Synthesis and anti-HIV activity of l-2′,3′-Dideoxy-4′-selenonucleosides (l-4′-Se-ddNs)

Jinha Yu; Gyudong Kim; Dnyandev B. Jarhad; Hong Rae Kim; Lak Shin Jeong

doi:10.1007/s12272-019-01157-6

Synthesis and anti-HIV activity of l-2′,3′-Dideoxy-4′-selenonucleosides (l-4′-Se-ddNs)

Jinha Yu, Gyudong Kim, Dnyandev B. Jarhad, Hong Rae Kim, Lak Shin Jeong

Pharmaceutical Sciences

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

1 Scopus citations

Abstract

Based on the potent anti-HIV activity of l-2′,3′-dideoxycytidine (l-ddC), l-2′,3′-dideoxy-4′-selenonucleosides (l-4′-Se-ddNs) have been synthesized from natural chiral template, l-glutamic acid, using Pummerer-type condensation as a key step. All synthesized compounds were assayed for anti-HIV-1 activity, but none of them did show any significant antiviral activity up to 100 μM, probably due to conformational differences between l-ddC and l-4′-Se-ddC, induced by the bulky selenium atom, which might play an important role in phosphorylation by cellular kinase.

Original language	English
Pages (from-to)	780-789
Number of pages	10
Journal	Archives of Pharmacal Research
Volume	42
Issue number	9
DOIs	https://doi.org/10.1007/s12272-019-01157-6
State	Published - 1 Sep 2019

Keywords

Antiviral
l-2′,3′-Dideoxy-4′-selenonucleosides
l-4′-Se-ddC
l-Nucleoside
Pummerer-type condensation

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1007/s12272-019-01157-6

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title = "Synthesis and anti-HIV activity of l-2′,3′-Dideoxy-4′-selenonucleosides (l-4′-Se-ddNs)",

abstract = "Based on the potent anti-HIV activity of l-2′,3′-dideoxycytidine (l-ddC), l-2′,3′-dideoxy-4′-selenonucleosides (l-4′-Se-ddNs) have been synthesized from natural chiral template, l-glutamic acid, using Pummerer-type condensation as a key step. All synthesized compounds were assayed for anti-HIV-1 activity, but none of them did show any significant antiviral activity up to 100 μM, probably due to conformational differences between l-ddC and l-4′-Se-ddC, induced by the bulky selenium atom, which might play an important role in phosphorylation by cellular kinase.",

keywords = "Antiviral, l-2′,3′-Dideoxy-4′-selenonucleosides, l-4′-Se-ddC, l-Nucleoside, Pummerer-type condensation",

author = "Jinha Yu and Gyudong Kim and Jarhad, {Dnyandev B.} and Kim, {Hong Rae} and Jeong, {Lak Shin}",

note = "Funding Information: Acknowledgements This research was supported by grants from Mid-career Research Program (2016R1A2B3010164) and Basic Science Research Program (2018R1D1A1A02085459) of the National Research Foundation (NRF), Korea. Antiviral assay by C.-K. Lee (KRICT) is greatly appreciated. Publisher Copyright: {\textcopyright} 2019, The Pharmaceutical Society of Korea.",

year = "2019",

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doi = "10.1007/s12272-019-01157-6",

language = "English",

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TY - JOUR

T1 - Synthesis and anti-HIV activity of l-2′,3′-Dideoxy-4′-selenonucleosides (l-4′-Se-ddNs)

AU - Yu, Jinha

AU - Kim, Gyudong

AU - Jarhad, Dnyandev B.

AU - Kim, Hong Rae

AU - Jeong, Lak Shin

N1 - Funding Information: Acknowledgements This research was supported by grants from Mid-career Research Program (2016R1A2B3010164) and Basic Science Research Program (2018R1D1A1A02085459) of the National Research Foundation (NRF), Korea. Antiviral assay by C.-K. Lee (KRICT) is greatly appreciated. Publisher Copyright: © 2019, The Pharmaceutical Society of Korea.

PY - 2019/9/1

Y1 - 2019/9/1

N2 - Based on the potent anti-HIV activity of l-2′,3′-dideoxycytidine (l-ddC), l-2′,3′-dideoxy-4′-selenonucleosides (l-4′-Se-ddNs) have been synthesized from natural chiral template, l-glutamic acid, using Pummerer-type condensation as a key step. All synthesized compounds were assayed for anti-HIV-1 activity, but none of them did show any significant antiviral activity up to 100 μM, probably due to conformational differences between l-ddC and l-4′-Se-ddC, induced by the bulky selenium atom, which might play an important role in phosphorylation by cellular kinase.

AB - Based on the potent anti-HIV activity of l-2′,3′-dideoxycytidine (l-ddC), l-2′,3′-dideoxy-4′-selenonucleosides (l-4′-Se-ddNs) have been synthesized from natural chiral template, l-glutamic acid, using Pummerer-type condensation as a key step. All synthesized compounds were assayed for anti-HIV-1 activity, but none of them did show any significant antiviral activity up to 100 μM, probably due to conformational differences between l-ddC and l-4′-Se-ddC, induced by the bulky selenium atom, which might play an important role in phosphorylation by cellular kinase.

KW - Antiviral

KW - l-2′,3′-Dideoxy-4′-selenonucleosides

KW - l-4′-Se-ddC

KW - l-Nucleoside

KW - Pummerer-type condensation

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U2 - 10.1007/s12272-019-01157-6

DO - 10.1007/s12272-019-01157-6

M3 - Article

C2 - 31041687

AN - SCOPUS:85065241443

SN - 0253-6269

VL - 42

SP - 780

EP - 789

JO - Archives of Pharmacal Research

JF - Archives of Pharmacal Research

IS - 9

ER -

Synthesis and anti-HIV activity of l-2′,3′-Dideoxy-4′-selenonucleosides (l-4′-Se-ddNs)

Abstract

Keywords

UN SDGs

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