The chemistry of irreversible capture

Advanced Drug Delivery Reviews

Volumn 60, Issue 12, 2008, Pages 1383-1388

  Meares, Claude F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Affinity label; Antibody; Bifunctional chelating agent; DOTA; Macrocycle; Mutagenesis; Protein engineering; Receptor

Indexed keywords

ANTIBODIES; BINDING ENERGY; BIOCHEMISTRY; BIOMOLECULES; CELL MEMBRANES; CHELATION; COMPLEXATION; LIGANDS; MOLECULES; SYNTHESIS (CHEMICAL);

BINDING SPECIFICITIES; BIOLOGICAL MOLECULES; CELL SURFACES; CHEMICAL SYNTHESES; DELIVERY SYSTEMS; ELSEVIER (CO); FAB' FRAGMENTS; GENETIC MANIPULATIONS; LIGAND BINDING SITES; SINGLE CHAIN FV; SMALL MOLECULES; SPECIFIC RECOGNITION;

BINDING SITES;

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID; CARCINOEMBRYONIC ANTIGEN; IMMUNOGLOBULIN F(AB) FRAGMENT; INDIUM 111; MITOMYCIN A; MITOMYCIN C; MONOCLONAL ANTIBODY; MONOCLONAL ANTIBODY 2D12.5; MONOCLONAL ANTIBODY CHA255; MONOCLONAL ANTIBODY ZCE025; N [4 (3 BROMOANILINO) 6 QUINAZOLINYL]ACRYLAMIDE; PENICILLIN G; WORTMANNIN;

AFFINITY LABELING; ANTIBODY AFFINITY; ANTIBODY SPECIFICITY; BINDING SITE; CROSS LINKING; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG TARGETING; HUMAN; LIGAND BINDING; METAL BINDING; MOLECULAR PROBE; PRIORITY JOURNAL; PROTEIN ENGINEERING; REVIEW; SITE DIRECTED MUTAGENESIS;

AFFINITY LABELS; ANTIBODIES; ANTIBODY AFFINITY; CHELATING AGENTS; DRUG DELIVERY SYSTEMS; PROTEIN ENGINEERING;

EID: 46849112799     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.addr.2008.04.010     Document Type: Review

References (32)

1. Reardan D.T., Meares C.F., Goodwin D.A., McTigue M., David G.S., Stone M.R., Leung J.P., Bartholomew R.M., and Frincke J.M. Antibodies against metal chelates. Nature 316 (1985) 265-268
2. Stickney D.R., Anderson L.D., Slater J.B., Ahlem C.N., Kirk G.A., Schweighardt S.A., and Frincke J.M. Bifunctional antibody: a binary radiopharmaceutical delivery system for imaging colorectal carcinoma. Cancer Res. 51 (1991) 6650-6655
3. Love R.A., Villafranca J.E., Aust R.M., Nakamura K.K., Jue R.A., Major J.G., Radhakrishnan R., and Butler W.F. How the anti-(metal chelate) antibody CHA255 is specific for the metal ion of its antigen: X-ray structures for two Fab'/hapten complexes with different metals in the chelate. Biochemistry 32 (1993) 10950-10959
4. Chmura A.J., Orton M.S., and Meares C.F. Antibodies with infinite affinity. Proc. Natl. Acad. Sci. U. S. A. 98 (2001) 8480-8484
5. Baker B.R., Lee W.W., Tong E., and Ross L.O. 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 (1961) 3713-3714
6. Schoellmann G., and Shaw E. Direct evidence for the presence of histidine in the active center of chymotrypsin. Biochemistry 2 (1963) 252-255
7. Wofsy L., Metzger H., and Singer S.J. Affinity labeling-A general method for labeling the active sites of antibody and enzyme molecules. Biochemistry 1 (1962) 1031-1039
8. 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. 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 (1998) 12022-12027
9. Yocum R.R., Waxman D.J., Rasmussen J.R., and Strominger J.L. 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 (1979) 2730-2734
10. Chmura A.J., Schmidt B.D., Corson D.T., Traviglia S.T., and Meares C.F. Electrophilic chelating agents for binding of metal chelates to engineered antibodies. J. Control. Release 78 (2002) 249-258
11. Corneillie T.M., Whetstone P.A., Lee K.C., Wong J.P., and Meares C.F. Converting weak binders into infinite binders. Bioconjug. Chem. 15 (2004) 1389-1391
12. Corneillie T.M., Lee K.C., Whetstone P.A., Wong J.P., and Meares C.F. Irreversible engineering of the multielement-binding antibody 2D12.5 and its complementary ligands. Bioconjug. Chem. 15 (2004) 1392-1402
13. Corneillie T.M., Whetstone P.A., and Meares C.F. Irreversibly binding anti-metal chelate antibodies: artificial receptors for pretargeting. J. Inorg. Biochem. 100 (2006) 882-890
14. Butlin N.G., and Meares C.F. Antibodies with infinite affinity: origins and applications. Acc. Chem. Res. 39 (2006) 780-787
15. Fersht A. Enzyme Structure and Mechanism. 2nd Ed. (1985), Freeman, New York 56-63
16. Pollack S.J., Nakayama G.R., and Schultz P.G. Introduction of nucleophiles and spectroscopic probes into antibody combining sites. Science (Washington, DC) 242 (1988) 1038-1040
17. Salerno A., and Lawrence D.S. Covalent modification with concomitant inactivation of the cAMP-dependent protein kinase by affinity labels containing only L-amino acids. J. Biol. Chem. 268 (1993) 13043-13049
18. Yan X.W., Corbin J.D., Francis S.H., and Lawrence D.S. Precision targeting of protein kinases-an affinity label that inactivates the cGMP- but not the cAMP-dependent protein kinase. J. Biol. Chem. 271 (1996) 1845-1848
19. Levitsky K., Ciolli C.J., and Belshaw P.J. Selective inhibition of engineered receptors via proximity-accelerated alkylation. Org. Lett. 5 (2003) 693-696
20. Chen G., Heim A., Riether D., Yee D., Milgrom Y., Gawinowicz M.A., and Sames D. Reactivity of functional groups on the protein surface: development of epoxide probes for protein labeling. J. Am. Chem. Soc. 125 (2003) 8130-8133
21. Blanca M., Cornejo-Garcia J.A., Torres M.J., and Mayorga C. Specificities of B cell reactions to drugs. The penicillin model. Toxicology 209 (2005) 181-184
22. Nicholas R.A., and Strominger J.L. Site-directed mutants of a soluble form of penicillin-binding protein 5 from Escherichia coli and their catalytic properties. J. Biol. Chem. 263 (1988) 2034-2040
23. Wymann M.P., Bulgarelli-Leva G., Zvelebil M.J., Pirola L., Vanhaesebroeck B., Waterfield M.D., and Panayotou G. Wortmannin inactivates phosphoinositide 3-kinase by covalent modification of Lys-802, a residue involved in the phosphate transfer reaction. Mol. Cell. Biol. 16 (1996) 1722-1733
24. Wipf P., and Halter R.J. Chemistry and biology of wortmannin. Org. Biomol. Chem. 3 (2005) 2053-2061
25. Norman B.H., Paschal J., and Vlahos C.J. Synthetic studies on the furan ring of wortmannin. Bioorg. Med. Chem. Lett. 5 (1995) 1183-1186
26. Kunz K.R., Iyengar B.S., Dorr R.T., Alberts D.S., and Remers W.A. Structure-activity relationships for mitomycin C and mitomycin A analogues. J. Med. Chem. 34 (1991) 2281-2286
27. Boamah E.K., White D.E., Talbott K.E., Arva N.C., Berman D., Tomasz M., and Bargonetti J. Mitomycin-DNA adducts induce p53-dependent and p53-independent cell death pathways. ACS Chem. Biol. 2 (2007) 399-407
28. Corneillie T.M., Fisher A.J., and Meares C.F. Crystal structures of two complexes of the rare-Earth-DOTA-binding antibody 2D12.5: ligand generality from a chiral system. J. Am. Chem. Soc. 125 (2003) 15039-15048
29. Corneillie T.M., Whetstone P.A., Fisher A.J., and Meares C.F. A rare earth-DOTA-binding antibody: probe properties and binding affinity across the lanthanide series. J. Am. Chem. Soc. 125 (2003) 3436-3437
30. Krusemark C.J., and Belshaw P.J. Covalent labelling of fusion proteins in live cells via an engineered receptor-ligand pair. Org. Biomol. Chem. 5 (2007) 2201-2204
31. Noll D.M., and Clarke N.D. Covalent capture of a human O(6)-alkylguanine alkyltransferase-DNA complex using N(1),O(6)-ethanoxanthosine, a mechanism-based crosslinker. Nucleic Acids Res. 29 (2001) 4025-4034
32. Heinis C., Schmitt S., Kindermann M., Godin G., and Johnsson K. Evolving the substrate specificity of O6-alkylguanine-DNA alkyltransferase through loop insertion for applications in molecular imaging. ACS Chem. Biol. 1 (2006) 575-584