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Volumn 125, Issue 1-2, 2012, Pages 49-59

An LC-MS/MS method for concurrent determination of nicotine metabolites and the role of CYP2A6 in nicotine metabolite-mediated oxidative stress in SVGA astrocytes

Author keywords

Astrocytes; CYP2A6; LC MS MS; Nicotine; Oxidative stress

Indexed keywords

COTININE; CYTOCHROME P450 1A1; CYTOCHROME P450 2A6; KETONE DERIVATIVE; MESSENGER RNA; NICOTINE; NICOTINE DERIVED NITROSAMINE KETONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; SUPEROXIDE DISMUTASE; TRYPTAMINE; UNCLASSIFIED DRUG;

EID: 84864977581     PISSN: 03768716     EISSN: 18790046     Source Type: Journal    
DOI: 10.1016/j.drugalcdep.2012.03.015     Document Type: Article
Times cited : (33)

References (44)
  • 1
    • 0029152207 scopus 로고
    • Enhanced production of human immunodeficiency virus type 1 by in vitro-infected alveolar macrophages from otherwise healthy cigarette smokers
    • Abbud R.A., Finegan C.K., Guay L.A., Rich E.A. Enhanced production of human immunodeficiency virus type 1 by in vitro-infected alveolar macrophages from otherwise healthy cigarette smokers. J. Infect. Dis. 1995, 172:859-863.
    • (1995) J. Infect. Dis. , vol.172 , pp. 859-863
    • Abbud, R.A.1    Finegan, C.K.2    Guay, L.A.3    Rich, E.A.4
  • 2
    • 33645052737 scopus 로고    scopus 로고
    • Human immunodeficiency virus infection and acquired immunodeficiency syndrome dementia complex: role of cells of monocyte-macrophage lineage
    • Aquaro S., Ronga L., Pollicita M., Antinori A., Ranazzi A., Perno C.F. Human immunodeficiency virus infection and acquired immunodeficiency syndrome dementia complex: role of cells of monocyte-macrophage lineage. J. Neurovirol. 2005, 11(Suppl. 3):58-66.
    • (2005) J. Neurovirol. , vol.11 , Issue.SUPPL. 3 , pp. 58-66
    • Aquaro, S.1    Ronga, L.2    Pollicita, M.3    Antinori, A.4    Ranazzi, A.5    Perno, C.F.6
  • 3
    • 65249154248 scopus 로고    scopus 로고
    • Pharmacology of nicotine: addiction, smoking-induced disease, and therapeutics
    • Benowitz N.L. Pharmacology of nicotine: addiction, smoking-induced disease, and therapeutics. Annu. Rev. Pharmacol. Toxicol. 2009, 49:57-71.
    • (2009) Annu. Rev. Pharmacol. Toxicol. , vol.49 , pp. 57-71
    • Benowitz, N.L.1
  • 4
    • 0032189363 scopus 로고    scopus 로고
    • Preferential effects of nicotine and 4-(N-methyl-N-nitrosamine)-1-(3-pyridyl)-1-butanone on mitochondrial glutathione S-transferase A4-4 induction and increased oxidative stress in the rat brain
    • Bhagwat S.V., Vijayasarathy C., Raza H., Mullick J., Avadhani N.G. Preferential effects of nicotine and 4-(N-methyl-N-nitrosamine)-1-(3-pyridyl)-1-butanone on mitochondrial glutathione S-transferase A4-4 induction and increased oxidative stress in the rat brain. Biochem. Pharmacol. 1998, 56:831-839.
    • (1998) Biochem. Pharmacol. , vol.56 , pp. 831-839
    • Bhagwat, S.V.1    Vijayasarathy, C.2    Raza, H.3    Mullick, J.4    Avadhani, N.G.5
  • 5
    • 0030049490 scopus 로고    scopus 로고
    • Iron and oxidative stress as a mechanism for the enhanced production of human immunodeficiency virus by alveolar macrophages from otherwise healthy cigarette smokers
    • Boelaert J.R., Piette J., Weinberg G.A., Sappey C., Weinberg E.D. Iron and oxidative stress as a mechanism for the enhanced production of human immunodeficiency virus by alveolar macrophages from otherwise healthy cigarette smokers. J. Infect. Dis. 1996, 173:1045-1047.
    • (1996) J. Infect. Dis. , vol.173 , pp. 1045-1047
    • Boelaert, J.R.1    Piette, J.2    Weinberg, G.A.3    Sappey, C.4    Weinberg, E.D.5
  • 7
    • 15244354633 scopus 로고    scopus 로고
    • A rapid LC-MS-MS method for the determination of nicotine and cotinine in serum and saliva samples from smokers: validation and comparison with a radioimmunoassay method
    • Byrd G.D., Davis R.A., Ogden M.W. A rapid LC-MS-MS method for the determination of nicotine and cotinine in serum and saliva samples from smokers: validation and comparison with a radioimmunoassay method. J. Chromatogr. Sci. 2005, 43:133-140.
    • (2005) J. Chromatogr. Sci. , vol.43 , pp. 133-140
    • Byrd, G.D.1    Davis, R.A.2    Ogden, M.W.3
  • 8
    • 0037258380 scopus 로고    scopus 로고
    • Liquid chromatographic/tandem mass spectrometric method for the determination of the tobacco-specific nitrosamine metabolite NNAL in smokers' urine
    • Byrd G.D., Ogden M.W. Liquid chromatographic/tandem mass spectrometric method for the determination of the tobacco-specific nitrosamine metabolite NNAL in smokers' urine. J. Mass Spectrom. 2003, 38:98-107.
    • (2003) J. Mass Spectrom. , vol.38 , pp. 98-107
    • Byrd, G.D.1    Ogden, M.W.2
  • 9
    • 33644602478 scopus 로고    scopus 로고
    • Synergistic DNA damage and lipid peroxidation in cultured human white blood cells exposed to 4-(methyl-nitrosamino)-1-(3-pyridyl)-1-butanone and ultraviolet A
    • Chuang C.H., Hu M.L. Synergistic DNA damage and lipid peroxidation in cultured human white blood cells exposed to 4-(methyl-nitrosamino)-1-(3-pyridyl)-1-butanone and ultraviolet A. Environ. Mol. Mutagen. 2006, 47:73-81.
    • (2006) Environ. Mol. Mutagen. , vol.47 , pp. 73-81
    • Chuang, C.H.1    Hu, M.L.2
  • 11
    • 77950370516 scopus 로고    scopus 로고
    • Development and validation of a fast and sensitive bioanalytical method for the quantitative determination of glucocorticoids-quantitative measurement of dexamethasone in rabbit ocular matrices by liquid chromatography tandem mass spectrometry
    • Earla R., Boddu S.H., Cholkar K., Hariharan S., Jwala J., Mitra A.K. Development and validation of a fast and sensitive bioanalytical method for the quantitative determination of glucocorticoids-quantitative measurement of dexamethasone in rabbit ocular matrices by liquid chromatography tandem mass spectrometry. J. Pharm. Biomed. Anal. 2010, 52:525-533.
    • (2010) J. Pharm. Biomed. Anal. , vol.52 , pp. 525-533
    • Earla, R.1    Boddu, S.H.2    Cholkar, K.3    Hariharan, S.4    Jwala, J.5    Mitra, A.K.6
  • 13
    • 67650475221 scopus 로고    scopus 로고
    • Tobacco carcinogen induces microglial activation and subsequent neuronal damage
    • Ghosh D., Mishra M.K., Das S., Kaushik D.K., Basu A. Tobacco carcinogen induces microglial activation and subsequent neuronal damage. J. Neurochem. 2009, 110:1070-1081.
    • (2009) J. Neurochem. , vol.110 , pp. 1070-1081
    • Ghosh, D.1    Mishra, M.K.2    Das, S.3    Kaushik, D.K.4    Basu, A.5
  • 14
    • 0033591845 scopus 로고    scopus 로고
    • Tobacco smoke carcinogens and lung cancer
    • Hecht S.S. Tobacco smoke carcinogens and lung cancer. J. Natl. Cancer Inst. 1999, 91:1194-1210.
    • (1999) J. Natl. Cancer Inst. , vol.91 , pp. 1194-1210
    • Hecht, S.S.1
  • 15
    • 0033749374 scopus 로고    scopus 로고
    • 2'-Hydroxylation of nicotine by cytochrome P450 2A6 and human liver microsomes: formation of a lung carcinogen precursor
    • Hecht S.S., Hochalter J.B., Villalta P.W., Murphy S.E. 2'-Hydroxylation of nicotine by cytochrome P450 2A6 and human liver microsomes: formation of a lung carcinogen precursor. Proc. Natl. Acad. Sci. U.S.A. 2000, 97:12493-12497.
    • (2000) Proc. Natl. Acad. Sci. U.S.A. , vol.97 , pp. 12493-12497
    • Hecht, S.S.1    Hochalter, J.B.2    Villalta, P.W.3    Murphy, S.E.4
  • 17
    • 84859991085 scopus 로고    scopus 로고
    • A LC-MS/MS method for concurrent determination of nicotine metabolites and role of CYP2A6 in nicotine metabolism in U937 macrophages: implications in oxidative stress in HIV + smokers
    • Jin M., Earla R., Shah A., Earla R.L., Gupte R., Mitra A.K., Kumar A., Kumar S. A LC-MS/MS method for concurrent determination of nicotine metabolites and role of CYP2A6 in nicotine metabolism in U937 macrophages: implications in oxidative stress in HIV + smokers. J. Neuroimmune Pharmacol. 2011, 7:289-299.
    • (2011) J. Neuroimmune Pharmacol. , vol.7 , pp. 289-299
    • Jin, M.1    Earla, R.2    Shah, A.3    Earla, R.L.4    Gupte, R.5    Mitra, A.K.6    Kumar, A.7    Kumar, S.8
  • 19
    • 33645109957 scopus 로고    scopus 로고
    • Induction and recovery time course of rat brain CYP2E1 after nicotine treatment
    • Joshi M., Tyndale R.F. Induction and recovery time course of rat brain CYP2E1 after nicotine treatment. Drug Metab. Dispos. 2006, 34:647-652.
    • (2006) Drug Metab. Dispos. , vol.34 , pp. 647-652
    • Joshi, M.1    Tyndale, R.F.2
  • 21
    • 77955718138 scopus 로고    scopus 로고
    • Rat brain CYP2B induction by nicotine is persistent and does not involve nicotinic acetylcholine receptors
    • Khokhar J.Y., Miksys S.L., Tyndale R.F. Rat brain CYP2B induction by nicotine is persistent and does not involve nicotinic acetylcholine receptors. Brain Res. 2010, 1348:1-9.
    • (2010) Brain Res. , vol.1348 , pp. 1-9
    • Khokhar, J.Y.1    Miksys, S.L.2    Tyndale, R.F.3
  • 22
    • 32144443980 scopus 로고    scopus 로고
    • CYP2B6 is expressed in African Green monkey brain and is induced by chronic nicotine treatment
    • Lee A.M., Miksys S., Palmour R., Tyndale R.F. CYP2B6 is expressed in African Green monkey brain and is induced by chronic nicotine treatment. Neuropharmacology 2006, 50:441-450.
    • (2006) Neuropharmacology , vol.50 , pp. 441-450
    • Lee, A.M.1    Miksys, S.2    Palmour, R.3    Tyndale, R.F.4
  • 23
    • 79251478773 scopus 로고    scopus 로고
    • Ethanol induction of CYP2A5: permissive role for CYP2E1
    • Lu Y., Zhuge J., Wu D., Cederbaum A.I. Ethanol induction of CYP2A5: permissive role for CYP2E1. Drug Metab. Dispos. 2011, 39:330-336.
    • (2011) Drug Metab. Dispos. , vol.39 , pp. 330-336
    • Lu, Y.1    Zhuge, J.2    Wu, D.3    Cederbaum, A.I.4
  • 24
    • 78149361342 scopus 로고    scopus 로고
    • Determination of nicotine and nicotine metabolites in urine by hydrophilic interaction chromatography-tandem mass spectrometry: potential use of smokeless tobacco products by ice hockey players
    • Marclay F., Saugy M. Determination of nicotine and nicotine metabolites in urine by hydrophilic interaction chromatography-tandem mass spectrometry: potential use of smokeless tobacco products by ice hockey players. J. Chromatogr. A 2010, 1217:7528-7538.
    • (2010) J. Chromatogr. A , vol.1217 , pp. 7528-7538
    • Marclay, F.1    Saugy, M.2
  • 25
    • 0030885491 scopus 로고    scopus 로고
    • A major role for CYP2A6 in nicotine C-oxidation by human liver microsomes
    • Messina E.S., Tyndale R.F., Sellers E.M. A major role for CYP2A6 in nicotine C-oxidation by human liver microsomes. J. Pharmacol. Exp. Ther. 1997, 282:1608-1614.
    • (1997) J. Pharmacol. Exp. Ther. , vol.282 , pp. 1608-1614
    • Messina, E.S.1    Tyndale, R.F.2    Sellers, E.M.3
  • 26
    • 0034017040 scopus 로고    scopus 로고
    • Regional and cellular induction of nicotine-metabolizing CYP2B1 in rat brain by chronic nicotine treatment
    • Miksys S., Hoffmann E., Tyndale R.F. Regional and cellular induction of nicotine-metabolizing CYP2B1 in rat brain by chronic nicotine treatment. Biochem. Pharmacol. 2000, 59:1501-1511.
    • (2000) Biochem. Pharmacol. , vol.59 , pp. 1501-1511
    • Miksys, S.1    Hoffmann, E.2    Tyndale, R.F.3
  • 27
    • 0038119910 scopus 로고    scopus 로고
    • Smoking, alcoholism and genetic polymorphisms alter CYP2B6 levels in human brain
    • Miksys S., Lerman C., Shields P.G., Mash D.C., Tyndale R.F. Smoking, alcoholism and genetic polymorphisms alter CYP2B6 levels in human brain. Neuropharmacology 2003, 45:122-132.
    • (2003) Neuropharmacology , vol.45 , pp. 122-132
    • Miksys, S.1    Lerman, C.2    Shields, P.G.3    Mash, D.C.4    Tyndale, R.F.5
  • 28
    • 33750296572 scopus 로고    scopus 로고
    • Nicotine induces brain CYP enzymes: relevance to Parkinson's disease
    • Miksys S., Tyndale R.F. Nicotine induces brain CYP enzymes: relevance to Parkinson's disease. J. Neural Transm. Suppl. 2006, 177-180.
    • (2006) J. Neural Transm. Suppl. , pp. 177-180
    • Miksys, S.1    Tyndale, R.F.2
  • 29
    • 77649190286 scopus 로고    scopus 로고
    • A novel validated procedure for the determination of nicotine, eight nicotine metabolites and two minor tobacco alkaloids in human plasma or urine by solid-phase extraction coupled with liquid chromatography-electrospray ionization-tandem mass spectrometry
    • Miller E.I., Norris H.R., Rollins D.E., Tiffany S.T., Wilkins D.G. A novel validated procedure for the determination of nicotine, eight nicotine metabolites and two minor tobacco alkaloids in human plasma or urine by solid-phase extraction coupled with liquid chromatography-electrospray ionization-tandem mass spectrometry. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 2010, 878:725-737.
    • (2010) J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. , vol.878 , pp. 725-737
    • Miller, E.I.1    Norris, H.R.2    Rollins, D.E.3    Tiffany, S.T.4    Wilkins, D.G.5
  • 32
    • 84860466380 scopus 로고    scopus 로고
    • HIV-1 gp120 induces antioxidant response element-mediated expression in primary astrocytes: role in HIV associated neurocognitive disorder
    • (epub ahead of print)
    • Reddy P.V., Gandhi N., Samikkannu T., Saiyed Z., Agudelo M., Yndart A., Khatavkar P., Nair M.P. HIV-1 gp120 induces antioxidant response element-mediated expression in primary astrocytes: role in HIV associated neurocognitive disorder. Neurochem. Int. 2011, (epub ahead of print).
    • (2011) Neurochem. Int.
    • Reddy, P.V.1    Gandhi, N.2    Samikkannu, T.3    Saiyed, Z.4    Agudelo, M.5    Yndart, A.6    Khatavkar, P.7    Nair, M.P.8
  • 33
    • 49549112067 scopus 로고    scopus 로고
    • Potentiation of HIV-1 expression in microglial cells by nicotine: involvement of transforming growth factor-beta 1
    • Rock R.B., Gekker G., Aravalli R.N., Hu S., Sheng W.S., Peterson P.K. Potentiation of HIV-1 expression in microglial cells by nicotine: involvement of transforming growth factor-beta 1. J. Neuroimmune Pharmacol. 2008, 3:143-149.
    • (2008) J. Neuroimmune Pharmacol. , vol.3 , pp. 143-149
    • Rock, R.B.1    Gekker, G.2    Aravalli, R.N.3    Hu, S.4    Sheng, W.S.5    Peterson, P.K.6
  • 34
    • 0036301269 scopus 로고    scopus 로고
    • Cytochrome P450 expression in human hepatocytes and hepatoma cell lines: molecular mechanisms that determine lower expression in cultured cells
    • Rodriguez-Antona C., Donato M.T., Boobis A., Edwards R.J., Watts P.S., Castell J.V., Gomez-Lechon M.J. Cytochrome P450 expression in human hepatocytes and hepatoma cell lines: molecular mechanisms that determine lower expression in cultured cells. Xenobiotica 2002, 32:505-520.
    • (2002) Xenobiotica , vol.32 , pp. 505-520
    • Rodriguez-Antona, C.1    Donato, M.T.2    Boobis, A.3    Edwards, R.J.4    Watts, P.S.5    Castell, J.V.6    Gomez-Lechon, M.J.7
  • 35
    • 0032708337 scopus 로고    scopus 로고
    • Iron metabolism and HIV infection: reciprocal interactions with potentially harmful consequences?
    • Savarino A., Pescarmona G.P., Boelaert J.R. Iron metabolism and HIV infection: reciprocal interactions with potentially harmful consequences?. Cell. Biochem. Funct. 1999, 17:279-287.
    • (1999) Cell. Biochem. Funct. , vol.17 , pp. 279-287
    • Savarino, A.1    Pescarmona, G.P.2    Boelaert, J.R.3
  • 36
    • 0028787779 scopus 로고
    • Activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human lung microsomes by cytochromes P450, lipoxygenase, and hydroperoxides
    • Smith T.J., Stoner G.D., Yang C.S. Activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human lung microsomes by cytochromes P450, lipoxygenase, and hydroperoxides. Cancer Res. 1995, 55:5566-5573.
    • (1995) Cancer Res. , vol.55 , pp. 5566-5573
    • Smith, T.J.1    Stoner, G.D.2    Yang, C.S.3
  • 37
    • 0031827820 scopus 로고    scopus 로고
    • Nicotine-induced modulation of T Cell function. Implications for inflammation and infection
    • Sopori M.L., Kozak W., Savage S.M., Geng Y., Kluger M.J. Nicotine-induced modulation of T Cell function. Implications for inflammation and infection. Adv. Exp. Med. Biol. 1998, 437:279-289.
    • (1998) Adv. Exp. Med. Biol. , vol.437 , pp. 279-289
    • Sopori, M.L.1    Kozak, W.2    Savage, S.M.3    Geng, Y.4    Kluger, M.J.5
  • 38
    • 82755161978 scopus 로고    scopus 로고
    • Reactive astrocytes give neurons less support: implications for Alzheimer's disease
    • e421-423, e413
    • Steele M.L., Robinson S.R. Reactive astrocytes give neurons less support: implications for Alzheimer's disease. Neurobiol. Aging 2012, 33:423. e421-423, e413.
    • (2012) Neurobiol. Aging , vol.33 , pp. 423
    • Steele, M.L.1    Robinson, S.R.2
  • 39
    • 70349333698 scopus 로고    scopus 로고
    • The Nrf2-ARE cytoprotective pathway in astrocytes
    • Vargas M.R., Johnson J.A. The Nrf2-ARE cytoprotective pathway in astrocytes. Expert Rev. Mol. Med. 2009, 11:e17.
    • (2009) Expert Rev. Mol. Med. , vol.11
    • Vargas, M.R.1    Johnson, J.A.2
  • 40
    • 21144437181 scopus 로고    scopus 로고
    • Metabolic activation of the tobacco carcinogen 4-(methylnitrosamino)-(3-pyridyl)-1-butanone by cytochrome P450 2A13 in human fetal nasal microsomes
    • Wong H.L., Zhang X., Zhang Q.Y., Gu J., Ding X., Hecht S.S., Murphy S.E. Metabolic activation of the tobacco carcinogen 4-(methylnitrosamino)-(3-pyridyl)-1-butanone by cytochrome P450 2A13 in human fetal nasal microsomes. Chem. Res. Toxicol. 2005, 18:913-918.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 913-918
    • Wong, H.L.1    Zhang, X.2    Zhang, Q.Y.3    Gu, J.4    Ding, X.5    Hecht, S.S.6    Murphy, S.E.7
  • 41
    • 78650178488 scopus 로고    scopus 로고
    • Human CYP2A6 is regulated by nuclear factor-erythroid 2 related factor 2
    • Yokota S., Higashi E., Fukami T., Yokoi T., Nakajima M. Human CYP2A6 is regulated by nuclear factor-erythroid 2 related factor 2. Biochem. Pharmacol. 2011, 81:289-294.
    • (2011) Biochem. Pharmacol. , vol.81 , pp. 289-294
    • Yokota, S.1    Higashi, E.2    Fukami, T.3    Yokoi, T.4    Nakajima, M.5
  • 42
    • 0035024678 scopus 로고    scopus 로고
    • Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro
    • Zhang W., Kilicarslan T., Tyndale R.F., Sellers E.M. Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro. Drug Metab. Dispos. 2001, 29:897-902.
    • (2001) Drug Metab. Dispos. , vol.29 , pp. 897-902
    • Zhang, W.1    Kilicarslan, T.2    Tyndale, R.F.3    Sellers, E.M.4
  • 43
    • 35548981393 scopus 로고    scopus 로고
    • CYP2A13: variable expression and role in human lung microsomal metabolic activation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone
    • Zhang X., D'Agostino J., Wu H., Zhang Q.Y., von Weymarn L., Murphy S.E., Ding X. CYP2A13: variable expression and role in human lung microsomal metabolic activation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. J. Pharmacol. Exp. Ther. 2007, 323:570-578.
    • (2007) J. Pharmacol. Exp. Ther. , vol.323 , pp. 570-578
    • Zhang, X.1    D'Agostino, J.2    Wu, H.3    Zhang, Q.Y.4    von Weymarn, L.5    Murphy, S.E.6    Ding, X.7
  • 44
    • 76749151814 scopus 로고    scopus 로고
    • Role of CYP2A5 in the clearance of nicotine and cotinine: insights from studies on a Cyp2a5-null mouse model
    • Zhou X., Zhuo X., Xie F., Kluetzman K., Shu Y.Z., Humphreys W.G., Ding X. Role of CYP2A5 in the clearance of nicotine and cotinine: insights from studies on a Cyp2a5-null mouse model. J. Pharmacol. Exp. Ther. 2010, 332:578-587.
    • (2010) J. Pharmacol. Exp. Ther. , vol.332 , pp. 578-587
    • Zhou, X.1    Zhuo, X.2    Xie, F.3    Kluetzman, K.4    Shu, Y.Z.5    Humphreys, W.G.6    Ding, X.7


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