Phase II drug metabolizing enzymes

Biomedical Papers

Volumn 154, Issue 2, 2010, Pages 103-116

  Jancova, Petra ^a   Anzenbacher, Pavel ^a   Anzenbacherova, Eva ^a  

^a PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

Catechol O methyl transferase; Glutathione S transferases; N acetyltransferases; Phase II biotransformation; Sulfotransferases; Thiopurine S methyl transferase; UDP glucuronosyltransferases

Indexed keywords

EID: 84969884406     PISSN: 12138118     EISSN: 12138118     Source Type: Journal    
DOI: 10.5507/bp.2010.017     Document Type: Article

References (140)

1. Anzenbacher P, Anzenbacherova E. Cytochromes P450 and metabolism xenobiotics. Cell Mol Life Sci 2001; 58(5-6):737-747.
2. Glatt H. Sulfotransferases in the bioactivation of xenobiotics. Chem Biol Interact 2000; 129(1-2):141-170.
3. Wells PG, Mackenzie PI, Chowdhury JR, Guillemette C, Gregory PA, Ishii Y, Hansen AJ, Kessler FK, Kim PM, Chowdhury NR, Ritter JK. Glucuronidation and the UDP-glucuronosyltransferases in health and disease. Drug Metab Dispos 2004; 32(3):281-290.
4. Kiang TKL, Ensom MHH, Chang TKH. UDP-glucurono syl transferases and clinical drug-drug interactions. Pharmacol Ther 2005; 106(1):97-132.
5. Cashman JR, Perotti BYT, Berkman CE, Lin J. Pharmacokinetics and molecular detoxication. Environ Health Perspect 1996; 104:23-40.
6. Fisher MB, Paine MF, Strelevitz T, Wrighton SA. The role of hepatic and extrahepatic UDP-glucuronosyltransferases in human drug metabolism. Drug Metabol Rev 2001; 33(3-4):273-297.
7. Mackenzie PI, Rogers A, Treloar J, Jorgensen BR, Miners JO, Meech R. Identification of UDP glycosyltransferase 3A1 as a UDP N-acetylglucosaminyltransferase. J Biol Chem 2008; 283(52):36205-36210.
8. Burchell B, Brierley CH, Rance D. Specificity of human UDPglucuronosyltransferases and xenobiotic glucuronidation. Life Sci 1995; 57(20):1819-1831.
9. Mackenzie PI, Bock KW, Burchell B, Guillemette C, Ikushiro S, Iyanagi T, Miners JO, Owens IS, Nebert DW. Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 2005; 15(10):677-685.
10. Miners JO, Knights KM, Houston JB, Mackenzie PI. In vitro-in vivo correlation for drugs and other compounds eliminated by glucuronidation in humans: pitfalls and promises. Biochem Pharm 2006; 71(11):1531-1539.
11. Court MH, Hazarika S, Krishnaswamy S, Finel M, Williams JA. Novel polymorphic human UDP-glucuronosyltransferase (UGT) 2A3: Cloning, functional characterization of enzyme variants, comparative tissue expression, and gene induction. Mol Pharmacol 2008; 74(3):744-754.
12. Patten CJ. New technologies for assessing UDP-glucuronosyltransferase (UGT) metabolism in drug discovery and development. Drug Discov Today Tech 2006; 3(1):73-78.
13. Sneitz N, Court MH, Zhang X, Laajanen K, Yee KK, Dalton P, Ding X, Finel M. Human UDP-glucuronosyltransferase UGT2A2: cDNA construction, expression, and functional characterization in comparison with UGT2A1 and UGT2A3. Pharmacogenet Genomics 2009; [Epub ahead of print].
14. Gregory PA, Lewinsky RH, Gardner-Stephen DA, Mackenzie PI. Regulation of UDP glucuronosyltransferases in the gastrointestinal tract. Toxicol Appl Pharmacol 2004; 199: 354-363.
15. Tukey RH, Strassburg CP. Genetic multiplicity of the human UDPglucuronosyltransferases and regulation in the gastrointestinal tract. Mol Pharmacol 2001; 59: 405-414.
16. Cheng Z, Radominska-Pandya A, and Tephly TR. Studies on the substrate specificity of human intestinal UDP-glucuronosyltransferases 1A8 and 1A10. Drug Metab Dispos 1999; 27: 1165-1170.
17. Sutherland L, Ebner T, Burchell B. The expression of UDPglucuronosyltransferases of the UGT1 family in human liver and kidney and in response to drugs. Biochem Pharmacol 1993; 45(2):295-301.
18. King CD, Rios GR, Assouline JA, Tephly TR. Expression of UDPglucuronosyltransferases (UGTs) 2B7 and 1A6 in the human brainand identification of 5-hydroxytryptamine as a substrate. Arch Biochem Biophys 1999; 365(1):156-162.
19. Collier AC, Ganley NA, Tingle MD, Blumenstein M, Marvin KW, Paxton JW, Mitchell MD, Keelan JA. UDP-glucuronosyltransferase activity, expression and cellular localization in human placenta at term. Biochem Pharmacol 2002; 63(3):409-419.
20. Tukey RH and Strassburg CP. Human UDP-glucurono syltransferases: metabolism, expression, and disease. Annu Rev Pharmacol Toxicol 2000; 40: 581-616.
21. Wang X, Chowdhury JR, Chowdhury NR. Bilirubin metabolism: Applied physiology. Curr Paediatr 2006; 16(1):70-74.
22. Coffman BL, King CD, Rios GR, Tephly TR. The glucuronidation of opioids, other xenobiotics, and androgens by human UGT2B7Y (268) and UGT2B7H (268). Drug Metab Dispos 1998; 26(1):73-77.
23. King CD, Rios GR, Green MD, Tephly TR. UDPglucuronosyltransferases. Curr Drug Metab 2000; 1(2):143-161.
24. Wen Z, Martin DE, Bullock P, Lee KH, Smith PC. Glucuronidation of anti-HIV drug candidate bevirimat: identification of human UDP-glucuronosyltransferases and species differences. Drug Metab Dispos 2007; 35(3):440-448.
25. Chen Y, Xie S, Chen S, Zeng S. Glucuronidation of flavonoids by recombinant UGT1A3 and UGT1A9. Biochem Pharmacol 2008; 76(3):416-425.
26. Lewinsky RH, Smith PA, Mackenzie PI. Glucuronidation of bioflavonoids by human UGT1A10: structure-function relationships. Xenobiotica 2005; 35(2):117-129.
27. Uchaipichat V, Mackenzie PI, Elliot DJ, Miners JO. Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) probes for human udp-glucuronosyltransferases. Drug Metab Dispos 2006; 34(3):449-456.
28. Uchaipichat V, Winner LK, Mackenzie PI, Elliot DJ, Williams JA, Miners JO. Quantitative prediction of in vivo inhibitory interactions involving glucuronidated drugs from in vitro data: the effect of fluconazole on zidovudine glucuronidation. Br J Clin Pharmacol 2006; 61(4):427-439.
29. Ghosal A, Hapangama N, Yuan Y, Achanfuo-Yeboah J, Iannucci R, Chowdhury S, Alton K, Patrick JE, Zbaida S. Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of posaconazole (Noxafil). Drug Metab Dispos 2004; 32(2):267-271.
30. Caraco Y, Sheller J, Wood AJ. Pharmacogenetic determinants of codeine induction by rifampin: the impact on codeine's respiratory, psychomotor and miotic effects. J Pharmacol Exp Ther 1997; 281(1):330-336.
31. Guillemette, C. Pharmacogenomics of human UDPglucuronosyltransferase enzymes. Pharmacogenomics J 2003; 3(3):136-158.
32. Mori A, Maruo Y, Iwai M, Sato H, Takeuchi Y. UDP-glucuronosyltransferase 1A4 polymorphisms in a Japanese population and kinetics of clozapine glucuronidation. Drug Metab Dispos 2005; 33(5):672-675.
33. Jinno H, Saeki M, Saito Y, Tanaka-Kagawa T, Hanioka N, Sai K, Kaniwa N, Ando M, Shirao K, Minami H, Ohtsu A, Yoshida T, Saijo N, Ozawa S, Sawada J. Functional characterization of human UDP-glucuronosyltransferase 1A9 variant, D256N, found in Japanese cancer patients. J Pharmacol Exp Ther 2003; 306(2):688-693.
34. Iida A, Saito S, Sekine A, Mishima C, Kitamura Y, Kondo K, Harigae S, Osawa S, Nakamura Y. Catalog of 86 single-nucleotide polymorphisms (SNPs) in three uridine diphosphate glycosyltransferase genes: UGT2A1, UGT2B15, and UGT8. J Hum Genet 2002; 47(10):505-510.
35. Kadakol A, Ghosh SS, Sappal BS, Sharma G, Roy Chowdhury J, Roy Chowdhury N. Genetic lesions of bilirubin uridine-diphosphoglucuronate glucuronosyltransferase (UGT1A1) causing Crigler-Najjar and Gilbert syndromes: correlation of genotype to phenotype. Hum Mutat 2000; 16(4): 297-306.
36. Arias IM, Gartner LM, Cohen M, Ezzer JB, Levi AJ. Chronic nonhemolytic unconjugated hyperbilirubinemia with glucuronyl transferase deficiency. Clinical, biochemical, pharmacologic and genetic evidence for heterogeneity. Am J Med 1969; 47(3):395-409.
37. Labrune P, Myara A, Hennion C, Gout JP, Trivin F, Odievre M. Crigler-Najjar type II disease inheritance: a family study. J Inherit Metab Dis 1989; (3):302-306.
38. Ehmer U, Lankisch TO, Erichsen TJ, Kalthoff S, Freiberg N, Wehmeier M, Manns MP, Strassburg CP. Rapid allelic discrimination by TaqMan PCR for the detection of the Gilbert's syndrome marker UGT1A1*28. J Mol Diagn 2008; 10(6):549-552.
39. Matal J, Jancova P, Siller M, Masek V, Anzenbacherova E, Anzenbacher P. Interspecies comparison of the glucuronidation processes in the man, monkey, pig, dog and rat. Neuro Endocrinol Lett 2008; 29(5):738-743.
40. Kaji H, Kume T. Characterization of af loqualone N-glucuronidation: species differences and identification of human UDP-glucuronosyltransferase isoform(s). Drug Metab Dispos 2005; 33(1):60-67.
41. Court MH, Greenblatt DJ. Biochemical basis for deficient paracetamol glucuronidation in cats: an interspecies comparison of enzyme constraint in liver microsomes. J Pharm Pharmacol 1997; 49(4):446-449.
42. Court MH, Greenblatt DJ. Molecular basis for deficient acetaminophen glucuronidation in cats. An interspecies comparison of enzyme kinetics in liver microsomes. Biochem Pharmacol 1997; 53(7):1041-1047.
43. Krishnaswamy S, Duan SX, Von Moltke LL, Greenblatt DJ, Sudmeier JL, Bachovchin WW, Court MH. Serotonin (5-hydroxytryptamine) glucuronidation in vitro: assay development, human liver microsome activities and species differences. Xenobiotica 2003; 33(2):169-180.
44. Habuchi O. Diversity and functions of glycosaminoglycan sulfotransferases. Biochim Biophys Acta 2000; 1474(2):115-127.
45. Senggunprai L, Yoshinari K, Yamazoe Y. Selective role of sulfotransferase 2A1 (SULT2A1) in the N-sulfoconjugation of quinolone drugs in humans. Drug Metab Dispos 2009; 37(8):1711-1717.
46. Strott CA. Sulfonation and molecular action. Endocr Rev 2002; 23(5):703-732.
47. Strassburg CP, Strassburg A, Kneip S, Barut A, Tukey RH, Rodeck B, Manns MP. Developmental aspects of human hepatic drug glucuronidation in young children and adults. Gut 2002; 50(2):259-265.
48. Ring JA, Ghabrial H, Ching MS, Smallwood RA, Morgan DJ. Fetal hepatic drug elimination. Pharmacol Ther 1999; 84(3):429-445.
49. Glatt H, Meinl W. Pharmacogenetics of soluble sulfotransferases (SULTs). Naunyn Schmiedebergs Arch Pharmacol 2004; 369(1):55-68.
50. Gamage N, Barnett A, Hempel N, Duggleby RG, Windmill KF, Martin JL, McManus ME. Human sulfotransferases and their role in chemical metabolism. Toxicol Sci 2006; 90(1):5-22.
51. Surh Y-J. Bioactivation of benzylic and allylic alcohols via sulfoconjugation. Chem Biol Interact 1998; 109(1-3):221-235.
52. Lindsay J, Wang LL, Li Y, Zhou SF. Structure, function and polymorphism of human cytosolic sulfotransferases. Curr Drug Metab 2008; 9(2):99-105.
53. Weinshilboum RM, Otterness DM, Aksoy IA, Wood TC, Her C, Raftogianis RB. Sulfation and sulfotransferases 1: Sulfotransferase molecular biology: cDNAs and genes. FASEB J 1997; 11(1):3-14.
54. Falany CN, Xie X, Wang J, Ferrer J, Falany JL. Molecular cloning and expression of novel sulphotransferase-like cDNAs from human and rat brain. Biochem J 2000; 346 Pt 3:857-864.
55. Sakakibara Y, Suiko M, Pai TG, Nakayama T, Takami Y, Katafuchi J, Liu MC. Highly conserved mouse and human brain sulfotransferases: molecular cloning, expression, and functional characterization. Gene 2002; 285(1-2):39-47.
56. Takahashi S, Sakakibara Y, Mishiro E, Kouriki H, Nobe R, Kurogi K, Yasuda S, Liu MC, Suiko M. Molecular cloning, expression and characterization of a novel mouse SULT6 cytosolic sulfotransferase. J Biochem 2009; 146(3):399-405.
57. Dajani R, Hood AM, Coughtrie MW. A single amino acid, glu146, governs the substrate specificity of a human dopamine sulfotransferase, SULT1A3. Mol Pharmacol 1998; 54(6):942-948.
58. Meinl W, Meerman JH, Glatt H. Differential activation of promutagens by alloenzymes of human sulfotransferase 1A2 expressed in Salmonella typhimurium. Pharmacogenetics 2002; 12(9):677-689.
59. Dajani R, Cleasby A, Neu M, Wonacott AJ, Jhoti H, Hood AM, Modi S, Hersey A, Taskinen J, Cooke RM, Manchee GR, Coughtrie MW. X-ray crystal structure of human dopamine sulfotransferase, SULT1A3. Molecular modeling and quantitative structure-activity relationship analysis demonstrate a molecular basis for sulfotransferase substrate specificity. J Biol Chem 1999; 274(53):37862-37868.
60. Fujita K, Nagata K, Ozawa S, Sasano H, Yamazoe Y. Molecular cloning and characterization of rat ST1B1 and human ST1B2 cDNAs, encoding thyroid hormone sulfotransferases. J Biochem 1997; 122(5):1052-1061.
61. Pai TG, Sugahara T, Suiko M, Sakakibara Y, Xu F, Liu MC. Differential xenoestrogen-sulfating activities of the human cytosolic sulfotransferases: molecular cloning, expression, and purification of human SULT2B1a and SULT2B1b sulfotransferases. Biochim Biophys Acta 2002; 1573(2):165-170.
62. Li X, Clemens DL, Anderson RJ. Sulfation of iodothyronines by human sulfotransferase 1C1 (SULT1C1)*. Biochem Pharmacol 2000; 60(11):1713-1716.
63. Yoshinari K, Nagata K, Shimada M, Yamazoe Y. Molecular characterization of ST1C1-related human sulfotransferase. Carcinogenesis 1998; 19(5):951-953.
64. Falany CN, Krasnykh V, Falany JL. Bacterial expression and characterization of a cDNA for human liver estrogen sulfotransferase. J Steroid Biochem Mol Biol 1995; 52(6):529-539.
65. Comer KA, Falany JL, Falany CN. Cloning and expression of human liver dehydroepiandrosterone sulphotransferase. Biochem J 1993; 289(Pt 1):233-240.
66. Javitt NB, Lee YC, Shimizu C, Fuda H, Strott CA. Cholesterol and hydroxycholesterol sulfotransferases: identification, distinction from dehydroepiandrosterone sulfotransferase, and differential tissue expression. Endocrinology 2001; 142(7):2978-2984.
67. Wang LQ, James MO. Inhibition of sulfotransferases by xenobiotics. Curr Drug Metab 2006; 7(1):83-104.
68. Vietri M, Pietrabissa A, Mosca F, Spisni R, Pacifici GM. Curcumin is a potent inhibitor of phenol sulfotransferase (SULT1A1) in human liver and extrahepatic tissues. Xenobiotica 2003; 33(4):357-363.
69. De Santi C, Pietrabissa A, Mosca F, Rane A, Pacifici GM. Inhibition of phenol sulfotransferase (SULT1A1) by quercetin in human adult and foetal livers. Xenobiotica 2002; 32(5):363-368.
70. Nishimuta H, Ohtani H, Tsujimoto M, Ogura K, Hiratsuka A, Sawada Y. Inhibitory effects of various beverages on human recombinant sulfotransferase isoforms SULT1A1 and SULT1A3. Biopharm Drug Dispos 2007; 28(9):491-500.
71. King RS, Ghosh AA, Wu J. Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents. Curr Drug Metab 2006; 7(7):745-753.
72. Maiti S, Chen X, Chen G. All-trans retinoic acid induction of sulfotransferases. Basic Clin Pharmacol Toxicol 2005; 96(1):44-53.
73. Chen X, Baker SM, Chen G. Methotrexate induction of human sulfotransferases in Hep G2 and Caco-2 cells. J Appl Toxicol 2005; 25(5):354-360.
74. Chen Y, Huang C, Zhou T, Chen G. Genistein induction of human sulfotransferases in HepG2 and Caco-2 cells. Basic Clin Pharmacol Toxicol 2008; 103(6):553-559.
75. Arslan S, Silig Y, Pinarbasi H. An investigation of the relationship between SULT1A1 Arg(213)His polymorphism and lung cancer susceptibility in a Turkish population. Cell Biochem Funct 2009; 27(4):211-215.
76. Huang SK, Chiu AW, Pu YS, Huang YK, Chung CJ, Tsai HJ, Yang MH, Chen CJ, Hsueh YM. Arsenic methylation capability, myeloperoxidase and sulfotransferase genetic polymorphisms, and the stage and grade of urothelial carcinoma. Urol Int 2009; 82(2):227-234.
77. Bardakci F, Arslan S, Bardakci S, Binatli AO, Budak M. Sulfotransferase 1A1 (SULT1A1) polymorphism and susceptibility to primary brain tumors. J Cancer Res Clin Oncol 2008; 134(1):109-114.
78. Tsoi C, Falany CN, Morgenstern R, Swedmark S. Identification of a new subfamily of sulphotransferases: cloning and characterization of canine SULT1D1. Biochem J 2001; 356(Pt 3):891-897.
79. Yoshinari K, Nagata K, Ogino M, Fujita K, Shiraga T, Iwasaki K, Hata T, Yamazoe Y. Molecular cloning and expression of an amine sulfotransferase cDNA: a new gene family of cytosolic sulfotransferases in mammals. J Biochem 1998; 123(3):479-486.
80. Nagata K, Yamazoe Y. Pharmacogenetics of sulfotransferase. Annu Rev Pharmacol Toxicol 2000; 40:159-176.
81. Wang PC, Buu NT, Kuchel O, Genest J. Conjugation patterns of endogenous plasma catecholamines in human and rat. A new specific method for analysis of glucuronide-conjugated catecholamines. J Lab Clin Med 1983; 101(1):141-151.
82. Dunn RT 2nd, Klaassen CD. Tissue-specific expression of rat sulfotransferase messenger RNAs. Drug Metab Dispos 1998; 26(6):598-604.
83. Hein DW, McQueen CA, Grant DM, Goodfellow GH, Kadlubar FF, Weber WW. Pharmacogenetics of the arylamine N-acetyltransferases: a symposium in honor of Wendell W. Weber. Drug Metab Dispos 2000; 28(12):1425-1432.
84. Watanabe M, Sofuni T, Nohmi T. Nohmi. Involvement of Cys69 residue in the catalytic mechanism of N-hydroxyarylamine O-acetyltransferase of Salmonella typhimurium. Sequence similarity at the amino acid level suggests a common catalytic mechanism of acetyltransferase for S. typhimurium and higher organisms. J Biol Chem 1992; 267(12):8429-8436.
85. Payton M, Auty R, Delgoda R, Everett M, Sim E. Cloning and characterization of arylamine N-acetyltransferase genes from Mycobacterium smegmatis and Mycobacterium tuberculosis: increased expression results in isoniazid resistance. J Bacteriol 1999; 181(4):1343-1347.
86. Kawamura A, Graham J, Mushtaq A, Tsiftsoglou SA, Vath GM, Hanna PE, Wagner CR, Sim E. Eukaryotic arylamine N-acetyltransferase. Investigation of substrate specificity by highthroughput screening. Biochem Pharmacol 2005; 69(2):347-359.
87. Grant DM, Blum M, Beer M, Meyer UA. Monomorphic and polymorphic human arylamine N-acetyltransferases: a comparison of liver isozymes and expressed products of two cloned genes. Mol Pharmacol 1991; 39(2):184-191.
88. Kukongviriyapan V, Phromsopha N, Tassaneeyakul W, Kukongviriyapan U, Sripa B, Hahnvajanawong V, Bhudhisawasdi V. Inhibitory effects of polyphenolic compounds on human arylamine N-acetyltransferase 1 and 2. Xenobiotica 2006; 36(1):15-28.
89. Chen GW, Chung JG, Hsieh CL, Lin JG. Effects of the garlic components diallyl sulfide and diallyl disulfide on arylamine N-acetyltransferase activity in human colon tumour cells. Food Chem Toxicol 1998; 36(9-10):761-770.
90. Lin JG, Chen GW, Su CC, Hung CF, Yang CC, Lee JH, Chung JG. Effects of garlic components diallyl sulfide and diallyl disulfide on arylamine N-acetyltransferase activity and 2-aminofluorene-DNA adducts in human promyelocytic leukemia cells. Am J Chin Med 2002; 30(2-3):315-325.
91. Butcher NJ, Tetlow NL, Cheung C, Broadhurst GM, Minchin RF. Induction of human arylamine N-acetyltransferase type I by androgens in human prostate cancer cells. Cancer Res 2007; 67(1):85-92.
92. Agúndez JA. Polymorphisms of human N-acetyltransferases and cancer risk. Curr Drug Metab 2008; 9(6):520-531.
93. Lammer EJ, Shaw GM, Iovannisci DM, Finnell RH. Periconceptional multivitamin intake during early pregnancy, genetic variation of acetyl-N-transferase 1 (NAT1), and risk for orofacial clefts. Birth Defects Res A Clin Mol Teratol 2004; 70(11):846-852.
94. Kawamura A, Westwood I, Wakefield L, Long H, Zhang N, Walters K, Redfield C, Sim E. Mouse N-acetyltransferase type 2, the homologue of human N-acetyltransferase type 1. Biochem Pharmacol 2008; 75(7):1550-1560.
95. Walraven JM, Doll MA, Hein DW. Identification and characterization of functional rat arylamine N-acetyltransferase 3: comparisons with rat arylamine N-acetyltransferases 1 and 2. J Pharmacol Exp Ther 2006; 319(1):369-375.
96. Collins JM. Inter-species differences in drug properties. Chem Biol Interact 2001; 134(3):237-242.
97. Hearse DJ, Weber WW. Multiple N-acetyltransferases and drug metabolism. Tissue distribution, characterization and significance of mammalian N-acetyltransferase. Biochem J 1973; 132(3):519-526.
98. van Bladeren PJ. Glutathione conjugation as a bioactivation reaction. Chem Biol Interact 2000; 129(1-2):61-76.
99. Sheehan D, Meade G, Foley VM, Dowd CA. Structure, function and evolution of glutathione transferases: implications for classification of non-mammalian members of an ancient enzyme superfamily. Biochem J 2001; 360(Pt 1):1-16.
100. Soboll S, Grundel S, Harris J, Kolb-Bachofen V, Ketterer B, Sies H. The content of glutathione and glutathione S-transferases and the glutathione peroxidase activity in rat liver nuclei determined by a non-aqueous technique of cell fractionation. Biochem J 1995; 311(Pt 3):889-894.
101. Morel F, Rauch C, Petit E, Piton A, Theret N, Coles B, Guillouzo A. Gene and protein characterization of the human glutathione S-transferase kappa and evidence for a peroxisomal localization. J Biol Chem 2004; 279(16):16246-16253.
102. Armstrong RN. Structure, catalytic mechanism, and evolution of the glutathione transferases. Chem Res Toxicol 1997; 10(1):2-18.
103. Hayes JD, Strange RC. Glutathione S-transferase polymorphisms and their biological consequences. Pharmacology 2000; 61(3):154-166.
104. Kulkarni AA, Kulkarni AP. Retinoids inhibit mammalian glutathione transferases. Cancer Lett 1995; 91(2):185-189.
105. Ploemen JHTM, Van Ommen B, De Haan A, Venekamp JC, Van Bladeren PJ. Inhibition of human glutathione S-transferases by dopamine, α-methyldopa and their 5-S-glutathionyl conjugates. Chem Biol Interact 1994; 90(1):87-99.
106. Liu XP, Goldring CE, Wang HY, Copple IM, Kitteringham NR, Park BK. Extract of Ginkgo biloba induces glutathione-S-transferase subunit-P1 in vitro. Phytomedicine 2009; 16(5):451-455.
107. Williamson G, DuPont MS, Wanigatunga S, Heaney RK, Musk SRR, Fenwick GR, Rhodes MJC. Induction of glutathione S'- transferase activity in hepG2 cells by extracts from fruits and vegetables. Food Chem 1997; 60(2):157-160.
108. Hayes JD, Flanagan JU, Jowsey IR. Glutathione transferases. Annu Rev Pharmacol Toxicol 2005; 45:51-88.
109. Iida A, Saito S, Sekine A, Harigae S, Osawa S, Mishima C, Kondo K, Kitamura Y, Nakamura Y. Catalog of 46 single-nucleotide polymorphisms (SNPs) in the microsomal glutathione S-transferase 1 (MGST1) gene. J Hum Genet 2001; 46(10):590-594.
110. Reitz RH, Mendrala AL, Guengerich FP. In vitro metabolism of methylene chloride in human and animal tissues: use in physiologically based pharmacokinetic models. Toxicol Appl Pharmacol 1989; 97(2):230-246.
111. Sherratt PJ, Williams S, Foster J, Kernohan N, Green T, Hayes JD. Direct comparison of the nature of mouse and human GST T1-1 and the implications on dichloromethane carcinogenicity. Toxicol Appl Pharmacol 2002; 179(2):89-97.
112. Igarashi T, Tomihari N, Ohmori S, Ueno K, Kitagawa H, Satoh T. Comparison of glutathione S-transferases in mouse, guinea pig, rabbit and hamster liver cytosol to those in rat liver. Biochem Int 1986; 13(4):641-648.
113. Weinshilboum R. Thiopurine pharmacogenetics: clinical and molecular studies of thiopurine methyltransferase. Drug Metab Dispos 2001; 29(4 Pt 2):601-605.
114. Oselin K, Anier K. Inhibition of human thiopurine S-methyltransferase by various nonsteroidal anti-inflammatory drugs in vitro: a mechanism for possible drug interactions. Drug Metab Dispos 2007; 35(9):1452-1454.
115. Fessing MY, Krynetski EY, Zambetti GP, Evans WE. Functional characterization of the human thiopurine S-methyltransferase (TPMT) gene promoter. Eur J Biochem 1998; 256(3):510-517.
116. Otterness DM, Szumlanski CL, Wood TC, Weinshilboum RM. Human thiopurine methyltransferase pharmacogenetics. Kindred with a terminal exon splice junction mutation that results in loss of aktivity. J Clin Invest 1998; 101(5):1036-1044.
117. Klemetsdal B, Wist E, Aarbakke J. Gender difference in red blood cell thiopurine methyltransferase activity. Scand J Clin Lab Invest 1993; 53(7):747-749.
118. McLeod HL, Krynetski EY, Wilimas JA, Evans WE. Higher activity of polymorphic thiopurine S-methyltransferase in erythrocytes from neonates compared to adults. Pharmacogenetics 1995; 5(5):281-286.
119. Szumlanski CL and Weinshilboum RM. Sulphasalazine inhibition of thiopurine methyltransferase: possible mechanism for interaction with 6-mercaptopurine and azathioprine. Br J Clin Pharmacol 1995; 39(4):456-459.
120. Schaeffeler E, Fischer C, Brockmeier D, Wernet D, Moerike K, Eichelbaum M, Zanger UM, Schwab M. Comprehensive analysis of thiopurine S-methyltransferase phenotype-genotype correlation in a large population of German-Caucasians and identification of novel TPMT variants. Pharmacogenetics 2004; 14(7):407-417.
121. Ujiie S, Sasaki T, Mizugaki M, Ishikawa M, Hiratsuka M. Functional characterization of 23 allelic variants of thiopurine S-methyltransferase gene (TPMT*2 - *24). Pharmacogenet Genomics 2008; 18(10):887-893.
122. Feng Q, Vannaprasaht S, Peng Y, Angsuthum S, Avihingsanon Y, Yee VC, Tassaneeyakul W, Weinshilboum RM. Thiopurine S-methyltransferase pharmacogenetics: functional characterization of a novel rapidly degraded variant allozyme. Biochem Pharmacol 2010; 79(7):1053-1061.
123. Jones TS, Yang W, EvansWE, Relling MV. Using HapMap Tools in Pharmacogenomic Discovery: The Thiopurine Methyltransferase Polymorphism. Clin Pharmacol Ther 2007; 81(5):729-734.
124. White SD, Rosychuk RA, Outerbridge CA, Fieseler KV, Spier S, Ihrke PJ, Chapman PL. Thiopurine methyltransferase in red blood cells of dogs, cats, and horses. J Vet Intern Med 2000; 14(5):499-502.
125. Wang LN, Zhang L, Nan F, Cheng JQ, Bu H, Liang MZ, Lu YR. HPLC determination and diversity analysis of thiopurine methyltransferase activity in human and pig. Sichuan Da Xue Xue Bao Yi Xue Ban 2006; 37(3):460-463.
126. Shield AJ, Thomae BA, Eckloff BW, Wieben ED, Weinshilboum RM. Human catechol O-methyltransferase genetic variation: gene resequencing and functional characterization of variant allozymes. Mol Psychiatry 2004; 9(2):151-160.
127. Ulmanen I, Peränen J, Tenhunen J, Tilgmann C, Karhunen T, Panula P, Bernasconi L, Aubry J-P, and Lundström K. Expression and intracellular localization of catechol-Omethyltransferase in transfected mammalian cells. Eur J Biochem 1997; 243(1-2):452-459.
128. Taskinen J, Ethell BT, Pihlavisto P, Hood AM, Burchell B, Coughtrie MW. Conjugation of catechols by recombinant human sulfotransferases, UDP-glucuronosyltransferases, and soluble catechol O-methyltransferase: structure-conjugation relationships and predictive models. Drug Metab Dispos 2003; 31(9):1187-1197.
129. Lehmann L, Jiang L, Wagner J. Soy isoflavones decrease the catechol-O-methyltransferase-mediated inactivation of 4-hydroxyestradiol in cultured MCF-7 cells. Carcinogenesis 2008; 29(2):363-370.
130. Antonini A, Abbruzzese G, Barone P, Bonuccelli U, Lopiano L, Onofrj M, Zappia M, Quattrone8 A. COMT inhibition with tolcapone in the treatment algorithm of patients with Parkinson's disease (PD): relevance for motor and non-motor features. Neuropsychiatr Dis Treat 2008; 4(1):1-9.
131. Lachman HM, Papolos DF, Saito T, Yu YM, Szumlanski CL, Weinshilboum RM. Human catechol-O-methyltransferase pharmacogenetics: Description of a functional polymorphism and its potential application to neuropsychiatric disorders. Pharmacogenetics 1996; 6(3):243-250.
132. Park TW, Yoon KS, Kim JH, Park WY, Hirvonen A, Kang D. Functional catechol-O-methyltransferase gene polymorphism and susceptibility to schizophrenia. Eur Neuropsychopharmacol 2002; 12(4):299-303.
133. Egan MF, Goldberg TE, Kolachana BS, Callicott JH, Mazzanti CM, Straub RE, Goldman D, Weinberger DR. Effect of COMT Val108/158 Met genotype on frontal lobe function and risk for schizophrenia. Proc Natl Acad Sci U S A 2001; 98(12):6917-6922.
134. Glatt SJ, Faraone SV, Tsuang MT. Association between a functional catechol O-methyltransferase gene polymorphism andschizophrenia: meta-analysis of case-control and family-based studies. Am J Psychiatry 2003; 160(3):469-476.
135. Kunugi H, Nanko S, Ueki A, Otsuka E, Hattori M, Hoda F, Vallada HP, Arranz MJ, Collier DA. High and low activity alleles of catechol-O-methyltransferase gene: ethnic difference and possible association with Parkinson's disease. Neurosci Lett 1997; 221(2-3):202-204.
136. Yoritaka A, Hattori N, Yoshino H, Mizuno Y. Catechol-Omethyltransferase genotype and susceptibility to Parkinson's disease in Japan. J Neural Transm 1997; 104(11-12):1313-1317.
137. Tiihonen J, Hallikainen T, Lachman H, Saito T, Volavka J, Kauhanen J, Salonen JT, Ryynänen OP, Koulu M, Karvonen MK, Pohjalainen T, Syvälahti E, Hiet-aletal/et-ala J. Association between the functional variant of the catechol-O-methyltransferase (COMT) gene and type 1 alcoholism. Mol Psychiatry 1999; 4(3):286-289.
138. Kauhanen J, Hallikainen T, Tuomainen TP, Koulu M, Karvonen MK, Salonen JT, Tiihonen J. Association between the functional polymorphism of catechol-O-methyltransferase gene and alcohol consumption among social drinkers. Alcohol Clin Exp Res 2000; 24(2):135-139.
139. Wang T, Franke P, Neidt H, Cichon S, Knapp M, Lichtermann D, Maier W, Propping P, Nöthen MM. Association study of the lowactivity allele of catechol-O-methyltransferase and alcoholism using a family-based approach. Mol Psychiatry 2001; 6(1):109-111.
140. Chen J, Lipska BK, Halim N, Ma QD, Matsumoto M, Melhem S, Kolachana BS, Hyde TM, Herman MM, Apud J, Egan MF, Kleinman JE, Weinberger DR. Functional analysis of genetic variation in catechol-O-methyltransferase (COMT): effects on mRNA, protein, and enzyme activity in postmortem human brain. Am J Hum Genet 2004; 75(5):807-821.