  A. Poso,et al.  More potent inhibition of human CYP2A6 than mouse CYP2A5 enzyme activities by derivatives of phenylethylamine and benzaldehyde , 2003, Xenobiotica; the fate of foreign compounds in biological systems.

[20]  R. Tyndale,et al.  CYP2A6 genetic variation and potential consequences. , 2002, Advanced drug delivery reviews.

[21]  M. Nakajima,et al.  INTERINDIVIDUAL DIFFERENCES IN NICOTINE METABOLISM AND GENETIC POLYMORPHISMS OF HUMAN CYP2A6 , 2002, Drug metabolism reviews.

[22]  O Pelkonen,et al.  Polymorphisms of CYP2A6 and its practical consequences. , 2001, British journal of clinical pharmacology.

[23]  R. Tyndale,et al.  Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro. , 2001, Drug metabolism and disposition: the biological fate of chemicals.

[24]  R. Tyndale,et al.  Variable CYP2A6-mediated nicotine metabolism alters smoking behavior and risk. , 2001, Drug metabolism and disposition: the biological fate of chemicals.

[25]  O. Pelkonen,et al.  In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene. , 2001, Drug metabolism and disposition: the biological fate of chemicals.

[26]  Antti Poso,et al.  A comparative molecular field analysis of cytochrome P450 2A5 and 2A6 inhibitors , 2001, J. Comput. Aided Mol. Des..

[27]  M. Oscarson Genetic polymorphisms in the cytochrome P450 2A6 (CYP2A6) gene: implications for interindividual differences in nicotine metabolism. , 2001, Drug metabolism and disposition: the biological fate of chemicals.

[28]  N E Morton,et al.  The use of long PCR to confirm three common alleles at the CYP2A6 locus and the relationship between genotype and smoking habit , 2000, Annals of human genetics.

[29]  D E McRee,et al.  Microsomal cytochrome P450 2C5: comparison to microbial P450s and unique features. , 2000, Journal of inorganic biochemistry.

[30]  R. Tyndale,et al.  Inhibition of cytochrome P450 2A6 increases nicotine's oral bioavailability and decreases smoking , 2000, Clinical pharmacology and therapeutics.

[31]  O. Pelkonen,et al.  CYP2A6: a human coumarin 7-hydroxylase. , 2000, Toxicology.

[32]  G Klebe,et al.  Three-dimensional quantitative structure-activity relationship analyses using comparative molecular field analysis and comparative molecular similarity indices analysis to elucidate selectivity differences of inhibitors binding to trypsin, thrombin, and factor Xa. , 1999, Journal of medicinal chemistry.

[33]  R. Tyndale,et al.  A major role for CYP2A6 in nicotine C-oxidation by human liver microsomes. , 1997, The Journal of pharmacology and experimental therapeutics.

[34]  G. V. Paolini,et al.  Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes , 1997, J. Comput. Aided Mol. Des..

[35]  A. Parkinson,et al.  Inhibition of coumarin 7-hydroxylase activity in human liver microsomes. , 1997, Archives of biochemistry and biophysics.

[36]  P Willett,et al.  Development and validation of a genetic algorithm for flexible docking. , 1997, Journal of molecular biology.

[37]  Y. Funae,et al.  Role of human cytochrome P4502A6 in C-oxidation of nicotine. , 1996, Drug metabolism and disposition: the biological fate of chemicals.

[38]  S. Wrighton,et al.  In vitro-in vivo correlations of human (S)-nicotine metabolism. , 1995, Biochemical pharmacology.

[39]  G. Klebe,et al.  Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. , 1994, Journal of medicinal chemistry.

[40]  R. Cramer,et al.  Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. , 1988, Journal of the American Chemical Society.

[41]  A. Aitio A simple and sensitive assay of 7-ethoxycoumarin deethylation. , 1978, Analytical biochemistry.

[42]  O. Pelkonen,et al.  Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. , 2005, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[43]  Alan D. Lopez,et al.  Potential health gains from reducing multiple risk factors , 2004 .

[44]  F. Lombardo,et al.  Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. , 2001, Advanced drug delivery reviews.

[45]  J Gynther,et al.  Pronounced differences in inhibition potency of lactone and non-lactone compounds for mouse and human coumarin 7-hydroxylases (CYP2A5 and CYP2A6). , 2000, Xenobiotica; the fate of foreign compounds in biological systems.

[46]  Gerhard Klebe,et al.  Comparative Molecular Similarity Index Analysis (CoMSIA) to study hydrogen-bonding properties and to score combinatorial libraries , 1999, J. Comput. Aided Mol. Des..

[47]  N. Benowitz Pharmacology of nicotine: addiction and therapeutics. , 1996, Annual review of pharmacology and toxicology.

[48]  R. Cramer,et al.  Recent advances in comparative molecular field analysis (CoMFA). , 1989, Progress in clinical and biological research.