Tütüne Özgü Kanserojen Nitrozaminlerin Biyolojik Örneklerde Tayini için Kullanılan Analitik Yöntemlerin İncelenmesi

Yıl 2021, , 77 - 92, 01.05.2021

Sinem Çolak

https://doi.org/10.5281/zenodo.4843549

Öz

Tütüne özgü nitrozaminler (TSNA) nikotinin kimyasal reaksiyonları sonucu oluşmaktadır ve çoğu kanserojendir. Biyolojik örneklerde bu nitrozamin miktarlarının takibi, hastalık ve kanser riski için önemli bilgiler sağlayabilir. Ancak, TSNA’ların biyolojik örneklerdeki konsantrasyonlarının düşük olması ve örneklerde matris etkisinin fazlalığı hassas ektraksiyon ve analiz yöntemleri gerektirmektedir. Bu çalışma, şu anda mevcut olan yöntem ve kullanılan cihazlara genel bir bakış açısı sunmaktadır. Ayrıca, farklı biyolojik matrislerde TSNA ölçen çeşitli çalışmalar için analitik prosedürlerin kapsamlı bir özetini sağlamaktadır. Her yöntemin avantaj ve dezavantajlarının yanı sıra biyolojik örneklerdeki analitik zorluklar da çalışmada vurgulanmış ve bunların giderilmesi için benimsenen yaklaşımlar tartışılmıştır. Geleneksel yöntemlerin yanında yeni geliştirilen nanomalzemeler ve biyosensörler de çalışmada sunulmuştur.

Anahtar Kelimeler

TSNA, Biyolojik örnek, LC-MS

Kaynakça

• [1] Hecht, S.S. and Hoffmann, D. (1988). Tobacco-specific nitrosamines, an important group of carcinogens in tobacco and tobacco smoke. Carcinogenesis, 9: 875-884.
• [2] International Agency for Research on Cancer (IARC) (1978). Some N-nitroso compounds. IARC Monographs on the Evaluation of Risks to Humans, 17: ISBN-109283212177.
• [3] Sugeçti, S. (2021). Pathophysiological effects of Klebsiella pneumoniae infection on Galleria mellonella as an invertebrate model organism. Archives of Microbiology https://doi.org/10.1007/s00203-021-02346-y.
• [4] Xue, J., Yang, S., Seng, S. (2014). Mechanisms of Cancer Induction by Tobacco-Specific NNK and NNN. Cancers, 6:1138-1156.
• [5] Sleiman, M., Maddalena, R.L, et al. H. (2009). Rapid and sensitive gas chromatography–ion-trap tandem mass spectrometry method for the determination of tobacco-specific N-nitrosamines in secondhand smoke. Journal of Chromatography A, 1216(45):7899-7905.
• [6] Lin, R.K., Hsieh, Y.S, Lin, P., et al. (2010). The tobaccospecific carcinogen NNK induces DNA methyltransferase 1 accumulation and tumor suppressor gene hypermethylation in mice and lung cancer patients. Journal of Clinical Investigation,120:521-532.
• [7] Hebels, D.G.A.J, Briede,´J.J., Khampang R, Kleinjans, J.C.S., de Kok, T.M.C.(2010). Radical Mechanisms in Nitrosamine- and Nitrosamide-Induced Whole-Genome Gene Expression Modulations in Caco-2 Cells. Toxıcologıcal Scıences, 116 (1):194–205.
• [8] Cogliano, V. J., Baan, R., Straif, K., et al. (2011). Preventable exposures associated with human cancers. J Natl Cancer I, 103(24): 1827-1839.
• [9] Kwak, S., Choi, Y.S., Na, H.G., et al. (2020). Effect of Tobacco-specific Nitrosamines on MUC5AC Expression in Human Airway Epithelial Cells. Journal of Rhinology, 27(1):34-40.
• [10] Stepanov, I., Carmella, S.G., Briggs, A., et al. (2009a). Presence of the carcinogen N′-nitrosonornicotine in the urine of some users of oral nicotine replacement therapy products. Cancer Research, 69: 8236-8240.
• [11] Wang, L., Yang, C., Zhang, Q., et al. (2013). SPE–HPLC–MS/MS method for the trace analysis of tobacco-specific N-nitrosamines and 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanol in rabbit plasma using tetraazacalix[2]arene[2]triazine-modified silica as a sorbent J. Sep. Sci. 36:2664–2671.
• [12] Zhao, B., Wang, S., Wang, J., et al. (2012). Analysis of N'-nitrosonornicotine and its metabolites in rabbit blood with liquid chromatography/tandem mass spectrometric method, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 899:103–108.
• [13] Lang, H., Wang, S., Zhang, Q., Zhao, B., et al. (2013). Simultaneous determination of NNK and its seven metabolites in rabbit blood by hydrophilic interaction liquid chromatography-tandem mass spectrometry. Anal. Bioanal. Chem., 405:2083–2089.
• [14] Gabr, R.Q, Elsherbiny, M.E., Somayaji, V., Pollak, P.T., Brocks, D.R.A. (2011). liquid chromatography- mass spectrometry method for nicotine and cotinine; utility in screening tobacco exposure in patients taking amiodarone, Biomed. Chromatogr., 25:1124–1131.
• [15] Stepanov, I., Hecht, S.S. (2008). Detection and Quantitation of N′-Nitrosonornicotine in Human Toenails by Liquid Chromatography-Electrospray Ionization-Tandem Mass Spectrometry. Cancer Epidemiology Biomarkers & Prevention. 17(4):945-948.
• [16] Florek, E., Pıekoszewskı, W., Basıor, A., et al. (2011). Effect Of Maternal Tobacco Smokıng Or Exposure To Second-Hand Smoke On The Levels Of 4-(Methylnıtrosamıno)-1-(3-Pyrıdyl)-1-Butanol (NNAL) In Urıne Of Mother And The Fırst Urıne Of Newborn. Journal Of Physıology And Pharmacology, 62(3):377-383.
• [17] Ortuño, R.P., Martínez-Sánchez, J.M., Fu, M., Fernández, E., Pascual, J.A.(2016). Evaluation of tobacco specific nitrosamines exposure by quantification of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human hair of non-smokers. Sci Rep, 26(6):25043.
• [18] Loukotková, L., VonTungeln, L.S., et al. (2018). A simple and highly sensitive UPLC-ESI-MS/MS method for the simultaneous quantification of nicotine, cotinine, and the tobacco-specific carcinogens N’-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)- 1-butanone in serum samples. Journal of Chromatography B, 1072:229–234.
• [19] Biotage, (2013). Application Note AN787: Extraction of Nicotine and Metabolites from Urine, Serum, Plasma and Whole Blood Using ISOLUTE® SLE+ Prior to LC-MS/MS Analysis, (2017) http://www.biotage.com/literature/search?keywords%5B%5D%5B%5D=527.
• [20] Xia, B., Xia, Y., Wong, J., et al. (2014). Quantitative Analysis of Five Tobacoo Specific NNitrosamines in Urine by Liquid Chromatography-Atmospheric Pressure Ionization Tandom Mass Spectrometry. Biomed. Chromatogr., 28:375–384.
• [21] Hu, A.F., Jiang, J., Zhou, G.J., Yang J. et al. (2014). Characteristic fragmentation behavior of tobacco‐specific N‐nitrosamines using electrospray ionization multistage tandem mass spectrometry incorporating deuterium labeling. Rapid Commun Mass Spect., 28(15):1658-64.
• [22] Sepehr, E., Woodling, K.A, Bryant, M.S.(2018). Rapid quantitation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and its metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in rat urine using ultra-fast liquid chromatography mass spectrometry (UFLC/MS/MS). Journal of Lıquıd Chromatography & Related Technologıes, 4(8): 422–429.
• [23] Widstrand, C., BoydJohan, B., Rees, B.A.(2006). Efficient Extraction of Toxic Compounds From Complex Matrices Using Molecularly Imprinted Polymers. American Laboratory, 39(17).
• [24] Hou, H., Zhang, X., Tian, Y., et al. (2012). Development of a method for the determination of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in urine of nonsmokers and smokers using liquid chromatography/tandem mass spectrometry. J Pharm Biomed Anal., 7(63):17-22.
• [25] Kavvadias, D., Scherer, G., Urban, M., et al. (2009). Simultaneous determination of four tobacco-specific N-nitrosamines (TSNA) in human urine. J Chromatogr B Analyt Technol Biomed Life Sci., 877(11-12):1185-92.
• [26] Yao, L., Yang, J., Guan, Y., et al.(2012). Development, validation, and application of a liquid chromatography-tandem mass spectrometry method for the determination of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in human hair. Anal Bioanal Chem, 404:2259–66.
• [27] Li, Y.Y., Wan, M.M., Zhu, J.H., (2014). Cleaning carcinogenic nitrosamine with zeolites. A review, Environ. Chem. Lett. 1:139–152.
• [28] Li, S.H., Sun, X.D., Wang, Y.Z., et al. (2017). Novel mesoporous composite with zeolite-like selectivity to capture tobacco specific nitrosamine NNK Chemical Engineering Journal (IF 10.652) Pub Date:2017-09-17, DOI: 10.1016/j.cej.2017.09.090.
• [29] Sun, X.D., Shi, C.L., Li, S.H., et al. (2018). New shape-selectivity discovered on graphene-based materials in catching tobacco specific nitrosamines. J. Hazard. Mater., 358:234–242.
• [30] Xu, T.G., Shi, R., Lu, N., Zhang, J., et al. (2018). Adsorption of tobacco-specific nitrosamine 4-(methylnitrosamino)-1- (3-pyridyl)-1-butanone from aqueous solution with graphene aerogel. IOP Conf. Ser.: Mater. Sci. Eng., 324, 012028.
• [31] Yong-Qiang P., Xiao-Jing, C., et al. (2019). Magnetic solid-phase extraction of tobacco-specific N-nitrosamines using magnetic graphene composite as sorbent. J Sep Sci 42:3119–25.
• [32] Jiang, H. (2020) Investigation of Carcinogenic Compounds in Tobacco Smoke. International Journal of Pharma Medicine and Biological Sciences, 9:3.
• [33] Shi, C.L., Li, S.H., Sun, X.D. (2018). New activated carbon sorbent with the zeolite-like selectivity to capture tobacco-specific nitrosamines in solution. Chemical Engineering Journal, 339:170-179.
• [34] Xu, T.G, Shi, R. Lu, N., Zhang,J., Bai, R.S., Yang, Z.D., Zhou,J. (2018). Adsorption of tobacco-specific nitrosamine 4-(methylnitrosamino) -1- (3-pyridyl)-1-butanone from aqueous solution with graphene aerogel. IOP Conference Series: Materials Science and Engineering, 324 012028.
• [35] Skarydova, L., Zverinova, M., et al. (2012). Simple Identification of Novel Carbonyl Reducing Enzymes in the Metabolism of the Tobacco Specific Carcinogen NNK Drug Metabolism Letters, 6:3.
• [36] Lee, H.L., Wang, C., Lin, S., Hsieh, D.P. (2007). Liquid Chromatography/Tandem Mass Spectrometric Method for the Simultaneous Determination of Tobacco-Specific Nitrosamine NNK and its Five Metabolites. Talanta, 73(1): 76–80.
• [37] Martínez-Sáncheza, J.M., Ballbè, M., Ortu˜no, R.P., et al. (2019). Secondhand exposure to aerosol from electronic cigarettes:pilot study of assessment of tobacco-specific nitrosamine (NNAL) in urine. Gac Sanit., 33(6):575–578.
• [38] Dobrinas, M., Choong, E., Noetzli, M., Cornuz, J. et al.(2011). Quantification of nicotine, cotinine, trans-3′-hydroxycotinine and varenicline in human plasma by a sensitive and specific UPLC–tandem mass-spectrometry procedure for a clinical study on smoking cessation, J. Chromatogry B, 879:3574–3582.
• [39] Baumann, F., Regenthal, R., Burgos-Guerrero L.L., et al. (2010). Determination of nicotine and cotinine in human serum by means of LC/MS, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 878:107–111.
• [40] Li, P., Beck, W.D., et al. (2012). Quantitation of cotinine and its metabolites in rat plasma and brain tissue by hydrophilic interactionchromatography tandem mass spectrometry (HILIC-MS/MS), J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 907:117–125.
• [41] Hendrickx, S., et al. (2015). Recent advances in the application of hydrophilic interaction chromatography for the analysis of biological matrices, Bioanalysis, 7:2927–2945.
• [42] Isokawa, M., Kanamori, T., Funatsu, T., Tsunoda, M. (2014). Recent advances in hydrophilic interaction chromatography for quantitative analysis of endogenous and pharmaceutical compounds in plasma samples. Bioanalysis, 6:2421–2439.
• [43] Gilar, M., Olivova, P., Daly, A.E., Gebler, J.C. (2005). Orthogonality of separation in two-dimensional liquid chromatography. Anal Chem., 77:6426–34.
• [44] Zhou, Y., Zhang, H., Wang, X., et al. (2019). Development of a heart-cutting supercritical fluid chromatography-high-performance liquid chromatography coupled to tandem mass spectrometry for the determination of four tobacco-specific nitrosamines in mainstream smoke. Analytical and Bioanalytical Chemistry, 411:2961–2969.
• [45] Lisko, J.G., Stanfill, S.B., et al. (2013). Application of GC-MS/MS for the analysis of tobacco alkaloids in cigarette filler and various tobacco species. Analytical Chemistry, 85:3380–3384.
• [46] Xu, N., Goodrich, L.E., Lehnert, N., et al. (2010). Five- and Six- Coordinate Adducts of Nitrosamines with Ferric Porphyrins: Structural Models for the Type II Interactions of Nitrosamines with Ferric Cytochrome P450. Inorganic Chemistry, 49(10):4405-4419.
• [47] Su, X., Bromberg, L., Tan, K.J., Jamison, T.F., et al. (2017). Electrochemically Mediated Reduction of Nitrosamines by Hemin-Functionalized Redox Electrodes. Environmental Science and Technology Letters, 4: 161-167.
• [48] Su, X., Bromberg, L., Tan, K.J., Jamison, T.F., et al. (2017). Electrochemically Mediated Reduction of Nitrosamines by Hemin-Functionalized Redox Electrodes. Supporting Information
• [49] Zhao, H., He, H., Shi, L., Cai, X., et al. (2018). Electrochemical detection of 4- (methylnitrosamino)-1-(3-pyridyl)-1-butanone using a cytochrome P450 2E1 decorated biosensor. Journal of Electroanalytical Chemistry, 816: 62-67.