Biotin reagents for antibody pretargeting. 7. Investigation of chemically inert biotinidase blocking functionalities for synthetic utility

Bioconjugate Chemistry

Volumn 17, Issue 6, 2006, Pages 1514-1522

  Wilbur, D Scott ^a   Hamlin, Donald K ^a   Chyan, Ming Kuan ^a  

^a UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; BINDING ENERGY; CARBOXYLATION; COENZYMES; DISSOCIATION; ETHERS; METHANOL; SYNTHESIS (CHEMICAL);

AMINOBUTYRIC ACIDS; BLOCKINGS; CARBOXYLATE GROUPS; HYDROXYMETHYL GROUPS; IN-VIVO; METHYL ETHERS; MULTISTEPS; SARCOSINE; STABILIZING GROUPS; SYNTHETIC UTILITY;

AMINO ACIDS;

2 AMINOBUTYRIC ACID; 4 AMINOBUTYRIC ACID; ASPARTIC ACID; BIOTIN DERIVATIVE; BIOTINIDASE; CARBOXYLIC ACID; CYANOCOBALAMIN; ENZYME INHIBITOR; ETHER DERIVATIVE; REAGENT; SARCOSINE; SERINE; SERINE DERIVATIVE; STREPTAVIDIN; VALINE;

ARTICLE; BINDING AFFINITY; CHEMICAL BOND; DISSOCIATION; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPOPHILICITY; RADIOIODINATION; SERUM; SYNTHESIS;

EID: 33845200615     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060084m     Document Type: Article

References (36)

1. Goodwin, D. A., and Meares, C. F. (1997) Pretargeting: General Principles. Cancer (Suppl.) 80, 2675-2680.
2. Zhu, H., Jain, R. K., and Baxter, L. T. (1998) Tumor Pretargeting for Radioimmunodetection and Radioimmunotherapy. J. Nucl. Med. 39, 65-76.
3. Stoldt, H. S., Aftab, F., Chinol, M., Paganelli, G., Luca, F., Testori, A., and Geraghty, J. G. (1997) Pretargeting Strategies for Radioimmunoguided Tumour Localisation and Therapy. Eur. J. Cancer 33, 186-192.
4. Wright, L. D., Driscoll, C. A., and Boger, W. P. (1954) Biocytinase, an enzyme concerned with hydrolytic cleavage of biocytin. Proc. Soc. Exp. Biol. Med. 86, 335-7.
5. Wolf, B., Hymes, J., and Heard, G. S. (1990) Biotinidase Methods Enzymol. 184, 103-111.
6. Oizumi, J., and Hayakawa, K. (1993) Biocytin-specific 110-kDa biotinidase from human serum. Clin. Chim. Acta. 215, 63-71.
7. Hymes, J., Fleischhauer, K., and Wolf, B. (1997) Biotinidase in Serum and Tissues. Methods Enzymol. 279, 422-434.
8. Pispa, J. (1965) Animal Biotinidase. Ann. Med. Expl. Biol. Fenniae 43, 3-40.
9. Ballard, T. D., Wolff, J., Griffin, J. B., Stanley, J. S., van Calcar, S., and Zempleni, J. (2002) Biotinidase catalyzes debiotinylation of histones. Eur. J. Nutr. 41, 78-84.
10. Chauhan, J., and Dakshinamurti, K. (1988) Role of Human Serum Biotinidase as Biotin-Binding Protein. Biochem. J. 256, 265-270.
11. Stanley, C. M., Hymes, J., and Wolf, B. (2004) Identification of alternatively spliced human biotinidase mRNAs and putative localization of endogenous biotinidase. Mol. Genet. Metab. 81, 300-12.
12. Zempleni, J. (2005) Uptake, localization, and noncarboxylase roles of biotin. Annu. Rev. Nutr. 25, 175-96.
13. Hayakawa, K., Yoshikawa, K., Oizumi, J., and Yamauchi, K. (1997) Determination of Biotinidase Activity with Biotinyl-6-aminoquinoline as Substrate. Methods Enzymol. 279, 435-442.
14. Wolf, B., and McVoy, J. S. (1983) A sensitive radioassay for biotinidase activity: deficient activity in tissues of serum biotinidase-deficient individuals. Clin. Chim. Acta 135, 275-281.
15. Livaniou, E., Kakabakos, S. E., Evangelatos, S. A., Evangelatos, G. P., and Ithakissios, D. S. (1997) Determination of Serum Biotinidase Activity with Radioiodinated Biotinylamide Analogs. Methods Enzymol. 279, 442-451.
16. Chauhan, J., and Dakshinamurti, K. (1986) Purification and Characterization of Human Serum Biotinidase. J. Biol. Chem. 261, 4268-4275.
17. Nilsson, L., and Kagedal, B. (1994) Lipoamidase and biotinidase activities in the rat: tissue distribution and intracellular localization. Eur. J. Clin. Chem. Clin. Biochem. 32, 501-9.
18. Nilsson, L., and Kagedal, B. (1993) Co-purification of human serum lipoamidase and biotinidase: evidence that the two enzyme activities are due to the same enzyme protein. Biochem. J. 291 (Pt 2), 545-51.
19. Gustavson, L. M., Srinivasan, A., Fritzberg, A. R., Reno, J. M., and Axworthy, D. B. (1994) NeoRx Corporation, US Patent 5,283,342.
20. Rosebrough, S. F. (1993) Plasma Stability and Pharmacokinetics of Radiolabeled Deferoxamine-Biotin Derivatives. J. Pharmacol. Exp. Ther. 265, 408-415.
21. Foulon, C. F., Alston, K. L., and Zalutsky, M. R. (1998) Astatine-211-Labeled Biotin Conjugates Resistant to Biotinidase for Use in Pretargeting Radioimmunotherapy. Nucl. Med. Biol. 25, 81-88.
22. Wilbur, D. S., Hamlin, D. K., Pathare, P. M., and Weerawarna, S. A. (1997) Biotin reagents for antibody pretargeting. Synthesis, radioiodination and in vitro evaluation of water soluble, biotinidase resistant biotin derivatives. Bioconjugate Chem. 8, 572-584.
23. Wilbur, D. S., Hamlin, D. K., Chyan, M. K., Kegley, B. B., and Pathare, P. M. (2001) Biotin reagents for antibody pretargeting. 5. Additional studies of biotin conjugate design to provide biotinidase stability. Bioconjugate Chem. 12, 616-23.
24. Axworthy, D. B., Theodore, L. J., Gustavson, L. M., and Reno, J. M. (1997) NeoRx Corporation, US Patent 5,608,060.
25. Wilbur, D. S., Chyan, M.-K., Pathare, P. M., Hamlin, D. K., Frownfelter, M. B., and Kegley, B. B. (2000) Biotin Reagents for Antibody Pretargeting. 4. Selection of Biotin Conjugates for in Vivo Application Based on Their Dissociation Rate from Avidin and Streptavidin. Bioconjugate Chem. 11, 569-583.
26. Wilbur, D. S., Pathare, P. M., Hamlin, D. K., Frownfelter, M. B., Kegley, B. B., Leung, W. Y., and Gee, K. R. (2000) Evaluation of biotin-Dye conjugates for use in an HPLC assay to assess relative binding of biotin derivatives with avidin and streptavidin. Bioconjugate Chem. 11, 584-98.
27. Wilbur, D. S., Hamlin, D. K., Vessella, R. L., Stray, J. E., Buhler, K. R., Stayton, P. S., Klumb, L. A., Pathare, P. M., and Weerawarna, S. A. (1996) Antibody fragments in tumor pretargeting. Evaluation of biotinylated Fab' colocalization with recombinant streptavidin and avidin. Bioconjugate Chem. 7, 689-702.
28. Wilbur, D. S., Hamlin, D. K., Buhler, K. R., Pathare, P. M., Vessella, R. L., Stayton, P. S., and To, R. (1998) Streptavidin in antibody pretargeting. 2. Evaluation of methods for decreasing localization of streptavidin to kidney while retaining its tumor binding capacity. Bioconjugate Chem. 9, 322-330.
29. Bhuniya, S., Park, S. M., and Kim, B. H. (2005) Biotin-amino acid conjugates: an approach toward self-assembled hydrogelation. Org. Lett. 7, 1741-4.
30. Wilbur, D. S., Hamlin, D. K., and Chyan, M.-K. (2005) Addition of Methionine to Radiohalogenation Reactions of Biotin Derivatives Decreases Formation of Biotin Sulfoxide by Oxidants. J. Labelled Compd. Radiopharm. 48, S305 (abstract).
31. Bogusiewicz, A., Mock, N. I., and Mock, D. M. (2005) A biotin-protein bond with stability in plasma. Anal. Biochem. 337, 98-102.
32. Visintin, C., Aliev, A. E., Riddall, D., Baker, D., Okuyama, M., Hoi, P. M., Hiley, R., and Selwood, D. L. (2005) Membrane receptor probes: solid-phase synthesis of biotin-Asp-PEG-arvanil derivatives. Org. Lett. 7, 1699-702.
33. Fritzberg, A. R., Beaumier, P. L., Bottino, B. J., and Reno, J. M. (1994) Approaches to improved antibody- and peptide-mediated targeting for imaging and therapy of cancer. J. Controlled Release 28, 167-173.
34. Rusckowski, M., Fogarasi, M., Fritz, B., and Hnatowich, D. J. (1997) Effect of Endogenous Biotin on the Applications of Streptavidin and Biotin in Mice. Nucl. Med. Biol. 24, 263-268.
35. Wang, H., and Pevsner, J. (1999) Detection of endogenous biotin in various tissues: novel functions in the hippocampus and implications for its use in avidin-biotin technology. Cell Tissue Res. 296, 511-6.
36. Theodore, L. J., Fritzberg, A. R., Schultz, J. E., and Axworthy, D. B. (2000) Evolution of a Pretarget Radioimmunotherapeutic Regimen. In Radioimmunotherapy of Cancer (Abrams, P. G., and Fritzberg, A. R., Eds.) pp 195-221, Marcel Dekker, New York.