Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase

Sidath C. Kumarapperuma; Yanjie Sun; Marjan Jeselnik; Kiwon Chung; William B. Parker; Colleen B. Jonsson; Jeffrey B. Arterburn

doi:10.1016/j.bmcl.2007.03.018

Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase

Sidath C. Kumarapperuma, Yanjie Sun, Marjan Jeselnik, Kiwon Chung, William B. Parker, Colleen B. Jonsson, Jeffrey B. Arterburn

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

14 Scopus citations

Abstract

The conversion of ribavirin to the monophosphate by adenosine kinase is the rate-limiting step in activation of this broad spectrum antiviral drug. Variation of the 3-substituents in a series of bioisosteric and homologated 1-β-d-ribofuranosyl-1,2,4-triazoles has marked effects on activity with the human adenosine kinase, and analysis of computational descriptors and binding models offers insight for the design of novel substrates.

Original language	English (US)
Pages (from-to)	3203-3207
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	17
Issue number	11
DOIs	https://doi.org/10.1016/j.bmcl.2007.03.018
State	Published - Jun 1 2007
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by Department of Defense USAMRC Grant No. W81XWH-04-C-0055 (C.J.), and NIH INBRE RR016480 (J.A.).

Keywords

Adenosine kinase
Antiviral
Bioisostere
Ribavirin
Triazole

Publisher link

10.1016/j.bmcl.2007.03.018

Find It

Find It at U of M Libraries

Cite this

@article{eb744787a139409cacc7e0f43ff0646a,

title = "Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase",

abstract = "The conversion of ribavirin to the monophosphate by adenosine kinase is the rate-limiting step in activation of this broad spectrum antiviral drug. Variation of the 3-substituents in a series of bioisosteric and homologated 1-β-d-ribofuranosyl-1,2,4-triazoles has marked effects on activity with the human adenosine kinase, and analysis of computational descriptors and binding models offers insight for the design of novel substrates.",

keywords = "Adenosine kinase, Antiviral, Bioisostere, Ribavirin, Triazole",

author = "Kumarapperuma, {Sidath C.} and Yanjie Sun and Marjan Jeselnik and Kiwon Chung and Parker, {William B.} and Jonsson, {Colleen B.} and Arterburn, {Jeffrey B.}",

note = "Funding Information: This work was supported by Department of Defense USAMRC Grant No. W81XWH-04-C-0055 (C.J.), and NIH INBRE RR016480 (J.A.).",

year = "2007",

month = jun,

day = "1",

doi = "10.1016/j.bmcl.2007.03.018",

language = "English (US)",

volume = "17",

pages = "3203--3207",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "11",

}

TY - JOUR

T1 - Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase

AU - Kumarapperuma, Sidath C.

AU - Sun, Yanjie

AU - Jeselnik, Marjan

AU - Chung, Kiwon

AU - Parker, William B.

AU - Jonsson, Colleen B.

AU - Arterburn, Jeffrey B.

N1 - Funding Information: This work was supported by Department of Defense USAMRC Grant No. W81XWH-04-C-0055 (C.J.), and NIH INBRE RR016480 (J.A.).

PY - 2007/6/1

Y1 - 2007/6/1

N2 - The conversion of ribavirin to the monophosphate by adenosine kinase is the rate-limiting step in activation of this broad spectrum antiviral drug. Variation of the 3-substituents in a series of bioisosteric and homologated 1-β-d-ribofuranosyl-1,2,4-triazoles has marked effects on activity with the human adenosine kinase, and analysis of computational descriptors and binding models offers insight for the design of novel substrates.

AB - The conversion of ribavirin to the monophosphate by adenosine kinase is the rate-limiting step in activation of this broad spectrum antiviral drug. Variation of the 3-substituents in a series of bioisosteric and homologated 1-β-d-ribofuranosyl-1,2,4-triazoles has marked effects on activity with the human adenosine kinase, and analysis of computational descriptors and binding models offers insight for the design of novel substrates.

KW - Adenosine kinase

KW - Antiviral

KW - Bioisostere

KW - Ribavirin

KW - Triazole

UR - http://www.scopus.com/inward/record.url?scp=34247893961&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34247893961&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2007.03.018

DO - 10.1016/j.bmcl.2007.03.018

M3 - Article

C2 - 17379518

AN - SCOPUS:34247893961

SN - 0960-894X

VL - 17

SP - 3203

EP - 3207

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 11

ER -

Structural effects on the phosphorylation of 3-substituted 1-β-d-ribofuranosyl-1,2,4-triazoles by human adenosine kinase

Abstract

Bibliographical note

Keywords

Publisher link

Find It

Other files and links

Fingerprint

Cite this