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Prediction of long-term polysorbate degradation according to short-term degradation kinetics

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Article: 2232486 | Received 11 Apr 2023, Accepted 29 Jun 2023, Published online: 06 Jul 2023

References

  • Li X, Wang F, Li H, Richardson DD, Roush DJ. The measurement and control of high-risk host cell proteins for polysorbate degradation in biologics formulation. Antib Ther. 2022;5(1):42–13. doi:10.1093/abt/tbac002. PMID: 35155990.
  • Dwivedi M, Blech M, Presser I, Garidel P. Polysorbate degradation in biotherapeutic formulations: identification and discussion of current root causes. Int J Pharm. 2018;552:422–36. doi:10.1016/j.ijpharm.2018.10.008. PMID: 30300706.
  • Martos A, Koch W, Jiskoot W, Wuchner K, Winter G, Friess W, Hawe A. Trends on analytical characterization of polysorbates and their degradation products in biopharmaceutical formulations. J Pharm Sci. 2017;106:1722–35. doi:10.1016/j.xphs.2017.03.001. PMID: 28302541.
  • Glucklich N, Carle S, Buske J, Mader K, Garidel P. Assessing the polysorbate degradation fingerprints and kinetics of lipases - how the activity of polysorbate degrading hydrolases is influenced by the assay and assay conditions. Eur J Pharm Sci. 2021;166:105980. doi:10.1016/j.ejps.2021.105980. PMID: 34419573.
  • Larson NR, Wei Y, Prajapati I, Chakraborty A, Peters B, Kalonia C, Hudak S, Choudhary S, Esfandiary R, Dhar P, et al. Comparison of polysorbate 80 hydrolysis and oxidation on the aggregation of a monoclonal antibody. J Pharm Sci. 2020;109:633–39. doi:10.1016/j.xphs.2019.10.069. PMID: 31758949.
  • Jahn M, Zerr A, Fedorowicz FM, Brigger F, Koulov A, Mahler HC. Measuring lipolytic activity to support process improvements to manage lipase-mediated polysorbate degradation. Pharm Res. 2020;37:118. doi:10.1007/s11095-020-02812-0. PMID: 32495187.
  • Kishore RS, Pappenberger A, Dauphin IB, Ross A, Buergi B, Staempfli A, Mahler HC. Degradation of polysorbates 20 and 80: studies on thermal autoxidation and hydrolysis. J Pharm Sci. 2011;100:721–31. doi:10.1002/jps.22290. PMID: 20803573.
  • Kishore RS, Kiese S, Fischer S, Pappenberger A, Grauschopf U, Mahler HC. The degradation of polysorbates 20 and 80 and its potential impact on the stability of biotherapeutics. Pharm Res. 2011;28:1194–210. doi:10.1007/s11095-011-0385-x. PMID: 21369824.
  • Zhang S, Riccardi C, Kamen D, Xiao H, Li N. Monitoring polysorbate hydrolysis in therapeutic proteins using an ultrasensitive extraction-free fatty acid quantitation method. Anal Biochem. 2022;637:114472. doi:10.1016/j.ab.2021.114472. PMID: 34801481.
  • Saggu M, Demeule B, Jiang L, Kammerer D, Nayak PK, Tai M, Xiao N, Tomlinson A. Extended characterization and impact of visible fatty acid particles - a case study with a mab product. J Pharm Sci. 2021;110:1093–102. doi:10.1016/j.xphs.2020.11.027. PMID: 33271136.
  • Glucklich N, Dwivedi M, Carle S, Buske J, Mader K, Garidel P. An in-depth examination of fatty acid solubility limits in biotherapeutic protein formulations containing polysorbate 20 and polysorbate 80. Int J Pharm. 2020;591:119934. doi:10.1016/j.ijpharm.2020.119934. PMID: 33059015.
  • Doshi N, Martin J, Tomlinson A. Improving prediction of free fatty acid particle formation in biopharmaceutical drug products: incorporating ester distribution during polysorbate 20 degradation. Mol Pharm. 2020;17:4354–63. doi:10.1021/acs.molpharmaceut.0c00794. PMID: 32941040.
  • Honemann MN, Wendler J, Graf T, Bathke A, Bell CH. Monitoring polysorbate hydrolysis in biopharmaceuticals using a QC-ready free fatty acid quantification method. J Chromatogr B Analyt Technol Biomed Life Sci. 2019;1116:1–8. doi:10.1016/j.jchromb.2019.03.030. PMID: 30951966.
  • Tomlinson A, Demeule B, Lin B, Yadav S. Polysorbate 20 degradation in biopharmaceutical formulations: quantification of free fatty acids, characterization of particulates, and insights into the degradation mechanism. Mol Pharm. 2015;12:3805–15. doi:10.1021/acs.molpharmaceut.5b00311. PMID: 26419339.
  • Doshi N, Demeule B, Yadav S. Understanding particle formation: solubility of free fatty acids as polysorbate 20 degradation byproducts in therapeutic monoclonal antibody formulations. Mol Pharm. 2015;12:3792–804. doi:10.1021/acs.molpharmaceut.5b00310. PMID: 26419285.
  • Li X, Chandra D, Letarte S, Adam GC, Welch J, Yang RS, Rivera S, Bodea S, Dow A, Chi A, et al. Profiling active enzymes for polysorbate degradation in biotherapeutics by activity-based protein profiling. Anal Chem. 2021;93:8161–69. doi:10.1021/acs.analchem.1c00042. PMID: 34032423.
  • Zhang S, Riccardi C, Kamen D, Reilly J, Mattila J, Bak H, Xiao H, Li N. Identification of the specific causes of polysorbate 20 degradation in monoclonal antibody formulations containing multiple lipases. Pharm Res. 2022;39(1):75–87. doi:10.1007/s11095-021-03160-3. PMID: 34981317.
  • Zhang S, Xiao H, Li N. Degradation of polysorbate 20 by sialate O-Acetylesterase in monoclonal antibody formulations. J Pharm Sci. 2021;110(12):3866–73. doi:10.1016/j.xphs.2021.09.001. PMID: 34487744.
  • Graf T, Tomlinson A, Yuk IH, Kufer R, Spensberger B, Falkenstein R, Shen A, Li H, Duan D, Liu W, et al. Identification and characterization of polysorbate-degrading enzymes in a monoclonal antibody formulation. J Pharm Sci. 2021;110(11):3558–67. doi:10.1016/j.xphs.2021.06.033. PMID: 34224732.
  • Zhang S, Xiao H, Molden R, Qiu H, Li N. Rapid polysorbate 80 degradation by liver carboxylesterase in a monoclonal antibody formulated drug substance at early stage development. J Pharm Sci. 2020;109:3300–07. doi:10.1016/j.xphs.2020.07.018. PMID: 32721471.
  • Chiu J, Valente KN, Levy NE, Min L, Lenhoff AM, Lee KH. Knockout of a difficult-to-remove CHO host cell protein, lipoprotein lipase, for improved polysorbate stability in monoclonal antibody formulations. Biotechnol Bioeng. 2017;114:1006–15. doi:10.1002/bit.26237. PMID: 27943242.
  • McShan AC, Kei P, Ji JA, Kim DC, Wang YJ. Hydrolysis of polysorbate 20 and 80 by a range of carboxylester hydrolases. PDA J Pharm Sci Technol. 2016;70:332–45. doi:10.5731/pdajpst.2015.005942. PMID: 27020650.
  • Hall T, Sandefur SL, Frye CC, Tuley TL, Huang L. Polysorbates 20 and 80 degradation by group XV lysosomal phospholipase A2 Isomer X1 in monoclonal antibody formulations. J Pharm Sci. 2016;105:1633–42. doi:10.1016/j.xphs.2016.02.022. PMID: 27056628.
  • Labrenz SR. Ester hydrolysis of polysorbate 80 in mAb drug product: evidence in support of the hypothesized risk after the observation of visible particulate in mAb formulations. J Pharm Sci. 2014;103:2268–77. doi:10.1002/jps.24054. PMID: 24942482.
  • Zhang J, He J, Smith KJ. Fatty acids can induce the formation of proteinaceous particles in monoclonal antibody formulations. J Pharm Sci. 2022;111:655–62. doi:10.1016/j.xphs.2021.10.008. PMID: 34666046.
  • Molden R, Hu M, Yen ES, Saggese D, Reilly J, Mattila J, Qiu H, Chen G, Bak H, Li N. Host cell protein profiling of commercial therapeutic protein drugs as a benchmark for monoclonal antibody-based therapeutic protein development. MAbs. 2021;13:1955811. doi:10.1080/19420862.2021.1955811. PMID: 34365906.
  • Jones M, Palackal N, Wang F, Gaza-Bulseco G, Hurkmans K, Zhao Y, Chitikila C, Clavier S, Liu S, Menesale E, et al. “High-risk” host cell proteins (HCPs): a multi-company collaborative view. Biotechnol Bioeng. 2021;118:2870–85. doi:10.1002/bit.27808. PMID: 33930190.
  • Gao X, Rawal B, Wang Y, Li X, Wylie D, Liu YH, Breunig L, Driscoll D, Wang F, Richardson DD. Targeted host cell protein quantification by LC–MRM enables biologics processing and product characterization. Anal Chem. 2020;92(1):1007–15. doi:10.1021/acs.analchem.9b03952. PMID: 31860266.
  • Chen Y, Xu CF, Stanley B, Evangelist G, Brinkmann A, Liu S, McCarthy S, Xiong L, Jones E, Sosic Z, et al. A highly sensitive LC-MS/MS method for targeted quantitation of lipase host cell proteins in biotherapeutics. J Pharm Sci. 2021;110:3811–18. doi:10.1016/j.xphs.2021.08.024. PMID: 34461112.
  • Cheng Y, Hu M, Zamiri C, Carcelen T, Demeule B, Tomlinson A, Gu J, Yigzaw Y, Kalo M, Yu XC. A rapid high-sensitivity reversed–phase ultra high performance liquid chromatography mass spectrometry method for assessing polysorbate 20 degradation in protein therapeutics. J Pharm Sci. 2019;108(9):2880–86. doi:10.1016/j.xphs.2019.04.029. PMID: 31054888.
  • Zhang R, Wang Y, Tan L, Zhang HY, Yang M. Analysis of polysorbate 80 and its related compounds by RP-HPLC with ELSD and MS detection. J Chromatogr Sci. 2012;50:598–607. doi:10.1093/chromsci/bms035. PMID: 22542890.
  • Hvattum E, Yip WL, Grace D, Dyrstad K. Characterization of polysorbate 80 with liquid chromatography mass spectrometry and nuclear magnetic resonance spectroscopy: specific determination of oxidation products of thermally oxidized polysorbate 80. J Pharm Biomed Anal. 2012;62:7–16. doi:10.1016/j.jpba.2011.12.009. PMID: 22260967.
  • Borisov OV, Ji JA, Wang YJ, Vega F, Ling VT. Toward understanding molecular heterogeneity of polysorbates by application of liquid chromatography–mass spectrometry with computer-aided data analysis. Anal Chem. 2011;83(10):3934–42. doi:10.1021/ac2005789. PMID: 21491950.
  • Hewitt D, Zhang T, Kao YH. Quantitation of polysorbate 20 in protein solutions using mixed-mode chromatography and evaporative light scattering detection. J Chromatogr A. 2008;1215:156–60. doi:10.1016/j.chroma.2008.11.017. PMID: 19036378.
  • Khossravi M, Kao YH, Mrsny RJ, Sweeney TD. Analysis methods of polysorbate 20: a new method to assess the stability of polysorbate 20 and established methods that may overlook degraded polysorbate 20. Pharm Res. 2002;19:634–39. doi:10.1023/a:1015306112979. PMID: 12069166.
  • Puschmann J, Evers DH, Muller-Goymann CC, Herbig ME. Development of a design of experiments optimized method for quantification of polysorbate 80 based on oleic acid using UHPLC-MS. J Chromatogr A. 2019;1599:136–43. doi:10.1016/j.chroma.2019.04.015. PMID: 31003714.
  • Dahotre S, Tomlinson A, Lin B, Yadav S. Novel markers to track oxidative polysorbate degradation in pharmaceutical formulations. J Pharm Biomed Anal. 2018;157:201–07. doi:10.1016/j.jpba.2018.05.031. PMID: 29803911.
  • Borisov OV, Ji JA, John Wang Y. Oxidative degradation of polysorbate surfactants studied by liquid chromatography–Mass spectrometry. J Pharm Sci. 2015;104(3):1005–18. doi:10.1002/jps.24314. PMID: 28756834.
  • Zhang S, Xiao H, Li N. Ultrasensitive method for profiling host cell proteins by coupling limited digestion to ProteoMiner technology. Anal Biochem. 2022;657:114901. doi:10.1016/j.ab.2022.114901. PMID: 36130653.