Total solid-phase synthesis of 1,4,7,10-tetraazacyclododecane-N,N',N'',N'''-tetraacetic acid-functionalized peptides for radioimmunotherapy

Bioconjugate Chemistry

Volumn 10, Issue 2, 1999, Pages 316-320

  Peterson, James J ^a   Pak, Roger H ^a   Meares, Claude F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RESINS; SYNTHESIS (CHEMICAL);

DEPROTECTION; FUNCTIONALIZATIONS; FUNCTIONALIZED; MACROCYCLICS; PEPTIDE AMIDES; RADIOIMMUNOTHERAPY; SOLID PHASE SYNTHESIS; TETRAACETIC ACID; TOTAL SOLIDS;

PEPTIDES;

EID: 0033104341     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc980118t     Document Type: Article

References (16)

1. Desreux, J. F. (1980) Nuclear magnetic resonance spectroscopy of lanthanide complexes with a tetraacetic tetraaza macrocycle. Unusual conformation properties. Inorg. Chem. 19, 1319-1324.
2. Loncin, M. F., Desreux, J. F., and Merciny, E. (1986) Coordination of lanthanides by two polyamino polycarboxylic macrocycles: Formation of highly stable lanthanide complexes. Inorg. Chem. 25, 2646-2648.
3. Lewis, M. R., Raubitschek, A., and Shively, J. E. (1994) A facile, water soluble method for modification of proteins with DOTA. Use of elevated temperature and optimized pH to achieve high specific activity and high chelate stability in radiolabeled immunoconjugates. Bioconjugate Chem. 5, 565-576.
4. Moi, M. K., Meares, C. F., and DeNardo, S. J. (1988) The peptide way to macrocyclic bifunctional chelating agents: Synthesis of 2-(p-nitrobenzyl)-1,4,7,10-tetraazacyclododecane- N,N′,N″,N‴-tetraacetic acid and study of its yttrium(III) complex. J. Am. Chem. Soc. 110, 6266-6267.
5. Renn, O., and Meares, C. F. (1992) Large scale synthesis of the bifunctional chelating agent 2-(p-nitrobenzyl)-1,4,7,10- tetraazacyclododecane-N,N′,N″,N‴-tetraacetic acid, and the determination of its enantiomeric purity by chiral chromatography. Bioconjugate Chem. 3, 563-569.
6. Cox, J. P. L., Craig, A. S., Helps, I. M., Jankowski, K. J., Parker, D., Eaton, M. A. W., Millican, A. T., Millar, K., Beeley, N. R. A., and Boyce, B. A. (1990) Synthesis of C- and N-functionalized derivatives of 1,4,7-triazacyclononane-1,4,7- triyltriacetic acid (NOTA), 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayltetraacetic acid (DOTA), and diethylenetriaminepentaacetic acid (DTPA): Bifunctional complexing agents for the derivatization of antibodies. J. Chem. Soc., Perkin Trans. 1, 2567-2576.
7. Sieving, P. F., Watson, A. D., and Rocklage, S. M. (1990) Preparation and characterization of paramagnetic polychelates and their protein conjugates. Bioconjugate Chem. 1, 65-71.
8. Sherry, A. D., Brown, R. D., III, Geraldes, C. F. G. C., Koenig, S. H., Kuan, K.-T., and Spiller, M. (1989) Synthesis and characterization of the gadolinium(3+) complex of DOTA- propylamide: A model DOTA-protein conjugate. Inorg. Chem. 28, 620-622.
9. 90Y labeling of proteins. Nucl. Med. Biol. 19, 239-244.
10. Li, M., and Meares, C. F. (1993) Synthesis, metal chelate stability studies, and enzyme digestion of a peptide-linked DOTA derivative and its corresponding radiolabeled immunoconjugates. Bioconjugate Chem. 4, 275-283.
11. Meares, C. F., McCall, M. J., Reardan, D. T., Goodwin, D. A., Diamante, C. I., and McTigue, M. (1984) Conjugation of antibodies with bifunctional chelating agents: Isothiocyantate and bromoacetamide reagents, methods of analysis, and subsequent addition of metal ions. Anal. Biochem. 142, 68-78.
12. Kruper, W. J., Rudolf, P. R., and Langhoff, C. A. (1993) Unexpected selectivity in the alkylation of polyazamacrocycles. J. Org. Chem. 58, 3869-3876.
13. Peterson, J. J., and Meares, C. F. (1998) Cathepsin substrates as cleavable peptide linkers in bioconjugates, selected from a fluorescence quench combinatorial library. Bioconjugate Chem. 9, 618-626.
14. Hudson, D. (1988) Methodological implications of simultaneous solid-phase peptide synthesis. 1. Comparison of different coupling procedures. J. Org. Chem. 53, 617-624.
15. Perich, J. (1992) Efficient solid-phase synthesis of mixed Thr(P)-, Ser(P)- and Tyr(P)-containing phosphopeptides by "global" "phosphite-triester" phosphorylation. Int. J. Pept. Protein Res. 40, 134-140.
16. Liberatore, F. A., Comeau, R. D., McKearin, J. M., Pearson, D. A., Belonga, B. Q., III, Brocchini, S. J., Kath, J., Phillips, T., Oswell, K., and Lawton, R. G. (1990) Site-directed chemical modification and cross-linking of a monoclonal antibody using equilibrium transfer alkylating cross-link reagents. Bioconjugate Chem. 1, 36-50.