Toward Top-Down Determination of PEGylation Site Using MALDI In-Source Decay MS Analysis

Journal of the American Society for Mass Spectrometry

Volumn 20, Issue 2, 2009, Pages 326-333

  Yoo, Chul ^a   Suckau, Detlev ^b   Sauerland, Volker ^b   Ronk, Michael ^a   Ma, Minhui ^a  

^a AMGEN INC   (United States)

^b BRUKER DALTONIK GMBH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FRAGMENT IONS; HIGH RESOLUTIONS; LASER DESORPTION/IONIZATION; LINEAR POLYETHYLENE GLYCOLS; MOLECULAR LEVELS; PEGYLATION; SAMPLE TREATMENTS; SIDE CHAINS; STRUCTURAL ASPECTS; TOP DOWNS;

DESORPTION; ETHYLENE GLYCOL; GLYCOLS; OLIGOMERS; POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES; POLYMERS;

AMINES;

PEPTIDES; POLYETHYLENE GLYCOLS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 58249086365     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2008.10.013     Document Type: Article

References (48)

1. Veronese F.M., and Pasut G. PEGylation, Successful Approach to Drug Delivery. Drug Discov. Today 10 (2005) 1451-1458
2. Roberts M.J., Bentley M.D., and Harris J.M. Chemistry for Peptide and Protein PEGylation. Adv. Drug Delivery Rev. 54 (2002) 459-476
3. Harris J.M., and Chess R.B. Effect of PEGylation on Pharmaceuticals. Nat. Rev. Drug Discov. 2 (2003) 214-221
4. Greenwald R.B., Choe Y.H., McGuire J., and Conover C.D. Effective Drug Delivery by PEGylated Drug Conjugates. Adv. Drug Delivery Rev. 55 (2003) 217-250
5. Molineux G. Pegylation: Engineering Improved Biopharmaceuticals for Oncology. Pharmacotherapy 23 (2003) 3S-8S
6. Yang Z., Wang J., Lu Q., Xu J., Kobayashi Y., Takakura T., Takimoto A., Yoshioka T., Lian C., Chen C., Zhang D., Zhang Y., Li S., Sun X., Tan Y., Yagi S., Frenkel E.P., and Hoffman R.M. PEGylation Confers Greatly Extended Half-Life and Attenuated Immunogenicity to Recombinant Methioninase in Primates. Cancer Res. 64 (2004) 6673-6678
7. Kinstler O., Molineux G., Treuheit M., Ladd D., and Gegg C. Mono-N-Terminal Poly(Ethylene Glycol)-Protein Conjugates. Adv. Drug Delivery Rev. 54 (2002) 477-485
8. Rajan R.S., Li T., Aras M., Sloey C., Sutherland W., Arai H., Briddell R., Kinstler O., Lueras A.M.K., Zhang Y., Yeghnazar H., Treuheit M., and Brems D.N. Modulation of Protein Aggregation by Polyethylene Glycol Conjugation: GCSF as a Case Study. Protein Sci. 15 (2006) 1063-1075
9. Ramon J., Saez V., Baez R., Aldana R., and Hardy E. PEGylated interferon-z2b: A Branched 40 K Polyethylene Glycol Derivative. Pharmaceut. Res. 22 (2005) 1374-1386
10. DeNardo S.J., Yao Z., Lam K.S., Lamborn K.R., O-Donnell R.T., and Denardo G.L. Effect of Molecular Size of Pegylated Peptide on the Pharmacokinetics and Tumor Targeting in Lymphoma-Bearing Mice. Clin. Cancer Res. 9 (2003) 3854s-3864s
11. Bagal D., Zhang H., and Schnier P.D. Gas-Phase Proton-Transfer Chemistry Coupled with TOF Mass Spectrometry and Ion Mobility-MS for the Facile Analysis of Poly(Ethylene Glycols) and PEGylated Polypeptide Conjugates. Anal. Chem. 80 (2008) 2408-2418
12. Vestling M.M., Murphy C.M., Keller D.A., Fenselau C., Dedinas J., Ladd D.L., and Olsen M.A. A Strategy for Characterization of Polyethylene Glycol-Derivatized Superoxide Dismutase. Drug Metab. Dispos. 21 (1993) 911-917
13. Iafelice R., Cristoni S., Caccia D., Russo R., Rossi-Bernardi L., Lowe K.C., and Perrella M. Identification of the Sites of Deoxyhemoglobin PEGylation. Biochem. J. 403 (2007) 189-196
14. Stigsnaes P., Frokjaer S., Bjerregaard S., van de Weert M., Kingshott P., and Moeller E.H. Characterization and Physical Stability of PEGylated Glucagon. Int. J. Pharm. 330 (2007) 89-98
15. Roberts M.J., and Harris J.M. Attachment of Degradable Poly(Ethylene Glycol) to Proteins Has the potential to Increase a Therapeutic Efficacy. J. Pharm. Sci. 87 (1998) 1440-1445
16. Karas M., and Hillenkamp F. Laser Desorption Ionization of Proteins with Molecular Masses Exceeding 10,000 Daltons. Anal. Chem. 60 (1988) 2299-2301
17. Tanaka K., Wak H., Ido Y., Akita S., Yoshida Y., and Yoshida T. Protein and Polymer Analyses up to m/z 100 000 by Laser Ionization Time-of-Flight Mass Spectrometry. Rapid Commun. Mass Spectrom. 2 (1988) 151-153
18. Karas M., Gluckmann M., and Schafer J. Ionization in Matrix-Assisted Laser Desorption/Ionization: Singly Charged Molecular Ions are the lucky Survivors. J. Mass Spectrom. 35 (2000) 1-12
19. Giannakopulos A.E., Thomas N., Colburn A.W., Reynolds D.J., Raptakis E.N., Makarov A.A., and Derrick P.J. Tandem Time-of-Flight Mass Spectrometer (TOF-TOF) with a Quadratic-Field Ion Mirror. Rev. Sci. Instrum. 73 (2002) 2115-2123
20. Schriemer D.C., and Li L. Detection of High Molecular Weight Narrow Polydisperse Polymers up to 1.5 Million Daltons by MALDI Mass Spectrometry. Anal. Chem. 68 (1996) 2721-2725
21. Schriemer D.C., and Li L. Mass Discrimination in the Analysis of Polydisperse Polymers by MALDI Time-of-Flight Mass Spectrometry. 1. Sample Preparation and Desorption/Ionization Issues. Anal. Chem. 69 (1997) 4169-4175
22. Schriemer D.C., and Li L. Mass Discrimination in the Analysis of Polydisperse Polymers by MALDI Time-of-Flight Mass Spectrometry. 2. Instrumental Issues. Anal. Chem. 69 (1997) 4176-4183
23. Nielen M.W.F. MALDI Time-of-Flight Mass Spectrometry of Synthetic Polymers. Mass Spectrom. Rev. 18 (1999) 309-344
24. Cotter R.J., Griffith W., and Jelinek C. Tandem Time-of-Flight (TOF/TOF) Mass Spectrometry and the Curve-Field Reflectron. J. Chromatogr. B 855 (2007) 2-13
25. Suckau D., Resemann A., Schuerenberg M., Hufnagel P., Franzen J., and Holle A. A novel MALDI LIFT-TOF/TOF Mass Spectrometer for Proteomics. Anal. Bioanal. Chem. 376 (2003) 952-965
26. Macht M., Asperger A., and Deininger S.-O. Comparison of Laser-Induced Dissociation and High-Energy Collision-Induced Dissociation Using Matrix-Assisted Laser Desorption/Ionization Tandem Time-of-Flight (MALDI-TOF/TOF) for Peptide and Protein Identification. Rapid Commun. Mass Spectrom. 18 (2004) 2093-2105
27. Yoo C., Zhao J., Pal M., Hersberger K., Huber C.G., Simeone D.M., Beer D.G., and Lubman D.M. Automated Integration of Monolith-Based Protein Separation with On-Plate Digestion for Mass Spectrometric Analysis of Esophageal Adenocarcinoma Human Epithelial Samples. Electrophoresis 27 (2006) 3643-3451
28. Demirev P.A., Feldman A.B., Kowalski P., and Lin J.S. Top-Down Proteomics for Rapid Identification of Intact Microorganisms. Anal. Chem. 77 (2005) 7455-7461
29. Liu Z., and Schey K. Optimization of a MALDI-TOF/TOF Mass Spectrometer for Intact Protein Analysis. J. Am. Soc. Mass Spectrom. 16 (2005) 482-490
30. Samyn B., Debyser G., Sergeant K., Devreese B., and Beeumen J.V. A Case Study of de Novo Sequence Analysis of N-Sulfonated Peptides by MALDI-TOF/TOF Mass Spectrometry. J. Am. Soc. Mass Spectrom. 15 (2004) 1838-1852
31. Hardouin J. Protein Sequence Information by Matrix-Assisted Laser Desorption/Ionization In-Source Decay Mass Spectrometry. Mass Spectrom. Rev. 26 (2007) 672-682
32. Hardouin J., Hubert-Roux M., Delmas A.F., and Lange C. Identification of Isoenzymes Using Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry. Rapid Commun. Mass Spectrom. 20 (2006) 725-732
33. Suckau D., and Resemann A. T3-Sequencing: Targeted Characterization of the N- and C-Termini of Undigested Proteins by Mass Spectrometry. Anal. Chem. 75 (2003) 5817-5824
34. Lennon J.J., and Walsh K.A. Direct Sequence Analysis of Proteins by In-Source Fragmentation During Delayed Ion Extraction. Protein Sci. 6 (1997) 2446-2453
35. Brown R.S., and Lennon J.J. Sequence-Specific Fragmentation of Matrix-Assisted Laser-Desorbed Protein/Peptide Ions. Anal. Chem. 67 (1995) 3990-3999
36. Schnaible V., Wefing S., Resemann A., Suckau D., Bucker A., Wolf-Kummeth S., and Hoffmann D. Screening for Disulfide Bonds in Proteins by MALDI In-Source Decay and LIFT-TOF/TOF MS. Anal. Chem. 74 (2002) 4980-4988
37. Demeure K., Quinton L., Gabelica V., and Pauw E.D. Rational Selection of the Optimum MALDI Matrix for Top-Down Proteomics by In-Source Decay. Anal. Chem. 79 (2007) 8678-8685
38. Takayama M. In-Source Decay Characteristics of Peptides in Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry. J. Am. Soc. Mass Spectrom. 12 (2001) 420-427
39. Kocher T., Engstrom A., and Zubarev R.A. Fragmentation of Peptides in MALDI In-Source Decay Mediated by Hydrogen Radicals. Anal. Chem. 77 (2005) 172-177
40. Gegg, C.; Miranda, L.; Walker, K.; Johnson, E.; Holder, J. R.; Wright, M. E.; D'Amico, D. C. WO 2007/048026.
41. Holle A., Haase A., Kayser M., and Hohndorf J. Optimizing UV Laser Focus Profiles for Improved MALDI Performance. J. Mass Spectrom. 41 (2006) 705-716
42. Na D.H., and Lee K.C. Capillary Electrophoretic Characterization of PEGylated Human Parathyroid Hormone with Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass spectrometry. Anal. Biochem. 331 (2004) 322-328
43. Na D.H., Park M.O., Choi S.Y., Kim Y.S., Lee S.S., Yoo S.D., Lee H.S., and Lee K.C. Identification of the Modifying Sites of Mono-PEGylated Salmon Calcitonins by Capillary Electrophoresis and MALDI-TOF Mass Spectrometry. J. Chromatogr. B 754 (2001) 259-263
44. Dou H., Zhang M., Zhang Y., and Yin C. Synthesis and Purification of mono-PEGylated insulin. Chem. Biol. Drug Design 69 (2007) 132-138
45. Veronese F.M. Peptide and Protein PEGylation: A Review of Problems and Solution. Biomaterials 22 (2001) 405-417
46. Esposito P., Barbero L., Caccia P., D'Antonio M., Pizuet G., and Veronese F.M. PEGylation of Growth Hormone-Releasing Hormone (GRF) Analogues. Adv. Drug Delivery Rev. 55 (2003) 1279-1291
47. Kaufmann R., Kirsch D., and Spengler B. Sequencing of Peptides in a Time-of-Flight Mass Spectrometer: Evaluation of Postsource Decay Following Matrix-Assisted Laser Desorption Ionization (MALDI). Int. J. Mass. Spectrom. Ion Processes 131 (1994) 355-385
48. Quinton L., Demeure K., Dobson R., Gilles N., Gabelica V., and Pauw E.D. New Method for Characterizing Highly Disulfide-Bridged Peptides in Complex Mixtures: Application to Toxin Identification from Crude Venoms. J. Proteome Res. 6 (2007) 3216-3223