Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 36, 2006 - Issue 9
166
Views
15
CrossRef citations to date
0
Altmetric
Original

Transesterification of p-hydroxybenzoate esters (parabens) by human intestinal (Caco-2) cells

, , , , &
Pages 739-749 | Received 27 Dec 2005, Accepted 06 Apr 2006, Published online: 11 Aug 2009

References

  • Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein–dye binding. Analytical Biochemistry 1976; 72: 248–254
  • Brunet J-L, Maresca M, Fantini J, Belzunces LP. Human intestinal absorption of imidacloprid with Caco-2 cells as enterocyte model. Toxicology and Applied Pharmacology 2004; 194: 1–9
  • Brzezinski MR, Abraham TL, Stone CL, Dean RA, Bosron WF. Purification and characterization of a human liver cocaine carboxylesterase that catalyzes the production of benzoylecgonine and the formation of cocaethylene from alcohol and cocaine. Biochemical Pharmacology 1994; 48: 1747–1755
  • Chou RC, Wyss R, Huselton CA, Wiegand U-W. A potentially new metabolic pathway: Ethyl esterification of acitretin. Xenobiotica 1992; 22: 993–1002
  • Darbre PD, Aljarrah A, Miller WR, Coldham NG, Sauer MJ, Pope GS. Concentrations of parabens in human breast tumours. Journal of Applied Toxicology 2004; 24: 5–13
  • Delie F, Rubas W. A human colonic cell line sharing similarities with enterocytes as a model to examine oral absorption: Advantages and limitations of the Caco-2 model. Critical Reviews in Therapeutic Drug Carrier Systems 1997; 14: 221–286
  • Ege S. Carboxylic acids and their derivatives I. Acyl-transfer reactions. Organic chemistry, 4th ed, S Ege. MAL Houghton Mifflin. ch. 14, Boston 1999
  • Halsted CH, Robles EA, Mezey E. Distribution of ethanol in the human gastrointestinal tract. American Journal of Clinical Nutrition 1973; 26: 831–834
  • Karlsson J, Artursson P. A method for the determination of cellular permeability coefficients and aqueous boundary layer thickness in monolayers of intestinal epithelial (Caco-2) cells grown in permeable filter chambers. International Journal of Pharmaceutics 1991; 71: 55–64
  • Knights KM, Gasser R, Klemisch W. In vitro metabolism of acitretin by human liver microsomes: Evidence of an acitretinoyl-coenzyme: A thioester conjugate in the transesterification to etretinate. Biochemical Pharmacology 2000; 60: 507–516
  • Krishna G, Chen K-J, Lin C-C, Nomeir AA. Permeability of lipophilic compounds in drug discovery using in vitro human absorption model, Caco-2. International Journal of Pharmaceutics 2001; 222: 77–89
  • Nakagawa Y, Moldeus P. Mechanism of p-hydroxybenzoate ester-induced mitochondrial dysfunction and cytotoxicity in isolated rat hepatocytes. Biochemical Pharmacology 1998; 55: 1907–1914
  • Oh SY, Fujii M, Takeda Y, Yoda K, Utoguchi N, Matsumoto M, Watanabe Y. The effect of ethanol on the simultaneous transport and metabolism of methyl p-hydroxybenzoate in excised skin of Yucatan micropig. International Journal of Pharmaceutics 2002; 236: 35–42
  • Perry JJ, Staley JT, Lory S. Cellular energy derived from chemicals. Microbial life, JJ Perry, JT Staley, S Lory. Sinauer Associates. ch. 8, Boston, MA 2002
  • Pohorecky LA, Brick J. Pharmacology of ethanol. Pharmacology and Therapeutics 1988; 36: 335–427
  • Soni MG, Burdock GA, Taylor SL, Greenberg NA. Safety assessment of propyl paraben: A review of the published literature. Food and Chemical Toxicology 2001; 39: 513–532
  • Soni MG, Carabin IG, Burdock GA. Safety assessment of esters of p-hydroxybenzoic acid (parabens). Food and Chemical Toxicology 2005; 43: 985–1015
  • Soni MG, Taylor SL, Greenberg NA, Burdock GA. Evaluation of the health aspects of methyl paraben: A review of the published literature. Food and Chemical Toxicology 2002; 40: 1335–1373
  • Valkova N, Lepine F, Labrie L, Dupont M, Beaudet R. Purification and characterization of PrbA, a new esterase from Enterobacter cloacae hydrolyzing the esters of 4-hydroxybenzoic acid (parabens). Journal of Biological Chemistry 2003; 278: 12779–12785
  • Yee S. In vitro permeability across Caco-2 cells (colonic) can predict in vivo (small intestinal) absorption in man – fact or myth. Pharmaceutical Research 1997; 14: 763–766

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.