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Synthesis of Radioiodine Labeled Dibenzyl Disulfide for Evaluation of Tumor Cell Uptake

Synthesis of Radioiodine Labeled Dibenzyl Disulfide for Evaluation of Tumor Cell Uptake

Eun Kyoung Ryu, Yearn Seong Choe, Sang Sung Byun, Kyung-Han Lee, Dae Yoon Chi, Yong Choi, Byung-Tae Kim

Bioorg Med Chem. 2004 Mar 1;12(5):859-64.

PMID: 14980597

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP150607	Benzyl disulfide		150-60-7	Price

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