1. Synthesis of radioiodine-labeled 2-phenylethyl 1-thio-β-d-galactopyranoside for imaging of LacZ gene expression
- Author
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Choi, Joon Hun, Choe, Yearn Seong, Lee, Kyung-Han, Choi, Yong, Kim, Sang Eun, and Kim, Byung-Tae
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GENE expression , *IODINE isotopes - Abstract
A potent inhibitor of β-galactosidase (EC 3.2.1.23), 2-phenylethyl 1-thio-β-d-galactopyranoside (PETG), was radioiodinated for noninvasive imaging of LacZ gene expression. In order to introduce radioiodine to the phenyl ring of PETG, 2-(4-bromophenyl)ethanethiol was prepared and attached to the C-1 position of β-d-galactose pentaacetate under conditions that resulted in the exclusive formation of the β anomer. The bromo group of PETG was converted to the tributylstannyl group where radioiododemetallation was carried out. Radioiodine-labeled PETG tetraacetate was purified by HPLC, which can be used as a prodrug for biological evaluation or hydrolyzed to 2-(4-[123I/125I]iodophenyl)ethyl 1-thio-β-d-galactopyranoside ([123I/125I]7) under basic conditions. The resulting radioiodine-labeled PETG was obtained in overall 62% radiochemical yield (decay-corrected) and with specific activity of 46–74 GBq/μmol. [Copyright &y& Elsevier]
- Published
- 2003
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