A novel ternary ligand system for 99mTc-labeling of hydrazino nicotinamide-modified biologically active molecules using imine-N-containing heterocycles as coligands

Bioconjugate Chemistry

Volumn 9, Issue 5, 1998, Pages 583-595

  Liu, Shuang ^a   Scott Edwards, D ^a   Harris, Anthony R ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHELATION; CHLORINE COMPOUNDS; GLYCOPROTEINS; MIXTURES; MOLECULES; PLATELETS; PYRIDINE; SYNTHESIS (CHEMICAL); TECHNETIUM;

CO-LIGANDS; DIASTEREOMERS; HETEROCYCLES; HIGH SPECIFIC ACTIVITIES; LABELINGS; LIGAND SYSTEM; NICOTINIC ACID; RADIOMETRICS; SULPHONIC ACIDS; TECHNETIUM-; ISONICOTINIC ACID;

LIGANDS;

EID: 0345055302     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc9800116     Document Type: Article

References (67)

1. 99mTc-protein conjugates. Bioconjugate Chem. 2, 334-336.
2. Abrams, M. J., Juweid, M., tenKate, C. I., Schwartz, D. A., Hauser, M. M., Gaul, F. E., Fuccello, A. J., Rubin, R. H., Strauss, H. W., and Fischman, A. J. (1990) Technetium-99m-human polyclonal IgG radiolabeled via the hydrazino nicotinamide derivative for imaging focal sites of infection in rats. J. Nucl. Med. 31, 2022-2028.
3. Babich, J. W., Solomon, H., Pike, M. C., Kroon, D., Graham, W., Abrams, M. J., Tompkins, R. G., Rubin, R. H., and Fischman, A. J. (1993) Technetium-99m-labeled hydrazino nicotinamide derivatized chemotactic peptide analogues for imaging focal sites of bacterial infection. J. Nucl. Med. 34, 1964-1974.
4. 99mTc-labeled hydrazino nicotinic acid derivatized chemotactic peptides. Nucl. Med. Biol. 22, 25-30.
5. Fischman, A. J., Babich, J. W., and Rubin, R. H. (1994) Infection imaging with technetium-99m-labeled chemotactic peptide analogues. Semin. Nucl. Med. 24, 154-168.
6. Fischman, A. J., Babich, J. W., and Strauss, H. W. (1993) A ticket to ride: peptide radiopharmaceuticals. J. Nucl. Med. 34, 2253-2263.
7. Fischman, A. J., Rauh, D., Solomon, H., Babich, J. W., Tompkins, R. G., Kroon, D., Strauss, H. W., and Rubin, H. R. (1993) In vivo bioactivity and biodistribution of chemotactic peptide analogues in nonhuman primates. J Nucl. Med. 34, 2130-2134.
8. 111In IgG. Nucl. Med. Biol. 22, 643-648.
9. Babich, J. W., Solomon, H., Pike, M. C., Kroon, D., Graham, W., Abrams, M. J., Tompkins, R. G., Rubin, R. H., Barrow, and Fischman, A. J. (1993) Technetium-99m-labeled hydrazino nicotinamide derivatized chemotactic peptide analogues for imaging focal sites of bacterial infection. J. Nucl. Med. 34, 1964-1974.
10. Mäcke, H. R., and Behe, M. (1996) New octreotide derivatives labeled with technetium-99m. J. Nucl. Med. 37, 29P (abstract 107).
11. Behe, M., and Mäcke, H. R. (1995) New somatostatin analogues labeled with technetium-99m. Eur. J. Nucl. Med. 22, 791 (abstract 267).
12. Dewanjee, M. K., Ghalfouripour, A. K., Subramanian, M., Hanna, M., Kapadvanjwala, M., Serafini, A. N., Ezuddin, S., Lopez, D., and Sfakianakis, G. N. (1994) Labeling antisense deoxyoligonucleotide with Tc-99m and hybridation with c-myc oncogene mRNA in P388 leukemic cells. J. Labelled Compd. and Radiopharm. 35, 40-42.
13. Dewanjee, M. K., Abrams, M. J., Wu, S. M., Kapadvanjwala, M., Serafini, A. N., and Sfakianakis, G. N. (1995) Technetium-99m labeled single-strand DNA probe for imaging thrombin in viscera formed during cardiopulmonary bypass. J. Nucl. Med. 36, 16P (abstract 54).
14. Hnatowich, D. J., Winnard, P., Jr., Virzi, F., Fogarsi, M., Sano, T., Smith, C. L., Cantor, C. L., and Rusckowski, M. (1995) Technetium-99m labeling of DNA oligonucleotides. J. Nucl. Med. 36, 2306-2314.
15. 99mTc labeling of hydrazino nicotinamide modified human polyclonal IgG. J. Nucl. Med. 35, 105P (abstract 418).
16. 99mTc]Tricine: a useful precursor complex for the radiolabeling of hydrazinonicotinate protein conjugates. Bioconjugate Chem. 6, 635-638.
17. 99mTc using aminocarboxylates as coligands. Bioconjugate Chem. 7, 63-71.
18. Edwards, D. S., Barrett, J. A., Liu, S., Ziegler, M. C., Mazaika, T., Vining, M., Bridger, G., Higgins, J., III, and Abrams, M. J. (1996) A stabilized Tc-99m complex of a chemotactic peptide-HYNIC conjugate for imaging infection. Eur. J. Nucl. Med. 23, 1142 (abstract Omo440).
19. 99mTc. Bioconjugate Chem. 8, 146-154.
20. Kuntz, E. (1981) Catalytic hydroformylation of olefins. U.S. Patent 4,248,802.
21. Sworin, M., Rajopadhye, M., Harris, T. D., Edwards, D. S., Cheesman, E., and Liu, S. (1996) Stable reagents for the preparation of radiopharmaceuticals. PCT International Application, WO 96/40637.
22. Rajopadhye, M, Harris, T. D., Yu, K., Glowacka, D., Damphousse, P. R., Barrett, J. A., Heminway, S. J., Edwards, D. S., and Carroll, T. R. (1997) Synthesis, evaluation and Tc-99m complexation of a hydrazinonicotinyl conjugate of a GP IIb/IIIa antagonist cyclic peptide for the detection of deep vein thrombosis. Bioorg. Med. Chem. Lett. 7, 955-960.
23. Goodbody, A. E., Ballinger, J., Tran, L. L., Sumner-Smith, M., Lau, F., Meghji, K., and Pollak, A. (1994) A new Tc-99m labeled peptide inflammation imaging agent. Eur. J. Nucl. Med. 21, 790 (abstract 262).
24. Cavelier, V., Goodbody, A. E., Tran, L. L., Bossuyt, A., and Thornback, J. (1996) Human dosimetry of Tc99m-RP128, a potential inflammation imaging agent. Eur. J. Nucl. Med. 23, 1131 (abstract OMo398).
25. Peers, S. H., Tran, L. L., Eriksson, S. J., Ballinger, J., and Goodbody, A. E. (1995) Imaging a model of colitis with RP128, a Tc-99m-chelated tuftsin Antagonist. J. Nucl. Med. 36, 114P (abstract 465).
26. Maina, T., Stolz, B., Albert, R., Bruns, C., Koch, P., and Macke. (1994) Synthesis, radiochemistry and biological evaluation of a new somatostatin analogue (SDZ 219-387) labeled with technetium-99m. Eur. J. Nucl. Med. 21, 437-444.
27. 1]-octreotide, a new octreotide derivative with high affinity for somatostatin receptors. in Technetium and Rhenium in Chemistry and Nuclear Medicine (M. Nicolini, G. Banoli, and U. Mazzi, Eds.) pp 395-400, Vol. 4, SGEditorali, Padova.
28. 111In-DTPA-octreotide. Pept. Res. 9, 144-150.
29. Vallabhajosula, S., Moyer, B. R., Lister-James, J., McBride, W. J., Lipszyc, H., Lee, H., Bastidas, D., and Dean, R. T. (1996) Preclinical evaluation of technetium-99m-labeled somatostatin receptor binding peptides. J. Nucl. Med. 37, 1016-1022.
30. Pearson, D. A., Lister-James, J., McBride, W. J., Wilson, D. M., Martel, L. J., Civitello, E. R., Taylor, J. E., Moyer, B. R., and Dean, R. T. (1996) Somatostatin receptor-binding peptides labeled with technetium-99m: chemistry and initial biological studies. J. Med. Chem. 39, 1361-1371.
31. 99mTc]chelator-peptide conjugate. Bioconjugate Chem. 7, 196-202.
32. 99mTc]chelator-peptide conjugates. Bioconjugate Chem. 7, 203-208.
33. Barrett, J. A, Bresnick, M., Crocker, A. C., Damphousse, D. J., Heminway, S. J., Mazaika, T. J., Kagan, M., Lazewatsky, J. L., Edwards, D. S., Liu, S., Harris, T. D., Rajpladhye, M., and Carroll, T. R. (1998) RP431: a technetium-99m-labeled platelet GP IIbIIIa receptor antagonist as a thrombus imaging agent. J. Nucl. Med. (In press).
34. 99mTc. Bioconjuate Chem. 8, 155-160.
35. Lister-James, J., Knight, L. C., Mauer, A. H., Bush, L. R., Moyer, B. R., and Dean, R. T. (1996) Thrombus imaging with technetium-99m-labeled, activated platelet receptor binding peptide. J. Nucl. Med. 37, 775-781.
36. Muto, P., Lastoria, S., Varrella, P., Vergara, E., Salvatore, M., Morgano, G., Lister-James, J., Bernardy, J. D., Dean, R. T., Wencker, D., and Boer, J. S. (1995) Detecting deep venous thrombosis with technetium-99m-labeled synthetic peptide P280. J. Nucl. Med. 36, 1384-1391.
37. Pearson, D. A., Lister-James, J., McBride, W. J., Wilson, D. M., Martel, L. J., Civitello, E. R., and Dean, R. T. (1996) Thrombus imaging using technetium-99m labeled high potency GPIIb/IIIa receptor antagonists. Chemistry and initial biological studies. J. Med. Chem. 39, 1372-1382.
38. Lister-James, J., Vallabhajosula, S., Moyer, B. R., Pearson, D. A., McBride, B. J., De Rosch, M. A., Bush, L. R., Machac, J., and Dean, R. T. (1997) Pre-clinical evaluation of technetium-99m platelet receptor-binding peptide. J. Nucl. Med. 38, 105-111.
39. 99mTc-labeling of highly potent small peptides. Bioconjugate Chem. 8, 621-636.
40. 99mTc. Q. J. Nucl. Med. 40, 221-233.
41. Lanteingne, D., and Hnatowich, D. J. (1984) The labeling of DTPA coupled proteins. Int. J. Radiat. Isot. 35, 617-621.
42. Breitz, H. B., Weiden, P. L., Vanderheyden, J.-L., Appelbaum, J. W., Bjorn, M. J., Fer, M. F., Wolf, S. B., Ratliff, B. A., Seiler, C. A., Foisie, D. C., Fisher, D. R., Schroff, R. W., Fritzberg, A. R., and Abrams, P. G. (1992) Clinical experience with rhenium-186-labeled monoclonal antibodies for radioimmunotherapy: results of phase I trials. J. Nucl. Med. 33, 1099-1112.
43. Schroff, R. W., Weiden, P. L., Appelbaum, J. W., Fer, M. F., Breitz, H. B., Vanderheyden, J.-L., Ratliff, B. A., Fisher, D. R., Foisie, D. C., Hanelin, L. G., Morgan, A. C., Jr., Fritzberg, A. R., and Abrams, P. G. (1990) Rhenium-186 labeled antibody in patients with cancer: Report of a pilot phase I study. Antibody, Immunoconjugates, Radiopharm. 3, 99-111.
44. 3S triamidethiols as bifunctional chelating agents for labeling small peptides with technetium-99m. in Technetium and Rhenium in Chemistry and Nuclear Medicine (M. Nicolini, G. Banoli, and U. Mazzi, Eds.) pp 383-393, Vol. 4, SGEditorali, Padova.
45. Fritzberg, A. R., Abrams, P. G., Beaumier, P. L., Kasina, S., Morgan, A. C., Rao, T. N., Reno, J. M., Sanderson, J. A., Srinivasan, A., and Wilbur, D. S. (1988) Specific and stable labeling of antibodies with technetium-99m with a diamide dithiolate chelating agent. Proc. Natl. Acad. Sci. U.S.A. 85, 4025-4029.
46. Eary, J. F., Schroff, R. W., Abrams, P. G., Fritzberg, A. R., Morgan, A. C., Kasina, S., Reno, J. M., Srinivasan, A., Woodhouse, C. S., Wilbur, D. S., Natale, R. B., Collins, C., Stehlin, J. S., Mitchell, M., Nelp, W. B. (1989) Successful imaging of malignant melanoma with technetium-99m-labeled monoclonal antibodies. J. Nucl. Med. 30, 25-32.
47. Kasina, S., Rao, T. N., Srinivasan, A., Sanderson, J. A., Fitzner, J. N., Reno, J. M., Beaumier, P. L., and Fritzberg, A. R. (1991) Development and biological evaluation of a kit for preformed chelate technetium-99m radiolabeling of an antibody Fab fragment using a diamide dimercaptide chelating agent. J. Nucl. Med. 32, 1445-1451.
48. 1A receptor imaging agents, in Technetium and Rhenium in Chemistry and Nuclear Medicine (M. Nicolini, G. Banoli, and U. Mazzi, Eds.) pp 383-393, Vol. 4, SGEditorali, Padova.
49. 99mTc-labeling. J. Labelled Compd. Radiopharm. 29, 1283-1291.
50. Eisenhut, M., Lehmann, W. D., Becker, W., Behr, T., Elser, H., Strittmater, W., Steinsträsser, A., Baum, R. P., Valerius, T., Repp, R., and Deo, Y. (1996) Bifunctional NHS-BAT ester for antibody conjugation and stable technetium-99m labeling: conjugation chemistry, immunoreactivity and kit formulation. J. Nucl. Med. 37, 362-370.
51. Baidoo, K. E., and Lever, S. Z. (1990) Synthesis of a diaminedithiol bifunctional chelating agent for incorporation of technetium-99m into biomolecules. Bioconjugate Chem. 1, 132-137.
52. DiZio, J. P., Fiashi, R., Davison, A., Jones, A. G., and Katzenellenbogen, J. A. (1991) Progestin-rhenium complexes: metal labeled steriods with high receptor binding affinity, potential receptor-directed agents for diagnostic imaging or therapy. Bioconjugate Chem. 2, 352-366.
53. DiZio, J. P., Anderson, C. J., Davison, A., Ehrhardt, G. J., Carlson, K. E., Welch, M. J., and Katzenellenbogen, J. A. (1992) Technetium- and rhenium-labeled progestins: synthesis, receptor binding and in vivo distribution of an β-substituted progestin labeled with technetium-99 and rhenium-186. J. Nucl. Med. 33, 558-569.
54. Baidoo, K. E., Scheffel, U., Finley, P., Lever, S. Z., and Wagner, H. N., Jr. (1994) No carrier added (NCA) Tc-99m-diaminedithiolate derivatives of chemotactic peptides for imaging inflammation. J. Nucl. Med. 35, 19P (abstract 67).
55. 3 PITC. Bioconjugate Chem. 2, 160-170.
56. 2. Bioconjugate Chem. 2, 407-414.
57. 99mTc labeling of hydrazino nicotinamide modified proteins. J. Labelled Compd. Radiopharm. 35, 1-2.
58. 4N)]. Inorg. Chim. Acta 252, 421-426.
59. 4N)]. Inorg. Chim. Acta 252, 427-430.
60. 2. Inorg. Chim. Acta 185, 7-15.
61. Archer, C. M., Dilworth, J. R., Jobanputra, P., Thompson, R. M., McPartlin, M., Povey, D. C., Smith, G. W., and Kelly, J. D. (1990) Development of new technetium cores containing technetium-nitrogen multiple bonds. Synthesis and characterization of some diazenido-, hydrazido- and imido-complexes of technetium. Polyhedron 9, 1497-1502.
62. 3)] Z. Naturforsch. 46, 449-452.
63. 2O. J. Chem. Soc., Dalton Trans. 897-904.
64. 4]. J. Chem. Soc., Dalton Trans. 1251-1256.
65. 2]. Technetium and Rhenium in Chemistry and Nuclear Medicine (M. Nicolini, G. Bandoli, and U. Mazzi, Eds.) pp 95-108, Vol. 3, Cortina International, Verona.
66. 2. Technetium and Rhenium in Chemistry and Nuclear Medicine (M. Nicolini, G. Bandoli, and U. Mazzi, Eds.) pp 65-68, Vol. 3, Cortina International, Verona.
67. Liu, S and Edwards, D. S. Unpublished results.