Preparation and biologic evaluation of a novel radioiodinated benzylpiperazine, 123I-MEL037, for malignant melanoma

Journal of Nuclear Medicine

Volumn 48, Issue 8, 2007, Pages 1348-1356

  Pham, Tien Q ^a   Berghofer, Paula ^a   Liu, Xiang ^a   Greguric, Ivan ^a   Dikic, Branko ^a   Ballantyne, Patrice ^a   Mattner, Filomena ^a   Nguyen, Vu ^a   Loc'h, Christian ^a   Katsifis, Andrew ^a  

^a AUSTRALIAN NUCLEAR SCIENCE AND TECHNOLOGY ORGANISATION   (Australia)

Author keywords

A375 tumor; B16 tumor; Iodobenzylpiperazines; Melanoma; Small animal SPECT

Indexed keywords

2 [2 [4 (4 IODOBENZYL)PIPERAZIN 1 YL] 2 OXOETHYL]ISOINDOLINE 1,3 DIONE I 123; HALOPERIDOL; IODINE 123; LYSERGIDE; MEL 037; MELANIN; N SEC BUTYL 1 (2 CHLOROPHENYL) N METHYL 3 ISOQUINOLINECARBOXAMIDE; NALOXONE; PENTAZOCINE; PIPERAZINE DERIVATIVE; QUINUCLIDINYL BENZILATE; RADIOLIGAND; SPIPERONE; TRITIUM; UNCLASSIFIED DRUG;

AMELANOTIC MELANOMA; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BAGG ALBINO MOUSE; BINDING COMPETITION; BRAIN; CONTROLLED STUDY; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG SYNTHESIS; DRUG UPTAKE; FEMALE; HEART; HUMAN; HUMAN CELL; IN VIVO STUDY; ISOTOPE LABELING; KIDNEY; LUNG; MELANOMA; MOUSE; NONHUMAN; NUDE MOUSE; PRIORITY JOURNAL; TISSUE DISTRIBUTION; TUMOR XENOGRAFT;

ANIMALS; FEMALE; HALOPERIDOL; IODINE RADIOISOTOPES; MELANOMA; MICE; MICE, INBRED BALB C; MICE, INBRED C57BL; PIPERAZINES; RADIOPHARMACEUTICALS; TISSUE DISTRIBUTION; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 34547793555     PISSN: 01615505     EISSN: None     Source Type: Journal    
DOI: 10.2967/jnumed.107.041673     Document Type: Article

References (38)

1. Baade P, Coory M. Trends in melanoma mortality in Australia: 1950-2002 and their implications for melanoma control. Aust N Z J Public Health. 2005;29:383-386.
2. Allen BJ, Rizvi S, Li Y, Tian Z, Ranson M. In vitro and preclinical targeted alpha therapy for melanoma, breast, prostate and colorectal cancers. Crit Rev Oncol Hematol. 2001;39:139-146.
3. Coderre JA, Packer S, Fairchild RG, et al. Iodothiouracil as a melanoma localizing agent. J Nucl Med. 1986;27:1157-1164.
4. 188Re-labeled alpha-melanocyte stimulating hormone peptide analogs for melanoma therapy. Int J Cancer. 2002;101:480-487.
5. Inoue S, Hasegawa K, Ito S, Wakamatsu K, Fujita K. Antimelanoma activity of chloroquine, an antimalarial agent with high affinity for melanin. Pigment Cell Res. 1993;6:354-358.
6. Link EM, Blower PJ, Costa DC, et al. Early detection of melanoma metastases with radioiodinated methylene blue. Eur J Nucl Med. 1998;25:1322-1329.
7. Michelot JM, Moreau MF, Veyre AJ, et al. Phase II scintigraphic clinical trial of malignant melanoma and metastases with iodine-123-N-(2- diethylaminoethyl 4-iodobenzamide). J Nucl Med. 1993;34:1260-1266.
8. 123,131I]iodobenzamides by animal and cell-culture studies. J Labelled Comp Radiopharm. 1995;37:260-262.
9. Labarre P, Papon J, Moreau MF, Moins N, Veyre A, Madelmont JC. Evaluation in mice of some iodinated melanoma imaging agents using cryosectioning and multi-wire proportional counting. Eur J Nucl Med. 1999;26:494-498.
10. John CS, Bowen WD, Saga T, et al. A malignant melanoma imaging agent: synthesis, characterization, in vitro binding and biodistribution of iodine-125-(2-piperidinylaminoethyl)4-iodobenzamide. J Nucl Med. 1993;34:2169-2175.
11. Brandau W, Niehoff T, Pulawski P, et al. Structure distribution relationship of iodine-123-iodobenzamides as tracers for the detection of melanotic melanoma. J Nucl Med. 1996;37:1865-1871.
12. 123I-N-(2- Diethylaminoethyl)-2-iodobenzamide: a potential imaging agent for cutaneous melanoma staging. Eur J Nucl Med Mol Imaging. 2002;29:1478-1484.
13. Larisch R, Schulte KW, Vosberg H, Ruzicka T, Muller-Gartner HW. Differential accumulation of iodine-123-iodobenzamide in melanotic and amelanotic melanoma metastases in vivo. J Nucl Med. 1998;39:996-1001.
14. Salopek TG, Scott JR, Joshua AV, et al. Radioiodinated N-[3-(4-Morpholino)-propyl]-N-methyl-2-hydroxy-5-iodo-3-methylbenzylamine (ERC9): a new potential melanoma imaging agent. Eur J Nucl Med. 2001;28:408-417.
15. 123I-labeled piperidine-based sigma receptor ligands as potential melanoma imaging agents: initial studies in mouse tumor models. Nucl Med Biol. 1997;24:587-593.
16. 125 I]-N-(N-benzypiperidin-4yl)-4-iodobenzamide, a new σ receptor radiopharmaceutical: high-affinity binding to MCF-7 breast tumor cells. J Med Chem. 1994;37:1737-1739.
17. 125I]-N-(N-benzylpiperidin-4-yl)-4- iodobenzamide: a high affinity sigma receptor ligand for potential imaging of breast cancer. Cancer Res. 1995;55:3022-3027.
18. 123I]-1-(iodopropen-2-yl)-4-[(4- cyanophenoxy) methyl]piperidine. J Med Chem. 1997;40:1657-1667.
19. Nguyen VH, Kassiou M, Johnston GA, Christie MJ. Comparison of binding parameters of sigma 1 and sigma 2 binding sites in rat and guinea pig brain membranes: novel subtype-selective trishomocubanes. Eur J Pharmacol. 1996;311:233-240.
20. Labarre P, Papon J, Moreau MF, et al. Melanin affinity of N-(2-diethylaminoethyl)-4-iodobenzamide, an effective melanoma imaging agent. Melanoma Res. 2002;12:115-121.
21. Dittmann H, Coenen HH, Zolzer F, Dutschka K, Brandau W, Streffer C. In vitro studies on the cellular uptake of melanoma imaging aminoalkyl-iodobenzamide derivatives (ABA). Nucl Med Biol. 1999;26:51-56.
22. Vilner BJ, John CS, Bowen WD. Sigma-1 and sigma-2 receptors are expressed in a wide variety of human and rodent tumor cell lines. Cancer Res. 1995;55:408-413.
23. Bem WT, Thomas GE, Mamone JY, et al. Overexpression of sigma receptors in nonneural human tumors. Cancer Res. 1991;51:6558-6562.
24. Eisenhut M, Hull WE, Mohammed A, et al. Radioiodinated N-(2-diethylaminoethyl)benzamide derivatives with high melanoma uptake: structure-affinity relationships, metabolic fate, and intracellular localization. J Med Chem. 2000;43:3913-3922.
25. Moins N, Papon J, Seguin H, et al. Synthesis, characterization and comparative biodistribution study of a new series of p-iodine-125 benzamides as potential melanoma imaging agents. Nucl Med Biol. 2001;28:799-808.
26. Mansard S, Papon J, Moreau MF, et al. Uptake in melanoma cells of N-(2-diethylaminoethyl)-2-iodobenzamide (BZA2), an imaging agent for melanoma staging: relation to pigmentation. Nucl Med Biol. 2005;32:451-458.
27. 14C-I-BZA. J Nucl Med. 2005;46:1701-1706.
28. Chehade F, Michelot J, Hindie E, et al. Localization of N-(2-diethylaminoethyl)4-iodobenzamide in the pigmented mouse eye: a microanalytical study. Cell Mol Biol. 1996;42:343-350.
29. Van der Heijden A, van Dijk JE, Lemmens AG, Beynen AC. Spleen pigmentation in young C57BL mice is caused by accumulation of melanin. Lab Anim. 1995;29:459-463.
30. Nordenberg J, Perlmutter I, Lavie G, et al. Anti-proliferative activity of haloperidol in B16 mouse and human SK-MEL-28 melanoma cell lines. Int J Oncol. 2005;27:1097-1103.
31. Wei Z, Mousseau DD, Dai Y, Cao X, Li XM. Haloperidol induces apoptosis via the sigma2 receptor system and Bcl-XS. Pharmacogenomics J. 2006;6:279-288.
32. Gil-Ad I, Shtaif B, Levkovitz Y, et al. Phenothiazines induce apoptosis in a B16 mouse melanoma cell line and attenuate in vivo melanoma tumor growth. Oncol Rep. 2006;15:107-112.
33. Brent PJ, Pang GT. Sigma binding site ligands inhibit cell proliferation in mammary and colon carcinoma cell lines and melanoma cells in culture. Eur J Pharmacol. 1995;278:151-160.
34. Boyd CM, Lieberman LM, Beierwaltes WH, Varma VM. Diagnostic efficacy of a radioiodinated chloroquine analog in patients with malignant melanoma. J Nucl Med. 1970;11:479-486.
35. Tjalve H, Nilsson M, Larsson B. Studies on the binding of chlorpromazine and chloroquine to melanin in vivo. Biochem Pharmacol. 1981;30:1845-1847.
36. Salazar-Bookaman MM, Wainer I, Patil PN. Relevance of drug-melanin interactions to ocular pharmacology and toxicology. J Ocul Pharmacol. 1994;10:217-239.
37. Lyden A, Larsson B, Lindquist NG. Studies on the melanin affinity of haloperidol. Arch Int Pharmacodyn Ther. 1982;259:230-243.
38. Wolf M, Bauder-Wust U, Mohammed A, et al. Alkylating benzamides with melanoma cytotoxicity. Melanoma Res. 2004;14:353-360.