Photosensitizers form in histidine buffer and mediate the photodegradation of a monoclonal antibody

Journal of Pharmaceutical Sciences

Volumn 100, Issue 12, 2011, Pages 5142-5155

  Stroop, Steven D ^a   Conca, David M ^a   Lundgard, Robert P ^a   Renz, Mark E ^a   Peabody, Lynn M ^a   Leigh, Scott D ^a  

^a FIBROGEN INC   (United States)

Author keywords

Antibody; Fluorescence spectroscopy; Histidine; Mass spectrometry; Oxidation; Photodegradation; Photosensitizer; Protein formulation; Stability

Indexed keywords

6A HYDROXY 2 OXO OCTAHYDROPYROL[2,3 D]IMIDAZOLE 5 CARBOXYLIC ACID; BUFFER; CARBOXYLIC ACID DERIVATIVE; HISTIDINE; HYDROGEN PEROXIDE; IMMUNOGLOBULIN G; IMMUNOGLOBULIN HEAVY CHAIN; IMMUNOGLOBULIN LIGHT CHAIN; METHIONINE; MONOCLONAL ANTIBODY; OXYGEN; PHOTOSENSITIZING AGENT; SINGLE CHAIN FRAGMENT VARIABLE ANTIBODY; TRACE METAL; TRYPTOPHAN; UNCLASSIFIED DRUG;

ANTIGEN BINDING; ARTICLE; CAPILLARY ELECTROPHORESIS; CONTROLLED STUDY; DRUG FORMULATION; FLUORESCENT LIGHTING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGHT ABSORPTION; LIGHT EXPOSURE; MASS SPECTROMETRY; PH; PHOTODEGRADATION; PHOTOOXIDATION; PROTEIN DEGRADATION; PROTEIN STABILITY; ULTRAVIOLET RADIATION;

EID: 80054896994     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22714     Document Type: Article

References (21)

1. International Conference on Harmonization (ICH) Guideline for the Photo Stability Testing of New Drug Substances and Products, (Q1B), Nov 06, 1996.
2. Kerwin BA, Remmele RL Jr. 2007. Protect from light: Photodegradation and protein biologics. J Pharm Sci 96:1468-1479.
3. Igarashi N, Onoue S, Tsuda Y. 2007. Photoreactivity of amino acids: Tryptophan-induced photochemical events via reactive oxygen species generation. Analytical Sci 23:943-948.
4. Sarkar B, Das U, Bhattacharyya S, Bose SK. 1997. Studies on the aerobic photooxidation of cysteine using riboflavin as a sensitizer: Evidence for the photogeneration of a superoxide anion and hydrogen peroxide. Biol Pharm Bull 20:910-912.
5. Sluyterman LA. 1962. Photo-oxidation, sensitized by proflavine, of a number of protein constituents. Biochim Biophys Acta 60:557-561.
6. Weil L. 1965. On the mechanism of the Photo-oxidation of amino acids sensitized by methylene blue. Arch Biochem Biophys 110:57-68.
7. Suto D, Ikeda Y, Fujii J, Ohba Y. 2006. Structural analysis of amino acids, oxidized by reactive oxygen species and an Antibody against N-formylkynurenine. J Clin Biochem Nutr 38:1-5.
8. Agon VV, Bubb WA, Wright A, Hawkins CL, Davies MJ. 2006. Sensitizer-mediated photooxidation of histidine residues: Evidence for the formation of reactive side-chain peroxides. Free Radic Biol Med 40:698-710.
9. Wei Z, Feng J, Lin H-Y, Mullapudi S, Bishop E, Tous GI, Casas-Finet J, Hakki F, Strouse R, Schenerman MA. 2007. Identification of a single tryptophan residue as critical for binding activity in a humanized monoclonal antibody against respiratory syncytial virus. Anal Chem 79:2797-2805.
10. Qi P, Volkin DB, Zhao H, Nedved ML, Hughes R, Bass R, Yi SC, Panek ME, Wang D, Dalmonte P, Bond MD. 2009. Characterization of the photodegradation of a human IgG1 monoclonal antibody formulated as a high-concentration liquid dosage form. J Pharm Sci 98:3117-3130.
11. Chen B, Bautista R, Yu K, Zapata GA, Mulkerrin MG, Chamow SM. 2003. Influence of histidine on the stability and physical properties of a fully human antibody in aqueous and solid forms. Pharm Res 20:1952-1960.
12. Chignell CF, Sik RH, Bilski PJ. 2008. The photosensitizing potential of compact fluorescent vs incandescent light bulbs. Photochem Photobiol 84:1291-1293.
13. Gadgil HS, Pipes GD, Dillon TM, Treuheit MJ, Bondarenko PV. 2006. Improving mass accuracy of high performance liquid chromatography/electrospray ionization time-of-flight mass spectrometry of intact antibodies. J Am Soc Mass Spec 17:867-872.
14. Yan B, Valliere-Douglass J, Brady L, Steen S, Han M, Pace D, Elliott S, Yates Z, Han Y, Balland A, Wang W, Pettit D. 2007. Analysis of post-translational modifications in recombinant monoclonal antibody IgG1 by reversed-phase liquid chromatography/mass spectrometry. J Chrom A 1164:153-161.
15. Sinha S, Pipes G, Topp EM, Bondarenko PV, Treuheit MJ, Gadgil HS. 2008. Comparison of LC and LC/MS methods for quantifying N-glycosylation in recombinant IgGs. J Am Soc Mass Spectrom 19:1643-1654.
16. Rehder DS, Dillon TM, Pipes GD, Bonderenko PV. 2006. Reversed-phase liquid chromatography/mass spectrometry analysis of reduced monoclonal antibodies in pharmaceutics. J Chrom A 1102:164-175.
17. Bariola PA, Russell BA, Monahan SJ, Stroop SD. 2007. Identification and quantification of N alpha-acetylated Y. pestis fusion protein F1-V expressed in Escherichia coli using LCMS E. J Biotechnol 130:11-23.
18. Stroop SD. 2007. A modified peptide mapping strategy for quantifying site-specific deamidation by electrospray time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 21:830-836.
19. Valko M, Morris H, Cronin M. 2005. Metals, toxicity and oxidative stress. Curr Med Chem 12: 1161-208.
20. Pirie A. 1972. Fluorescence of N-formylkynurenine and of proteins exposed to sunlight. Biochem J 128:1365-367.
21. Wenworth Jr. P, Jones LH, Wentworth AD, Zhy X, Larsen NA, Wilson IA, Xu X, Goddard III WA, Janda KD, Eschenmoser A, Lerner RA. 2001. Antibody catalysis of the oxidation of water. Science 293:1806-1811.