Radioiodination and astatination of octreotide by conjugation labeling

Nuclear Medicine and Biology

Volumn 27, Issue 4, 2000, Pages 329-337

  Vaidyanathan, Ganesan ^a,c   Affleck, Donna ^a   Welsh, Philip ^a   Srinivasan, Ananth ^b   Schmidt, Michelle ^b   Zalutsky, Michael R ^a  

^a DUKE UNIVERSITY   (United States)

^b MALLINCKRODT PHARMACEUTICALS   (United States)

^c DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

Astatine 211; Conjugation radiohalogenation; Octreotide

Indexed keywords

ASTATINE; DIAGNOSTIC AGENT; OCTREOTIDE; RADIOACTIVE IODINE; IODINE DERIVATIVE; PENTETREOTIDE; SOMATOSTATIN RECEPTOR; SUCCINIMIDE DERIVATIVE;

ANIMAL; ARTICLE; CELL CULTURE; ISOTOPE LABELING; MOUSE; RAT; TISSUE DISTRIBUTION; ANIMAL CELL; ANIMAL TISSUE; CONJUGATION; DEHALOGENATION; DRUG MANUFACTURE; DRUG RECEPTOR BINDING; DRUG TUMOR LEVEL; INTERNALIZATION; MALE; NONHUMAN; PANCREAS TUMOR; RADIOCHEMISTRY; RADIOIODINATION; RADIOISOTOPE DISTRIBUTION; THYROID GLAND;

ANIMALS; ASTATINE; IODINE RADIOISOTOPES; ISOTOPE LABELING; MICE; OCTREOTIDE; RATS; TISSUE DISTRIBUTION; TUMOR CELLS, CULTURED;

EID: 0034186439     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(00)00098-6     Document Type: Article

References (48)

1. 1-Octreotide in vivo. Bioconjugate Chem. 9, 662-670.
2. Ali S. A., Warren S. D., Richter K. Y., Badger C. C., Eary J. F., Press O. W., Krohn K. A., Bernstein I. D. and Nelp W. B. (1990) Improving tumor retention of radioiodinated antibody: Aryl carbohydrate adducts. Cancer Res. 50(suppl), 783s-788s.
3. Anderson C. J., Jone L. A., Bass L. A., Sherman E. L. C., McCarthy D. W., Cutler P. D., Lanahan M. V., Cristel M. E., Lewis J. S. and Schwarz S. W. (1998) Radiotherapy, toxicity and dosimetry of copper-64-TETA-octreotide in tumor-bearing rats. J. Nucl. Med. 39, 1944-1951.
4. Anderson C. J., Pajeau T. S., Edwards W. B., Sherman E. L. C., Rogers B. E. and Welch M. J. (1995) In vitro and in vivo evaluation of copper-64-octreotide conjugates. J. Nucl. Med. 36, 2315-2325.
5. 1-octreotide. J. Nucl. Med. 37, 2002-2006.
6. 1]-octreotide, a potential radiopharmaceutical for imaging of somatostatin receptor-positive tumors: Synthesis, radiolabeling and in vitro validation. Life Sci. 49, 1583-1591.
7. Bakker W. H., Krenning E. P., Breeman W. A., Koper J. W., Kooij P. P., Reubi J.-C., Klijn J. G., Visser T. J., Docter R. and Lamberts S. W. (1990) Receptor scintigraphy with a radioiodinated somatostatin analogue: Radiolabeling, purification, biologic activity, and in vivo application in animals. J. Nucl. Med. 31, 1501-1509.
8. Bauer W., Briner U., Doepfner W., Haller R., Huguenin R., Marbach P., Petcher T. J. and Pless J. (1982) SMS 201-995: A very potent and selective octapeptide analogue of somatostatin with prolonged action. Life Sci. 31, 1133-1140.
9. 3 derivatives of octreotide in rats. Anticancer Res. 18, 83-90.
10. Buchsbaum D. J., Rogers B. E,. Khazaeli M. B., Mayo M. S., Milenic D. E., Kashmiri S. V., Anderson C. J., Chappell L. L., Brechbiel M. W. and Curiel D. T. (1999) Targeting strategies for cancer radiotherapy. Clin. Cancer Res. 5(suppl), 3048s-3055s.
11. Decristoforo C. and Mather S. J. (1999) Technetium-99m somatostatin analogues: Effect of labelling methods and peptide sequence. Eur. J. Nucl. Med. 26, 869-876.
12. 111In-labeled somatostatin analogues for tumor scintigraphy and radionuclide therapy. Cancer Res. 58, 437-441.
13. Dumas P. (1973) Dehalogenation of various analogs of phenolic iodides in normal and thyroidectomized rats. Biochem. Pharmacol. 22, 1599-1605.
14. Dumas P., Maziere B., Autissier N. and Michel R. (1973) Specificity of thyroidal and hepatic microsomal iodotyrosine deiodinase. Biochim. Biophys. Acta 293, 36-47.
15. Friedman H. S., Burger P. C., Bigner S. H., Trojanowski J. Q., Wikstrand C. J., Halperin E. C. and Bigner D. D. (1985) Establishment and characterization of the human medulloblastoma cell line and transplantable xenograft D283 Med. J. Neuropathol. Exp. Neurol. 44, 592-605.
16. Frühwald M. C., O'Dorisio M. S., Pietsch T. and Reubi J. C. (1999) High expression of somatostatin receptor subtype 2 (sst2) in medulloblastoma: Implications for diagnosis and therapy. Pediatr. Res. 45, 697-708.
17. Garg P. K., Alston K. L., Welsh P. C. and Zalutsky M. R. (1996) Enhanced binding and inertness to dehalogenation of α-melanotropic peptides labeled using N-succinimidyl 3-iodobenzoate. Bioconjugate Chem. 7, 233-239.
18. Garg S., Garg P. K. and Zalutsky M. R. (1991) N-Succinimidyl 5-(Trialkylstannyl)-3-pyridinecarboxylates: A new class of reagents for protein radioiodination. Bioconjugate Chem. 2, 50-56.
19. 3 as prosthetic groups for labeling amines and peptides: Approaches with pre- and postconjugate labeling. Nucl. Med. Biol. 25, 621-632.
20. 1)-octreotide, a potential radiopharmaceutical for quantitative somatostatin receptor imaging with PET: Synthesis, radiolabeling, in vitro validation and biodistribution in mice. Nucl. Med. Biol. 21, 819-825.
21. Hall E. J. (1994) Radiobiology for the Radiologist, pp. 153-164. Lippincott, Philadelphia.
22. 125I]octreotide by mouse and human pituitary tumor cells: Increase by unlabeled octreotide. Endocrinology 136, 3698-3706.
23. Kawai K., Fujibayashi Y., Saji H., Konishi J., Kubodera A. and Yokoyama A. (1990) Monoiodo-D-tyrosine, an artificial amino acid radiopharmaceutical for selective measurement of membrane amino acid transport in the pancreas. Nucl. Med. Biol. 17, 369-376.
24. 111in-DTPA-octreotide in the same patients: Biodistribution, kinetics, organ and tumor uptake. J. Nucl. Med. 40, 762-761.
25. Kwekkeboom D. J. and Krenning E. P. (1997) Radiolabeled somatostatin analog scintigraphy in oncology and immune diseases: An overview. Eur. Radiol. 7, 1103-1109.
26. Lamberts S. W. J., Bakker W. H., Reubi J. C. and Krenning E. P. (1990) Somatostatin receptor imaging in vivo localization of tumors with a radiolabeled somatostatin analog. J. Steroid Biochem. Mol. Biol. 37, 1079-1082.
27. 211At reaction. Appl. Radiat, Isot. 47, 135-143.
28. Lewis J. S., Lewis M. R., Srinivasan A., Schmidt M. A., Wang J. and Anderson C. J. (1999) Comparison of four 64Cu-labeled somatostatin analogues in vitro and in a tumor-bearing rat model: Evaluation of new derivatives for positron emission tomography imaging and targeted radiotherapy. J. Med. Chem. 42, 1341-1347.
29. 3-octreotate. A new somatostatin analog with improved target tissue uptake. Nucl. Med. Biol. 26, 267-273.
30. 111In-indium octreotide scan. Ann. Thorac. Surg. 67, 555-558.
31. Müller H. L., Frühwald M. C., Scheubeck M., Rendl J., Warmuth-Metz M., Sörensen N., Kühl J. and Reubi J. C. (1998) A possible role for somatostatin receptor scinitigraphy in the diagnosis and follow-up of children with medulloblastoma. J. Neuro-Oncol. 38, 27-40.
32. Olsen J. O., Pozderac R. V., Hinkle G., Hill T., O'Dorisio T. M., Schirmer W. J., Ellison E. C. and O'Dorisio M. S. (1995) Somatostatin receptor imaging of neuroendocrine tumors with indium-111 pentetreotide (Octreoscan). Semin. Nucl. Med. 25, 251-261.
33. Pittman R. C., Carew T. E., Glass C. K., Green S. R., Taylor C. A. Jr. and Attie A. D. A. (1983) A radioiodinated, intracellularly trapped ligand for determining the sites of plasma protein degradation in vivo. Biochem. J. 212, 791-800.
34. Pless J., Bauer W., Briner U., Doepfner W., Marbach P., Maurer R., Petcher T. J., Reubi J. C. and Vonderscher J. (1986) Chemistry and pharmacology of SMS 201-995, a long-acting octapeptide analogue of somatostatin. Scand. J. Gastroenterol. 119(suppl.), 54-64.
35. Raynor K. and Reisine T. (1989) Analogs of somatostatin selectively label distinct subtypes of somatostatin receptors in rat brain. J. Pharmacol. Exp. Ther. 251, 510-517.
36. Reist C. J., Archer G. E., Wikstrand C. J., Bigner D. D. and Zalutsky M. R. (1997) Improved targeting of an anti-epidermal growth factor receptor variant III monoclonal antibody in tumor xenografts after labeling using N-succinimidyl 5-iodo-3-pyridinecarboxylate. Cancer Res. 57, 1510-1515.
37. Reist C. J., Garg P. K., Alston K. L., Bigner D. D. and Zalutsky M. R. (1996) Radioiodination of internalizing monoclonal antibodies using N-succinimidyl 5-iodo-3-pyridinecarboxylate. Cancer Res. 56, 4970-4977.
38. Reubi J. C., Kvols L. K., Krenning E. P. and Lamberts S. W. J. (1990) Distribution of somatostatin receptors in normal and tumor tissue. Metabolism 39(suppl), 78-81.
39. 2 in ovarian carcinoma induced to express the gastrin releasing peptide receptor by adenoviral vector-mediated gene transfer. J. Nucl. Med. 38, 1221-1229.
40. Spradau T. W. and Katzenellenbogen J. A. (1998) Protein and peptide labeling with (cyclopentadienyl)tricarbonyl rhenium and technetium. Bioconjugate Chem. 9, 765-772.
41. 211At]astatobenzylguanidine on human neuroblastoma cells. Cancer Res. 54, 5414-5419.
42. Thakur M. L., Kolan H., Li J., Wiaderkiewicz R., Pallela V. R., Duggaraju R. and Schally A. V. (1997) Radiolabeled somatostatin analogs in prostrate cancer. Nud. Med. Biol. 24, 105-113.
43. Wilbur D. S. (1992) Radiohalogenation of proteins: An overview of radionuclides, labeling methods, and reagents for conjugate labeling. Bioconjugate Chem. 3, 433-470.
44. Zalutsky M. R. and Bigner D. D. (1996) Radioimmunotherapy with alpha-particle emitting radioimmunoconjugates. Acta Oncologica. 35, 373-379.
45. 2 fragments with the α-particle-emitting nuclide astatine-211: Preservation of immunoreactivity and in vivo localizing capacity. Proc. Natl. Acad. Sci. USA 86, 7149-7153.
46. Zalutsky M. R. and Narula A. S. (1987) A method for the radiohalogenation of proteins resulting in decreased thyroid uptake of radioiodine. Appl. Radiat, Isot. 38, 1051-1055.
47. 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.
48. Zalutsky M. R., Noska M. A., Colapinto E. V., Garg P. K. and Bigner D. D. (1989) Enhanced tumor localization and in vivo stability of a monoclonal antibody radioiodinated using N-succinimidyl 3-(tri-n-butylstannyl)benzoate. Cancer Res. 49, 5543-5549.