The degradation of polysorbates 20 and 80 and its potential impact on the stability of biotherapeutics

Pharmaceutical Research

Volumn 28, Issue 5, 2011, Pages 1194-1210

  Kishore, Ravuri S K ^a   Kiese, Sylvia ^a   Fischer, Stefan ^a   Pappenberger, Astrid ^a   Grauschopf, Ulla ^a   Mahler, Hanns Christian ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

auto oxidation; degradation; hydrolysis; polysorbate; protein formulations; surfactant

Indexed keywords

FATTY ACID; MONOCLONAL ANTIBODY; POLYOXYETHYLENE; POLYSORBATE 20; POLYSORBATE 80; PROTEIN;

ARTICLE; DRUG DEGRADATION; DRUG FORMULATION; DRUG STABILITY; DRUG STORAGE; FOURIER TRANSFORM MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MASS FRAGMENTOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STRESS; TEMPERATURE; TURBIDITY; ULTRAVIOLET RADIATION;

ANTIBODIES, MONOCLONAL; DRUG STABILITY; DRUG STORAGE; EXCIPIENTS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; OXIDATION-REDUCTION; POLYSORBATES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SURFACE PROPERTIES; SURFACE-ACTIVE AGENTS;

EID: 79955601001     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-011-0385-x     Document Type: Article

References (40)

1. A Hillgren J Lindgren M Alden 2002 Protection mechanism of Tween 80 during freeze-thawing of a model protein, LDH Int J Pharm. 237 57 69 11955804 10.1016/S0378-5173(02)00021-2 1:CAS:528:DC%2BD38XislyrsLY%3D (Pubitemid 34310479)
2. S Kiese A Pappenberger W Friess HC Mahler 2008 Shaken, not stirred: mechanical stress testing of an IgG1 antibody J Pharm Sci. 97 4347 4366 18240293 10.1002/jps.21328 1:CAS:528:DC%2BD1cXht1Sgt7vF
3. Jones LS, Bam NB, Randolph TW. Surfactant-stabilized protein formulations: a review of protein-surfactant interactions and novel analytical methodologies. In: Shahrokh Z, Cleland JL, Shire SJ, editors. Therapeutic proteins and peptide formulation and delivery. Washington: American Chemical Society; 1997. p. 206-22. (Pubitemid 127440675)
4. L Kreilgaard LS Jones TW Randolph S Frokjaer JM Flink MC Manning JF Carpenter 1998 Effect of Tween 20 on freeze-thawing- and agitation-induced aggregation of recombinant human factor XIII J Pharm Sci. 87 1597 1603 10189273 1:CAS:528:DyaK1cXmtlKgt78%3D (Pubitemid 28559648)
5. W Wang 2005 Protein aggregation and its inhibition in biopharmaceutics Int J Pharm. 289 1 30 15652195 10.1016/j.ijpharm.2004.11.014 1:CAS:528:DC%2BD2MXisFKjsg%3D%3D (Pubitemid 40093537)
6. HC Mahler W Friess U Grauschopf S Kiese 2009 Protein aggregation: pathways, induction factors and analysis J Pharm Sci. 98 2909 2934 18823031 10.1002/jps.21566 1:CAS:528:DC%2BD1MXptl2isb0%3D
7. H-C Mahler R Mueller W Friess A Delille S Matheus 2005 Induction and analysis of aggregates in a liquid IgG1-antibody formulation Eur J Pharm Biopharm 59 407 417 15760721 10.1016/j.ejpb.2004.12.004 1:CAS:528: DC%2BD2MXit1Chsr8%3D (Pubitemid 40342515)
8. Y-F Maaand CC Hsu 1997 Protein denaturation by combined effect of shear and air-liquid interface Biotechnol Bioeng 54 503 512 10.1002/(SICI)1097- 0290(19970620)54:6<503::AID-BIT1>3.0.CO;2-N (Pubitemid 27209319)
9. MEM Cromwell E Hilario F Jacobson 2006 Protein aggregation and bioprocessing Aaps J 8 E572 E579 17025275 10.1208/aapsj080366 1:CAS:528:DC%2BD28XhtVGltLnJ (Pubitemid 44458092)
10. JF Carpenter BS Chang W Garzon-Rodriguez TW Randolph 2002 Rational design of stable lyophilized protein formulations: theory and practice Pharm Biotechnol 13 109 133 11987749 1:CAS:528:DC%2BD38XntFeltbk%3D
11. JF Carpenter MJ Pikal BS Chang TW Randolph 1997 Rational design of stable lyophilized protein formulations: some practical advice Pharm Res 14 969 975 9279875 10.1023/A:1012180707283 1:CAS:528:DyaK2sXlslejtL4%3D (Pubitemid 27371393)
12. FO Ayorinde SV Gelain JH Johnson Jr LW Wan 2000 Analysis of some commercial polysorbate formulations using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry Rapid Commun Mass Spectrom 14 2116 2124 11114018 10.1002/1097-0231(20001130)14:22<2116::AID- RCM142>3.0.CO;2-1 1:CAS:528:DC%2BD3cXosVKrsbk%3D
13. JD Brandner 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 1049 1054 9876559 10.3109/03639049809089948 1:CAS:528:DyaK1cXmsVanurc%3D (Pubitemid 28460243)
14. S Frison-Norrieand P Sporns 2001 Investigating the molecular heterogeneity of polysorbate emulsifiers by MALDI-TOF MS J Agric Food Chem 49 3335 3340 10.1021/jf010096w (Pubitemid 32845065)
15. WR Wasylaschuk PA Harmon G Wagner AB Harman AC Templeton H Xu RA Reed 2007 Evaluation of hydroperoxides in common pharmaceutical excipients J Pharm Sci. 96 106 116 16917844 10.1002/jps.20726 1:CAS:528:DC%2BD2sXivFCitg%3D%3D (Pubitemid 46087343)
16. E Ha W Wang YJ Wang 2002 Peroxide formation in polysorbate 80 and protein stability J Pharm Sci 91 2252 2264 12226852 10.1002/jps.10216 1:CAS:528:DC%2BD38XntlCqtLY%3D
17. PA Harmon K Kosuda E Nelson M Mowery RA Reed 2006 A novel peroxy radical based oxidative stressing system for ranking the oxidizability of drug substances J Pharm Sci 95 2014 2028 16850394 10.1002/jps.20668 1:CAS:528:DC%2BD28XpsFehtbw%3D (Pubitemid 44433031)
18. BA Kerwin 2008 Polysorbates 20 and 80 used in the formulation of protein biotherapeutics: structure and degradation pathways J Pharm Sci. 97 2924 2935 17973307 10.1002/jps.21190 1:CAS:528:DC%2BD1cXpsVOrsro%3D
19. M Donbrow E Azaz A Pillersdorf 1978 Autoxidation of polysorbates J Pharm Sci 67 1676 1681 31449 10.1002/jps.2600671211 1:CAS:528:DyaE1MXns1CrtQ%3D%3D (Pubitemid 9086684)
20. M Donbrow R Hamburger E Azaz 1975 Surface tension and cloud point changes of polyoxyethylenic nonionic surfactants during autoxidation J Pharm Pharmacol 27 160 166 237997 1:CAS:528:DyaE2MXks1agurw%3D
21. M Donbrow R Hamburger E Azaz A Pillersdorf 1978 Development of acidity in nonionic surfactants: formic and acetic acid Analyst (London) 103 400 402 10.1039/an9780300400 1:CAS:528:DyaE1cXls1Ggs7w%3D
22. Kishore RSK, Pappenberger A, Dauphin IB, Ross A, Buergi B, Staempfli A, Mahler HC. Degradation of polysorbates 20 and 80: Studies on thermal auto-oxidation in bulk and hydrolysis in formulations. J Pharm Sci. 2011;100:721-31.
23. H-C Mahler F Senner K Maeder R Mueller 2009 Surface activity of a monoclonal antibody J Pharm Sci. 98 4525 4533 19655376 10.1002/jps.21776 1:CAS:528:DC%2BD1MXhtlCjsL%2FL
24. HC Mahler F Huber RSK Kishore J Reindl P Rückert R Müller 2010 Adsorption behavior of a surfactant and a monoclonal antibody to sterilizing-grade filters J Pharm Sci. 99 2620 2627 20091913 1:CAS:528:DC%2BC3cXkvVOktb0%3D
25. Kiese S. Protein aggregation: induction, analytical methods and inhibition in biopharmaceutical formulations. Faculty of Chemistry und Pharmacy Vol. Doctorate, Ludwig-Maximillians-Universität München Munich, Germany, 2009, p. 298.
26. Carey FA, Sundberg RJ. Advanced organic chemistry, Springer Verlag, 2007.
27. TR Bates CH Nightingale E Dixon 1973 Kinetics of hydrolysis of poly(oxyethylene) (20) sorbitan fatty acid ester surfactants J Pharm Pharmacol 25 470 477 4146586 1:CAS:528:DyaE3sXksFOls7c%3D
28. C Decker J Marchal 1974 Autoxydation radio-induite du poly (oxyéthylène) en solution aqueuse, 7. Cinétique de la consommation d'oxygène Die Makromolekulare Chemie 175 3531 3540 10.1002/macp.1974.021751218 1:CAS:528:DyaE2MXlvVCnsg%3D%3D
29. VL Dulogand G Storck 1966 Die oxydation von polyepoxiden mit molekularem sauerstoff Die Makromolekulare Chemie. 91 50 73 10.1002/macp.1966.020910104
30. Donbrow M. Stability of polyoxyethylene chain in non ionic surfactants. In: Schick MJ, editor. Nonionic surfactants: physical chemistry, vol. 23. new york: CRC; 1987. p. 1135.
31. J Yao DK Dokuru M Noestheden SS Park BA Kerwin J Jona D Ostovic DL Reid 2009 A quantitative kinetic study of polysorbate autoxidation: the role of unsaturated fatty acid ester substituents Pharm Res-Dord. 26 2303 2313 10.1007/s11095-009-9946-7 1:CAS:528:DC%2BD1MXpsF2it7c%3D
32. Zhou Y, Woo LK, Angelici RJ. Solid acid catalysis of tandem isomerization-lactonization of olefinic acids. Applied Catalysis A. 2007.
33. IS Shepherdand JS Showell 1969 The mechanism of the aqueous perchloric acid isomerization of oleic acid to -stearolactone Journal of the American Oil Chemists' Society. 46 479 481 10.1007/BF02544372
34. RL Arudi MW Sutherland BH Bielski 1983 Purification of oleic acid and linoleic acid J. Lipid Res 24 485 6854155 1:CAS:528:DyaL3sXktlyjsr4%3D
35. S Li C Schöneich RT Borchardt 2004 Chemical instability of protein pharmaceuticals: mechanisms of oxidation and strategies for stabilization Biotechnol Bioeng. 48 490 500 10.1002/bit.260480511
36. M Tomita M Irie T Ukita 1969 Sensitized photooxidation of histidine and its derivatives. Products and mechanism of the reaction Biochemistry 8 5149 5160 5365801 10.1021/bi00840a069 1:CAS:528:DyaE3cXjt1WqsQ%3D%3D
37. R Müller A Karle A Vogt H Kropshofer A Ross K Maeder H-C Mahler 2009 Evaluation of the immuno-stimulatory potential of stopper extractables and leachables by using dendritic cells as readout J. Pharm. Sci. 98 3548 3561 10.1002/jps.21672
38. NA Porter SE Cladwell KA Mills 1995 Mechanisms of free-radical oxidation of unsaturated lipids Amer Oil Chemists Soc. 30 277 290 1:CAS:528: DyaK2MXltFCqtLc%3D
39. EP O'Brien RI Dima B Brooks D Thirumalai 2007 Interactions between hydrophobic and ionic solutes in aqueous guanidinium chloride and urea solutions: lessons for protein denaturation mechanism J Am. Chem. Soc. 129 7346 7353 17503819 10.1021/ja069232+ (Pubitemid 46980813)
40. AB Mirgorodskaya EI Yatskevich LY Zakharova 2010 The solubilization of fatty acids in systems based on block copolymers and nonionic surfactants Russ J Phys Chem A. 84 2066 2070 10.1134/S0036024410120101 1:CAS:528: DC%2BC3cXhsVyiu7vJ