Synthesis, in vitro validation and in vivo pharmacokinetics of [125I]N-[2-(4-iodophenyl)ethyl]-N-methyl-2-(1-piperidinyl) ethylamine: A high-affinity ligand for imaging sigma receptor positive tumors

Nuclear Medicine and Biology

Volumn 23, Issue 6, 1996, Pages 761-766

  John, Christy S ^a   Gulden, Mary E ^a   Vilner, Bertold J ^b   Bowen, Wayne D ^b  

^a GEORGE WASHINGTON UNIVERSITY MEDICAL CENTER   (United States)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

IPEMP; sigma receptor radioligand; tumor imaging

Indexed keywords

HALOPERIDOL; IODINE 125; LIGAND; N [2 (3,4 DICHLOROPHENYL)ETHYL] N METHYL 2 (1 PYRROLIDINYL)ETHYLAMINE; N [2 (4 BROMOPHENYL)ETHYL] N METHYL 2 (1 PIPERIDINYL)ETHYLAMINE; N [2 (4 IODOPHENYL)ETHYL] N METHYL 2 (1 PIPERIDINYL)ETHYLAMINE; OPIATE; PENTAZOCINE; SIGMA OPIATE RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BREAST CANCER; CANCER CELL; CONTROLLED STUDY; DRUG SYNTHESIS; GUINEA PIG; INTRAVENOUS DRUG ADMINISTRATION; ISOTOPE LABELING; MELANOMA CELL; RAT; TUMOR SCINTISCANNING;

EID: 0030220443     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/0969-8051(96)00070-4     Document Type: Article

References (34)

1. 1. Bakker W. H., Krenning E. R., Breeman W. A., Koper J. W., Kooji 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 applications in animals. J. Nucl. Med. 31, 1501-1509.
2. 2. Bem W. T., Thomas G. E., Mamome J. Y., Homan S. M., Levy B. K., Johnson F. E. and Coscia C. J. (1991) Overexpression of sigma receptors in nonneural human tumors. Cancer Res. 51, 6558-6562.
3. 3. Booth R. G., Wyrick S. D., Baldessarini R. J., Kula N. S., Myers A. M. and Mailman R. B. (1993) New sigma-like receptor recognized by novel phenylaminotetralins: Ligand binding and functional studies. Mol. Pharmacol. 44, 1232-1239.
4. 3H](+)-Pentazocine: A potent and highly selective benzomorphan-based probe for sigma-1 receptors. Mol. Neuropharmacol. 3, 117-126.
5. 5. Bowen W. D. (1993) Biochemical pharmacology of sigma receptors. In: Aspects of Synaptic Transmission, Vol. II (Edited by Stone T. W.), pp. 113-136. Taylor and Francis, London.
6. 6. Bowen W. D., Vilner B. J., Lee K. S., He X.-S., de Costa B. R. and Weinberger D. R. (1995) A haloperidol-insensitive binding site for sigma-active arylarylethylenediamine-related compounds: A novel sigma receptor subtype? Society Neuroscience 21, 526 (Abstract 219.5).
7. 7. Brent P. J. and Pang G. T. (1995) Sigma binding site ligands inhibit cell proliferation in mammary and colon carcinoma cell lines and melanoma cells in culture. Eur. J. Pharmacol. 278, 151-160.
8. 8. de Costa B. R., Radesca L., Di Paolo L. and Bowen W. D. (1992a) Synthesis, characterization and biological evaluation of a novel class of N-(arylethyl)-N-alkyl-2-(1-pyrrolidinyl)ethylamines: Structural requirements and binding affinity at the sigma sites. J. Med. Chem. 35, 38-47.
9. 9. de Costa B. R., Radesca L., Dominguez C. D., Di Paolo L. and Bowen W. D. (1992b) Synthesis and receptor binding properties of fluoro-and iodo-substituted high affinity sigma receptor ligands: Identification of potential PET and SPECT sigma receptor imaging agents. J. Med. Chem. 35, 2221-2230.
10. 10. He X.-S., Bowen W. D., Lee K. S., Williams W., Weinburger D. R. and de Costa B. R. (1993) Synthesis and binding characteristics of potential SPECT imaging agents for sigma-1 and sigma-2 binding sites. J. Med. Chem. 36, 566-572.
11. 11. Hellewell S. B. and Bowen W. D. (1990) A sigma-like binding site in rat pheochromocytoma (PC 12) cells: Decreased affinity for (+)-benzomorphans and lower molecular weight suggests a different sigma receptor form from that in guinea pig brain. Brain Res. 527, 244-253.
12. 12. Hellewell S. B., Bruce A., Feinstein G., Orringer J., Williams W. and Bowen W. D. (1994) Rat liver and kidney contain high densities of sigma-1 and sigma-2 receptors: Characterization by ligand binding and photoaffinity labeling. Eur. J. Pharmacol. 268, 9-18.
13. 13. John C. S., Bowen W. D., Saga T., Kinuya S., Vilner B. J., Baumgold J., Paik C. H., Reba R. C., Neumann R. D., Varma V. M. and McAfee J.G. (1993a) A malignant melanoma imaging agent: Synthesis, characterization, in vitro binding and biodistribution of iodine-125-(2-pipendinylaminoethyl) 4-iodobenzamide. J. Nucl. Med. 34, 2169-2175.
14. 125I]N-(2-piperidinylaminoethyl)4-iodobenzamide and related analogs as sigma receptor imaging agents: High affinity binding to human malignant melanoma and rat C6 glioma cell lines. J. Labeled Compds. Radiopharm. 35, 242-244.
15. 15. John C. S., Moody T. W., Bowen W. D., Vilner B. J., Varma V. M. and McAfee J. G. (1994b) Sigma receptors are expressed in non-small-cell lung carcinoma: Potential use for tumor visualization. J. Nucl. Med. 35, 248 (Abstract).
16. 16. John C. S., Bowen W. D., Varma V. M., McAfee J. G. and Moody T. W. (1995a) Sigma receptors are expressed in human non-small-cell lung carcinoma. Life Sci. 56, 2385-2392.
17. 125I]N-(diethylaminoethyl)4-iodobenzamide: A potential ligand for imaging malignant melanoma. Nucl. Med. Biol. 20, 75-79.
18. 125I]-N-(N-benzylpiperidin-4-yl)-4-iodobenzamide, a new sigma receptor radiopharmaceutical: High affinity binding to MCF-7 breast tumor cells. J. Med. Chem. 37, 1737-1739.
19. 125I]-N-(N-benzylpiperidin-4-yl)-4-iodobenzamide: A high affinity sigma receptor ligand for potential imaging of breast cancer. Cancer Res. 55, 3022-3027.
20. 20. Katzenellenbogen J. A. (1992) The pharmacology of steroid radiopharmaceuticals: Specific and non-specific binding uptake selectivity. In: Radiopharmaceuticals: Chemistry and Pharmacology, (Edited by Nunn A.D.), pp. 297-331. Marcel Dekker, New York.
21. 123I-Tyr]-octreotide: The Rotterdam experience with more than 100 patients. Eur. J. Nucl. Med. 20, 716-731.
22. 22. Martin W. R., Eades C. E., Thompson J. A. and Huppler R. E. (1976) The effects of morphine and nalorpine-like drugs in the nondependent and morphine-dependent chronic spinal dog. J. Pharmacol. Exp. Ther. 197, 517-532.
23. 23. Mintun M. A., Welch M. J., Siegal B. A., Mathias C. J., Brodack J. W., McGuire A. H. and Katzenellenbogen J. A. (1988) Breast cancer: PET imaging of estrogen receptors. Radiology 45, 169-173.
24. 24. Quirion R., Bowen W. D., Itzhak Y., Junien J. L., Musacchio J. M., Rothman R. B., Su T-P., Tam S. W. and Taylor D. P. (1992) A proposal for the classification of sigma binding sites. Trends Pharmacol. Sci. 13, 85-86.
25. 25. Reubi J. C., Maurer R., von Werder K., Torhorst J., Klijn J. G. M., Lamberts S. W. J. (1987) Somatostatin receptors in human endocrine tumors. Cancer Res. 47, 551-558.
26. 26. Reubi J. C. (1995) In vitro identification of vasoactive intestinal peptide receptors in human tumors: Implications for tumor imaging. J. Nucl. Med. 36, 71 (Abstract).
27. 27. Su T-P. (1993) Delineating biochemical and functional properties of sigma receptors: Emerging concepts. Crit. Rev. Neurobiol. 7, 187-203.
28. 3H]tolyl)guanidine: A selective ligand that labels sigma type receptors for psychotomimetic opiates and antipsychotic drugs. Proc. Natl. Acad. Sci. USA 83, 8784-8788.
29. 29. Wolfe S. A., Gulp S. G. and DeSouza E. B. (1989) Sigma-receptors in endocrine organs: Identification, characterization, and autoradiographic localization in rat pituitary, adrenals, testis, and ovary. Endocrinology 124, 1160-1172.
30. 30. Thomas G. E., Szucs M., Mamone J. Y., Bem W. T., Rush M. D., Johnson F. E. and Coscia C. J. (1990) Sigma and opioid receptors in human brain tumors. Life Sci. 46, 1279-1286.
31. 31. Vilner B. J. and Bowen W. D. (1992) Characterization of sigma-like binding sites of NB41A3, S-20Y, and N1E-115 neuroblastomas, C6 glioma, and NG108-15 neuroblastoma-glioma hybrid cells: Further evidence for sigma-2 receptors. In: Multiple Sigma and PCP Receptor Ligands: Mechanisms for Neuromodulation and Neuroprotection? (Edited by Kamenka J. M. and Domino E. F.), pp. 341-353. NPP Books, Ann Arbor, MI.
32. 32. Vilner B. J., John C. S. and Bowen W. D. (1995) Sigma-1 and sigma-2 receptors are expressed in a wide variety of human and rodent tumor cell lines. Cancer Res. 55, 408-413.
33. 33. Vilner B. J. and Bowen W. D. (1993) Sigma receptor active neuroleptics are cytotoxic to C6 glioma cells in culture. Eur. J. Pharmacol. 244, 199-201.
34. 34. Vilner B. J., John C. S. and Bowen W. D. (1994) Iodobenzamides as novel sigma receptor ligands and potential imaging agents. Society Neuroscience 20, 746, 314.1 (Abstract).