Synthesis and biological activities of position one and three transposed analogs of the opioid peptide YKFA

John E. Burden; Peg Davis; Frank Porreca; Arno F. Spatola

doi:10.1016/S0960-894X(99)00625-3

Synthesis and biological activities of position one and three transposed analogs of the opioid peptide YKFA

John E. Burden, Peg Davis, Frank Porreca, Arno F. Spatola

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

13 Scopus citations

Abstract

Tyr-c[D-Lys-Phe-Ala], YKFA, is a potent opioid peptide analog with subnanomolar IC₅₀s toward mu and delta receptors. Transposing Phe and Tyr, a modification found to promote mu antagonist activity in opioid/somatostatin hybrids, gave surprisingly high mu agonist activities for several related analogs, considering the lack of a 1-position hydroxyl function.

Original language	English (US)
Pages (from-to)	3441-3446
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	9
Issue number	24
DOIs	https://doi.org/10.1016/S0960-894X(99)00625-3
State	Published - Dec 20 1999

Keywords

Agonists
Analgesics
Peptides and polypeptides
Receptors

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(99)00625-3

Cite this

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title = "Synthesis and biological activities of position one and three transposed analogs of the opioid peptide YKFA",

abstract = "Tyr-c[D-Lys-Phe-Ala], YKFA, is a potent opioid peptide analog with subnanomolar IC50s toward mu and delta receptors. Transposing Phe and Tyr, a modification found to promote mu antagonist activity in opioid/somatostatin hybrids, gave surprisingly high mu agonist activities for several related analogs, considering the lack of a 1-position hydroxyl function.",

keywords = "Agonists, Analgesics, Peptides and polypeptides, Receptors",

author = "Burden, {John E.} and Peg Davis and Frank Porreca and Spatola, {Arno F.}",

note = "Funding Information: Acknowledgement: This work was supported by grants from the U.S. Department of Education (through the GAANN Program) and by NIH GM33376. Amino acid analysis was performed by Mr. Benjamin van Osdol in the Department of Biochemistry at the University of Louisville Health Sciences Center, and electrospray mass spectrometry was performed at the University of Michigan Protein and Carbohydrate Structure Facility.",

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AU - Burden, John E.

AU - Davis, Peg

AU - Porreca, Frank

AU - Spatola, Arno F.

N1 - Funding Information: Acknowledgement: This work was supported by grants from the U.S. Department of Education (through the GAANN Program) and by NIH GM33376. Amino acid analysis was performed by Mr. Benjamin van Osdol in the Department of Biochemistry at the University of Louisville Health Sciences Center, and electrospray mass spectrometry was performed at the University of Michigan Protein and Carbohydrate Structure Facility.

PY - 1999/12/20

Y1 - 1999/12/20

N2 - Tyr-c[D-Lys-Phe-Ala], YKFA, is a potent opioid peptide analog with subnanomolar IC50s toward mu and delta receptors. Transposing Phe and Tyr, a modification found to promote mu antagonist activity in opioid/somatostatin hybrids, gave surprisingly high mu agonist activities for several related analogs, considering the lack of a 1-position hydroxyl function.

AB - Tyr-c[D-Lys-Phe-Ala], YKFA, is a potent opioid peptide analog with subnanomolar IC50s toward mu and delta receptors. Transposing Phe and Tyr, a modification found to promote mu antagonist activity in opioid/somatostatin hybrids, gave surprisingly high mu agonist activities for several related analogs, considering the lack of a 1-position hydroxyl function.

KW - Agonists

KW - Analgesics

KW - Peptides and polypeptides

KW - Receptors

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Synthesis and biological activities of position one and three transposed analogs of the opioid peptide YKFA

Abstract

Keywords

ASJC Scopus subject areas

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