Synthesis and biological activity of 125I/127I-phenylboronic acid derivatives.
Three iodinated phenylboronic acids have been synthesized: 4-iodophenylboronic acid (2a), 3-(4-iodobenzenesulfonamido)phenylboronic acid (5a) and 3-(5-dimethylamino-6-iodo-1-naphthalenesulfonamido)phenylboronic acid (6a). The corresponding no-carrier-added 125I derivatives 2b, 5b and 6b have been prepared in good yield by selective displacement of the tributylstannyl group. Compound 6b was concentrated in vitro preferentially in HT-29 human colon carcinoma cells compared to V79 Chinese hamster lung fibroblasts and showed selective retention in PaCa-2 human pancreatic cancer cells grown as solid tumor xenografts in the nude mouse.
Kinsey
B M
BM
Department of Radiology, Harvard Medical School, Shields Warren Radiation Laboratory, Boston, MA 02115.
Kassis
A I
AI
D000818:Animals; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000494:pharmacology; D002478:Cells, Cultured; D006224:Cricetinae; D003412:Cricetulus; D006801:Humans; D007457:Iodine Radioisotopes; D007462:Iodobenzenes / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000494:pharmacology; D051379:Mice; D008819:Mice, Nude; D009368:Neoplasm Transplantation; D009374:Neoplasms, Experimental / Q000209:etiology / Q000378:metabolism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000494:pharmacology; D014018:Tissue Distribution; D014407:Tumor Cells, Cultured
D001896:Boron Compounds; D007457:Iodine Radioisotopes; D007462:Iodobenzenes; D013449:Sulfonamides; C080455:3-(4-iodobenzenesulfonamido)phenylboronic acid; C080456:3-(5-dimethylamino-6-iodo-1-naphthalenesulfonamido)phenylboronic acid; C080454:4-iodophenylboronic acid