Nuclear Medicine and Biology
Volume 35, Issue 7 , Pages 769-781 , October 2008

Synthesis and evaluation of novel radioiodinated nicotinamides for malignant melanoma

Received 29 April 2008 ,Revised 23 May 2008 ,Accepted 31 May 2008.

References 

  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. Coenen HH, Brandau W, Dittmann H, Dutschka K, Niehoff T, Pulawski P, et al. Evaluation of melanoma seeking N-(dialkylamino)-alkyl [123,131I]iodobenzamides by animal and cell-culture studies. J Lab Comp Radiopharm. 1995;37:260–262
  3. John CS, Bowen WD, Saga T, Kinuya S, Vilner BJ, Baumgold J, 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
  4. 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
  5. Pham TQ, Greguric I, Liu X, Berghofer P, Ballantyne P, Chapman J, et al. Synthesis and evaluation of novel radioiodinated benzamides for malignant melanoma. J Med Chem. 2007;50:3561–3572
  6. Eisenhut M, Hull WE, Mohammed A, Mier W, Lay D, Just W, 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
  7. Brandau W, Niehoff T, Pulawski P, Jonas M, Dutschka K, Sciuk J, et al. Structure distribution relationship of iodine-123-iodobenzamides as tracers for the detection of melanotic melanoma. J Nucl Med. 1996;37:1865–1871
  8. Michelot JM, Moreau MF, Veyre AJ, Bonafous JF, Bacin FJ, Madelmont JC, 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
  9. Moins N, D'Incan M, Bonafous J, Bacin F, Labarre P, Moreau MF, et al. 123I-N-(2-Diethylaminoethyl)-2-iodobenzamide: a potential imaging agent for cutaneous melanoma staging. Eur J Nucl Med Mol Imaging. 2002;29:1478–1484
  10. Sillaire-Houtmann I, Bonafous J, Veyre A, Mestas D, D'Incan M, Moins N, et al. Phase 2 clinical study of 123I-N-(2-diethylaminoethyl)-2-iodobenzamide in the diagnostic of primary and metastatic ocular melanoma. J Fr Ophthalmol. 2004;27:34–39
  11. 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
  12. Salopek TG, Scott JR, Joshua AV, Smylie M, Logus JW, Morin CA, et al. Radioiodinated N-[3-(4-morpholino)propyl]-N-methyl-2-hydroxy-5-iodo-3-methyl benzylamine (ERC9): a new potential melanoma imaging agent. Eur J Nucl Med. 2001;28:408–417
  13. Nicholl C, Mohammed A, Hull WE, Bubeck B, Eisenhut M. Pharmacokinetics of iodine-123-IMBA for melanoma imaging. J Nucl Med. 1997;38:127–133
  14. Brown JM, Lemmon MJ, Horsman MR, Lee WW. Structure–activity relationships for tumour radiosensitization by analogues of nicotinamide and benzamide. Int J Radiat Biol. 1991;59:739–748
  15. Pero RW, Axelsson B, Siemann D, Chaplin D, Dougherty G. Newly discovered anti-inflammatory properties of the benzamides and nicotinamides. Mol Cell Biochem. 1999;193:119–125
  16. Girgis AS, Hosni HM, Barsoum FF. Novel synthesis of nicotinamide derivatives of cytotoxic properties. Bioorg Med Chem. 2006;14:4466–4476
  17. Moins N, Papon J, Seguin H, Gardette D, Moreau MF, Labarre P, 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(7):799–808
  18. Waterhouse RN. Determination of lipophilicity and its use as a predictor of blood–brain barrier penetration of molecular imaging agents. Mol Imaging Biol. 2003;5:376–389
  19. Chaki S, Tanaka M, Muramatsu M, Otomo S. NE-100, a novel potent sigma ligand, preferentially binds to sigma 1 binding sites in guinea pig brain. Eur J Pharmacol. 1994;251:R1–R2
  20. 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
  21. Salazar-Bookaman MM, Wainer I, Patil PN. Relevance of drug–melanin interactions to ocular pharmacology and toxicology. J Ocul Pharmacol. 1994;10:217–239
  22. Labarre P, Papon J, Moreau MF, Moins N, Bayle M, Veyre A, et al. Melanin affinity of N-(2-diethylaminoethyl)-4-iodobenzamide, an effective melanoma imaging agent. Melanoma Res. 2002;12:115–121
  23. 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
  24. 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
  25. Bem WT, Thomas GE, Mamone JY, Homan SM, Levy BK, Johnson FE, et al. Overexpression of sigma receptors in nonneural human tumors. Cancer Res. 1991;51:6558–6562
  26. Mansard S, Papon J, Moreau MF, Miot-Noirault E, Labarre P, Bayle M, 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. John CS, Vilner BJ, Geyer BC, Moody T, Bowen WD. Targeting sigma receptor-binding benzamides as in vivo diagnostic and therapeutic agents for human prostate tumors. Cancer Res. 1999;59:4578–4583
  28. John CS, Bowen WD, Varma VM, McAfee JG, Moody TW. Sigma receptors are expressed in human non-small cell lung carcinoma. Life Sci. 1995;56:2385–2392
  29. Chehade F, Michelot J, Hindie E, Papon J, Delabriolle-Vaylet C, Zhang L, et al. Localization of N-(2-diethylaminoethyl)4-iodobenzamide in the pigmented mouse eye: a microanalytical study. Cell Mol Biol. 1996;42:343–350
  30. Mohammed A, Nicholl C, Titsch U, Eisenhut M. Radioiodinated N-(alkylaminoalkyl)-substituted 4-methoxy-, 4-hydroxy-, and 4-aminobenzamides biological investigations for the improvement of melanoma-imaging agents. Nucl Med Biol. 1997;24:373–380
  31. Pham TQ, Berghofer P, Liu X, Greguric I, Dikic B, Ballantyne P, et al. Preparation and biologic evaluation of a novel radioiodinated benzylpiperazine, 123I-MEL037, for malignant melanoma. J Nucl Med. 2007;48:1348–1356
  32. Moreau MF, Papon J, Labarre P, Moins N, Borel M, Bayle M, et al. Synthesis, in vitro binding and biodistribution in B16 melanoma-bearing mice of new iodine-125 spermidine benzamide derivatives. Nucl Med Biol. 2005;32:377–384
  33. Wolf M, Bauder-Wust U, Haberkorn U, Mier W, Eisenhut M. Alkylating benzamides with melanoma cytotoxicity: role of melanin, tyrosinase, intracellular pH and DNA interaction. Melanoma Res. 2005;15:383–391
  34. Wolf M, Bauder-Wust U, Mohammed A, Schonsiegel F, Mier W, Haberkorn U, et al. Alkylating benzamides with melanoma cytotoxicity. Melanoma Res. 2004;14:353–360

PII: S0969-8051(08)00141-8

doi: 10.1016/j.nucmedbio.2008.05.011

Nuclear Medicine and Biology
Volume 35, Issue 7 , Pages 769-781 , October 2008