Biotin reagents in antibody pretargeting. 6. Synthesis and in vivo evaluation of astatinated and radioiodinated aryl- and nido-carboranyl-biotin derivatives

Bioconjugate Chemistry

Volumn 15, Issue 3, 2004, Pages 601-616

  Wilbur, D Scott ^a   Hamlin, Donald K ^a   Chyan, Ming Kuan ^a   Kegley, Brian B ^a   Quinn, Janna ^a   Vessella, Robert L ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; MAMMALS;

ATHYMIC MICE; BIOTIN MOIETY; BLOCKINGS; CARBORANES; DISTRIBUTION PROPERTY; IN-VITRO; IN-VIVO; STABILITY PROPERTIES; SYNTHESISED; VIVO EVALUATION;

COENZYMES;

1 N (BIOTINYL) 5 N [3' (NIDOCARBORANYL)PROPIONYL]LYSINE; 2 (N BIOTINYL) 4 [N' [13' (4'' IODOBENZOYL)AMINO] 4',7',10' TRIOXATRIDECANEAMINO]ASPARTATE; 3 [3' (IODONIDOCARBORANYL)PROPIONYL]AMINO 1 N [1' (N BIOTINYL) 5' LYSYLTHIOUREA]BENZENE; 3 [3' (IODONIDOCARBORANYL)PROPIONYL]AMINO 5 [1' (N BIOTINYL) 5' LYSYLTHIOUREA](3' DIMETHYLAMINOPROPYL)BENZAMIDE; 3 [3' (NIDOCARBORANYL)PROPIONYL]AMINO 1 N [1' (N BIOTINYL) 5' LYSYLTHIOUREA]BENZENE; 3 [3' (NIDOCARBORANYL)PROPIONYL]AMINO 5 [1' (N BIOTINYL) 5' LYSYLTHIOUREA](3' DIMETHYLAMINOPROPYL)BENZAMIDE; ANTIBODY; ASTATINE; ASTATINE 211; BIOTIN; BIOTIN DERIVATIVE; BIOTINIDASE; CARBORANE DERIVATIVE; IODINE 125; IODINE 131; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BIOACCUMULATION; COMPARATIVE STUDY; DRUG SCREENING; DRUG SYNTHESIS; HALOGENATION; ISOTOPE LABELING; MALE; MOLECULAR STABILITY; MOUSE; NONHUMAN; PLASMA CLEARANCE; RADIOIODINATION; STRUCTURE ANALYSIS;

ANIMALIA; STAPHYLOCOCCUS PHAGE 3A;

EID: 2542447254     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc034229q     Document Type: Article

References (57)

1. Wilbur, D. S. (1991) Potential use of alpha-emitting radionuclides in the treatment of cancer. Antibody Immunoconjugate Radiopharm. 4, 85-97.
2. Raju, M. R., Eisen, Y., Carpenter, S., and Inkret, W. C. (1991) Radiobiology of alpha particles. III. Cell inactivation by alpha-particle traversals of the cell nucleus. Radiat. Res. 128, 204-209.
3. Humm, J. L., and Chin, L. M. (1993) A Model of Cell Inactivation by Alpha-Particle Internal Emitters. Radiat. Res. 134, 143-150.
4. Allen, B. J. (1999) Targeted alpha therapy: evidence for potential efficacy of alpha-immunoconjugates in the management of micrometastatic cancer. Australas Radiol. 43, 480-486.
5. Akabani, G., Kennel, S. J., and Zalutsky, M. R. (2003) Microdosimetric analysis of α-particle-emitting targeted radiotherapeutics using histological images. J. Nucl. Med. 44, 792-805.
6. Hall, E. J. (1988) LET and RBE. Radiobiology for the Radiologist, pp 161-178, J. B. Lippincott Company, Philadelphia, PA.
7. Feinendegen, L. E., and McClure, J. J. (1997) Alpha-Emitters for Medical Therapy - Workshop of the United States Department of Energy. Radiat. Res. 148, 195-201.
8. Zalutsky, M. R., Zhao, X. G., Alston, K. L., and Bigner, D. (2001) High-level production of alpha-particle-emitting (211) At and preparation of (211)At-labeled antibodies for clinical use. J. Nucl. Med. 42, 1508-1515.
9. Zalutsky, M. R., and Vaidyanathan, G. (2000) Astatine-211-labeled radiotherapeutics: an emerging approach to targeted alpha-particle radiotherapy. Curr. Pharm. Des. 6, 1433-1455.
10. 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.
11. Goodwin, D. A., and Meares, C. F. (1997) Pretargeting: General Principles. Cancer (Suppl.) 80, 2675-2680.
12. Janssen, M. L., Oyen, W. J., Dijkgraaf, I., Massuger, L. F., Frielink, C., Edwards, D. S., Rajopadhye, M., Boonstra, H., Corstens, F. H., and Boerman, O. C. (2002) Tumor targeting with radiolabeled.alpha.v.beta.3 integrin binding peptides in a nude mouse model. Cancer Res. 62, 6146-6151.
13. Goodwin, D. A., and Meares, C. F. (2001) Advances in pretargeting biotechnology. Biotechnol. Adv. 19, 435-450.
14. Chinol, M., Grana, C., Gennari, R., Cremonesi, M., Geraghty, J. G., and Paganelli, G. (2000) Pretargeted Radioimmunotherapy of Cancer. Radioimmunotherapy of Cancer (Abrams, P. G., Fritzberg, A. R., Eds.) pp 169-193, Marcel Dekker, New York.
15. Axworthy, D. B., Reno, J. M., Hylarides, M. D., Mallett, R. W., Theodore, L. J., Gustavson, L. M., Su, F., Hobson, L. J., Beaumier, P. L., and Fritzberg, A. R. (2000) Cure of human carcinoma xenografts by a single dose of pretargeted yttrium-90 with negligible toxicity. Proc. Natl. Acad. Sci. U.S.A. 97, 1802-1807.
16. Press, O. W., Corcoran, M., Subbiah, K., Hamlin, D. K., Wilbur, D. S., Johnson, T., Theodore, L., Yau, E., Mallett, R., Meyer, D. L., and Axworthy, D. (2001) A comparative evaluation of conventional and pretargeted radioimmunotherapy of CD20-expressing lymphoma xenografts. Blood 98, 2535-2543.
17. 90Y-DOTA-Biotin. J. Nucl. Med. 41, 131-140.
18. 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.
19. 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, 616-623.
20. 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.
21. Zalutsky, M. R., and Narula, A. S. (1988) Astatination of Proteins using an N-Succinimidyl Tri-n-Butylstannyl Benzoate Intermediate. Appl. Radiat. Isot. 39, 227-232.
22. Wilbur, D. S., Hylarides, M. D., and Fritzberg, A. R. (1989) Reactions of organometallic compounds with astatine-211. Application to protein labeling. Radiochim. Acta 47, 137-142.
23. Hawthorne, M. F., and Maderna, A. (1999) Applications of radiolabeled boron clusters to the diagnosis and treatment of cancer. Chem. Rev. 99, 3421-3434.
24. Wilbur, D. S., Hamlin, D. K., and Srivastava, R. R. (1994) Radioiodinations of nido-Carboranes. Potential Hydrophilic Pendant Groups for Radiohalogenation of Biological Molecules. J. Labeled Compds. Radiopharm. 35, 199-201.
25. Wilbur, D. S., Hamlin, D. K., Livesey, J. C., Srivastava, R. R., Laramore, G. E., and Griffin, T. W. (1994) Synthesis and radioiodination of a nido-1,2-carboranyl derivative of 2-nitroimidazole. Nucl. Med. Biol. 21, 601-611.
26. Wilbur, D. S., Hamlin, D. K., Foulon, C. F., Zalutsky, M. R., and Pathare, P. M. (1997) Investigation of nido-Carboranes as Hydrophilic Pendant Groups for Astatination of Biomolecules. Application to an Astatinated Biotin Derivative. Proceedings of the 12th International Symposium on Radiopharmaceutical Chemistry, pp 76-78, Uppsala, Sweden.
27. Wilbur, D. S., Chyan, M.-K., Hamlin, D. K., Kegley, B. B., Risler, R., Pathare, P. M., Quinn, J., Vessella, R. L., Foulon, C., Zalutsky, M., Wedge, T. J., and Hawthorne, M. F. (2004) Reagents for Astatination of Biomolecules. Comparison of the in Vivo Distribution and Stability of Some Radioiodinated/Astatinated Benzamidyl- and nido-Carboranyl Compounds. Bioconjugate Chem. 15, 203-223.
28. Gamper, H. B., Reed, M. W., Cox, T., Virosco, J. S., Adams, A. D., Gall, A. A., Scholler, J. K., and Meyer, R. B. (1993) Facile Preparation of Nuclease Resistant 3′ Modified Oligodeoxynucleotides. Nucleic Acids Res. 21, 145-150.
29. 2. Nucl. Med. Biol. 20, 917-927.
30. 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.
31. 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.
32. 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, 616-623.
33. Boerman, O. C., van Schaijk, F. G., Oyen, W. J., and Corstens, F. H. (2003) Pretargeted radioimmunotherapy of cancer: progress step by step. J. Nucl. Med. 44, 400-411.
34. Theodore, L. J., Fritzberg, A. R., Schultz, J. E., and Axworthy, D. B. (2000) Evolution of a Pretarget Radioimmunotherapeutic Regimen. Radioimmunotherapy of Cancer (Abrams, P. G., Fritzberg, A. R., Eds.) pp 195-221, Marcel Dekker, New York.
35. Paganelli, G., Malcovati, M., and Fazio, F. (1991) Monoclonal Antibody pretargetting techniques for tumour localization: the avidin-biotin system. Nucl. Med. Commun. 12, 211-234.
36. Pagel, J. M., Hedin, N., Subbiah, K., Meyer, D., Mallet, R., Axworthy, D., Theodore, L. J., Wilbur, D. S., Matthews, D. C., and Press, O. W. (2003) Comparison of anti-CD20 and anti-CD45 antibodies for conventional and pretargeted radioimmunotherapy of B-cell lymphomas. Blood 101, 2340-2348.
37. Knox, S. J., Goris, M. L., Tempero, M., Weiden, P. L., Gentner, L., Breitz, H., Adams, G. P., Axworthy, D., Gaffigan, S., Bryan, K., Fisher, D. R., Colcher, D., Horak, I. D., and Weiner, L. M. (2000) Phase II trial of yttrium-90-DOTA-biotin pretargeted by NR-LU-10 antibody/streptavidin in patients with metastatic colon cancer. Clin. Cancer Res. 6, 406-414.
38. Green, N. M. (1990) Avidin and Streptavidin. Methods Enzymol. 184, 51-67.
39. 64Cu for tumor imaging and therapy. J. Nucl. Med. 44, 1284-1292.
40. Correa-Gonzalez, L., Arteaga de Murphy, C., Ferro-Flores, G., Pedraza-Lopez, M., Murphy-Stack, E., Mino-Leon, D., Perez-Villasenor, G., Diaz-Torres, Y., and Munoz-Olvera, R. (2003) Uptake of 153Sm-DTPA-bis-biotin and 99mTc-DTPA-bis-biotin in rat AS-30D-hepatoma cells. Nucl. Med. Biol. 30, 135-140.
41. Pispa, J. (1965) Animal Biotinidase. Ann. Med. Exptl. Bio. Fenniae 43, 3-40.
42. Wolf, B., Hymes, J., and Heard, G. S. (1990) Biotinidase. Methods Enzymol. 184, 103-111.
43. Hymes, J., Fleischhauer, K., and Wolf, B. (1997) Biotinidase in Serum and Tissues. Methods Enzymol. 279, 422-434.
44. 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.
45. 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.
46. 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, 584-598.
47. Kohrle, J. (2000) The deiodinase family: selenoenzymes regulating thyroid hormone availability and action. Cell. Mol. Life Sci. 57, 1853-1863.
48. Kabalka, G. W., and Varma, R. S. (1989) The Synthesis of Radiolabeled Compounds Via Organometallic Intermediates. Tetrahedron 45, 6601-6621.
49. Wilbur, D. S. (1992) Radiohalogenation of proteins: an overview of radionuclides, labeling methods, and reagents for conjugate labeling. Bioconjugate Chem. 3, 433-470.
50. 11]. Inorg. Chem. 24, 1911-1916.
51. Varadarajan, A., Sharkey, R. M., Goldenberg, D. M., and Hawthorne, M. F. (1991) Conjugation of Phenyl Isothiocyanate Derivatives of Carborane to Antitumor antibody and in Vivo Lacalization of Conjugates in Nude Mice. Bioconjugate Chem. 2, 102-110.
52. Hawthorne, M. F. (1991) Biochemical applications of boron cluster chemistry. Pure Appl. Chem. 63, 327-334.
53. Wilbur, D. S., Hamlin, D. K., Pathare, P. M., and Kegley, B. B. (1999) Synthesis of a nido-Carborane Derivative for use as a Protein Conjugate for Direct Radioiodination. J. Labelled Compd. Radiopharm. 42, S288-S290.
54. Olsen, F. P., and Hawthorne, M. F. (1965) Halodicarbaundecaborate(II) Ions. Inorg. Chem. 4, 1839-1840.
55. Hamilton, J. G., Durbin, P. W., and Parrott, M. (1954) The Accumulation and Destructive Action of Astatine211 (EKA-Iodine) in the Thyroid Gland of Rats and Monkeys. J. Clin. Endocrinol. Metab. 14, 1161-1178.
56. 125I]iodobenzoyl conjugate. Bioconjugate Chem. 2, 171-179.
57. Kerr, J. A. (1993) Strengths of Chemical Bonds. CRC Handbook of Chemistry and Physics (Lide, D. R., Ed.) pp 9-123-9-145, CRC Press, Boca raton.