Biotransformation of acrylates. Excretion of mercapturic acids and changes in urinary carboxylic acid profile in rat dosed with ethyl and 1-butyl acrylate

References

• Bladeren P. J., van Buys W., Breimer D. D., van DER Gen A. The synthesis of mercapturic acids and their esters. European Journal Medicinal Chemistry 1980; 15: 495–497
   Web of Science ®Google Scholar
• Chassaud L. F. The role of glutathione and glutathione S-transferases in the metabolism of chemical carcinogens and other electrophilic agents. Advances in Cancer Research, Y. Klein, S. Weinhouse. Academic, New York 1979; Vol. 29: 175–255
   Google Scholar
• DeBethizy J. D., Udinsky J. R., Scribner H. E., Frederick C. B. The disposition and metabolism of acrylic acid and ethyl acrylate in male Sprague-Dawley rats. Fundamental and Applied Toxicology 1987; 8: 549–561
   PubMedGoogle Scholar
• Delbressine L. P. C., Seutter-Berlage F., Seutter E. Identification of urinary mercapturic acids formed from acrylate, methacrylate and crotonate. Xenobiotica 1981; 11: 241–247
   PubMed Web of Science ®Google Scholar
• Frederick C. B., Potter D. W., Chang-Mateu M. I., Andersen M. E. A physiologically based pharmacokinetic and pharmacodynamic model to describe the oral dosing of rats with ethyl acrylate and its implications for risk assessment. Toxicology and Applied Pharmacology 1992; 114: 246–260
   PubMed Web of Science ®Google Scholar
• Ghanayem B. I., Burka L. T., Matthews H. B. Ethyl acrylate distribution, macromolecule binding, excretion and metabolism in male Fisher 344 rats. Fundamental and Applied Toxicology 1987; 9: 389–397
   PubMedGoogle Scholar
• Hashimoto K., Aldridge W. N. Biochemical studies on acrylamide, a neurotoxic agent. Biochemical Pharmacology 1970; 19: 2591–2604
   PubMed Web of Science ®Google Scholar
• Kiliani H. New from sugar chemistry. Chemische Berichte 1921; 54: 456–472, in German
   Google Scholar
• Klieger E., Schroeder E., Gibian H. Synthesisof peptides II. Preparation and application of dicyclohexylammonium salts of acylated amino acids and peptides. Annalen der Chemie 1961; 640: 157–167, in German
   Google Scholar
• Kopecky J., Linhart I., Stiborova A., Smejkal J. Biotransformation of acrylic acid esters in rat. I. Formation of mercapturic acids and their determination in urine. Pracovni Lékarstvi 1985; 37: 126–129, in Czech
   Google Scholar
• Kutzman R. S., Meyer G. J., Wolf A. P. The biodistribution and metabolic fate of [11C]acrylic acid in the rat after acute inhalation exposure or stomach intubation. Journal of Toxicology and Environmental Health 1982; 10: 969–979
   PubMed Web of Science ®Google Scholar
• Lixhart I., Hrabal R., Šmejkal J., Mitera J. Metabolic pathways of 1-butyl [3-13C]acrylate. Identification of urinary metabolites in rat using nuclear magnetic resonance and mass spectrometry. Chemical Research in Toxicology 1994; 7: 1–8
   PubMed Web of Science ®Google Scholar
• McCarthy T. J., Witz G. Structure-activity relationships of acrylate esters: reactivity towards glutathione and hydrolysis by carboxylesterase in vitro. Advances in Experimental Medicine and Biology 1991; 283: 333–335
   PubMedGoogle Scholar
• Miller R. R., Ayres J. A., Rampy L. W., McKenna M. J. Metabolism of acrylate esters in rat tissue homogenates. Fundamental and Applied Toxicology 1981; 1: 410–414
   PubMedGoogle Scholar
• Miwa H., Yamamoto M. High-performance liquid chromatographic analysis of serum short-chain fatty acids by direct derivatization. Journal of Chromatography, Biomedical Applications 1987; 421: 33–41
   PubMed Web of Science ®Google Scholar
• Miwa H., Yamamoto M., Asano T. High-performance liquid chromatographic analysis of hydroxymonocarboxylic acids and dicarboxylic acids in urine as their 2-nitrophenylhydrazides. Analytical Biochemistry 1990; 185: 17–23
   PubMed Web of Science ®Google Scholar
• Miwa H., Yamamoto M., Nishida T., Nunoi K., Kikuchi M. High-performance liquid chromatographic analysis of serum long-chain fatty acids by direct derivatization method. Journal of Chromatography, Biomedical Applications 1987; 416: 237–245
   PubMed Web of Science ®Google Scholar
• Norpoth K., Müller G. The determination of mercapturic acids in urine in workers exposed to xenobiotics. Zeitschrift für Gestammte Hygiene und ihre Grenzgebiete 1989; 35: 487–490
   PubMedGoogle Scholar
• Read R. R. β-Hydroxypropionic acid (hydracrylic acid). Organic Syntheses, Collective Volume 1941; 1: 321
   Google Scholar
• Sanders J. M., Burka L. T., Matthews H. B. Metabolism and disposition of n-butyl acrylate in male Fischer rats. Drug Metabolism and Disposition 1988; 16: 429–434
   PubMed Web of Science ®Google Scholar
• Stott W. T., McKenna M. J. Acrylate esters; hydrolysis of several glycol ether acetates and acrylate esters by nasal mucosal carboxylesterase in vitro. Fundamental and Applied Toxicology 1985; 5: 399–404
   PubMedGoogle Scholar
• Vagelos P. R., Earl J. M. Propionic acid metabolism II. Enzymatic synthesis of lactyl pantetheine. Journal of Biological Chemistry 1959; 234: 765–769
   PubMed Web of Science ®Google Scholar
• Winter S. M., Weber G. L., Gooley P. R., Mackenzie N. E., Sipes I. G. Identification and comparison of the urinary metabolites of [1,2,3-13C3] acrylic acid and [1,3,3-13C3]propionic acid in the rat by homonuclear 13C nuclear magnetic resonance spectroscopy. Drug Metabolism and Disposition 1992; 20: 655–672
   Web of Science ®Google Scholar
• Yancey M., Holland M. L., Stuart R., Wiesler D., Novotny M. Urinary profiles of organic acids and volatile metabolites during the starvation process in rats. Journal of Chromatography, Biomedical Applications 1986; 382: 3–18
   PubMed Web of Science ®Google Scholar