Structure-Activity Relationships of Acyclic Selenopurine Nucleosides as Antiviral Agents

Pramod K. Sahu; Tamima Umme; Jinha Yu; Gyudong Kim; Shuhao Qu; Siddhi D. Naik; Lak Shin Jeong

doi:10.3390/molecules22071167

Structure-Activity Relationships of Acyclic Selenopurine Nucleosides as Antiviral Agents

Pramod K. Sahu, Tamima Umme, Jinha Yu, Gyudong Kim, Shuhao Qu, Siddhi D. Naik, Lak Shin Jeong

Department of Pharmaceutical Sciences

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

9 Scopus citations

Abstract

A series of acyclic selenopurine nucleosides 3a-f and 4a-g were synthesized based on the bioisosteric rationale between oxygen and selenium, and then evaluated for antiviral activity. Among the compounds tested, seleno-acyclovir (4a) exhibited the most potent anti-herpes simplex virus (HSV)-1 (EC50 = 1.47 µM) and HSV-2 (EC50 = 6.34 µM) activities without cytotoxicity up to 100 µM, while 2,6-diaminopurine derivatives 4e-g exhibited significant anti-human cytomegalovirus (HCMV) activity, which is slightly more potent than the guanine derivative 4d, indicating that they might act as prodrugs of seleno-ganciclovir (4d).

Original language	English
Journal	Molecules
Volume	22
Issue number	7
DOIs	https://doi.org/10.3390/molecules22071167
State	Published - 12 Jul 2017

Keywords

acyclic selenopurine nucleoside
anti-herpetic
antiviral
prodrug

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title = "Structure-Activity Relationships of Acyclic Selenopurine Nucleosides as Antiviral Agents",

abstract = "A series of acyclic selenopurine nucleosides 3a-f and 4a-g were synthesized based on the bioisosteric rationale between oxygen and selenium, and then evaluated for antiviral activity. Among the compounds tested, seleno-acyclovir (4a) exhibited the most potent anti-herpes simplex virus (HSV)-1 (EC50 = 1.47 µM) and HSV-2 (EC50 = 6.34 µM) activities without cytotoxicity up to 100 µM, while 2,6-diaminopurine derivatives 4e-g exhibited significant anti-human cytomegalovirus (HCMV) activity, which is slightly more potent than the guanine derivative 4d, indicating that they might act as prodrugs of seleno-ganciclovir (4d).",

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T1 - Structure-Activity Relationships of Acyclic Selenopurine Nucleosides as Antiviral Agents

AU - Sahu, Pramod K.

AU - Umme, Tamima

AU - Yu, Jinha

AU - Kim, Gyudong

AU - Qu, Shuhao

AU - Naik, Siddhi D.

AU - Jeong, Lak Shin

PY - 2017/7/12

Y1 - 2017/7/12

N2 - A series of acyclic selenopurine nucleosides 3a-f and 4a-g were synthesized based on the bioisosteric rationale between oxygen and selenium, and then evaluated for antiviral activity. Among the compounds tested, seleno-acyclovir (4a) exhibited the most potent anti-herpes simplex virus (HSV)-1 (EC50 = 1.47 µM) and HSV-2 (EC50 = 6.34 µM) activities without cytotoxicity up to 100 µM, while 2,6-diaminopurine derivatives 4e-g exhibited significant anti-human cytomegalovirus (HCMV) activity, which is slightly more potent than the guanine derivative 4d, indicating that they might act as prodrugs of seleno-ganciclovir (4d).

AB - A series of acyclic selenopurine nucleosides 3a-f and 4a-g were synthesized based on the bioisosteric rationale between oxygen and selenium, and then evaluated for antiviral activity. Among the compounds tested, seleno-acyclovir (4a) exhibited the most potent anti-herpes simplex virus (HSV)-1 (EC50 = 1.47 µM) and HSV-2 (EC50 = 6.34 µM) activities without cytotoxicity up to 100 µM, while 2,6-diaminopurine derivatives 4e-g exhibited significant anti-human cytomegalovirus (HCMV) activity, which is slightly more potent than the guanine derivative 4d, indicating that they might act as prodrugs of seleno-ganciclovir (4d).

KW - acyclic selenopurine nucleoside

KW - anti-herpetic

KW - antiviral

KW - prodrug

UR - https://www.scopus.com/pages/publications/85038129516

U2 - 10.3390/molecules22071167

DO - 10.3390/molecules22071167

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C2 - 28704950

AN - SCOPUS:85038129516

SN - 1420-3049

VL - 22

JO - Molecules

JF - Molecules

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ER -

Structure-Activity Relationships of Acyclic Selenopurine Nucleosides as Antiviral Agents

Abstract

Keywords

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