Cysteinylated protein as reactive disulfide: An alternative route to affinity labeling

Bioconjugate Chemistry

Volumn 19, Issue 1, 2008, Pages 15-19

  Miao, Zheng ^a   McCoy, Mark R ^a   Singh, Diment D ^a   Barrios, Brianda ^a   Hsu, Oliver L ^a   Cheal, Sarah M ^a   Meares, Claude F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; BINDING SITES; COMPLEXATION; LIGANDS; MEDICAL APPLICATIONS; MONOMERS; SULFUR COMPOUNDS;

ALTERNATIVE ROUTES; ANTIBODY BINDING SITES; BIOLOGY AND MEDICINE; CHEMICAL DESIGNS; DISULFIDE LINKAGES; ELECTROPHILES; LABELINGS; RECEPTOR-LIGAND COMPLEX; STANDARD PRACTICES; SYNTHETIC LIGANDS;

AMINO ACIDS;

CYSTEINE; DISULFIDE; IMMUNOGLOBULIN F(AB) FRAGMENT; MONOMER; PROTEIN DERIVATIVE; THIOL DERIVATIVE;

AFFINITY LABELING; ARTICLE; BINDING AFFINITY; CONJUGATION; COVALENT BOND; DISULFIDE BOND; NONHUMAN; PROTEIN ENGINEERING; PROTEIN EXPRESSION;

EID: 38949163295     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc700330j     Document Type: Article

References (26)

1. Means, G. E., and Feeney, R. E. (1990) Chemical modifications of proteins: history and applications. Bioconjugate Chem. 1, 2-12.
2. Baker, B. R., Lee, W. W., Tong, E., and Ross, L. O. (1961) Potential anticancer agents. LXVI. Non-classical antimetabolites. III. 4-(Iodoacetamido)-salicylic acid, an exo alkylating irreversible inhibitor of glutamic dehydrogenase. J. Am. Chem. Soc. 83, 3713-3714.
3. Schoellmann, G., and Shaw, E. (1963) Direct evidence for the presence of histidine in the active center of chymotrypsin. Biochemistry 2, 252-255.
4. Wofsy, L., Metzger, H., and Singer, S. J. (1962) Affinity labeling-A general method for labeling the active sites of antibody and enzyme molecules. Biochemistry 1, 1031-1039.
5. Fry, D. W., Bridges, A. J., Denny, W. A., Doherty, A., Greis, K. D., Hicks, J. L., Hook, K. E., Keller, P. R., Leopold, W. R., Loo, J. A., McNamara, D. J., Nelson, J. M., Sherwood, V., Smaill, J. B., Trumpp-Kallmeyer, S., and Dobrusin, E. M. (1998) Specific, irreversible inactivation of the epidermal growth factor receptor and erbB2, by a new class of tyrosine kinase inhibitor. Proc. Natl. Acad. Sci. U.S.A. 95, 12022-12027.
6. Yocum, R. R., Waxman, D. J., Rasmussen, J. R., and Strominger, J. L. (1979) Mechanism of penicillin action: penicillin and substrate bind covalently to the same active site serine in two bacterial D-alanine carboxypeptidases. Proc. Natl. Acad. Sci. U.S.A. 76, 2730-2734.
7. Chmura, A. J., Orton, M. S., and Meares, C. F. (2001) Antibodies with infinite affinity. Proc. Natl. Acad. Sci. U.S.A. 98, 8480-8484.
8. Chmura, A. J., Schmidt, B. D., Corson, D. T., Traviglia, S. T., and Meares, C. F. (2002) Electrophilic chelating agents for binding of metal chelates to engineered antibodies. J. Controlled Release 78, 249-258.
9. Corneillie, T. M., Whetstone, P. A., Lee, K. C., Wong, J. P., and Meares, C. F. (2004) Converting weak binders into infinite binders. Bioconjugate Chem. 15, 1389-1391.
10. Corneillie, T. M., Lee, K. C., Whetstone, P. A., Wong, J. P., and Meares, C. F. (2004) Irreversible engineering of the multielement-binding antibody 2D12. 5 and its complementary ligands. Bioconjugate Chem. 15, 1392-1402.
11. Corneillie, T. M., Whetstone, P. A., and Meares, C. F. (2006) Irreversibly binding anti-metal chelate antibodies: Artificial receptors for pretargeting. J. Inorg. Biochem. 100, 882-890.
12. Butlin, N. G., and Meares, C. F. (2006) Antibodies with infinite affinity: origins and applications. Acc. Chem. Res. 39, 780-787.
13. Erlanson, D. A., Braisted, A. C., Raphael, D. R., Randal, M., Stroud, R. M., Gordon, E. M., and Wells, J. A. (2000) Site-directed ligand discovery. Proc. Natl. Acad. Sci. U.S.A. 97, 9367-9372.
14. Arkin, M. R., Randal, M., DeLano, W. L., Hyde, J., Luong, T. N., Oslob, J. D., Raphael, D. R., Taylor, L., Wang, J., McDowell, R. S., Wells, J. A., and Braisted, A. C. (2003) Binding of small molecules to an adaptive protein-protein interface. Proc. Natl. Acad. Sci. U.S.A. 100, 1603-1608.
15. Buck, E., and Wells, J. A. (2005) Disulfide trapping to localize small-molecule agonists and antagonists for a G protein-coupled receptor. Proc. Natl. Acad. Sci. U.S.A. 102, 2719-2724.
16. Pollack, S. J., Nakayama, G. R., and Schultz, P. G. (1988) Introduction of nucleophiles and spectroscopic probes into antibody combining sites. Science (Washington, DC) 242, 1038-1040.
17. Salerno, A., and Lawrence, D. S. (1993) Covalent modification with concomitant inactivation of the cAMP-dependent protein kinase by affinity labels containing only L-amino acids. J. Biol. Chem. 268, 13043-13049.
18. Yan, X. W., Corbin, J. D., Francis, S. H., and Lawrence, D. S. (1996) Precision targeting of protein kinases - An affinity label that inactivates the cGMP- but not the cAMP-dependent protein kinase. J. Biol. Chem. 271, 1845-1848.
19. Levitsky, K., Ciolli, C. J., and Belshaw, P. J. (2003) Selective inhibition of engineered receptors via proximity-accelerated alkylation. Org. Lett. 5, 693-696.
20. Chen, G., Heim, A., Riether, D., Yee, D., Milgrom, Y., Gawinowicz, M. A., and Sames, D. (2003) Reactivity of functional groups on the protein surface: development of epoxide probes for protein labeling. J. Am. Chem. Soc. 125, 8130-8133.
21. Blanca, M., Cornejo-Garcia, J. A., Torres, M. J., and Mayorga, C. (2005) Specificities of B cell reactions to drugs. The penicillin model. Toxicology 209, 181-184.
22. Gadgil, H. S., Bondarenko, P. V., Pipes, G. D., Dillon, T. M., Banks, D., Abel, J., Kleemann, G. R., and Treuheit, M. J. (2006) Identification of cysteinylation of a free cysteine in the Fab region of a recombinant monoclonal IgG1 antibody using Lys-C limited proteolysis coupled with LC/MS analysis. Anal. Biochem. 355, 165-174.
23. Odaka, M., Kiribuchi, K., Allison, W. S., and Yoshida, M. (1993) In vivo affinity label of a protein expressed in Escherichia coli. Coenzyme A occupied the AT(D)P binding site of the mutant F1-ATPase beta subunit (Y307C) through a disulfide bond. FEBS Lett. 336, 231-235.
24. Stimmel, J. B., Merrill, B. M., Kuyper, L. F., Moxham, C. P., Hutchins, J. T., Fling, M. E., and Kull, F. C., Jr. (2000) Site-specific conjugation on serine right-arrow cysteine variant monoclonal antibodies. J. Biol. Chem. 275, 30445-30450.
25. Weiss, U. (1947) N-Arylamides of mercaptoacetic acid. I. Analogs of a carbamylmercaptoacetanilide. J. Am. Chem. Soc. 69, 2682-2684.
26. Jones, D. P., Mody, V. C., Jr., Carlson, J. L., Lynn, M. J., and Sternberg, P., Jr. (2002) Redox analysis of human plasma allows separation of pro-oxidant events of aging from decline in antioxidant defenses. Free Rad. Biol. Med. 33, 1290-1300.