Benzotriazoles and benzothiazoles in human urine from several countries: A perspective on occurrence, biotransformation, and human exposure

Environment International

Volumn 59, Issue , 2013, Pages 274-281

  Asimakopoulos, Alexandros G ^a,b   Wang, Lei ^a   Thomaidis, Nikolaos S ^b   Kannan, Kurunthachalam ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

Benzothiazole; Benzotriazole; Biomonitoring; Hydroxy benzotriazole; Metabolism; Urine

Indexed keywords

BENZOTHIAZOLES; BENZOTRIAZOLES; BIOMONITORING; HYDROXY-BENZOTRIAZOLE; URINE;

AGRICULTURAL CHEMICALS; AZO DYES; DRY CLEANING; ISOMERS; METABOLISM; PHOTOSENSITIZERS; SOAPS (DETERGENTS);

BODY FLUIDS;

1 HYDROXYBENZOTRIAZOLE; 2 AMINOBENZOTHIAZOLE; 2 HYDROXYBENZOTHIAZOLE; 2 METHYLTHIOBENZOTHIAZOLE; 2 MORPHOLIN 4 YL BENZOTHIAZOLE; 2 THIOCYANOMETHYLTHIOBENZOTHIAZOLE; 4 HYDROXYBENZOTRIAZOLE; 4 METHOXYBENZOTRIAZOLE; 5 CHLOROBENZOTRIAZOLE; 5 HYDROXYBENZOTRIAZOLE; 5 METHOXYBENZOTRIAZOLE; BENZOTHIAZOLE; BENZOTHIAZOLE DERIVATIVE; BENZOTRIAZOLE; BENZOTRIAZOLE DERIVATIVE; CREATININE; EPSILON 5 BENZOTHIAZOLE; EPSILON 6 BENZOTHIAZOLE; TOLYLTRIAZOLE; UNCLASSIFIED DRUG; XYLYLTRIAZOLE;

BIOMONITORING; BIOTRANSFORMATION; CHEMICAL POLLUTANT; CONCENTRATION (COMPOSITION); METABOLISM; POLLUTION EXPOSURE; URINE;

ADOLESCENT; ADULT; AGED; ARTICLE; BIOTRANSFORMATION; CHEMICAL STRUCTURE; CHILD; CHINA; CREATININE BLOOD LEVEL; ENVIRONMENTAL EXPOSURE; FEMALE; GREECE; HUMAN; INDIA; JAPAN; KOREA; LIMIT OF DETECTION; MALE; PRESCHOOL CHILD; PRIORITY JOURNAL; RELATIVE DENSITY; SCHOOL CHILD; STRUCTURE ANALYSIS; UNITED STATES; URINALYSIS; URINE; VIET NAM;

1-HYDROXY-BENZOTRIAZOLE; 1-OH-BTR; 1H-BENZOTRIAZOLE; 1H-BTR; 2-AMINO-BENZOTHIAZOLE; 2-AMINO-BTH; 2-HYDROXY-BENZOTHIAZOLE; 2-M-BTH; 2-ME-S-BTH; 2-METHYLTHIO-BENZOTHIAZOLE; 2-MORPHOLIN-4-YL-BENZOTHIAZOLE; 2-OH-BTH; 2-SCNMES-BTH; 2-THIOCYANOMETHYLTHIO-BENZOTHIAZOLE; 4-HYDROXY-BENZOTRIAZOLE; 4-ME-1H-BTR; 4-METHYL-1H-BENZOTRIAZOLE; 4-OH-BTR; 5-CHLORO-1H-BENZOTRIAZOLE; 5-CL-1H-BTR; 5-HYDROXY-BENZOTRIAZOLE; 5-ME-1H-BTR; 5-METHYL-1H-BENZOTRIAZOLE; 5-OH-BTR; BENZOTHIAZOLE; BENZOTRIAZOLE; BIOMONITORING; BTH; HYDROXY-BENZOTRIAZOLE; LIMIT OF DETECTION; LLOQ; LOD; LOWER LIMIT OF QUANTIFICATION; METABOLISM; OR 5,6-DIME-1H-BTR, XYLYLTRIAZOLE; RELATIVE STANDARD DEVIATION; RSD; TOLYLTRIAZOLE; TTR; URINE; XTR;

ADOLESCENT; ADULT; AGED; AGED, 80 AND OVER; BENZOTHIAZOLES; BIOTRANSFORMATION; CHILD; CHILD, PRESCHOOL; CHINA; ENVIRONMENTAL EXPOSURE; FEMALE; GREECE; HUMANS; INDIA; JAPAN; MALE; MIDDLE AGED; REPUBLIC OF KOREA; TRIAZOLES; UNITED STATES; VIETNAM; YOUNG ADULT;

CHINA; GREECE; INDIA; JAPAN; KOREA; UNITED STATES; VIET NAM;

EID: 84880281648     PISSN: 01604120     EISSN: 18736750     Source Type: Journal    
DOI: 10.1016/j.envint.2013.06.007     Document Type: Article

References (63)

1. Anders E., Katritzky A.R., Malhotra N., Stevens J. A MO theoretical study on the rearrangement of 1-hydroxy- and 1- (acyloxy)-1,2,3-triazoles and their benzotriazole analogues: comparison of ab initio and semiempirical calculations. J Org Chem 1992, 57:3698-3705.
2. Asimakopoulos A.G., Bletsou A.A., Wu Q., Thomaidis N.S., Kannan K. Determination of benzotriazoles and benzothiazoles in human urine by liquid chromatography-tandem mass spectrometry. Anal Chem 2013, 85:441-448.
3. Asimakopoulos A.G., Ajibola A., Kannan K., Thomaidis N.S. LC-MS/MS determination of 1,2,3-benzotriazoles and 1,3-benzothiazoles in wastewater and sewage sludge. Sci Total Environ 2013, 452:163-171.
4. Carpinteiro I., Abuin B., Ramil M., Rodríguez I., Cela R. Simultaneous determination of benzotriazole and benzothiazole derivatives in aqueous matrices by mixed-mode solid-phase extraction followed by liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem 2012, 402:2471-2478.
5. Colucci D.F., Buyske D.A. The biotransformation of a sulfonamide mercaptan and to mercapturic acid and glucuronide conjugates. Biochem Pharmacol 1965, 14:457-466.
6. CPSC (U.S.Consumer Product Safety Commission) Sensory and pulmonary irritation studies of carpet system materials and their constituent chemicals [cited November 26, 2012]. http://www.cpsc.gov/LIBRARY/FOIA/FOIA98/os/3519926D.pdf.
7. De Wever H., Verachtert H. Biodegradation and toxicity of benzothiazoles. Water Res 1997, 31:2673-2684.
8. Domínguez C., Reyes-Contreras C., Bayona J.M. Determination of benzothiazoles and benzotriazoles by using ionic liquid stationary phases in gas chromatography mass spectrometry. Application to their characterization in wastewaters. J Chromatogr A 2012, 1230:117-122.
9. El Dareer S.M., Kalin J.R., Tillery K.F., Hill D.L., Barnett J.W. Disposition of 2-mercaptobenzothiazole and 2-mercaptobenzothiazole disulfide in rats dosed intravenously, orally, and topically and in Guinea pigs dosed topically. J Environ Sci Health 1989, 27:65-84.
10. Farré M., Pérez S., Kantiani L., Barceló D. Fate and toxicity of emerging pollutants, their metabolites and transformation products in the aquatic environment. Trends Anal Chem 2008, 27:991-1007.
11. Ferrario J.B., DeLeon I.R., Tracy R.E. Evidence for toxic anthropogenic chemicals in human thrombogenic coronary plaques. Arch Environ Contam Toxicol 1985, 14:529-534.
12. Fukuoka M., Tanaka A. The metabolic origin of the sulfur atom in the sulfhydryl group of 2-thiobenzothiazole metabolites derived from benzothiazyl sulfonamide in the rat. Arch Toxicol 1987, 61:158-160.
13. Fukuoka M., Satoh M., Tanaka A. Metabolism of 2-thiobenzothiazoles in the rat. Urinary, fecal and biliary metabolites of 2-benzothiazyl sulfenamides. Arch Toxicol 1995, 70:1-9.
14. Ginsberg G., Toal B., Kurland T. Benzothiazole toxicity assessment in support of synthetic turf field human health risk assessment. J Toxicol Environ Health A 2011, 74:1175-1183.
15. Gottschall D.W., Theodorides V.J., Wang R. The metabolism of benzimidazole anthelmintics. Parasitol Today 1990, 6:115-124.
16. Guidance for Industry Bioanalytical method validation; U.S. Department of Health and Human Services Food and Drug Administration; Center for Drug Evaluation and Research (CDER) Center for Veterinary Medicine (CVM) http://www.fda.gov/cder/guidance/index.htm.
17. Hart D.S., Davis L.C., Erickson L.E., Callender T.M. Sorption and partitioning parameters of benzotriazole compounds. Microchem J 2004, 77:9-17.
18. Hassan N., Verdes P.V., Ruso J.M. Assessment of interactions between four proteins and benzothiazole derivatives by DSC and CD. J Chem Thermodynamics 2011, 43:399-404.
19. Health Council of The Netherlands: Dutch Expert Committee on Occupational Standards (DECOS) 1,2,3-Benzotriazole 2000, Health Council of The Netherlands, The Hague, [publication no. 2000/14OSH].
20. Heavner D.L., Morgan W.T., Sears S.B., Richardson J.D., Byrd G.D., Ogden M.W. Effect of creatinine and specific gravity normalization techniques on xenobiotic biomarkers in smokers' spot and 24-h urines. J Pharmaceut Biomed Anal 2006, 40:928-942. [http://www.winning-homebrew.com/refractometer.html, cited January 15, 2013].
21. Janna H., Scrimshaw M.D., Williams R.J., Churchley J., Sumpter J.P. From dishwasher to tap? Xenobiotic substances benzotriazole and tolyltriazole in the environment. Environ Sci Technol 2011, 45:3858-3864.
22. Jover E., Matamoros V., Bayona J.M. Characterization of benzothiazoles, benzotriazoles and benzosulfonamides in aqueous matrixes by solid-phase extraction followed by comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry. J Chromatogr A 2009, 1216:4013-4019.
23. Kannan K., Tao L., Sinclair E., Pastva S.D., Jude D.J., Giesy J.P. Perfluorinated compounds in aquatic organisms at various trophic levels in a Great Lakes food chain. Arch Environ Contam Toxicol 2005, 48:559-566.
24. Katritzky A.R., Yannakopoulou K., Anders E., Stevens J., Szafran M. Ab initio and semiempirical calculations on the tautomeric equilibria of N-unsubstituted and N-substituted benzotriazoles. J Org Chem 1990, 55:5683.
25. Khan K.M., Rahim F., Halim S.A., Taha M., Khan M., Perveen S., et al. Synthesis of novel inhibitors of β-glucuronidase based on benzothiazole skeleton and study of their binding affinity by molecular docking. Bioorg Med Chem 2011, 19:4286-4294.
26. Kinae N., Kawashima H., Kawane R., Saitou M., Saitou S., Tomita I. Detection and isolation of mutagenic substances from sea water. J Pharm Dyn 1981, 4:5-63.
27. Leonard C.J. Toxicity of tolyltriazole to Bacillus microorganisms. M.Sc. Thesis submitted to the Faculty of the Graduate School of Engineering and Management of the Air Force Institute of Technology Air Education and Training Command 2000, Air Force Institute of Technology (AFIT), Ohio, USA.
28. Liu Y.-S., Ying G.-G., Shareef A., Kookana R.S. Simultaneous determination of benzotriazoles and ultraviolet filters in ground water, effluent and biosolid samples using gas chromatography-tandem mass spectrometry. J Chromatogr A 2011, 1218:5328-5335.
29. Liu Y.-S., Ying G.-G., Shareef A., Kookana R.S. Biodegradation of three selected benzotriazoles under aerobic and anaerobic conditions. Water Res 2011, 45:5005-5014.
30. Liu Y.-S., Ying G.-G., Shareef A., Kookana R.S. Occurrence and removal of benzotriazoles and ultraviolet filters in a municipal wastewater treatment plant. Environ Pollut 2012, 165:225-232.
31. Llompart M., Sanchez-Prado L., Lamas J.P., Garcia-Jares C., Roca E., Dagnac T. Hazardous organic chemicals in rubber recycled tire playgrounds and pavers. Chemosphere 2013, 90:423-431.
32. Loos R., Gawlik B.M., Locoro G., Rimaviciute E., Contini S., Bidoglio G. EU-wide survey of polar organic persistent pollutants in European river waters. Environ Pollut 2009, 157:561-568.
33. Loos R., Locoro G., Comero S., Contini S., Schwesig D., Werres F., et al. Pan-European survey on the occurrence of selected polar organic persistent pollutants in ground water. Water Res 2010, 44:4115-4126.
34. 2 analysis. Water Res 2010, 44:2325-2335.
35. Manninen A., Auriola S., Vartiainen M., Liesivuori J., Turunen T., Pasanen M. Determination of urinary 2-mercaptobenzothiazole (2-MBT), the main metabolite of 2-(thiocyanomethylthio)benzothiazole (TCMTB) in humans and rats. Arch Toxicol 1996, 70:579-584.
36. Matamoros V., Jover E., Bayona J.M. Occurrence and fate of benzothiazoles and benzotriazoles in constructed wetlands. Water Sci Technol 2010, 61:191-198.
37. Mawhinney D.B., Vanderford B.J., Snyder S.A. Transformation of 1H-benzotriazole by ozone in aqueous solution. Environ Sci Technol 2012, 46:7102-7111.
38. Ni H.-G., Lu F.-H., Luo X.-L., Tian H.Y., Zeng E.Y. Occurrence, phase distribution, and mass loadings of benzothiazoles in riverine runoff of the Pearl River delta, China. Environ Sci Technol 2008, 42:1892-1897.
39. Novak I., Abu-Izneid T., Kovač B., Klasinc L. Electronic structure and stability of benzotriazoles. J Phys Chem A 2009, 113:9751-9756.
40. Pena T., Vecino-Bello X., Casais C., Mejuto C., Cela R. Optimization of a dispersive liquid-liquid microextraction method for the analysis of benzotriazoles and benzothiazoles in water samples. Anal Bioanal Chem 2012, 402:1679-1695.
41. Perucca J., Bouby N., Valeix P., Bankri L. Sex difference in urine concentration across differing age, sodium intake, and level of kidney disease. Am J Physiol Regul Integr Comp Physiol 2007, 292:R700-R705.
42. Pervova M.G., Kirichenko V.E., Saloutin V.I. Determination of 1,2,3-benzotriazole in aqueous solutions and air by reaction-gas-liquid chromatography. J Anal Chem 2010, 65:276-279.
43. Reddy C.M., Quinn J.G. Environmental chemistry of benzothiazoles derived from rubber. Environ Sci Technol 1997, 31:2847-2853.
44. Reemtsma T. Determination of 2-substituted benzothiazoles of industrial use from water by liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 2000, 14:1612-1618.
45. Reemtsma T., Miehe U., Duennbier U., Jekel M. Polar pollutants in municipal wastewater and the water cycle: occur
46. Reemtsma T., Miehe U., Duennbier U., Jekel M. Polar pollutants in municipal wastewater and the water cycle: occurrence and removal of benzotriazoles. Water Res 2010, 44:596-604.
47. Remer T., Meubert A., Maser-Gluth C. Anthropometry based reference values for 24-h urinary creatinine excretion during growth and their use in endocrine and nutritional research. Am J Clin Nutr 2002, 75:561-569.
48. Richardson S.D. Environmental mass spectrometry: emerging contaminants and current issues. Anal Chem 2012, 84:747-778.
49. Schmeltz I., Hoffmann D. Nitrogen-containing compounds in tobacco and tobacco smoke. Chem Rev 1977, 77:295-311.
50. Seo K.W., Park M., Kim J.G., Kim T.W., Kim H.J. Effects of benzothiazole on the xenobiotic metabolizing enzymes and metabolism of acetaminophen. J Appl Toxicol 2000, 20:427-430.
51. Sorahan T. Bladder cancer risks in workers manufacturing chemicals for the rubber industry. Occup Med 2008, 58:496-501.
52. Sorahan T. Cancer risks in chemical production workers exposed to 2-mercaptobenzothiazole. Occup Environ Med 2009, 66:269-273.
53. Tangtian H., Bo L., Wenhua L., Shin P.K.S., Wu R.S.S. Estrogenic potential of benzotriazole on marine medaka (Oryzias melastigma). Ecotoxicol Environ Safe 2012, 80:327-332.
54. Technical Resources International Inc Summary of data for chemical selection: benzothiazole [cited November 26, 2012]. http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/Benzothiazole.pdf.
55. Thomaidis N.S., Asimakopoulos A.G., Bletsou A.A. Emerging contaminants: a tutorial mini-review. Global Nest J 2012, 14:72-79.
56. Van Leerdam J.A., Hogenboom A.C., Van der Kooi M.M.E., De Voogt P. Determination of polar 1H-benzotriazoles and benzothiazoles in water by solid-phase extraction and liquid chromatography LTQ FT orbitrap mass spectrometry. Int J Mass Spectrom 2009, 282:99-107.
57. Vetter W., Lorenz J. Determination of benzotriazoles in dishwasher tabs from Germany and estimation of the discharge into German waters. Environ Sci Pollut Res 2013, 20:4435-4450.
58. Wang X.S., Suskind R.R. Comparative studies of the sensitization potential of morpholine, 2-mercaptobenzothiazole and two of their derivatives in guinea pigs. Contact Dermatitis 1988, 19:11-15.
59. Wang L., Asimakopoulos A.G., Moon H.-B., Nakata H., Kannan K. Benzotriazole, benzothiazole, and benzophenone compounds in indoor dust from the United States and East Asian countries. Environ Sci Technol 2013, 47:4752-4759.
60. Weiss S., Reemtsma T. Determination of benzotriazole corrosion inhibitors from aqueous environmental samples by liquid chromatography-electrospray ionization-tandem mass spectrometry. Anal Chem 2005, 77:7415-7420.
61. Wilson K., Chissick H., Fowler A.M., Frearson F.J., Gittins M., Swinbourne F.J. Metabolism of benzothiazole I. Identification of ring-cleavage products. Xenobiotica 1991, 21:1179-1183.
62. Wolschke H., Xie Z., Möller A., Sturm R., Ebinghaus R. Occurrence, distribution and fluxes of benzotriazoles along the German large river basins into the North Sea. Water Res 2011, 45:6259-6266.
63. Yadav P.S., Devprakash, Senthilkumar G.P. Benzothiazole: different methods of synthesis and diverse biological activities. Int J Pharm Sci & Drug Res 2011, 3:1-7.