Comparative study of the hydrolytic metabolism of methyl-, ethyl-, propyl-, butyl-, heptyl- and dodecylparaben by microsomes of various rat and human tissues

References

• Abbas S, Greige-Gerges H, Karam N. (2010). Metabolism of parabens (4-hydroxybenzoic acid esters) by hepatic esterases and UDP-glucuronosyltransferases in man. Drug Metab Pharmacokinet 25:568–77
   PubMed Web of Science ®Google Scholar
• Aubert N, Ameller T, Legrand JJ. (2012). Systemic exposure to parabens: pharmacokinetics, tissue distribution, excretion balance and plasma metabolites of [14C]-methyl-, propyl- and butylparaben in rats after oral, topical or subcutaneous administration. Food Chem Toxicol 50:445–54
   PubMed Web of Science ®Google Scholar
• Bencharit S, Edwards CC, Morton CL, et al. (2006). Multisite promiscuity in the processing of endogenous substrates by human carboxylesterase 1. J Mol Biol 363:201–14
   PubMed Web of Science ®Google Scholar
• Cygler M, Schrag JD, Sussman JL, et al. (1993). Relationship between sequence conservation and three-dimensional structure in a large family of esterases, lipases, and related protein. Protein Sci 2:366–82
   PubMed Web of Science ®Google Scholar
• Darbre PD, Aljarrah A, Miller WR, et al. (2004). Concentrations of parabens in human breast tumours. J Appl Toxicol 24:5–13
   PubMed Web of Science ®Google Scholar
• Darbre PD, Byford JR, Shaw LE, et al. (2002). Oestrogenic activity of isobutylparaben in vitro and in vivo. J Appl Toxicol 22:219–26
   PubMed Web of Science ®Google Scholar
• Darbre PD, Byford JR, Shaw LE, et al. (2003). Oestrogenic activity of benzylparaben. J Appl Toxicol 23:43–51
   PubMed Web of Science ®Google Scholar
• Darbre P, Harvey PW. (2008). Paraben esters: review of recent studies of endocrine toxicity, absorption, esterase and human exposure, and discussion of potential human health risks. J Appl Toxicol 28:561–78
   PubMed Web of Science ®Google Scholar
• Francis SO, Mahlberg MJ, Johnson KR, et al. (2006). Melanoma chemoprevention. J Am Acad Dermatol 55:849–61
   PubMed Web of Science ®Google Scholar
• Frederiksen H, Taxvig C, Hass U, et al. (2008). Higher levels of ethyl paraben and butyl paraben in rat amniotic fluid than in maternal plasma after subcutaneous administration. Toxicol Sci 106:376–83
   PubMed Web of Science ®Google Scholar
• Golden R, Gandy J, Vollmer G. (2005). A review of the endocrine activity of parabens and implications for potential risks to human health. Crit Rev Toxicol 35:435–58
   PubMed Web of Science ®Google Scholar
• Handa O, Kokura S, Adachi S, et al. (2006). Methylparaben potentiates UV-induced damage of skin keratinocytes. Toxicology 227:62–72
   PubMed Web of Science ®Google Scholar
• Harvey PW, Darbre P. (2004). Endocrine disrupters and human health: could oestrogenic chemicals in body care cosmetics adversely affected breast cancer incidence in women? A review of evidence and call for further research. J Appl Toxicol 24:167–76
   PubMed Web of Science ®Google Scholar
• Harvey PW, Everett DJ. (2004). Significance of the detection of esters of p-hydroxybenzoic acid (parabens) in human breast tumours. J Appl Toxicol 24:1–4
   PubMed Web of Science ®Google Scholar
• Harville HM, Voorman R, Prusakiewicz JJ. (2007). Comparison of paraben stability in human and rat skin. Drug Metab Lett 1:17–21
   PubMedGoogle Scholar
• Holmes RS, Wright MW, Laulederkind SJF, et al. (2010). Recommended nomenclature for five mammalian carboxylesterase gene families: human, mouse, and rat genes and proteins. Mammal Genome 21:427–41
   PubMed Web of Science ®Google Scholar
• Hosokawa M. (2008). Structure and catalytic properties of carboxylesterase isozymes involved in metabolic activation of prodrugs. Molecules 13:412–31
   PubMed Web of Science ®Google Scholar
• Hosokawa M, Maki T, Satoh T. (1990). Characterization of molecular species of liver microsomal carboxylesterases of several animal species and humans. Arch Biochem Biophys 277:219–27
   PubMed Web of Science ®Google Scholar
• Imai T, Taketani M, Shii M, et al. (2006). Substrate specificity of carboxylesterase isozymes and their contribution to hyydrolase activity in human liver and small intestine. Drug Metab Dispos 34:1734–41
   PubMed Web of Science ®Google Scholar
• Janjua NR, Frederiksen H, Skakkeback NE, et al. (2008). Urinary excretion of phthalates and paraben after repeated whole-body topical application in humans. Int J Androl 31:118–30
   PubMed Web of Science ®Google Scholar
• Janjua NR, Mortensen GK, Andersson AM, et al. (2007). Systemic uptake of diethyl phthalate, dibutyl phthalate, and butyl paraben following whole-body topical application and reproductive and thyroid hormone levels in humans. Environ Sci Technol 41:5564–70
   PubMed Web of Science ®Google Scholar
• Jewell C, Bennett P, Mutch E, et al. (2007b). Inter-individual variability in esterases in human liver. Biochem Pharmacol 74:932–9
   PubMed Web of Science ®Google Scholar
• Jewell C, Prusakiewicz JJ, Ackermann C, et al. (2007a). Hydrolysis of a series of parabens by skin microsomes and cytosol from human and minipigs and in whole skin in short-term culture. Toxicol Appl Pharmacol 225:221–8
   PubMed Web of Science ®Google Scholar
• Langin D, Laurell H, Holst LS, et al. (1993). Gene organization and primary structure of human hormone-sensitive lipase: possible significance of a sequence homology with a lipase of Moraxella TA144, an Antarctic bacterium. Proc Natl Acad Sci USA 90:4897–901
   PubMed Web of Science ®Google Scholar
• Lobemeier C, Tschoetschel C, Westie S, Heymann E. (1996). Hydrolysis of parabens by extracts from differing layers of human skin. Biol Chem 377:647–51
   PubMed Web of Science ®Google Scholar
• Murrell VG, Vincent JM. (1950). Esters of 4-hydroxybenzoic acid and related compounds. V. Bacteriostatic action of n-alkyl 4-hydroxybenzoates. J Soc Chem Ind 69:109–13
   Google Scholar
• Nakamura Y, Sugihara K, Sone T, et al. (2007). The in vitro metabolism of a pyrethroid insecticide, permethrin, and its hydrolysis products in rats. Toxicology 235:176–84
   PubMed Web of Science ®Google Scholar
• Okubo T, Yokoyama Y, Kano K, Kano I. (2001). ER-dependent estrogenic activity of parabens assessed by proliferation of human breast cancer MCF-7 cells and expression of ERα and PR. Food Chem Toxicol 39:1225–32
   PubMed Web of Science ®Google Scholar
• Routledge EJ, Parker J, Odum J, et al. (1998). Some alkyl hydroxy benzoate preservatives (parabens) are estrogenic. Toxicol Appl Pharmacol 153:12–19
   PubMed Web of Science ®Google Scholar
• Sanghani SP, Sanghani PC, Schiel MA, Bosron WF. (2009). Human carboxylesterase: an update on CES1, CES2 and CES3. Protein Peptide Lett 16:1207–14
   PubMed Web of Science ®Google Scholar
• Satoh T, Hosokawa M. (1998). The mechanism carboxylesterases: from molecules to functions. Ann Rev Pharmacol Toxicol 38:257–88
   PubMed Web of Science ®Google Scholar
• Satoh T, Hosokawa M. (2006). Structure, function and regulation of carboxylesterases. Chemico-Biol Interact 162:195–211
   PubMed Web of Science ®Google Scholar
• Satoh T, Taylor P, Bosron WF, et al. (2002). Current progress on esterases: from molecular structure to function. Drug Metab Dispos 30:488–93
   PubMed Web of Science ®Google Scholar
• Soni MG, Carabin IG, Burdock GA. (2005). Safety assessment of esters of p-hydroxybenzoic acid (parabens). Food Chem Toxicol 43:985–1015
   PubMed Web of Science ®Google Scholar
• Tayama S, Nakagawa Y, Tayama K. (2008). Genotoxic effects of environmental estrogen-like compounds in CHO-K1 cells. Mutat Res 649:114–25
   PubMed Web of Science ®Google Scholar
• Terasaki M, Kamata R, Shiraishi F, Makino M. (2009). Evaluation of estrogenic activity of parabens and their chlorinated derivatives by using the yeast two-hybrid assay and the enzyme-linked immunosorbent assay. Environ Toxicol Chem 28:204–8
   PubMed Web of Science ®Google Scholar
• Tsukamoto H, Terada S. (1960). Metabolism of drugs. XXIII. Metabolic fate of p-hydroxybenzoic acid and its derivatives in rabbits. Chem Pharm Bull 8:1066–70
   Google Scholar
• Tsukamoto H, Terada S. (1962). Metabolism of drugs. XXVI. Metabolic fate of p-hydroxybenzoic acid and its derivatives in rabbits. Chem Pharm Bull 10:86–90
   Google Scholar
• Tsukamoto H, Terada S. (1964). Metabolism of drugs. XLVII. Metabolic fate of p-hydroxybenzoic acid and its derivatives in rabbits. Chem Pharm Bull 12:765–9
   PubMed Web of Science ®Google Scholar
• van Meeuwen JA, van Son O, Piersma AH, et al. (2008). Aromatase inhibiting and combined estrogenic effects of parabens and estrogenic effects of other additives in cosmetics. Toxicol Appl Pharmacol 230:372–82
   PubMed Web of Science ®Google Scholar
• Vistoli G, Pedretti A, Mazzolari A, Testa R. (2010). Homology modeling and metabolism prediction of human carboxylesterase-2 using docking analysis by GriDock: a parallelized tool based on AutoDock 4.0. J Comp Aided Mol Design 24:771–87
   PubMed Web of Science ®Google Scholar
• Vo TTB, Yoo YM, Choi KC, Jeung EB. (2010). Potential estrogenic effect(s) of parabens at the prepubertal stage of a postnatal female rat model. Reprod Toxicol 29:306–16
   PubMed Web of Science ®Google Scholar
• Yamaori S, Fujiyama N, Kushihara M, et al. (2006). Involvement of human blood arylesterases and liver microsomal carboxylesterases in nafamostat hydrolysis. Drug Metab Pharmacokinet 21:147–55
   PubMed Web of Science ®Google Scholar
• Yan B, Yang D, Brady M, Parkinson A. (1994). Rat kidney carboxylesterase. Cloning, sequencing, cellular localization, and relationship to rat liver hydrolase. J Biol Chem 269:29688–96
   PubMed Web of Science ®Google Scholar
• Ye X, Bishop AM, Reidy JA, et al. (2006). Parabens as urinary biomarkers of exposure in humans. Environ Health Perspect 114:1843–6
   PubMed Web of Science ®Google Scholar