Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake.
Benzyl 4-halobenzyl and ally benzyl disulfide were synthesized as diallyl disulfide analogues and their tumor growth inhibitory effects on the cancer cells (SNU C5 and MCF-7) were comparable to that of diallyl disulfide, indicating that the disulfide functional group was responsible for the tumor growth inhibitory effects. Cu(I)-assisted radioiodination of benzyl 4-bromobenzyl disulfide gave benzyl 4-[123I/125I]iodobenzyl disulfide in 30-40% radiochemical yield. The radiolabeled disulfide was taken up by the cancer cells in a time-dependent manner, and the uptake was inhibited by the pretreatment of S-methyl methanethiosulfonate (MMTS), phorone and diallyl disulfide. This study suggested that the radiolabeled dibenzyl disulfide was taken up by the cancer cells via thiol-disulfide exchange and retained inside the cells.
Department of Nuclear Medicine, Samsung Medical Center, Sungkyunkwan University School of Medicine, 50 Ilwon-dong, Kangnam-ku, Seoul 135-710, South Korea.
Eun Kyoung
EK
Ryu
Yearn Seong
YS
Choe
Sang Sung
SS
Byun
Kyung-Han
KH
Lee
Dae Yoon
DY
Chi
Yong
Y
Choi
Byung-Tae
BT
Kim
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D002455:Cell Division / Q000187:drug effects; D045744:Cell Line, Tumor; D002463:Cell Membrane Permeability; D004220:Disulfides / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D005737:Garlic / Q000737:chemistry; D006801:Humans; D007457:Iodine Radioisotopes; D007553:Isotope Labeling; D011849:Radioactive Tracers; D013329:Structure-Activity Relationship; D013440:Sulfides / Q000138:chemical synthesis* / Q000493:pharmacokinetics
D000970:Antineoplastic Agents; D001593:Benzyl Compounds; D004220:Disulfides; D007457:Iodine Radioisotopes; D011849:Radioactive Tracers; D013440:Sulfides; C492349:dibenzyl disulfide; C016367:benzyl sulfide