Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 39, 2009 - Issue 12
184
Views
13
CrossRef citations to date
0
Altmetric
Research Article

Transport and metabolism of the antitumour drug candidate 2′-benzoyloxycinnamaldehyde in Caco-2 cells

, , , , , , , , , , & show all
Pages 881-888 | Received 09 Jul 2009, Accepted 29 Jul 2009, Published online: 20 Nov 2009

References

  • Artursson P. (1990). Epithelial transport of drugs in cell culture. I: A model for studying the passive diffusion of drugs over intestinal absorptive (Caco-2) cells. J Pharm Sci 79:476–82.
  • Artursson P. (1991). Cell cultures as models for drug absorption across the intestinal mucosa. Crit Rev Ther Drug Carrier Syst 8:305–33.
  • Artursson P, Borchardt RT. (1997). Intestinal drug absorption and metabolism in cell cultures: Caco-2 and beyond. Pharm Res 14:1655–58.
  • Artursson P, Palm K, Luthman K. (2001). Caco-2 monolayers in experimental and theoretical predictions of drug transport. Adv Drug Deliv Rev 46:27–43.
  • Beedham C, Peet CF, Panoutsopoulos GI, Carter H, Smith JA. (1995). Role of aldehyde oxidase in biogenic amine metabolism. Prog Brain Res 106:345–53.
  • Center for Drug Evaluation and Research. (2000). Guidance for Industry: Waiver of in vivo bioavailability and bioequivalence studies for immediate-release solid oral dosage forms based on a biopharmaceutics classification system. Washington, DC: US Food and Drug Administration (USFDA).
  • Chanteux H, Van Bambeke F, Mingeot-Leclercq MP, Tulkens PM. (2005). Accumulation and oriented transport of ampicillin in Caco-2 cells from its pivaloyloxymethylester prodrug, pivampicillin. Antimicrob Agents Chemother 49:1279–88.
  • Clarke SE, Harrell AW, Chenery RJ. (1995). Role of aldehyde oxidase in the in vitro conversion of famciclovir to penciclovir in human liver. Drug Metab Dispos 23:251–4.
  • Cogburn J, Donovan M, Schasteen C. (1991). A model for human small intestinal absorptive cells. 1. Transport barrier Pharm Res 8:210–16.
  • Delie F, Rubas W. (1997). A human colonic cell line sharing similarities with enterocytes as a model to examine oral absorption: advantages and limitations of the Caco-2 model. Crit Rev Ther Drug Carrier Syst 14:221–86.
  • Fogh J, Fogh JM, Orfeo T. (1977). One hundred and twenty-seven cultured human tumor cell lines producing tumors in nude mice. J Nat Cancer Inst 59:221–26.
  • Gan LS, Thakker DR. (1997). Applications of the Caco-2 model in the design and development of orally active drugs: elucidation of biochemical and physical barriers posed by the intestinal epithelium. Adv Drug Deliv Rev 23:77–98.
  • Ganey PE, Takei Y, Kauffman FC, Thurman RG. (1990). Ethanol potentiates oxygen uptake and toxicity due to menadione bisulfite in perfused rat liver. Mol Pharmacol 38:959–64.
  • Han DC, Lee MY, Shin KD, Jeon SB, Kim JM, Son KW, Kim HC, Kim HM, Kwon BM. (2004). 2′-Benzoyloxycinnamladehyde induces apoptosis in human carcinoma via reactive oxygen species. J Biol Chem 279:6911–20.
  • Helander A, Tottmar O. (1987). Effects of ethanol, acetaldehyde and disulfiram on the metabolism of biogenic aldehydes in isolated human blood cells and platelets. Biochem Pharmacol 36:3981–5.
  • Hidalgo J, Raub TJ, Borchardt RT. (1989). Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability. Gastroenterology 96:736–49.
  • Hilgers A, Conradi R, Burton PS. (1990). Caco-2 cell monolayers as a model for drug transport across the intestinal mucosa. Pharm Res 7:902–10.
  • Hong SH, Kim J, Kim JM, Lee SY, Shi DS, Son KH, Han DC, Sung YK, Kwon BM. (2007). Apoptosis induction of 2′-hydroxycinnamladehyde as a proteasome inhibitor is associated with ER stress and mitochondrial perturbation in cancer cells. Biochem Pharmacol 74:557–65.
  • Imai T, Imoto M, Sakamoto H, Hashimoto M. (2005). Identification of esterases expressed in Caco-2 cells and effects of their hydrolyzing activity in predicting human intestinal absorption. Drug Metab Dispos 33:1185–90.
  • Kang TH, Hwang EI, Yun BS, Park KD, Kwon BM, Shin CS, Kim SU. (2007). Inhibition of chitin synthases and antifungal activities by 2′-benzoyloxycinnamladehyde from Pleuropterus ciliinervis and its derivatives. Biol Pharm Bull 30:598–602.
  • Kitamura S, Sugihara K, Ohta S. (2006). Drug-metabolizing ability of molybdenum hydroxylases. Drug Metab Pharmacokinet 21:83–98.
  • Kwon BM, Cho YK, Lee SH, Nam JY, Bok SH, Chun SK, Kim JA, Lee IR. (1996). 2′-Hydroxycinnamaldehyde from Stem Bark of Cinnamomum cassia. Planta Med 62:183–4.
  • Kwon BM, Lee SH, Cho YK, Bok SH. (1997). Synthesis and biological activity of cinnamaldehydes as angiogenesis inhibitors. Bioorg Med Chem Lett 7:2473–6.
  • Lee CW, Hong DH, Han SB, Park SH, Kim HK, Kwon BM, Kim HM. (1999). Inhibition of human tumor growth by 2′-hydroxy- and 2′-benzoyloxycinnamaldehydes. Planta Med 65:263–6.
  • Lee K, Kwon BM, Kim K, Ryu J, Oh SJ, Lee KS, Kwon MG, Park SK, Kang JS, Lee CW, Kim HM. (2009). Plasma pharmacokinetics and metabolism of the antitumour drug candidate 2′-benzoyloxycinnamaldehyde in rats. Xenobiotica 39:255–65.
  • Lee K, Thakker DR. (1999). Saturable transport of H2-antagonists ranitidine and famotidine across Caco-2 cell monolayers. J Pharm Sci 88:680–7.
  • Masaki K, Hashimoto M, Imai T. (2007). Intestinal first-pass metabolism via carboxylesterase in rat jejunum and ileum. Drug Metab Dispos 35:1089–95.
  • Menconi MJ, Unno N, Smith M, Aguirre DE, Fink MP. (1998). Nitric oxide donor-induced hyperpermeability of cultured intestinal epithelial monolayers: role of superoxide radical, hydroxyl radical, and peroxynitrite. Biochim Biophys Acta 1425:189–203.
  • Pinto M, Robine-Leon S, Appay M–D, Kedinger M, Triadou N, Dussaulx EB, Croix B, Simmon-Assmann P, Haffen K, Fogh J, Zweibaum A. (1983). Enterocyte-like differentiation and polarization of the human colon carcinoma cell line Caco-2 in culture. Biol Cell 47:323–30.
  • Press B, Di Grandi D. (2008). Permeability for intestinal absorption: Caco-2 assay and related issues. Curr Drug Metab 9:893–900.
  • Rashidi MR, Smith JA, Clarke SE, Beedham C. (1997). In vitro oxidation of famciclovir and 6-deoxypenciclovir by aldehyde oxidase from human, guinea pig, rabbit, and rat liver. Drug Metab Dispos 25:805–13.
  • Sun H, Chow EC, Liu S, Du Y, Pang KS. (2008). The Caco-2 cell monolayer: usefulness and limitations. Expert Opin Drug Metab Toxicol 4:395–411.
  • Tang J, Akao T, Nakamura N, Wang ZT, Takagawa K, Sasahara M, Hattori M. (2007). In vitro metabolism of isoline, a pyrrolizidine alkaloid from Ligularia duciformis, by rodent liver microsomal esterase and enhanced hepatotoxicity by esterase inhibitors. Drug Metab Dispos 35:1832–9.
  • Tantishaiyakul V, Wiwattanawongsa K, Pinsuwan S, Kasiwong S, Phadoongsombut N, Kaewnopparat S, Kaewnopparat N, Rojanasakul Y. (2002). Characterization of mefenamic acid-guaiacol ester: stability and transport across Caco-2 cell monolayers. Pharm Res 19:1013–18.
  • Van Breemen RB, Li Y. Caco-2 cell permeability assays to measure drug absorption. (2005). Expert Opin Drug Metab Toxicol 1:175–85.
  • White EJ, Clark JB. (1988). Menadione-treated synaptosomes as a model for post-ischaemic neuronal damage. Biochem J 253:425–33.
  • Wilson G, Hassan I, Dix C, Williamson I, Shah R, Mackay M, Artursson P. (1990). Transport and permeability properties of human Caco-2 cells: an in vitro model of the intestinal epithelial cell barrier. J Control Release 11:25–45.
  • Yoshigae Y, Imai T, Taketani M, Otagiri M. (1999). Characterization of esterases involved in the stereoselective hydrolysis of ester-type prodrugs of propranolol in rat liver and plasma. Chirality 11:10–13.

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.