Synthesis, biological activity and decomposition studies of amino acid phosphomonoester amidates of acyclovir

Timothy W. Abraham, Edward J. McIntee, Vidhya V. Iyer, Raymond F. Schinazi, Carston R. Wagner

Research output: Contribution to journalReview article

15 Citations (Scopus)

Abstract

Highly stable and water soluble amino acid phosphomonoester amidates of acyclovir (ACV) were synthesized and shown to function predominantly as prodrugs of ACV and not acyclovir monophosphate (ACV-MP) with activities within two fold of the amino acid prodrug of ACV, valaciclovir (VACV). Metabolism studies revealed that incubation of cell-free extracts of Vero cells with the L-leucine phosphomonoester amidate of ACV (3c), resulted in a burst of ACV-MP production followed by the rapid generation of ACV.

Original languageEnglish (US)
Pages (from-to)2079-2092
Number of pages14
JournalNucleosides and Nucleotides
Volume16
Issue number10-11
DOIs
StatePublished - Jan 1 1997

Fingerprint

Acyclovir
Bioactivity
Decomposition
Amino Acids
valacyclovir
Prodrugs
Vero Cells
Cell Extracts
Metabolism
Leucine
Cells
Water

Cite this

Synthesis, biological activity and decomposition studies of amino acid phosphomonoester amidates of acyclovir. / Abraham, Timothy W.; McIntee, Edward J.; Iyer, Vidhya V.; Schinazi, Raymond F.; Wagner, Carston R.

In: Nucleosides and Nucleotides, Vol. 16, No. 10-11, 01.01.1997, p. 2079-2092.

Research output: Contribution to journalReview article

Abraham, Timothy W. ; McIntee, Edward J. ; Iyer, Vidhya V. ; Schinazi, Raymond F. ; Wagner, Carston R. / Synthesis, biological activity and decomposition studies of amino acid phosphomonoester amidates of acyclovir. In: Nucleosides and Nucleotides. 1997 ; Vol. 16, No. 10-11. pp. 2079-2092.
@article{ae80b520fbda47b68cb68b755af39e86,
title = "Synthesis, biological activity and decomposition studies of amino acid phosphomonoester amidates of acyclovir",
abstract = "Highly stable and water soluble amino acid phosphomonoester amidates of acyclovir (ACV) were synthesized and shown to function predominantly as prodrugs of ACV and not acyclovir monophosphate (ACV-MP) with activities within two fold of the amino acid prodrug of ACV, valaciclovir (VACV). Metabolism studies revealed that incubation of cell-free extracts of Vero cells with the L-leucine phosphomonoester amidate of ACV (3c), resulted in a burst of ACV-MP production followed by the rapid generation of ACV.",
author = "Abraham, {Timothy W.} and McIntee, {Edward J.} and Iyer, {Vidhya V.} and Schinazi, {Raymond F.} and Wagner, {Carston R.}",
year = "1997",
month = "1",
day = "1",
doi = "10.1080/07328319708002557",
language = "English (US)",
volume = "16",
pages = "2079--2092",
journal = "Nucleosides and Nucleotides",
issn = "0732-8311",
publisher = "Taylor and Francis Ltd.",
number = "10-11",

}

TY - JOUR

T1 - Synthesis, biological activity and decomposition studies of amino acid phosphomonoester amidates of acyclovir

AU - Abraham, Timothy W.

AU - McIntee, Edward J.

AU - Iyer, Vidhya V.

AU - Schinazi, Raymond F.

AU - Wagner, Carston R.

PY - 1997/1/1

Y1 - 1997/1/1

N2 - Highly stable and water soluble amino acid phosphomonoester amidates of acyclovir (ACV) were synthesized and shown to function predominantly as prodrugs of ACV and not acyclovir monophosphate (ACV-MP) with activities within two fold of the amino acid prodrug of ACV, valaciclovir (VACV). Metabolism studies revealed that incubation of cell-free extracts of Vero cells with the L-leucine phosphomonoester amidate of ACV (3c), resulted in a burst of ACV-MP production followed by the rapid generation of ACV.

AB - Highly stable and water soluble amino acid phosphomonoester amidates of acyclovir (ACV) were synthesized and shown to function predominantly as prodrugs of ACV and not acyclovir monophosphate (ACV-MP) with activities within two fold of the amino acid prodrug of ACV, valaciclovir (VACV). Metabolism studies revealed that incubation of cell-free extracts of Vero cells with the L-leucine phosphomonoester amidate of ACV (3c), resulted in a burst of ACV-MP production followed by the rapid generation of ACV.

UR - http://www.scopus.com/inward/record.url?scp=0031470425&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0031470425&partnerID=8YFLogxK

U2 - 10.1080/07328319708002557

DO - 10.1080/07328319708002557

M3 - Review article

VL - 16

SP - 2079

EP - 2092

JO - Nucleosides and Nucleotides

JF - Nucleosides and Nucleotides

SN - 0732-8311

IS - 10-11

ER -