Characterization of Plasma Protein Binding and the Effect of the Vehicle of Docetaxel Formulations
DOI:
https://doi.org/10.29356/jmcs.v61i4.468Keywords:
Docetaxel, alpha-1-acid glycoprotein (AAG), Polysorbate 80, generics, protein binging.Abstract
In this study we provide evidence of the alpha-1-acid glycoprotein (AAG) binding to Docetaxel as a key assay to evaluate formulations from different manufactures. The comparison of generics to the innovator is an active field in Pharmaceutics. While quality control tests are based on the evaluation of the active drug, our results show protein binding and excipients (Polysorbate 80) also play a critical role. We designed an assay by electronic absorption spectroscopy to evaluate the Docetaxel binding to AAG and the influence of Polysorbate 80. We evaluated Docetaxel generics from India and Latin America, our results show some generics of Docetaxel do not match with the innovator. The assay here developed is a feasible and easy access technique that could be implemented as a quick scan of quality control of Docetaxel generics available worldwide.Downloads
References
Baker S.D.; Li J.; ten Tije A.J.; Figg W.D.; Graveland W.; Verweij J.; Sparreboom A. Clin Pharmacol Ther. 2005, 77, 43-53. DOI: https://doi.org/10.1016/j.clpt.2004.09.005
Vial J.; Cohen M.; Sassiat P.; Thiébaut D. Curr Med Res Opin. 2008, 24, 2019-2033. DOI: http://dx.doi.org/10.1185/03007990802207874 DOI: https://doi.org/10.1185/03007990802207874
Ng S.S., Figg W.D., Sparreboom A. Cancer Res. 2004, 64, 821-824. DOI: https://doi.org/10.1158/0008-5472.CAN-03-3391
Jill M Kolesar. J Oncol Pharm Practice. 2000, 6, 43-49. DOI: https://doi.org/10.1177/107815520000600202
Urien S.; Barré J.; Morin C.; Paccaly A.; Montay G.; Tillement J.P. Invest New Drugs. 1996, 14, 147-151. DOI: https://doi.org/10.1007/BF00210785
Sparreboom A.; Zhao M.; Brahmer J.R.; Verweij J.; Baker S.D. J Chromatogr B Analyt Technol Biomed Life Sci. 2002, 773, 183-190. DOI: https://doi.org/10.1016/S1570-0232(02)00167-8
Carstens M.G.; de Jong P.H.; van Nostrum C.F.; Kemmink J.; Verrijk R.; de Leede L.G.; Crommelin D.J.; Hennink W.E. Eur J Pharm Biopharm. 2008, 68, 596-606. DOI: https://doi.org/10.1016/j.ejpb.2007.08.014
Vasu Dev R.; Moses Babu J.; Vyas K.; Sai Ram P.; Ramachandra P.; Sekhar N.M.; Mohan Reddy D.N.; Srinivasa Rao N. J Pharm Biomed Anal. 2006, 40, 614-622. DOI: https://doi.org/10.1016/j.jpba.2005.10.037
Datamonitor. 2010 [cited 2013; Available from: http://www.datamonitor.com/store/News/sanofi_aventis_jevtana_positi o n e d _ t o _ h e l p _ o ff s e t _ t a x o t e r e _ d e c l i n e ? p r o d u c -tid=35244E18-A4E1-4435-8797-DEFE94A569BE.
EMEA. Europena Medicines Agency Evaluation of Medicines for Human. Assessment Report for Docetaxel Teva. .Procedure No.EMEA/H/C/1107.2010. 2010 [cited 2013; Available from: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/001107/WC500073418. PDF.
Malleswara Reddy, A., et al., Evaluation of the pharmaceutical quality of docetaxel injection using new stability indicating chromatographic methods for assay and impurities. Sci Pharm, 2010. 78(2): p. 215-31. DOI: https://doi.org/10.3797/scipharm.0912-14
Loos, W.J., et al., Clinical pharmacokinetics of unbound docetaxel: Role of polysorbate 80 and serum proteins. Clinical Pharmacology & Therapeutics, 2003. 74(4): p. 364-371. DOI: https://doi.org/10.1016/S0009-9236(03)00222-4
Aizawa, H., Morphology of polysorbate 80 (Tween 80) micelles in aqueous 1,4-dioxane solutions. . J Appl Crystallogr, 2009. 42: p. 592-596. DOI: https://doi.org/10.1107/S002188980902295X
Croy, S.R. and G.S. Kwon, Polysorbate 80 and Cremophor EL micelles deaggregate and solubilize nystatin at the core-corona interface. J Pharm Sci, 2005. 94(11): p. 2345-54. DOI: https://doi.org/10.1002/jps.20301
Engels, F.K., R.A. Mathot, and J. Verweij, Alternative drug formulations of docetaxel: a review. Anticancer Drugs, 2007. 18(2): p. 95-103. DOI: https://doi.org/10.1097/CAD.0b013e3280113338
Acharya, M.R., et al., Determination of fraction unbound docetaxel using microequilibrium dialysis. Anal Biochem, 2004. 331(1): p. 192-4. DOI: https://doi.org/10.1016/S0003-2697(04)00297-0
Goodman and Gilman, eds. Las bases farmacológicas de la terapéutica. 11 ed., ed. M.G. Hill. 2007.
Ascoli, G.A., C. Bertucci, and P. Salvadori, Ligand binding to a human serum albumin stationary phase: Use of same-drug competition to discriminate pharmacologically relevant interactions. Biomedical Chromatography, 1998. 12(5): p. 248-254. DOI: https://doi.org/10.1002/(SICI)1099-0801(199809/10)12:5<248::AID-BMC742>3.0.CO;2-9
Sugio, S., et al., Crystal structure of human serum albumin at 2.5 angstrom resolution. Protein Engineering, 1999. 12(6): p. 439-446. DOI: https://doi.org/10.1093/protein/12.6.439
Otagiri, M. and V.T.G. Chuang, Pharmaceutically Important Preand Posttranslational Modifications on Human Serum Albumin. Biological & Pharmaceutical Bulletin, 2009. 32(4): p. 527-534. DOI: https://doi.org/10.1248/bpb.32.527
Otosu, T., E. Nishimoto, and S. Yamashita, Multiple conformational state of human serum albumin around single tryptophan residue at various pH revealed by time-resolved fluorescence spectroscopy. J Biochem, 2010. 147(2): p. 191-200. DOI: https://doi.org/10.1093/jb/mvp175
Otagiri, M., A molecular functional study on the interactions of drugs with plasma proteins. Drug Metab Pharmacokinet, 2005. 20(5): p. 309-23. DOI: https://doi.org/10.2133/dmpk.20.309
Ghuman, J., et al., Structural basis of the drug-binding specificity of human serum albumin. J Mol Biol, 2005. 353(1): p. 38-52. DOI: https://doi.org/10.1016/j.jmb.2005.07.075
Schonfeld, D.L., et al., The 1.8-A crystal structure of alpha1-acid glycoprotein (Orosomucoid) solved by UV RIP reveals the broad drug-binding activity of this human plasma lipocalin. J Mol Biol, 2008. 384(2): p. 393-405. DOI: https://doi.org/10.1016/j.jmb.2008.09.020
Kawasaki, T., J. Koyama, and Yamashin.I, Isolation and Characterization of Alpha1-Acid Glycoprotein from Rat Serum. Journal of Biochemistry, 1966. 60(5): p. 554-&. DOI: https://doi.org/10.1093/oxfordjournals.jbchem.a128475
Fournier, T., N. Medjoubi-N, and D. Porquet, Alpha-1-acid glycoprotein. Biochimica Et Biophysica Acta-Protein Structure and Molecular Enzymology, 2000. 1482(1-2): p. 157-171. DOI: https://doi.org/10.1016/S0167-4838(00)00153-9
Routledge, P.A., The Plasma-Protein Binding of Basic Drugs. British Journal of Clinical Pharmacology, 1986. 22(5): p. 499-506. DOI: https://doi.org/10.1111/j.1365-2125.1986.tb02927.x
Williams, J.P., et al., alpha(1)-acid glycoprotein reduces local and remote injuries after intestinal ischemia in the rat. American Journal of Physiology-Gastrointestinal and Liver Physiology, 1997. 273(5): p. G1031-G1035. DOI: https://doi.org/10.1152/ajpgi.1997.273.5.G1031
ten Tije, A.J., et al., Pharmacological effects of formulation vehicles: implications for cancer chemotherapy. Clin Pharmacokinet, 2003. 42(7): p. 665-85. DOI: https://doi.org/10.2165/00003088-200342070-00005
Loos, W.J., et al., Influence of polysorbate 80 on unbound fractions of anticancer agents. European Journal of Cancer, 2002. 38: p. S38-S38. DOI: https://doi.org/10.1016/S0959-8049(02)80761-4
Cheng, H.X., et al., Interaction of the docetaxel with human serum albumin using optical spectroscopy methods. Journal of Luminescence, 2009. 129(10): p. 1196-1203. DOI: https://doi.org/10.1016/j.jlumin.2009.05.023
Márquez M., Quintanar L., and C.-H. G. Rev Mex Cienc Farm 2013. 44 (1) p. 45-51.
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
