Coumarin-based prodrugs 2. Synthesis and bioreversibility studies of an esterase-sensitive cyclic prodrug of DADLE, an opioid peptide

Binghe Wang; Wei Wang; Huijuan Zhang; Daxian Shan; Terrill D. Smith

doi:10.1016/S0960-894X(96)00526-4

Coumarin-based prodrugs 2. Synthesis and bioreversibility studies of an esterase-sensitive cyclic prodrug of DADLE, an opioid peptide

Binghe Wang
, Wei Wang
, Huijuan Zhang
, Daxian Shan
, Terrill D. Smith

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

34 Scopus citations

Abstract

A coumarin-based esterase-sensitive cyclic prodrug of an opioid peptide, DADLE, was prepared. The cyclic prodrug quickly released (t( 1/4 ) = 761 min) its original peptide, DADLE, upon esterase catalyzed hydrolysis. Such a system can be used for the preparation of cyclic prodrugs of other biologically active peptides aimed at improving their bioavailability.

Original language	English (US)
Pages (from-to)	2823-2826
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	6
Issue number	23
DOIs	https://doi.org/10.1016/S0960-894X(96)00526-4
State	Published - Dec 3 1996
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0960-894X(96)00526-4

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title = "Coumarin-based prodrugs 2. Synthesis and bioreversibility studies of an esterase-sensitive cyclic prodrug of DADLE, an opioid peptide",

abstract = "A coumarin-based esterase-sensitive cyclic prodrug of an opioid peptide, DADLE, was prepared. The cyclic prodrug quickly released (t( 1/4 ) = 761 min) its original peptide, DADLE, upon esterase catalyzed hydrolysis. Such a system can be used for the preparation of cyclic prodrugs of other biologically active peptides aimed at improving their bioavailability.",

author = "Binghe Wang and Wei Wang and Huijuan Zhang and Daxian Shan and Smith, \{Terrill D.\}",

note = "Funding Information: Acknowledgment: Financial support from the Presbyterian Health Foundation is gratefully acknowledged. We also acknowledge the technical assistance of Thao Pham and Bau Tran. Mass spectra were obtained at the Mass Spectrometry Laboratory for Biotechnology, North Carolina State University. Partial funding for the facility was obtained from the North Carolina Biotechnology Center and the National Science Foundation grant 9111391.",

year = "1996",

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doi = "10.1016/S0960-894X(96)00526-4",

language = "English (US)",

volume = "6",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Coumarin-based prodrugs 2. Synthesis and bioreversibility studies of an esterase-sensitive cyclic prodrug of DADLE, an opioid peptide

AU - Wang, Binghe

AU - Wang, Wei

AU - Zhang, Huijuan

AU - Shan, Daxian

AU - Smith, Terrill D.

N1 - Funding Information: Acknowledgment: Financial support from the Presbyterian Health Foundation is gratefully acknowledged. We also acknowledge the technical assistance of Thao Pham and Bau Tran. Mass spectra were obtained at the Mass Spectrometry Laboratory for Biotechnology, North Carolina State University. Partial funding for the facility was obtained from the North Carolina Biotechnology Center and the National Science Foundation grant 9111391.

PY - 1996/12/3

Y1 - 1996/12/3

N2 - A coumarin-based esterase-sensitive cyclic prodrug of an opioid peptide, DADLE, was prepared. The cyclic prodrug quickly released (t( 1/4 ) = 761 min) its original peptide, DADLE, upon esterase catalyzed hydrolysis. Such a system can be used for the preparation of cyclic prodrugs of other biologically active peptides aimed at improving their bioavailability.

AB - A coumarin-based esterase-sensitive cyclic prodrug of an opioid peptide, DADLE, was prepared. The cyclic prodrug quickly released (t( 1/4 ) = 761 min) its original peptide, DADLE, upon esterase catalyzed hydrolysis. Such a system can be used for the preparation of cyclic prodrugs of other biologically active peptides aimed at improving their bioavailability.

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IS - 23

ER -

Coumarin-based prodrugs 2. Synthesis and bioreversibility studies of an esterase-sensitive cyclic prodrug of DADLE, an opioid peptide

Abstract

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