Degradation of polysorbates 20 and 80: Studies on thermal autoxidation and hydrolysis

Journal of Pharmaceutical Sciences

Volumn 100, Issue 2, 2011, Pages 721-731

  Kishore, Ravuri S K ^a   Pappenberger, Astrid ^a   Dauphin, Isabelle Bauer ^a   Ross, Alfred ^a   Buergi, Beatrice ^a   Staempfli, Andreas ^a   Mahler, Hanns Christian ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

Biopharmaceutics; Chemical stability; Excipients; Formulation; Surfactants

Indexed keywords

POLYSORBATE 20; POLYSORBATE 80;

ARTICLE; AUTOOXIDATION; DRUG DEGRADATION; DRUG FORMULATION; DRUG HYDROLYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; THERMOGRAVIMETRY; ULTRAVIOLET SPECTROSCOPY;

EID: 78650573283     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22290     Document Type: Article

References (55)

1. Hillgren A, Lindgren J, Alden M. 2002. Protection mechanism of Tween 80 during freeze-thawing of a model protein, LDH. Int J Pharm 237(1-2):57-69.
2. Jones LS, Bam NB, Randolph TW. 1997. Surfactant-stabilized protein formulations: A review of protein-surfactant interactions and novel analytical methodologies. In Therapeutic proteins and protein formulation and delivery; Shahrokh Z, Cleland JL, Shire SJ, Eds. American Chemical Society, Washington, DC. pp 206-222.
3. Kiese S, Papppenberger A, Friess W, Mahler HC. 2008. Shaken, not stirred: Mechanical stress testing of an IgG1 antibody. J Pharm Sci 97(10):4347-4366.
4. Kreilgaard L, Jones LS, Randolph TW, Frokjaer S, Flink JM, Manning MC, Carpenter JF. 1998. Effect of Tween 20 on freeze-thawing- and agitation-induced aggregation of recombinant human factor XIII. J Pharm Sci 87(12):1597-1603.
5. Wang W. 2005. Protein aggregation and its inhibition in biopharmaceutics. Int J Pharm 289(1-2):1-30.
6. Duncan MR, Lee JM, Warchol MP. 1995. Influence of surfactants upon protein/peptide adsorption to glass and polypropylene. Int J Pharm 120(2):179-188.
7. Mahler HC, Huber F, Ravuri S K K, Reindl J, Rückert P, Müller R. 2010. Adsorption behaviour of a surfactant and a monoclonal antibody to sterilizing-grade filters. J Pharm Sci 99(6)2620-2627.
8. Maa Y-F, Hsu CC. 1998. Investigation on fouling mechanisms for recombinant human growth hormone sterile filtration. J Pharm Sci 87(7):808-812.
9. Cromwell MEM, Hilario E, Jacobson F. 2006. Protein aggregation and bioprocessing. AAPS J 8(3):E572-E579.
10. Mahler H-C, Mueller R, Friess W, Delille A, Matheus S. 2005. Induction and analysis of aggregates in a liquid IgG1-antibody formulation. Eur J Pharm Biopharm 59(3):407-417.
11. Maa Y-F, Hsu CC. 1997. Protein denaturation by combined effect of shear and air-liquid interface. Biotechnol Bioeng 54(6):503-512.
12. Eckhardt BM, Oeswein JQ, Bewley TA 1991. Effect of freezing on aggregation of human growth hormone. Pharm Res 8(11):1360-1364.
13. Carpenter JF, Chang BS, Garzon-Rodriguez W, Randolph TW. 2002. Rational design of stable lyophilized protein formulations: Theory and practice. Pharm Biotechnol 13:109-133.
14. Carpenter JF, Pikal MJ, Chang BS, Randolph TW. 1997. Rational design of stable lyophilized protein formulations: Some practical advice. Pharm Res 14(8):969-975.
15. Mahler HC, Friess W, Grauschopf U, Kiese S. 2009. Protein aggregation: Pathways, induction factors and analysis. J Pharm Sci 98(9):2909-2934.
16. Barnhart ER, Feinstein AR. 2009. Physician's desk reference for nonprescription drugs. Physician's Desk Reference, Thomson PDR, Toronto, Canada.
17. Bergueiro JR, Bao M, Casares JJ. 1978. Determination of Hlb of nonionic dispersants by NMR, Part 1. Tween and Span series. An Quim 74(3):529-530.
18. Silha J, Bares M, Zeman I, Smidrkal J. 1989. The Hlb number determination of polyoxyethylene surfactants. Collect Czech Chem C 54(4):945-952.
19. Lucy SCW, Philip FSL. 1974. CMC of polysorbates. J Pharm Sci 63(1):136-137.
20. Mittal KL. 1972. Determination of CMC [critical micelle concentration] of polysorbate 20 in aqueous solution by surface tension method. J Pharm Sci 61(8):1334-1335.
21. Patist A, Bhagwat SS, Penfield KW, Aikens P, Shah DO. 2000. On the measurement of critical micelle concentrations of pure and technical-grade nonionic surfactants. J Surfactants Deterg 3(1):53-58.
22. Hanns-Christian M, Frank S, Karsten M, Robert M. 2009. Surface activity of a monoclonal antibody. J Pharm Sci 98(12):4525-4533.
23. Ayorinde FO, Gelain SV, Johnson JH Jr, Wan LW. 2000. Analysis of some commercial polysorbate formulations using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 14(22):2116-2124.
24. Brandner JD. 1998. The composition of NF-defined emulsifiers: Sorbitan monolaurate, monopalmitate, monostearate, monooleate, polysorbate 20, polysorbate 40, polysorbate 60, and polysorbate 80. Drug Dev Ind Pharm 24(11):1049-1054.
25. Frison-Norrie S, Sporns P. 2001. Investigating the molecular heterogeneity of polysorbate emulsifiers by MALDI-TOF MS. J Agric Food Chem 49(7):3335-3340.
26. Kerwin BA. 2008. Polysorbates 20 and 80 used in the formulation of protein biotherapeutics: Structure and degradation pathways. J Pharm Sci 97(8):2924-2935.
27. Donbrow M, Azaz E, Pillersdorf A. 1978. Autoxidation of polysorbates. J Pharm Sci 67(12):1676-1681.
28. Donbrow M, Hamburger R, Azaz E. 1975. Surface tension and cloud point changes of polyoxyethylenic nonionic surfactants during autoxidation. J Pharm Pharmacol 27(3):160-166.
29. Donbrow M, Hamburger R, Azaz E, Pillersdorf A. 1978. Development of acidity in nonionic surfactants: Formic and acetic acid. Analyst (Lond) 103(1225):400-402.
30. Ha E, Wang W, Wang YJ. 2002. Peroxide formation in polysorbate 80 and protein stability. J Pharm Sci 91(10):2252-2264.
31. Bates TR, Nightingale CH, Dixon E. 1973. Kinetics of hydrolysis of poly(oxyethylene) (20) sorbitan fatty acid ester surfactants. J Pharm Pharmacol 25(6):470-477.
32. Mueller R, Karle A, Vogt A, Kropshofer H, Ross A, Maeder K, Mahler H-C. 2009. Evaluation of the immuno-stimulatory potential of stopper extractables and leachables by using dendritic cells as readout. J Pharm Sci 98(10):3548-3561.
33. Yao J, Dokuru DK, Noestheden M, Park SS, Kerwin BA, Jona J, Ostovic D, Reid DL. 2009. A quantitative kinetic study of polysorbate autoxidation: The role of unsaturated fatty acid ester substituents. Pharm Res 26(10):2303-2313.
34. Hamburger R, Azaz E, Donbrow M. 1975. Autoxidation of polyoxyethylenic nonionic surfactants and of polyethylene glycols. Pharm Acta Helv 50(1-2):10-17.
35. Magill A, Becker AR. 1984. Spectrophotometric method for quantitation of peroxides in sorbitan monooleate and monostearate. J Pharm Sci 73(11):1663-1664.
36. Segal R, Azaz E, Donbrow M. 1979. Peroxide removal from nonionic surfactants. J Pharm Pharmacol 31(1):39-40.
37. Wasylaschuk WR, Harmon PA, Wagner G, Harman AB, Templeton AC, Xu H, Reed RA. 2007. Evaluation of hydroperoxides in common pharmaceutical excipients. J Pharm Sci 96(1):106-116.
38. Gilardi-Lorenz FI. 2006. Analytical characterisation of the excipient polysorbate 80. Zurich, Switzerland: Swiss Federal Institute of Technology.
39. Hewitt D, Zhang T, Kao YH. 2008. Quantitation of polysorbate 20 in protein solutions using mixed-mode chromatography and evaporative light scattering detection. J Chromatogr A 1215(1-2):156-160.
40. 2+ in the presence of xylenol orange. Comparison with the TBA assay and an iodometric method. Lipids 26(10):853-856.
41. Meyers RA. 2000. Encyclopedia of analytical chemistry applications, theory and instrumentation. Chichester, UK: Wiley. pp 15.
42. Brown ME. 1988. Introduction to thermal analysis techniques and applications. Vol. VIII. Dordrecht, Netherlands: Kulwer Academic, pp 211S.
43. Atkins P, De Paula J. 2006. Atkins' physical chemistry. Oxford, UK
44. Santacesaria E, Gelosa D, Diserio M, Tesser R. 1991. Thermal-stability of nonionic polyoxyalkylene surfactants. J Appl Polym Sci 42(7):2053-2061.
45. Donbrow M. 1987. Stability of polyoxyethylene chain in non ionic surfactants. In Nonionic surfactants: Physical chemistry; Schick MJ, Ed. New York: CRC Press. pp 1135.
46. Claude C, Jean M 1973. Caractérisation de réactions primaires de dégradation oxydante au cours de l'autoxydation des polyoxyéthylènes à 25°C: Étude en solution aqueuse avec amorçage par radiolyse du solvant. I. Étude viscosimétrique: Stabilité des hydroperoxydes du polyoxyéthylène et cinétique de production des coupures. Makromol Chem 166(1):69-84.
47. Vyazovkin S. 1996. A unified approach to kinetic processing of nonisothermal data. Int J Chem Kinet 28(2):95-101.
48. Litwinienko G. 2001. Autooxidation of unsaturated fatty acids and their esters. J Therm Anal Calorim 65(2):639-646.
49. de Sainte Claire P. 2009. Degradation of PEO in the solid state: A theoretical kinetic model. Macromolecules 42(10):3469-3482.
50. Bateman L. 1954. Olefin oxidation. Quart Revs (Lond) 8:147-167.
51. 1H nuclear magnetic resonance in the study of edible oils and fats. Trend Food Sci Technol 12(9):328-338.
52. 1H NMR study. FEBS Lett 355(1):81-90.
53. Passi S, Picardo M, Deluca C, Nazzaroporro M, Rossi L, Rotilio G. 1993. Saturated dicarboxylic-acids as products of unsaturated fatty-acid oxidation. Biochim Biophys Acta 1168(2):190-198.
54. Picardo M, Deluca C, Nazzaroporro M, Breathnach AS, Passi S. 1993. Dicarboxylic-acids are by-products of unsaturated fatty-acids peroxidation and are able to scavenge hydroxyl radicals in vitro. J Invest Dermatol 100(4):458-458.
55. Leroy G, Peeters D, Wilante C. 1982. Le calcul de l'energie de stabilisation des especes chimiques. J Mol Struct 88(3-4):217-233.