Association of human cytochrome P450 1A1 (CYP1A1) and sulfotransferase 1A1 (SULT1A1) polymorphisms with differential metabolism and cytotoxicity of aminoflavone

Molecular Cancer Therapeutics

Volumn 9, Issue 10, 2010, Pages 2803-2813

  Zheng, Qiang ^a   Sha, Xianyi ^a,b   Liu, Jiansheng ^a   Heath, Elisabeth ^a   LoRusso, Patricia ^a   Li, Jing ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

5 AMINO 6,8 DIFLUORO 2 (3 FLUOROPHENYL) 7 METHYL 4H 1 BENZOPYRAN 4 ONE; AMINOFLAVONE; ANTINEOPLASTIC AGENT; CYTOCHROME P450 1A1; SULFOTRANSFERASE 1A1; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL DIFFERENTIATION; CYTOTOXICITY; DRUG METABOLISM; DRUG STRUCTURE; ENZYME ACTIVITY; GENETIC POLYMORPHISM; HYDROXYLATION; METABOLISM; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANIMALS; ARYLSULFOTRANSFERASE; BASE SEQUENCE; CELL LINE; CRICETINAE; CRICETULUS; CYTOCHROME P-450 CYP1A1; DNA PRIMERS; HUMANS; POLYMORPHISM, GENETIC;

EID: 77958077431     PISSN: 15357163     EISSN: 15388514     Source Type: Journal    
DOI: 10.1158/1535-7163.MCT-10-0597     Document Type: Article

References (44)

1. Kuffel MJ, Schroeder JC, Pobst LJ, et al. Activation of the antitumor agent aminoflavone (NSC 686288) is mediated by induction of tumor cell cytochrome P450 1A1/1A2. Mol Pharmacol 2002;62:143-53.
2. Loaiza-Perez AI, Kenney S, Boswell J, et al. Sensitivity of renal cell carcinoma to aminoflavone: role of CYP1A1. J Urol 2004;17:1688-97.
3. Meng LH, Kohlhagen G, Liao ZY, Antony S, Sausville E, Pommier Y. DNA-protein cross-links and replication-dependent histone H2AX phosphorylation induced by aminoflavone (NSC 686288), a novel anticancer agent active against human breast cancer cells. Cancer Res 2005;65:5337-43.
4. Meng LH, Shankavaram U, Chen C, et al. Activation of aminoflavone (NSC 686288) by a sulfotransferase is required for the antiproliferative effect of the drug and for induction of histone γ-H2AX. Cancer Res 2006;66:9656-64.
5. Meng LH, Kohn KW, Pommier Y. Dose-response transition from cell cycle arrest to apoptosis with selective degradation of Mdm2 and p21WAF1/CIP1 in response to the novel anticancer agent, aminoflavone (NSC 686,288). Oncogene 2007;26:4806-16.
6. Loaiza-Perez AI, Kenney S, Boswell J, et al. Aryl hydrocarbon receptor activation of an antitumor aminoflavone: basis of selective toxicity for MCF-7 breast tumor cells. Mol Cancer Ther 2004;3:715-25.
7. Szklarz GD, Paulsen MD. Molecular modeling of cytochrome P450 1A1: enzyme-substrate interactions and substrate binding affinities. J Biomol Struct Dyn 2002;20:155-62.
8. Cascorbi I, Brockmoller J, Roots I. A C4887A polymorphism in exon 7 of human CYP1A1: population frequency, mutation linkages, and impact on lung cancer susceptibility. Cancer Res 1996;56:4965-9.
9. Mrozikiewicz PM, Cascorbi I, Brockmoller J, Roots I. CYP1A1 mutations 4887A, 4889G, 5639C and 6235C in the Polish population and their allelic linkage, determined by peptide nucleic acid-mediated PCR clamping. Pharmacogenetics 1997;7:303-7.
10. Aynacioglu AS, Cascorbi I, Mrozikiewicz PM, Roots I. High frequency of CYP1A1 mutations in a Turkish population. Arch Toxicol 1998;72:215-8.
11. Kawajiri K, Nakachi K, Imai K, Watanabe J, Hayashi S. The CYP1A1 gene and cancer susceptibility. Crit Rev Oncol Hematol 1993;14:77-87.
12. Schwarz D, Kisselev P, Cascorbi I, Schunck WH, Roots I. Differential metabolism of benzo[a]pyrene and benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1 variants. Carcinogenesis 2001;22:453-9.
13. Kisselev P, Schunck WH, Roots I, Schwarz D. Association of CYP1A1 polymorphisms with differential metabolic activation of 17β-estradiol and estrone. Cancer Res 2005;65:2972-8.
14. Schwarz D, Kisselev P, Schunck WH, et al. Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. Pharmacogenetics 2000;10:519-30.
15. Whitlock JP, Jr. Induction of cytochrome P4501A1. Annu Rev Pharmacol Toxicol 1999;39:103-25.
16. Nebert DW, Ingelman-Sundberg M, Daly AK. Genetic epidemiology of environmental toxicity and cancer susceptibility: human allelic polymorphisms in drug-metabolizing enzyme genes, their functional importance, and nomenclature issues. Drug Metab Rev 1999;31:467-87.
17. Sato M, Sato T, Izumo T, Amagasa T. Genetic polymorphism of drug-metabolizing enzymes and susceptibility to oral cancer. Carcinogenesis 1999;20:1927-31.
18. Esteller M, Garcia A, Martinez-Palones JM, Xercavins J, Reventos J. Germ line polymorphisms in cytochrome-P450 1A1 (C4887 CYP1A1) and methylenetetrahydrofolate reductase (MTHFR) genes and endometrial cancer susceptibility. Carcinogenesis 1997;18:2307-11.
19. Carlini EJ, Raftogianis RB, Wood TC, et al. Sulfation pharmacogenetics: SULT1A1 and SULT1A2 allele frequencies in Caucasian, Chinese and African-American subjects. Pharmacogenetics 2001;11:57-68.
20. Raftogianis RB, Wood TC, Otterness DM, Van Loon JA, Weinshilboum RM. Phenol sulfotransferase pharmacogenetics in humans: association of common SULT1A1 alleles with TS PST phenotype. Biochem Biophys Res Commun 1997;239:298-304.
21. Nagar S, Walther S, Blanchard RL. Sulfotransferase (SULT) 1A1 polymorphic variants *1, *2, and *3 are associated with altered enzymatic activity, cellular phenotype, and protein degradation. Mol Pharmacol 2006;69:2084-92.
22. Donato MT, Gomez-Lechon MJ, Castell JV. A microassay for measuring cytochrome P450IA1 and P450IIB1 activities in intact human and rat hepatocytes cultured on 96-well plates. Anal Biochem 1993;213:29-33.
23. Lubet RA, Nims RW, Mayer RT, Cameron JW, Schechtman LM. Measurement of cytochrome P-450 dependent dealkylation of alkoxyphenoxazones in hepatic S9s and hepatocyte homogenates: effects of dicumarol. Mutat Res 1985;142:127-31.
24. Doehmer J. Predicting drug metabolism-dependent toxicity for humans with a genetically engineered cell battery. Altern Lab Anim 2006;34:561-75.
25. Doehmer J, Oesch F. V79 Chinese hamster cells genetically engineered for stable expression of cytochromes P450. Methods Enzymol 1991;206:117-23.
26. Zhang ZY, Fasco MJ, Huang L, Guengerich FP, Kaminsky LS. Characterization of purified human recombinant cytochrome P4501A1-Ile462 and -Val462: assessment of a role for the rare allele in carcinogenesis. Cancer Res 1996;56:3926-33.
27. Chernogolov A, Behlke J, Schunck WH, Roots I, Schwarz D. Human CYP1A1 allelic variants: baculovirus expression and purification, hydrodynamic, spectral, and catalytical properties and their potency in the formation of all-trans-retinoic acid. Protein Expr Purif 2003;28:259-69.
28. Schwarz D, Kisselev P, Honeck H, Cascorbi I, Schunck WH, Roots I. Co-expression of human cytochrome P4501A1 (CYP1A1) variants and human NADPH-cytochrome P450 reductase in the baculovirus/insect cell system. Xenobiotica 2001;31:345-56.
29. Chen C, Meng L, Ma X, et al. Urinary metabolite profiling reveals CYP1A2-mediated metabolism of NSC686288 (aminoflavone). J Pharmacol Exp Ther 2006;318:1330-42.
30. Petersen DD, McKinney CE, Ikeya K, et al. Human CYP1A1 gene: cosegregation of the enzyme inducibility phenotype and an RFLP. Am J Hum Genet 1991;48:720-5.
31. Kiyohara C, Nakanishi Y, Inutsuka S, et al. The relationship between CYP1A1 aryl hydrocarbon hydroxylase activity and lung cancer in a Japanese population. Pharmacogenetics 1998;8:315-23.
32. Landi MT, Bertazzi PA, Shields PG, et al. Association between CYP1A1 genotype, mRNA expression and enzymatic activity in humans. Pharmacogenetics 1994;4:242-6.
33. Williams PA, Cosme J, Sridhar V, Johnson EF, McRee DE. Mammalian microsomal cytochrome P450 monooxygenase: structural adaptations for membrane binding and functional diversity. Mol Cell 2000;5:121-31.
34. Raftogianis RB, Wood TC, Weinshilboum RM. Human phenol sulfotransferases SULT1A2 and SULT1A1: genetic polymorphisms, allozyme properties, and human liver genotype-phenotype correlations. Biochem Pharmacol 1999;58:605-16.
35. Gamage NU, Duggleby RG, Barnett AC, et al. Structure of a human carcinogen-converting enzyme, SULT1A1. Structural and kinetic implications of substrate inhibition. J Biol Chem 2003;278:7655-62.
36. Desta Z, Ward BA, Soukhova NV, Flockhart DA. Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther 2004;310:1062-75.
37. Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM. Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4′-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos 2002;30:869-74.
38. Davis W, Venitt S, Phillips DH. The metabolic activation of tamoxifen and α-hydroxytamoxifen to DNA-binding species in rat hepatocytes proceeds via sulphation. Carcinogenesis 1998;19:861-6.
39. Dasaradhi L, Shibutani S. Identification of tamoxifen-DNA adducts formed byα-sulfate tamoxifen and α-acetoxytamoxifen. Chem Res Toxicol 1997;10:189-96.
40. Gjerde J, Hauglid M, Breilid H, et al. Effects of CYP2D6 and SULT1A1 genotypes including SULT1A1 gene copy number on tamoxifen metabolism. Ann Oncol 2008;19:56-61.
41. Goetz MP, Rae JM, Suman VJ, et al. Pharmacogenetics of tamoxifen biotransformation is associated with clinical outcomes of efficacy and hot flashes. J Clin Oncol 2005;23:9312-8.
42. Rae JM, Goetz MP, Hayes DF, et al. CYP2D6 genotype and tamoxifen response. Breast Cancer Res 2005;7:E6.
43. Nowell S, Sweeney C, Winters M, et al. Association between sulfotransferase 1A1 genotype and survival of breast cancer patients receiving tamoxifen therapy. J Natl Cancer Inst 2002;94:1635-40.
44. Schroth W, Goetz MP, Hamann U, et al. Association between CYP2D6 polymorphisms and outcomes among women with early stage breast cancer treated with tamoxifen. JAMA 2009;302:1429-36.