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

doi:10.4155/fmc.15.102

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

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

8 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-S_N2 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 language	English
Pages (from-to)	1643-1655
Number of pages	13
Journal	Future Medicinal Chemistry
Volume	7
Issue number	13
DOIs	https://doi.org/10.4155/fmc.15.102
State	Published - Sep 2015

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© 2015 Future Science Ltd.

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

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. ",

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

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doi = "10.4155/fmc.15.102",

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T1 - Design, synthesis and cellular metabolism study of 4′-selenonucleosides

AU - Yu, Jinha

AU - Sahu, Pramod K.

AU - Kim, Gyudong

AU - Qu, Shuhao

AU - Choi, Yoojin

AU - Song, Jayoung

AU - Lee, Sang Kook

AU - Noh, Minsoo

AU - Park, Sunghyouk

AU - Jeong, Lak Shin

PY - 2015/9

Y1 - 2015/9

N2 - 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.

AB - 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.

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JO - Future Medicinal Chemistry

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

Abstract

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