Benzylmorpholine Analogs as Selective Inhibitors of Lung Cytochrome P450 2A13 for the Chemoprevention of Lung Cancer in Tobacco Users
详细信息    查看全文
  • 作者:Linda C. Blake (1)
    Anuradha Roy (2)
    David Neul (3)
    Frank J. Schoenen (4)
    Jeffrey Aubé (1) (4)
    Emily E. Scott (1)
  • 关键词:chemopreventative ; cytochrome P450 2A13 ; cytochrome P450 2A6 ; lung cancer ; tobacco
  • 刊名:Pharmaceutical Research
  • 出版年:2013
  • 出版时间:September 2013
  • 年:2013
  • 卷:30
  • 期:9
  • 页码:2290-2302
  • 全文大小:835KB
  • 参考文献:1. Guengerich FP. Human Cytochrome P450 Enzymes. In: de Ortiz Montellano PR, editor. Cytochrome P450: Structure, Mechanism, and Biochemistry. New York: Kluwer Academic/Plenum; 2005. p. 377-30. CrossRef
    2. Tomao F, Spinelli G, Vici P, Pisanelli GC, Cascialli G, Frati L, / et al. Current role and safety profile of aromatase inhibitors in early breast cancer. Expert Rev Anticancer Ther. 2011;11(8):1253-3. CrossRef
    3. Vasaitis TS, Bruno RD, Njar VC. CYP17 inhibitors for prostate cancer therapy. J Steroid Biochem Mol Biol. 2011;125(1-):23-1. CrossRef
    4. Cvetkovic RS, Goa KL. Lopinavir/ritonavir: a review of its use in the management of HIV infection. Drugs. 2003;63(8):769-02. CrossRef
    5. Elion R, Cohen C, Gathe J, Shalit P, Hawkins T, Liu HC, / et al. Phase 2 study of cobicistat / versus ritonavir each with once-daily atazanavir and fixed-dose emtricitabine/tenofovir df in the initial treatment of HIV infection. AIDS. 2011;25(15):1881-. CrossRef
    6. Mathias AA, German P, Murray BP, Wei L, Jain A, West S, / et al. Pharmacokinetics and pharmacodynamics of GS-9350: a novel pharmacokinetic enhancer without anti-HIV activity. Clin Pharmacol Ther. 2010;87(3):322-. CrossRef
    7. World Health Organization. Cancer. http://www.who.int/mediacentre/factsheets/fs297/en/ (accessed 11/14/08).
    8. American Cancer Society. Cancer Facts and Figures 2012, Atlanta, 2012.
    9. Center for Disease Control. Smoking and Tobacco Use. http://www.cdc.gov/tobacco/data_statistics/fact_sheets/index.htm.
    10. Hecht SS, Kassie F, Hatsukami DK. Chemoprevention of lung carcinogenesis in addicted smokers and ex-smokers. Nat Rev Cancer. 2009;9(7):476-8. CrossRef
    11. Hecht SS. Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines. Chem Res Toxicol. 1998;11(6):559-03. CrossRef
    12. Hecht SS. DNA adduct formation from tobacco-specific N-nitrosamines. Mutat Res. 1999;424(1-):127-2.
    13. Wang H, Tan W, Hao B, Miao X, Zhou G, He F, / et al. Substantial reduction in risk of lung adenocarcinoma associated with genetic polymorphism in CYP2A13, the most active cytochrome P450 for the metabolic activation of tobacco-specific carcinogen NNK. Cancer Res. 2003;63(22):8057-1.
    14. Zhang X, Su T, Zhang QY, Gu J, Caggana M, Li H, / et al. Genetic polymorphisms of the human CYP2A13 gene: identification of single-nucleotide polymorphisms and functional characterization of an Arg257Cys variant. J Pharmacol Exp Ther. 2002;302(2):416-3. CrossRef
    15. Weng Y, Fang C, Turesky RJ, Behr M, Kaminsky LS, Ding X. Determination of the role of target tissue metabolism in lung carcinogenesis using conditional cytochrome P450 reductase-null mice. Cancer Res. 2007;67(16):7825-2. CrossRef
    16. Zhou X, D’Agostino J, Xie F, Ding X. Role of CYP2A5 in the Bioactivation of the Lung Carcinogen 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanone in Mice. J Pharmacol Exp Ther. 2012;341(1):233-1. CrossRef
    17. Hecht SS, Trushin N, Rigotty J, Carmella SG, Borukhova A, Akerkar S, / et al. Complete inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced rat lung tumorigenesis and favorable modification of biomarkers by phenethyl isothiocyanate. Cancer Epidemiol Biomarkers Prev. 1996;5(8):645-2.
    18. Morse MA, Eklind KI, Toussaint M, Amin SG, Chung FL. Characterization of a glucuronide metabolite of 4-(methyl-nitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and its dose-dependent excretion in the urine of mice and rats. Carcinogenesis. 1990;11(10):1819-3. CrossRef
    19. Rendic S. Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002;34(1-):83-48. CrossRef
    20. He XY, Shen J, Ding X, Lu AY, Hong JY. Identification of critical amino acid residues of human CYP2A13 for the metabolic activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco-specific carcinogen. Drug Metab Dispos. 2004;32(12):1516-1. CrossRef
    21. Su T, Bao Z, Zhang Q-Y, Smith TJ, Hong J-Y, Ding X. Human cytochrome P450 CYP2A13: predominant expression in the respiratory tract and its high efficiency metabolic activation of a tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 2000;60(18):5074-.
    22. Smith BD, Sanders JL, Porubsky PR, Lushington GH, Stout CD, Scott EE. Structure of the human lung cytochrome P450 2A13. J Biol Chem. 2007;282(23):17306-3. CrossRef
    23. DeVore NM, Smith BD, Urban MJ, Scott EE. Key residues controlling phenacetin metabolism by human cytochrome P450 2A enzymes. Drug Metab Dispos. 2008;36(12):2582-0. CrossRef
    24. Shen AL, Porter TD, Wilson TE, Kasper CB. Structural analysis of the FMN binding domain of NADPH-cytochrome P-450 oxidoreductase by site-directed mutagenesis. J Biol Chem. 1989;264(13):7584-.
    25. DeVore NM, Smith BD, Wang JL, Lushington GH, Scott EE. Key residues controlling binding of diverse ligands to human cytochrome P 450 2A enzymes. Drug Metab Dispos. 2009;37(6):1319-7. CrossRef
    26. DeVore NM, Scott EE. Structures of cytochrome P450 17A1 with prostate cancer drugs abiraterone and TOK-001. Nature. 2012;482(7383):116-. CrossRef
    27. Devore NM, Meneely KM, Bart AG, Stephens ES, Battaile KP, Scott EE. Structural comparison of cytochromes P450 2A6, 2A13, and 2E1 with pilocarpine. FEBS J. 2011.
    28. Rahnasto M, Raunio H, Poso A, Juvonen RO. More potent inhibition of human CYP2A6 than mouse CYP2A5 enzyme activities by derivatives of phenylethylamine and benzaldehyde. Xenobiotica. 2003;33(5):529-9. CrossRef
    29. von Weymarn LB, Murphy SE. CYP2A13-catalysed coumarin metabolism: comparison with CYP2A5 and CYP2A6. Xenobiotica. 2003;33(1):73-1. CrossRef
    30. Ohta H, Yuyama Y, Uozumi Y, Yamada YMA. In-water dehydrative alkylation of ammonia and amines with alcohols by a polymeric bimetallic catalyst. Org Lett. 2011;13(15):3892-. CrossRef
    31. Long TR, Maity PK, Samarakoon TB, Hanson PR. ROMP-derived oligomeric phosphates for application in facile benzylation. Org Lett. 2010;12(13):2904-. CrossRef
    32. Abdel-Magid AF, Carson KG, Harris BD, Maryanoff CA, Shah RD. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. studies on direct and indirect reductive amination procedures. J Org Chem. 1996;61(11):3849-2. CrossRef
    33. Marcia de Figueiredo R, Thoret S, Huet C, Dubois J. Palladium-catalyzed intramolecular arylation of N-Benzyl-2-iodoimidazoles: a facile and rapid access to 5H-imidazo[2,1-a]isoindoles. Synthesis. 2007;2007(4):529-0.
    34. Ding X, Kaminsky LS. Human extrahepatic cytochromes P450: function in xenobiotic metabolism and tissue-selective chemical toxicity in the respiratory and gastrointestinal tracts. Annu Rev Pharmacol Toxicol. 2003;43:149-3. CrossRef
    35. Wei Y, Li L, Zhou X, Zhang Q-Y, Dunbar A, Liu F, / et al. Generation and characterization of a novel Cyp2A(4/5)bgs-Null Mouse Model. Drug Metab Dispos. 2013;41:132-0. CrossRef
  • 作者单位:Linda C. Blake (1)
    Anuradha Roy (2)
    David Neul (3)
    Frank J. Schoenen (4)
    Jeffrey Aubé (1) (4)
    Emily E. Scott (1)

    1. Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence, Kansas, 66045, USA
    2. High Throughput Screening Laboratory, University of Kansas, 2034 Becker Drive, Lawrence, Kansas, 66047, USA
    3. Pharmacokinetics, Dynamics and Metabolism, Pfizer Inc., La Jolla, California, 92121, USA
    4. University of Kansas Specialized Chemistry Center, University of Kansas, 2034 Becker Drive, Lawrence, Kansas, 66047, USA
文摘

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700