Synthesis of l-(p-Isothiocyanatobenzyl) Derivatives of DTPA and EDTA. Antibody Labeling and Tumor-Imaging Studies

Inorganic Chemistry

Volumn 25, Issue 16, 1986, Pages 2772-2781

  Brechbiel, Martin W ^a   Gansow, Otto A ^a   Atcher, Robert W ^a   Schlom, Jeffrey ^b   Esteban, Jose ^b   Simpson, Diane E ^b   Colcher, David ^b  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MONOCLONAL ANTIBODY IN 111; RADIOISOTOPE;

1 (4 ISOTHIOCYANATOBENZYLIDENE)EDETIC ACID; 1 (4 ISOTHIOCYANATOBENZYLIDENE)PENTETIC ACID; ANIMAL EXPERIMENT; BIOLOGICAL MODEL; BLADDER; BLOOD AND HEMOPOIETIC SYSTEM; DIAGNOSIS; DRUG BINDING; DRUG BLOOD LEVEL; DRUG COMPARISON; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG PURIFICATION; DRUG SCREENING; DRUG SYNTHESIS; DRUG TISSUE LEVEL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTRAVENOUS DRUG ADMINISTRATION; KIDNEY; LIVER; MOUSE; NONHUMAN; PENTETIC ACID ISOBUTYLCARBOXYCARBONIC ACID ANHYDRIDE; PENTETIC ANHYDRIDE; SPLEEN;

EID: 0022968394     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/ic00236a024     Document Type: Article

References (70)

1. Scheinberg, D. A.; Strand, M.; Gansow, O. A. In Monoclonal Antibodies in Drug Development; August, J. T., Ed.; American Society for Pharmacology and Experimental Therapeutics: Bethesda, MD, 181; pp 159–171.
2. Scheinberg, D. A.; Strand, M.; Gansow, O. A. Science (Washington, D.C.) 1982, 215, 1511–1513.
3. Goldenberg, D. M., Ed. Cancer Res. 1980, 40, part 2 and references therein.
4. Belitsky, P.; Ghose, T.; Aquino, J.; Tai, J.; MacDonald, A. J. Radiology (Easton, Pa.) 1978, 126, 516–517.
5. Mach, J. P.; Carrel, S.; Forni, M.; Ritschard, J.; Donath, A.; Alberto, P. N. Engl. J. Med. 1981, 303, 5–10.
6. Scheinberg, D. A.; Strand, M. Cancer Res. 1982, 42, 44–49.
7. Spencer, R. P., Ed. Therapy in Nuclear Medicine; Greene and Stratton: New York, 1978; Chapters 1–3.
8. O'Brien, H. A. In Radioimmunoimaging and Radioimmunotherapy; Burchiel, S. W., Rhodes, B. A., Eds.; Elsevier: New York, 1983; pp 207–222.
9. Rainsbury, R. M.; Ott, R. S., et al. Lancet 2 1983, 934–938.
10. Murray, J. L.; Rosenblum, M. G.; Sobel, R. E.; Cancer Res. 1985, 45, 2376–2381.
11. Bunn, P. A.; Carrasquillo, J. A.; Keenan, A. M. Lancet 2 1984, 1219–1221.
12. Larson, S. M.; Carrasquillo, J. A. In Yearbook of Nuclear Medicine: Times-Mirror: Chicago, 1985; pp. 17–27.
13. Keenan, A. M.; Harbert, J. C.; Larson, S. M. J. Nucl. Med. 1985, 26, 531–537.
14. Larson, S. M.; Carrasquillo, J. A.; Reynolds, J. C. Cancer Invest. 1984, 2, 363–381.
15. Krejcarek, G. E.; Tucker, K. L. Biochem. Biophys. Rev. Commun. 1977, 77, 581–585.
16. Eckelman, W. C.; Chang, H. P.; Reba, R. C. Cancer Res. 1980, 40, 3036–3042.
17. Dazz, J. Swiss Patent 17, 930, 1966. British Patent 1, 161, 461, 1976. U.S. Patent 3, 660, 388, 1972.
18. Hnatowich, D. J.; Layne, M. W.; Childs, R. L. Int. J. Appl. Radiat. Isot. 1982, 33, 327–332.
19. Yeh, S. M.; Sherman, D. G.; Meares, C. F. Anal. Biochem. 1979, 100, 152–159.
20. Meares, C. F.; Goodwin, D. A.; Leung, C.-S.H.; Girgis, A. Y.; Sylvester, D. J.; Nunn, A. D.; Lavender, P. J. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 3803–3806.
21. DeRiemer, L. H.; Meares, C. F.; Goodwin, D. A.; Diamanti, C. I. J. Med. Chem. 1979, 22, 1019–1023.
22. DeRiemer, L. H.; Meares, C. F.; Goodwin, D. A.; Diamanti, C. I. J. Labelled Compd. Radiopharm. 1981, 18, 1517–1534.
23. Paik, C. H.; Eckelman, W. C.; Lei, K. S.; Friend, K. E. J. Nucl. Med. 1981, 22, 32.
24. Meares, C. F.; McCall, M. J.; Reardon, D. T.; Goodwin, D. A.; Diamanti, C. I.; McTigue, M. Anal. Biochem. 1984, 142, 68–78.
25. Altman, J.; Shoef, N.; Wilchek, M.; Warshawsky, A. J. Chem. Soc. Perkin Trans. 1 1984, 59–62.
26. Gansow, O. A.; Kausar, A. R.; Triplett, K. B. J. Heterocycl. Chem. 1981, 18, 297–302.
27. Gansow, O. A.; Kausar, A. R. Inorg. Chim. Acta 1983, 72, 39–41.
28. Gansow, O. A.; Kausar, A. R. Inorg. Chem. 1984, 91, 213–215.
29. Gansow, O. A.; Atcher, R. W.; Link, D. C.; et al. ACS Symp. Ser. 1984, No. 241, 215–227.
30. Paik, C. H.; Herman, D. E.; Eckelman, W. C.; Reba, R. C. J. Radidoanal. Chem. 1980, 57, 553–564.
31. Kawamura, A. In Fluorescent Antibody Techniques and Their Applications', Kawamura, A., Ed., University of Tokyo: Tokyo, 1969; Chapter 3.
32. Mizusawa, E. A.; Thompson, M. R.; Hawthorne, M. F. Inorg. Chem. 1985, 24, 1911–1916.
33. Griffith, O. H.; Waggoner, A. S. Acc. Chem. Res. 1969, 2, 17–24.
34. Saito, K.; Tsuchimoto, M. J. Inorg. Nucl. Chem. 1963, 25, 1245–1252.
35. Omori, T.; Kimizuka, R.; Yoshihara, K.; Yagi, M. J. Radioanal. Nucl. Chem. 1984, 82, 269–273.
36. Colcher, D.; Horan-Hand, P.; Nuti, M.; Schlom, J. Proc. Nat. Acad. Sci. U.S.A. 1981, 78, 3199–3203.
37. Nuti, M.; Teramoto, Y. A., et al. Int. J. Cancer 1982, 29, 539–545.
38. Stramignoni, O.; Bowen, R.; et al. Int. J. Cancer 1983, 31, 543–552.
39. (a) Szpak, C.; Johnston, N.; Acta Cytol. 1984, 28, 256–367. (b) Paterson, A. J.; Schlom, J.; Int. J. Cancer 1986, 37, 659–666.
40. Colcher, D.; Keenan, A. M.; Cancer Res. 1984, 44, 5744-5751; J. Nucl. Med. 1984, 25, 1197–1203.
41. Vaughn, J. R.; Eichler, J. A. J. Am. Chem. Soc. 1953, 75, 5556–5560.
42. Chambers, R. W.; Carpenter, F. K. J. Am. Chem. Soc. 1955, 77, 1522-1526.
43. Brown, H. C.; Keim, P. J. Org. Chem. 1973, 38, 912–916.
44. Udenfriend, S.; Stein, S.; Bohlen, P.; Dairman, W. Science (Washington, D.C.) 1972, 178, 871–872.
45. (a) Itoh, M.; Hagiwara, D.; Kamiya, T. Tetrahedron Lett. 1975, 4393 – 4394. (b) Kuroiwa, K.; Narita, K.; Isowa, Y. Bull. Chem. Soc. Jpn. 1973, 46, 1269–1272.
46. Bara, Y. A.; Friedrich, A.; Hehlein, W.; Kessler, H.; Kandor, P.; Molter, M.; Veith, H.-J. Chem. Ber. 1978, 111, 1029–1044.
47. Meikle, R. W. Nature (London) 1962, 196, 61–62.
48. Eckelman, W. C.; Karesh, S. M.; Reba, R. C. J. Pharm. Sci. 1975, 64, 704–706.
49. Goodwin, D. A.; Meares, C. F.; McCall, M. J. J. Nucl. Med. 1985, 26, 493–502.
50. Colcher, D.; Zalutsky, M.; Kaplan, W.; Kufe, D.; Austin, F.; Schlom, J. Cancer Res. 1983, 43, 736–742.
51. Esteban, J.; Schlom, J.; Simpson, D.; Brechbiel, M.; Atcher, R.; Gansow, O. A.; Colcher, D., manuscript in preparation.
52. Paik, C. H.; Murphy, P. R., et al. J. Nucl. Med. 1983, 24, 1158–1164.
53. Paik, C. H.; Murphy, P. R., et al. J. Nucl. Med. 1983, 24, 932–936.
54. Gansow, O. A., unpublished results.
55. (a) Zogbi, S. S.; Newman, R. D.; Gottschalk, A. Int. J. Nucl. Med. Biol. 1985, 12, 159–166. (b) Zogbi, S. S.; Newman, R. D.; Gottschalk, A. Invest. Radiol. in press.
56. Hosain, F.; McIntyre, P. A.; Kattadiyil, P.; Stern, H. S.; Wagner, H. N. Clin. Chim. Acta 1969, 24, 69–75.
57. Gansow, O. A.; Strand, M. U.S. Patent 4, 454
58. Glazer, A. N. Chemical Modification of Proteins; Elsevier: New York, 1976.
59. Brechbiel, M.; Gansow, O. A., submitted for publication.
60. Martell, A. E., Smith, R. M. Critical Stability Constants; Plenum: New York, 1974; Vol. 1.
61. Jackowatz, J. G.; Beatty, B. G., et al. Cancer Res. 1985, 45, 5700–5706.
62. Paxton, R. J.; Jakowatz, B. G., et al. Cancer Res. 1985, 45, 5694–5699.
63. Otsuka, F.; Welch, M. Int. J. Nucl. Med. Biol. 1985, 12, 331–333.
64. Chanchai, J.; Shimi, J.; et al. Int. J. Nucl. Med. Biol. 1985, 12, 289–293.
65. Anderson, W. T.; Strand, M. Cancer. Res. 1985, 45, 2154–2158.
66. Reba, R. C.; Hosain, F.; Wagner, H. Radiology (Easton, Pa.) 1968, 90, 147–149.
67. Gobuty, A. H.; Kim, E. E.; Weiner, R. E. J. Nucl. Med. 1985, 26, 545–547.
68. Yeh, S. M.; Meares, C. F.; Goodwin, D. A. J. Radioanal. Chem. 1979, 53, 327–336.
69. Kozak, R. W.; Atcher, R. W.; Gansow, O. A.; Friedman, A. M.; Hines, J. J.; Waldmann, T. A. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 474–478.
70. Strand, M.; et al., private communication.