Design, synthesis and cellular metabolism study of 4′-selenonucleosides

Jinha Yu, Pramod K. Sahu, Gyudong Kim, Shuhao Qu, Yoojin Choi, Jayoung Song, Sang Kook Lee, Minsoo Noh, Sunghyouk Park, Lak Shin Jeong

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

Background: 4′-seleno-homonucleosides were synthesized as next-generation nucleosides, and their cellular phosphorylation was studied to confirm the hypothesis that bulky selenium atom can sterically hinder the approach of cellular nucleoside kinase to the 5′-OH for phosphorylation. Results: 4′-seleno-homonucleosides (n = 2), with one-carbon homologation, were synthesized through a tandem seleno-Michael addition-SN2 ring cyclization. LC-MS analysis demonstrated that they were phosphorylated by cellular nucleoside kinases, resulting in anticancer activity. Conclusion: The bulky selenium atom played a key role in deciding the phosphorylation by cellular nucleoside kinases. </inline-graphic.

Original languageEnglish
Pages (from-to)1643-1655
Number of pages13
JournalFuture Medicinal Chemistry
Volume7
Issue number13
DOIs
StatePublished - Sep 2015

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