Quantification of thiazolidine-4-carboxylic acid in toxicant-exposed cells by isotope-dilution liquid chromatography-mass spectrometry reveals an intrinsic antagonistic response to oxidative stress-induced toxicity

Chemical Research in Toxicology

Volumn 28, Issue 3, 2015, Pages 394-400

  Liu, Jingjing ^a   Chan, Wan ^a,b  

^a Environmental Science Programs   (Hong Kong)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROFORMIC ACID ETHYL ESTER; FORMALDEHYDE; HYDROXYL RADICAL; TIMONACIC; EDETIC ACID; FE(II)-EDTA; FERROUS ION; HYDROGEN PEROXIDE; HYPOCHLORITE SODIUM; THIAZOLIDINE DERIVATIVE; THIAZOLIDINE-4-CARBOXYLIC ACID;

ABSORPTION; ACCURACY; ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; DERIVATIZATION; DILUTION; ESCHERICHIA COLI; EXPOSURE; GAS CHROMATOGRAPHY; HYDROPHOBICITY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; NONHUMAN; OXIDATIVE STRESS; PROTON TRANSPORT; REACTION TIME; RISK ASSESSMENT; SOLID PHASE EXTRACTION; DRUG EFFECTS; METABOLISM;

ESCHERICHIA COLI;

CHROMATOGRAPHY, LIQUID; EDETIC ACID; ESCHERICHIA COLI; FERROUS COMPOUNDS; HYDROGEN PEROXIDE; MASS SPECTROMETRY; OXIDATIVE STRESS; SODIUM HYPOCHLORITE; THIAZOLIDINES;

EID: 84924859768     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx500342w     Document Type: Article

References (32)

1. Mantovani, A. (2009) Cancer: inflaming metastasis Nature 457, 36-37
2. Dedon, P. C. (2008) The chemical toxicology of 2-deoxyribose oxidation in DNA Chem. Res. Toxicol. 21, 206-219
3. Pang, B., Zhou, X., Yu, H., Dong, M., Taghizadeh, K., Wishnok, J. S., Tannenbaum, S. R., and Dedon, P. C. (2007) Lipid peroxidation dominates the chemistry of DNA adduct formation in a mouse model of inflammation Carcinogenesis 28, 1807-1813
4. Jiang, T., Zhou, X., Taghizadeh, K., Dong, M., and Dedon, P. C. (2007) N-Formylation of lysine in histone proteins as a secondary modification arising from oxidative DNA damage Proc. Natl. Acad. Sci. U.S.A. 104, 60-65
5. OBrien, P. J., Siraki, A. G., and Shangari, N. (2005) Aldehyde sources, metabolism, molecular toxicity mechanisms, and possible effects on human health Crit. Rev. Toxicol. 35, 609-662
6. Chan, W., Luo, H. B., Zheng, Y., Cheng, Y. K., and Cai, Z. (2007) Investigation of the metabolism and reductive activation of carcinogenic aristolochic acids in rats Drug Metab. Dispos. 35, 866-874
7. Berhane, K., Widersten, M., Engstrom, A., Kozarich, J. W., and Mannervik, B. (1994) Detoxication of base propenals and other alpha, beta-unsaturated aldehyde products of radical reactions and lipid peroxidation by human glutathione transferases Proc. Natl. Acad. Sci. U.S.A. 91, 1480-1484
8. De la Fuente, M., Ferrandez, M. D., Del Rio, M., Sol Burgos, M., and Miquel, J. (1998) Enhancement of leukocyte functions in aged mice supplemented with the antioxidant thioproline Mech. Ageing Dev. 104, 213-225
9. Roberts, J. C., Nagasawa, H. T., Zera, R. T., Fricke, R. F., and Goon, D. J. (1987) Prodrugs of l -cysteine as protective agents against acetaminophen-induced hepatotoxicity. 2-(Polyhydroxyalkyl)- and 2-(polyacetoxyalkyl)thiazolidine-4(R)-carboxylic acids J. Med. Chem. 30, 1891-1896
10. Correa, R., Del Rio, M., and De La Fuente, M. (1999) Improvement of murine immune functions in vitro by thioproline Immunopharmacology 44, 281-291
11. Chao, T. F., Leu, H. B., Huang, C. C., Chen, J. W., Chan, W. L., Lin, S. J., and Chen, S. A. (2012) Thiazolidinediones can prevent new onset atrial fibrillation in patients with non-insulin dependent diabetes Int. J. Cardiol. 156, 199-202
12. Kumagai, H., Mukaisho, K., Sugihara, H., Miwa, K., Yamamoto, G., and Hattori, T. (2004) Thioproline inhibits development of esophageal adenocarcinoma induced by gastroduodenal reflux in rats Carcinogenesis 25, 723-729
13. Suo, M., Mukaisho, K., Shimomura, A., Sugihara, H., and Hattori, T. (2006) Thioproline prevents carcinogenesis in the remnant stomach induced by duodenal reflux Cancer Lett. 237, 256-262
14. Shin, H. S., Ahn, H. S., and Lee, B. H. (2007) Determination of thiazolidine-4-carboxylates in urine by chloroformate derivatization and gas chromatography-electron impact mass spectrometry J. Mass Spectrom. 42, 1225-1232
15. Alary, J., Carrera, G., Escrieut, C., and Periquet, A. (1989) Determination of 2-carboxy thiazolidine-4-carboxylic acid in biological fluids by ion-exchange chromatography J. Pharm. Biomed. Anal. 7, 715-723
16. Lankelma, J., Penders, P. G., Leyva, A., and Pinedo, H. M. (1981) Determination of thioproline in plasma using high performance liquid chromatography Cancer Lett. 12, 131-137
17. Alary, J., Carrera, G., De Saint Blanquat, G., Anglade, F., and Escrieut, C. (1989) Reversed-phase ion-pair high-performance liquid chromatographic determination of 2-carboxythiazolidine-4-carboxylic acid in plasma J. Chromatogr. 496, 485-492
18. Leung, E. M. and Chan, W. (2014) A novel reversed-phase HPLC method for the determination of urinary creatinine by pre-column derivatization with ethyl chloroformate: comparative studies with the standard Jaffe and isotope-dilution mass spectrometric assays Anal. Bioanal. Chem. 406, 1807-1812
19. Li, J., Leung, E. M., Choi, M. M., and Chan, W. (2013) Combination of pentafluorophenylhydrazine derivatization and isotope dilution LC-MS/MS techniques for the quantification of apurinic/apyrimidinic sites in cellular DNA Anal. Bioanal. Chem. 405, 4059-4066
20. Ye, Y., Liu, H., Horvatovich, P., and Chan, W. (2013) Liquid chromatography-electrospray ionization tandem mass spectrometric analysis of 2-alkylcyclobutanones in irradiated chicken by precolumn derivatization with hydroxylamine J. Agric. Food Chem. 61, 5758-5763
21. Kubec, R., Svobodova, M., and Velisek, J. (2000) Distribution of S-alk(en)ylcysteine sulfoxides in some allium species. Identification of a new flavor precursor: S-ethylcysteine sulfoxide (Ethiin) J. Agric. Food Chem. 48, 428-33
22. Kanne, D. B., Dick, R. A., Tomizawa, M., and Casida, J. E. (2005) Neonicotinoid nitroguanidine insecticide metabolites: synthesis and nicotinic receptor potency of guanidines, aminoguanidines, and their derivatives Chem. Res. Toxicol. 18, 1479-1484
23. Dabrowska, M. and Starek, M. (2014) Analytical approaches to determination of carnitine in biological materials, foods and dietary supplements Food Chem. 142, 220-232
24. Mudiam, M. K., Chauhan, A., Singh, K. P., Gupta, S. K., Jain, R., Ch, R., and Murthy, R. C. (2013) Determination of t,t-muconic acid in urine samples using a molecular imprinted polymer combined with simultaneous ethyl chloroformate derivatization and pre-concentration by dispersive liquid-liquid microextraction Anal. Bioanal. Chem. 405, 341-349
25. Cunha, S. C., Faria, M. A., and Fernandes, J. O. (2011) Gas chromatography-mass spectrometry assessment of amines in port wine and grape juice after fast chloroformate extraction/derivatization J. Agric. Food Chem. 59, 8742-8753
26. Mudiam, M. K., Ratnasekhar, C., Jain, R., Saxena, P. N., Chauhan, A., and Murthy, R. C. (2012) Rapid and simultaneous determination of twenty amino acids in complex biological and food samples by solid-phase microextraction and gas chromatography-mass spectrometry with the aid of experimental design after ethyl chloroformate derivatization J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 907, 56-64
27. Chan, C. T., Dyavaiah, M., DeMott, M. S., Taghizadeh, K., Dedon, P. C., and Begley, T. J. (2010) A quantitative systems approach reveals dynamic control of tRNA modifications during cellular stress PLoS Genet. 6, e1001247
28. 2+-EDTA J. Am. Chem. Soc. 132, 6145-6153
29. Chen, B., Bohnert, T., Zhou, X., and Dedon, P. C. (2004) 5β-(2-Phosphoryl-1,4-dioxobutane) as a product of 5β-oxidation of deoxyribose in DNA: elimination as trans -1,4-dioxo-2-butene and approaches to analysis Chem. Res. Toxicol. 17, 1406-1413
30. Chao, T., Peng, J. F., Liu, J. F., Jiang, G. B., and Zou, H. (2004) Determination of hydroxyl radicals in advanced oxidation processes with dimethyl sulfoxide trapping and liquid chromatography Anal. Chim. Acta 527, 73-80
31. Chesney, J. A., Eaton, J. W., and Mahoney, J. R., Jr. (1996) Bacterial glutathione: a sacrificial defense against chlorine compounds J. Bacteriol. 178, 2131-2135
32. - system: identification of diimino-imidazole and amino-imidazolone nucleosides Nucleic Acids Res. 30, 2555-2564