Page 95 - Read Online
P. 95
Goyal et al. J Cancer Metastasis Treat 2021;7:18 https://dx.doi.org/10.20517/2394-4722.2020.143 Page 11 of 12
26. He X, Feng S. Role of metabolic enzymes P450 (CYP) on activating procarcinogen and their polymorphisms on the risk of cancers.
Curr Drug Metab 2015;16:850-63. DOI PubMed
27. Hrycay EG, Bandiera SM. Involvement of cytochrome P450 in reactive oxygen species formation and cancer. Cytochrome P450
Function and Pharmacological Roles in Inflammation and Cancer. Elsevier; 2015. pp. 35-84. DOI PubMed
28. Shimada T, Oda Y, Gillam EM, Guengerich FP, Inoue K. Metabolic activation of polycyclic aromatic hydrocarbons and other
procarcinogens by cytochromes P450 1A1 and P450 1B1 allelic variants and other human cytochromes P450 in Salmonella
typhimurium NM2009. Drug Metab Dispos 2001;29:1176-82. PubMed
29. Williams DE, Shigenaga MK, Castagnoli N Jr. The role of cytochromes P-450 and flavin-containing monooxygenase in the
metabolism of (S)-nicotine by rabbit lung. Drug Metab Dispos 1990;18:418-28. PubMed
30. Bao Z, He XY, Ding X, Prabhu S, Hong JY. Metabolism of nicotine and cotinine by human cytochrome P450 2A13. Drug Metab
Dispos 2005;33:258-61. DOI PubMed
31. Peterson LA, Trevor A, Castagnoli N Jr. Stereochemical studies on the cytochrome P-450 catalyzed oxidation of (S)-nicotine to the
(S)-nicotine delta 1'(5')-iminium species. J Med Chem 1987;30:249-54. DOI PubMed
32. Gorrod JW, Hibberd AR. The metabolism of nicotine-delta 1'(5')-iminium ion, in vivo and in vitro. Eur J Drug Metab Pharmacokinet
1982;7:293-8. DOI PubMed
33. Centers for Disease Control and Prevention - Data and Statistics, F. F. a. F. S., Smoking & Tobacco Use.
https://www.cdc.gov/tobacco/data_statistics/fact_sheets/fast_facts/index.htm.
34. Baker TB, Piper ME, Stein JH, et al. Effects of nicotine patch vs Varenicline vs combination nicotine replacement therapy on smoking
cessation at 26 weeks: A randomized clinical trial. JAMA 2016;315:371-9. DOI PubMed PMC
35. N a t i o n a l I n s t i t u t e o n D r u g A b u s e . T o b a c c o , N . , a n d E C i g a r e t t e s , I s N i c o t i n e A d d i c t i v e ?
https://www.drugabuse.gov/publications/research-reports/tobacco/nicotine-addictive. [Last accessed on 1 Dec 2020].
36. Mcmorrow MJ, Foxx RM. Nicotine's role in smoking: An analysis of nicotine regulation. Psychological Bulletin 1983;93:302-27.
PubMed
37. Sellers EM, Kaplan HL, Tyndale RF. Inhibition of cytochrome P450 2A6 increases nicotine's oral bioavailability and decreases
smoking. Clin Pharmacol Ther 2000;68:35-43. DOI PubMed
38. Sellers EM, Ramamoorthy Y, Zeman MV, Djordjevic MV, Tyndale RF. The effect of methoxsalen on nicotine and 4-
(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism in vivo. Nicotine Tob Res 2003;5:891-9. DOI PubMed
39. Pianezza ML, Sellers EM, Tyndale RF. Nicotine metabolism defect reduces smoking. Nature 1998;393:750. DOI PubMed
40. Rao Y, Hoffmann E, Zia M, et al. Duplications and defects in the CYP2A6 gene: identification, genotyping, and in vivo effects on
smoking. Mol Pharmacol 2000;58:747-55. DOI PubMed
41. Ezzeldin N, El-Lebedy D, Darwish A, et al. Association of genetic polymorphisms CYP2A6*2 rs1801272 and CYP2A6*9 rs28399433
with tobacco-induced lung Cancer: case-control study in an Egyptian population. BMC Cancer 2018;18:525. DOI PubMed PMC
42. Foroozesh M, Jiang Q, Sridhar J, et al. Design, synthesis, and evaluation of a family of propargyl pyridinyl ethers as potential
cytochrome P450 inhibitors. J Undergrad Chem Res 2013;12:91-4. PubMed PMC
43. Shimada T, Takenaka S, Kakimoto K, et al. Structure-function studies of naphthalene, phenanthrene, biphenyl, and their derivatives in
interaction with and oxidation by cytochromes P450 2A13 and 2A6. Chem Res Toxicol 2016;29:1029-40. DOI PubMed PMC
44. Shimada T, Takenaka S, Murayama N, et al. Oxidation of pyrene, 1-hydroxypyrene, 1-nitropyrene and 1-acetylpyrene by human
cytochrome P450 2A13. Xenobiotica 2016;46:211-24. DOI PubMed PMC
45. Kramlinger VM, von Weymarn LB, Murphy SE. Inhibition and inactivation of cytochrome P450 2A6 and cytochrome P450 2A13 by
menthofuran, β-nicotyrine and menthol. Chem Biol Interact 2012;197:87-92. DOI PubMed PMC
46. Prasopthum A, Pouyfung P, Sarapusit S, Srisook E, Rongnoparut P. Inhibition effects of Vernonia cinerea active compounds against
cytochrome P450 2A6 and human monoamine oxidases, possible targets for reduction of tobacco dependence. Drug Metab
Pharmacokinet 2015;30:174-81. DOI PubMed
47. Nakajima M, Itoh M, Yamanaka H, et al. Isoflavones inhibit nicotine C-oxidation catalyzed by human CYP2A6. J Clin Pharmacol
2006;46:337-44. DOI PubMed
48. Gilardi G, Meharenna YT, Tsotsou GE, Sadeghi SJ, Fairhead M, Giannini S. Molecular Lego: design of molecular assemblies of P450
enzymes for nanobiotechnology. Biosensors and Bioelectronics 2002;17:133-45. DOI PubMed
49. Dodhia VR, Fantuzzi A, Gilardi G. Engineering human cytochrome P450 enzymes into catalytically self-sufficient chimeras using
molecular Lego. J Biol Inorg Chem 2006;11:903-16. DOI PubMed
50. Castrignanò S, Ortolani A, Sadeghi SJ, Di Nardo G, Allegra P, Gilardi G. Electrochemical detection of human cytochrome P450 2A6
inhibition: a step toward reducing dependence on smoking. Anal Chem 2014;86:2760-6. DOI PubMed
51. Denton TT, Srivastava P, Xia Z, et al. Identification of the 4-position of 3-alkynyl and 3-heteroaromatic substituted pyridine
methanamines as a key modification site eliciting increased potency and enhanced selectivity for cytochrome P-450 2A6 inhibition. J
Med Chem 2018;61:7065-86. DOI PubMed PMC
52. Denton TT, Zhang X, Cashman JR. Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. Biochem
Pharmacol 2004;67:751-6. DOI PubMed
53. Denton TT, Zhang X, Cashman JR. 5-substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as
selective inhibitors of cytochrome P-450 2A6. J Med Chem 2005;48:224-39. DOI PubMed
54. Yano JK, Denton TT, Cerny MA, Zhang X, Johnson EF, Cashman JR. Synthetic inhibitors of cytochrome P-450 2A6: inhibitory
activity, difference spectra, mechanism of inhibition, and protein cocrystallization. J Med Chem 2006;49:6987-7001. DOI PubMed
55. Liu J, Taylor SF, Dupart PS, et al. Pyranoflavones: a group of small-molecule probes for exploring the active site cavities of