Inhibition of rat hepatic CYP2E1 by quinacrine: Molecular modeling investigation and effects on 4-(methyl nitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced mutagenicity

Archives of Toxicology

Volumn 83, Issue 6, 2009, Pages 571-580

  Karamanakos, Petros Nikolaos ^a,d   Trafalis, D T P ^b   Geromichalos, G D ^c   Pappas, P ^a   Harkitis, P ^a   Konstandi, M ^a   Marselos, M ^a  

^a UNIVERSITY OF IOANNINA   (Greece)

^b METAXA CANCER HOSPITAL   (Greece)

^c THEAGENIO CANCER HOSPITAL   (Greece)

^d KUOPIO UNIVERSITY HOSPITAL   (Finland)

Author keywords

CYP2E1; Inhibition; Molecular modeling; Mutagenicity; NNK; Quinacrine

Indexed keywords

4 (METHYL NITROSAMINO) 1 (3 PYRIDYL) 1 BUTANONE; CYTOCHROME P450 2E1; DISULFIRAM; ISONIAZID; MEPACRINE; MUTAGENIC AGENT; NITROSAMINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG PROTEIN BINDING; ENZYME ACTIVITY; GENOTOXICITY; INHIBITION KINETICS; LIVER; MALE; MOLECULAR MODEL; MUTAGENICITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT; SISTER CHROMATID EXCHANGE; WESTERN BLOTTING;

ADULT; ANIMALS; ANTIMUTAGENIC AGENTS; BINDING SITES; BLOTTING, WESTERN; CYTOCHROME P-450 CYP2E1; DISULFIRAM; ENZYME INHIBITORS; FEMALE; GENE EXPRESSION REGULATION, ENZYMOLOGIC; HUMANS; ISONIAZID; MALE; MODELS, MOLECULAR; MUTAGENS; NITROSAMINES; PROTEIN BINDING; QUINACRINE; RATS; RATS, WISTAR; SISTER CHROMATID EXCHANGE;

NICOTIANA TABACUM; RATTUS; RATTUS NORVEGICUS;

EID: 67651172890     PISSN: 03405761     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00204-008-0350-6     Document Type: Article

References (42)

1. HM Bolt PH Roos R Thier 2003 The cytochrome P-450 isoenzyme CYP2E1 in the biological processing of industrial chemicals: consequences for occupational and environmental medicine Int Arch Occup Environ Health 76 174 185
2. JF Brady F Xiao MH Wang Y Li SM Ning JM Gapac CS Yang 1991 Effects of disulfiram on hepatic P450IIE1, other microsomal enzymes, and hepatotoxicity in rats Toxicol Appl Pharmacol 108 366 373
3. AI Cederbaum D Wu M Mari J Bai 2001 CYP2E1-dependent toxicity and oxidative stress in HepG2 cells Free Radic Biol Med 31 1539 1543
4. JJ Clarke DC Sokal AM Cancel DB Campen R Gudi VO Wagner RH San D Jacobson-Kram 2001 Re-evaluation of the mutagenic potential of quinacrine dihydrochloride dehydrate Mutat Res 494 41 53
5. K Doh-Ura T Iwaki B Caughey 2000 Lysosomotropic agents and cysteine protease inhibitors inhibit scrapie-associated prion protein accumulation J Virol 74 894 4897
6. DI Eneanya JR Bianchine DO Duran BD Andresen 1981 The actions and metabolic fate of disulfiram Annu Rev Pharmacol Toxicol 21 575 596
7. FP Guengerich DH Kim M Iwasaki 1991 Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects Chem Res Toxicol 4 168 179
8. SS Hecht 1998 Biochemistry, biology, and carcinogenicity of tobacco-specific N nitrosamines Chem Res Toxicol 11 559 603
9. SS Hecht 1999 DNA adduct formation from tobacco-specific N-nitrosamines Mutat Res 424 127 142
10. SS Hecht D Hoffmann 1989 The relevance of tobacco-specific nitrosamines to human cancer Cancer Surv 8 273 294
11. SS Hecht D Lin A Castonguay 1983 Effects of o-deuterium substitution on the mutagenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) Carcinogenesis 4 305 310
12. F Heinemann HJ Assion 1996 Hepatotoxic side-effect of chlormethiazole Pharmacopsychiatry 29 196 197
13. Hoffmann D, Hecht SS (1990) Advances in tobacco carcinogenesis. In: Cooper CS, Grover PL (eds) Handbook of experimental pharmacology. Springer, Heidelberg
14. DA Hungerford 1965 Leucocytes cultured from small inocula of whole blood and the preparation of metaphase chromosome by treatment with hypotonic KCI Stain Technol 40 333 338
15. I Johansson E Eliasson C Norsten M Ingelman-Sundberg 1986 Hydroxylation of acetone by ethanol- and acetone-inducible cytochrome P-450 in liver microsomes and reconstituted membranes FEBS Lett 196 59 64
16. DR Koop 1992 Oxidative and reductive metabolism by cytochrome P450 2E1 FASEB J 6 724 730
17. B Lambert A Lindblad M Nordenskjold B Werelius 1978 Increased frequency of sister chromatid exchanges in cigarette smokers Hereditas 88 147 149
18. OH Lowry NJ Rosebrough AL Farr RJ Randall 1951 Protein measurement with Folin phenol reagent J Biol Chem 193 265 275
19. D Maron BN Ames 1983 Revised methods for the salmonella mutagenicity test Mutat Res 113 173 215
20. T Nakajima E Elovaara SS Park HV Gelboin E Hietanen H Vainio 1989 Immunochemical characterization of cytochrome P-450 isozymes responsible for benzene oxidation in the rat liver Carcinogenesis 10 1713 1717
21. DR Nelson L Koymans T Kamataki JJ Stegeman R Feyereisen DJ Waxman MR Waterman O Gotoh MJ Coon RW Estabrook IC Gunsalus DW Nebert 1996 P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature Pharmacogenetics 6 1 42
22. P Perry PS Wolff 1974 New Giemsa method for the differential staining of sister chromatids Nature 251 156 158
23. LA Reinke MJ Moyer 1985 p-Nitrophenol hydroxylation. A microsomal oxidation which is highly inducible by ethanol Drug Metab Dispos 13 548 552
24. S Reyes LA Herrera P Ostrosky J Sotelo 2001 Quinacrine enhances carmustine therapy of experimental rat glioma Neurosurgery 49 969 973
25. A Rivenson D Hoffmann B Prokopczyk S Amin SS Hecht 1988 Induction of lung and exocrine pancreas tumors in F344 rats by tobacco-specific and Areca-derived N-nitrosamines Cancer Res 48 6912 6917
26. C Rodriguez-Antona M Ingelman-Sunberg 2006 Cytochrome P450 pharmacogenetics and cancer Oncogene 25 1679 1691
27. Schneidman-Duhovny D, Nussinov R, Wolfson HJ (2002) Efficient unbound docking of rigid molecules. In: Guido R, Gusfield D (eds) Proceedings of the 2nd Workshop on Algorithms in Bioinformatics (WABI) Rome, Italy, Lecture Notes in Computer Science. Springer, Berlin
28. D Schneidman-Duhovny Y Inbar V Polak M Shatsky I Halperin H Benyamini A Barzilai O Dror N Haspel R Nussinov HJ Wolfson 2003 Taking geometry to its edge: fast unbound rigid (and high-bent) docking Proteins 52 107 112
29. W Schulemann 1932 Synthetic anti-malarial preparations Proc R Soc Med 25 897 905
30. TJ Smith Z Guo FJ Gonzalez FP Guengerich GD Stoner CS Yang 1992 Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in human lung and liver microsomes and cytochromes P-450 expressed in hepatoma cells Cancer Res 52 1757 1763
31. TJ Smith GD Stoner CS Yang 1995 Activation of 4-(methylnitrosamino)-1-(3- pyridyl)-1-butanone (NNK) in human lung microsomes by cytochromes P450, lipoxygenase, and hydroperoxides Cancer Res 55 5566 5573
32. GB Smith A Castonguay PJ Donnelly KR Reid D Petsikas TE Massey 1999 Biotransformation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3- pyridyl)-1-butanone (NNK) in freshly isolated human lung cells Carcinogenesis 20 1809 1818
33. GB Smith JR Bend LL Bedard KR Reid D Petsikas TE Massey 2003 Biotransformation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in peripheral human lung microsomes Drug Metab Dispos 31 1134 1141
34. M Spatzenegger H Liu Q Wang A Debarber DR Koop JR Halpert 2003 Analysis of differential substrate selectivities of CYP2B6 and CYP2E1 by site-directed mutagenesis and molecular modeling J Pharmacol Exp Ther 304 477 487
35. DT Trafalis C Sambani V Kapsimali J Economidou T Politis P Catsoulacos 1995 Effects of homo-aza-steroids on acute non-lymphocytic leukaemia cell proliferation in vitro Br J Haematol 91 907 914
36. DTP Trafalis GD Geromichalos N Bountouroglou D Koumbi M Kontos D Sougias P Dalezis P Karamanakos A Papageorgiou C Camoutsis AE Athanassiou 2005 A preclinical survey on efficacy of lactandrate in the treatment of colon carcinoma J BUON 10 227 234
37. DT Trafalis D Tsavdaridis C Camoutsis V Karayiani D Mourelatos P Dalezis A Athanassiou GA Pangalis A Papageorgiou 2005 Preclinical studies on NSC290205 aza-steroid alkylator activity in combination with adriamycin against lymphoid leukaemia Br J Haematol 128 343 350
38. WM Valentine V Amarnath K Amarnath DG Graham 1995 Characterization of protein adducts produced by N-methyldithiocarbamate and N-methyldithiocarbamate esters Chem Res Toxicol 8 254 261
39. Williams PA, Cosme J, Sridhar V, Johnson EF, McRee DE (2000a) Structure of mammalian cytochrome P4502C5. In: Protein data bank. http://www.rcsb.org/pdb/ explore/explore.do?structureId=1DT6. Cited 27 September 2000
40. PA Williams J Cosme V Sridhar EF Johnson DE McRee 2000 Microsomal cytochrome P450 2C5: comparison to microbial P450s and unique features J Inorg Biochem 81 183 190
41. DK Winters AI Cederbaum 1992 Time course characterization of the induction of cytochrome P-4502E1 by pyrazole and 4-methylpyrazole Biochem Biophys Acta 1117 15 24
42. CH Yun GP Miller FP Guengerich 2001 Oxidations of p-alkoxyacylanilides catalyzed by human cytochrome P450 1A2: structure-activity relationships and simulation of rate constants of individual steps in catalysis Biochemistry 40 4521 4530