Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 39, 2009 - Issue 2
268
Views
14
CrossRef citations to date
0
Altmetric
Research Article

In vitro and in vivo phase II metabolism of combretastatin A-4: Evidence for the formation of a sulphate conjugate metabolite

, &
Pages 148-161 | Received 28 Jul 2008, Accepted 20 Oct 2008, Published online: 01 Feb 2009

References

  • Aprile S, Del Grosso E, Tron GC, Grosa G. 2007. In vitro metabolism study of combretastatin A-4 in rat and human liver microsomes. Drug Metabolism and Disposition 35:2252–2261.
  • Brown RT, Fox BW, Hadfield JA, McGown AT, Mayalarp SP, Pettit GR, Woods JA. 1995. Synthesis of water-soluble sugar derivatives of combretastatin A-4. Journal of the Chemical Society Perkin Transaction 577–581.
  • De Santi C, Pietrabissa A, Mosca F, Pacifici GM. 2000. Glucuronidation of resveratrol, a natural product present in grape and wine, in the human liver. Xenobiotica 30:1047–1054.
  • Dowlati A, Robertson K, Cooney M, Petros WP, Stratford M, Jesberger J, Rafie N, Overmoyer B, Makkar V, Stambler B, Taylor A, Waas J, Lewin JS, McCrae KR, Remick SC. 2002. A Phase I pharmacokinetic and translational study of the novel vascular targeting agent combretastatin A-4 phosphate on a single-dose intravenous schedule in patients with advanced cancer. Cancer Research 62:3408–3416.
  • Fisher MB, Campanale K, Ackermann BL, Vandenbranden M, Wrighton SA. 2000. In vitro glucuronidation using human liver microsomes and the pore-forming peptide alamethicin. Drug Metabolism and Disposition 28:560–566.
  • Grosa G, Galli U, Rolando B, Fruttero R, Gervasio G, Gasco A. 2004. Identification of 2,3-diaminophenazine and of o-benzoquinone dioxime as the major in vitro metabolites of benzofuroxan. Xenobiotica 34:345–352.
  • Hsieh HP, Liou JP, Mahindroo N. 2005. Pharmaceutical design of antimitotic agents based on combretastatins. Current Pharmaceutical Design 11:1655–1677.
  • Kirwan IG, Loadman PM, Swaine DJ, Antoney DA, Pettit GR, Lippert III JW, Shnyder SD, Cooper PA, Bibby MC. 2004. Comparative preclinical pharmacokinetic and metabolic studies of the combretastatin prodrugs combretastatin A4 phosphate and A1 phosphate. Clinical Cancer Research 10:1446–1453.
  • McGown AT, Fox BV. 1989. Structural and biochemical comparison of the antimitotic agents colchicine, combretastatin-A4 and amphetinile. Anti-Cancer Drug Design 3:249–254.
  • Mealy NE, Lupone B, Balcell M. 2006. Drugs under development for the treatment of breast cancer: combretastatin A-4 phosphate. Drugs of the Future 31:547–548.
  • Omura T, Sato S. 1964. The carbon monoxide-binding pigment of liver microsomes. Journal of Biological Chemistry 239:2370–2378.
  • Pettit GR, Singh SB, Hamel E, Lin CM, Alberts DS, Garciakendall D. 1989. Antineoplastic agent 145. Isolation and structure of the strong cell-growth and tubulin inhibitor combretastatin-A4. Experientia 45:209–211.
  • Pettit GR, Temple C, Narayanan VL, Varma R, Simpson MJ, Boyd MR. 1995. Antineoplastic agents 322. Synthesis of combretastatin A-4 prodrugs. Anti-Cancer Drug Design 10:299–309.
  • Rustin GJS, Galbraith SM, Anderson H, Stratford M, Folkes LK, Sena L, Gumbrell L, Price PM. 2003. Phase I clinical trial of weakly combretastatin A4 phosphate: clinical and pharmacokinetic results. Journal of Clinical Oncology 21:2815–282.
  • Soars MG, Mattiuz EL, Jackson DA, Kulanthaivel P, Ehlhardt WJ, Wrighton SA. 2002. Biosynthesis of drug glucuronides for use as authentic standards. Journal of Pharmacological and Toxicological Methods 47:161–168.
  • Stratford MRL, Dennis ML. 1999. Determination of combretastatin A-4 and its phosphate ester pro-drug in plasma by high-performance liquid chromatography. Journal of Chromatography B 721:77–85.
  • Tozer GM, Prise VE, Wilson J, Cemazar M, Shan S, Dewhirst MW, Barber PR, Vojnovic B, Chaplin DJ. 2001. Mechanisms associated with tumor vascular shut-down induced by combretastatin A-4 phosphate: intravital microscopy and measurement of vascular permeability. Cancer Research 61:6413–6422.
  • Wang LX, Heredia A, Song H, Zhang Z, Yu B, Davis C, Redfield R. 2004. Resveratrol glucuronides as the metabolites of resveratrol in humans: characterization, synthesis, and anti-HIV activity. Journal of Pharmaceutical Sciences 93:2448–2457.
  • Yu C, Shin YG, Chow A, Li Y, Kosmeder JW, Lee YS, Hirschelman WH, Pezzuto JM, Mehta RG, Van Breemen RB. 2002. Human, rat, and mouse metabolism of resveratrol. Pharmaceutical. Research 19:1907–1914.

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.