Amino acid analysis of peptide loading ratios in conjugate vaccines: A comparison of direct electrochemical detection and 6-aminoquinolyl-N- hydroxysuccinimidyl carbamate pre-column derivatization methods

Bioconjugate Chemistry

Volumn 19, Issue 1, 2008, Pages 322-326

  Nahas, Deborah D ^a   Palladino, Jennifer S ^a   Joyce, Joseph G ^a   Hepler, Robert W ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL DETECTION; HYDROLYSIS; PEPTIDES;

6-AMINOQUINOLYL-N-HYDROXYSUCCINIMIDYL CARBAMATES; AMINO ACID ANALYSIS; AMINO-ACIDS; CARRIER PROTEINS; CONJUGATE VACCINE; DERIVATIZATION METHOD; ELECTROCHEMICAL DETECTION; LOADING RATIO; PEPTIDE LOADING; PRE-COLUMN DERIVATISATION;

AMINO ACIDS;

6 AMINOQUINOLYL N HYDROXYSUCCINIMIDYLCARBAMATE; AMINO ACID; AMINOCAPROIC ACID; BUFFER; CARBAMIC ACID DERIVATIVE; CARBOHYDRATE; CYSTEINE DERIVATIVE; HOMOCYSTEINE; OUTER MEMBRANE PROTEIN; PEPTIDE DERIVATIVE; S CARBOXYMETHYLHOMOCYSTEINE; S DICARBOXYETHYLCYSTEINE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG; VACCINE;

AMINO ACID ANALYSIS; AMINO ACID COMPOSITION; ARTICLE; COVALENT BOND; DERIVATIZATION; DRUG CONJUGATION; DRUG SYNTHESIS; ELECTROCHEMICAL ANALYSIS; HYDROLYSIS; NEISSERIA MENINGITIDIS; NONHUMAN; QUANTITATIVE ANALYSIS; TEMPERATURE;

NEISSERIA MENINGITIDIS;

EID: 38949206865     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc700232z     Document Type: Article

References (23)

1. Fan, J., Liang, X., Horton, M. S., Perry, H. C., Citron, M. P., Heidecker, G. J., Fu, T.-M., Joyce, J., Przysiecki, C. T., Keller, P. M., Garsky, V. M., Ionescu, R., Rippeon, Y., Shi, L., Chastain, M. A., Condra, J. H., Davies, M.-E., Liao, J., Emini, E. A., and Shiver, J. W. (2004) Preclinical study of influenza virus A M2 peptide conjugate vaccines in mice, ferrets, and rhesus monkeys. Vaccine 22, 2993-3003.
2. Girard, M. P., Preziosi, M. P., Aguado, M. T., and Kieny, M. P. (2006) A review of vaccine research and development: meningococcal disease. Vaccine 24, 4692-4700.
3. Hatsukami, D. K., Rennard, S., Jorenby, D., Fiore, M., Koopmeiners, J., de Vos, A., Horwith, G., and Pentel, P. R. (2005) Safety and immunogenicity of a nicotine conjugate vaccine in current smokers. Clin. Pharmacol. Ther. 78, 456-467.
4. Pérez-Melgosa, M., Ochs, H. D., Linsley, P. S., Laman, J. D., van Meurs, M., Flavell, R. A., Ernst, R. K., Miller, S. I., and Wilson, C. B. (2001) Carrier-mediated enhancement of cognate T cell help: the basis for enhanced immunogenicity of meningococcal outer membrane protein polysaccharide conjugate vaccine. Eur. J. Immunol. 31, 2373-2381.
5. El Bashir, H., Heath, P. T., Papa, T., Ruggeberg, J. U., Johnson, N., Sinha, R., Balfour, G., and Booy, R. (2006) Antibody responses to meningococcal (groups A, C, Y and W135) polysaccharide diphtheria toxoid conjugate vaccine in children who previously received meningococcal C conjugate vaccine. Vaccine 24, 2544-2549.
6. Donnelly, J. J., Deck, R. R., and Liu, M. A. (1990) Immunogenicity of a Haemophilus influenzae polysaccharide-Neisseria meningitidis outer membrane protein complex conjugate vaccine. J. Immunol. 145, 3071-3079.
7. Bianchi, E., Liang, X., Ingallinella, P., Finotto, M., Chastain, M. A., Fan, J., Fu, T. M., Song, H. C., Horton, M. S., Freed, D. C., Manger, W., Wen, E., Shi, L., Ionescu, R., Price, C., Wenger, M., Emini, E. A., Cortese, R., Ciliberto, G., Shiver, J. W., and Pessi, A. (2005) Universal influenza B vaccine based on the maturational cleavage site of the hemagglutinin precursor. J. Virol. 79, 7380-7388.
8. Joyce, J., Cook, J., Chabot, D., Hepler, R., Shoop, W., Xu, Q., Stambaugh, T., Aste-Amezaga, M., Wang, S., Indrawati, L., Bruner, M., Friedlander, A., Keller, P., and Caulfield, M. (2006) Immunogenicity and protective efficacy of Bacillus anthracis poly-gamma-D-glutamic acid capsule covalently coupled to a protein carrier using a novel triazine-based conjugation strategy. J. Biol. Chem. 281, 4831-4843.
9. Lindberg, A. A. (1999) Glycoprotein conjugate vaccines. Vaccine 17, S28-S36.
10. Liu, M. A., Friedman, A., Oliff, A. I., Tai, J., Martinez, D., Deck, R. R., Shieh, J. T., Jenkins, T. D., Donnelly, J. J., and Hawe, L. A. (1992) A vaccine carrier derived from + with mitogenic activity for lymphocytes. Proc. Natl. Acad. Sci. U.S.A. 89, 4633-4637.
11. Massari, P., Henneke, P., Ho, Y., Latz, E., Golenbock, D. T., and Wetzler, L. M. (2002) Cutting edge: immune stimulation by neisserial porins is toll-like receptor 2 and MyD88 dependent. J. Immunol. 168, 1533-1537.
12. Shuler, K. R., Dunham, R. G., and Kanda, P. (1992) A simplified method for determination of peptide-protein molar ratios using amino acid analysis. J. Immunol. Methods 156, 137-149.
13. Tsao, J. L., Lin, X., Lackland, H., Tous, G., Wu, Y. L., and Stein, S. (1991) Internally standardized amino acid analysis for determining peptide/carrier protein coupling ratio. Anal. Biochem. 197, 137-142.
14. Marburg, S., Jorn, D., Tolman, R. L., Arison, B., McCauley, J., Kniskern, P. J., Hagopian, A., and Vella, P. P. (1986) Bimolecular chemistry of macromolecules: synthesis of bacterial polysaccharide conjugates with Neisseria meningitidis membrane protein. J. Am. Chem. Soc. 108, 5282-5287.
15. Millipore Corporation (1993) Waters AccQTag Chemistry Package Instruction Manual, Manual Number WAT052874, Millipore Corporation, Milford, PA.
16. Cohen, S. A. (2003) Amino acid analysis using pre-column derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate. Analysis of hydrolyzed proteins and electroblotted samples. Methods Mol. Biol. 211, 143-154.
17. Cohen, S. A. (2000) Amino acid analysis using precolumn derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate. Methods Mol. Biol. 159, 39-47.
18. De Antonis, K. M., Brown, P. R., and Cohen, S. A. (1994) High-performance liquid chromatographic analysis of synthetic peptides using derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate. Anal. Biochem. 223, 191-197.
19. Strydom, D. J., and Cohen, S. A. (1994) Comparison of amino acid analyses by phenylisothiocyanate and 6-aminoquinolyl-n-hydroxysuccinimidyl carbamate precolumn derivatization. Anal. Biochem. 222, 19-28.
20. Clarke, A. P., Jandik, P., Rocklin, R. D., Liu, Y., and Avdalovic, N. (1999) An integrated amperometry waveform for the direct, sensitive detection of amino acids and amino sugars following anion-exchange chromatography. Anal. Chem. 71, 2774-2781.
21. Yu, H., Ding, Y.-S., and Mou, S.-F. (2003) Some factors affecting separation and detection of amino acids by high-performance anion-exchange chromatography with integrated pulsed amperometric detection. J. Chromatogr. A 997, 145-153.
22. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J. (1951) Protein measurement with the folin phenol reagent. J. Biol. Chem. 193, 265-275.
23. Smyth, D. J., Blumenfield, O. O., and Konigsberg, W. (1964) Reactions of N-ethylmaleimide with peptides and amino acids. Biochem. J. 91, 589-595.