Synthesis, characterization and comparative biodistribution study of a new series of p-iodine-125 benzamides as potential melanoma imaging agents.
Iodobenzamides are reported to possess some affinity for melanoma. In order to identify the compound having the most appropriate pharmacokinetic properties as a potential melanoma imaging agent, thirteen new [125I]radioiodobenzamides with a butylene amide-amine spacer and various substituents on the terminal amino group were investigated. Their synthesis, radioiodination and biodistribution in B16 melanoma bearing C57BL6 mice are described and compared to [125I] labeled N-(2-diethylaminoethyl)-4-iodobenzamide ([125I]BZA), our reference compound. Changes in the terminal amino constituents induced modifications of lipophilicity, tumor uptake and organ distribution. The dimethylaminobutyl iodobenzamide appeared to be the most promising radiopharmaceutical imaging agent for the detection of melanoma and its metastases.
Moins
N
N
INSERM U484, 63005, Clermont-Ferrand, France. moins@inserm484.u-clermont1.fr
Papon
J
J
Seguin
H
H
Gardette
D
D
Moreau
M F
MF
Labarre
P
P
Bayle
M
M
Michelot
J
J
Gramain
J C
JC
Madelmont
J C
JC
Veyre
A
A
D000818:Animals; D001549:Benzamides / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000633:toxicity; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D007202:Indicators and Reagents; D007457:Iodine Radioisotopes; D007553:Isotope Labeling; D007928:Lethal Dose 50; D008297:Male; D008546:Melanoma, Experimental / Q000000981:diagnostic imaging* / Q000378:metabolism; D051379:Mice; D008810:Mice, Inbred C57BL; D011877:Radionuclide Imaging; D019275:Radiopharmaceuticals / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000633:toxicity; D014018:Tissue Distribution
D001549:Benzamides; D007202:Indicators and Reagents; D007457:Iodine Radioisotopes; D019275:Radiopharmaceuticals