General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability

Xiaoxu Li; John Stephen Taylor

doi:10.1016/j.bmc.2003.11.016

General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability

Xiaoxu Li
, John Stephen Taylor

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

12 Scopus citations

Abstract

To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg ₉. The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg ₉Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described.

Original language	English
Pages (from-to)	545-552
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	12
Issue number	3
DOIs	https://doi.org/10.1016/j.bmc.2003.11.016
State	Published - Feb 1 2004

Keywords

Arg peptide
Fluorescein
Fluorogenic ester
Prodrug

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10.1016/j.bmc.2003.11.016

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title = "General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability",

abstract = "To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg 9. The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg 9Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described.",

keywords = "Arg peptide, Fluorescein, Fluorogenic ester, Prodrug",

author = "Xiaoxu Li and Taylor, \{John Stephen\}",

note = "Funding Information: This work was financially supported by an NIH grant (RO1-CA92477). Mass spectrometry was provided by the Washington University Mass Spectrometry Resource (Grant No. P41RR0954).",

year = "2004",

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doi = "10.1016/j.bmc.2003.11.016",

language = "English",

volume = "12",

pages = "545--552",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

number = "3",

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TY - JOUR

T1 - General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability

AU - Li, Xiaoxu

AU - Taylor, John Stephen

N1 - Funding Information: This work was financially supported by an NIH grant (RO1-CA92477). Mass spectrometry was provided by the Washington University Mass Spectrometry Resource (Grant No. P41RR0954).

PY - 2004/2/1

Y1 - 2004/2/1

N2 - To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg 9. The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg 9Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described.

AB - To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg 9. The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg 9Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described.

KW - Arg peptide

KW - Fluorescein

KW - Fluorogenic ester

KW - Prodrug

UR - https://www.scopus.com/pages/publications/0347761410

U2 - 10.1016/j.bmc.2003.11.016

DO - 10.1016/j.bmc.2003.11.016

M3 - Article

C2 - 14738963

AN - SCOPUS:0347761410

SN - 0968-0896

VL - 12

SP - 545

EP - 552

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 3

ER -

General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability

Abstract

Keywords

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