Synthesis and biological activities of YkFA analogues: Effects of position 4 substitutions and altered ring size on in vitro opioid activity

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

doi:10.1016/S0960-894X(01)00706-5

Synthesis and biological activities of YkFA analogues: Effects of position 4 substitutions and altered ring size on in vitro opioid activity

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

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

13 Scopus citations

Abstract

Substitution in position 4 of the potent opioid peptide YkFA with aliphatic hydrophobic residues resulted in compounds that retained low nanomolar activities at both μ and δ opioid receptors, while ring contraction by incorporation of diaminobutyric acid in position 2 resulted in a more pronounced decrease in potency at both receptors for the ψ[CH₂NH] pseudopeptide as compared to the all amide parent.

Original language	English (US)
Pages (from-to)	213-216
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	12
Issue number	2
DOIs	https://doi.org/10.1016/S0960-894X(01)00706-5
State	Published - Jan 21 2002

ASJC Scopus subject areas

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

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title = "Synthesis and biological activities of YkFA analogues: Effects of position 4 substitutions and altered ring size on in vitro opioid activity",

abstract = "Substitution in position 4 of the potent opioid peptide YkFA with aliphatic hydrophobic residues resulted in compounds that retained low nanomolar activities at both μ and δ opioid receptors, while ring contraction by incorporation of diaminobutyric acid in position 2 resulted in a more pronounced decrease in potency at both receptors for the ψ[CH2NH] pseudopeptide as compared to the all amide parent.",

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

note = "Funding Information: This work was supported by grants from the US 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. ",

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AU - Davis, Peg

AU - Porreca, Frank

AU - Spatola, Arno F.

N1 - Funding Information: This work was supported by grants from the US 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.

PY - 2002/1/21

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N2 - Substitution in position 4 of the potent opioid peptide YkFA with aliphatic hydrophobic residues resulted in compounds that retained low nanomolar activities at both μ and δ opioid receptors, while ring contraction by incorporation of diaminobutyric acid in position 2 resulted in a more pronounced decrease in potency at both receptors for the ψ[CH2NH] pseudopeptide as compared to the all amide parent.

AB - Substitution in position 4 of the potent opioid peptide YkFA with aliphatic hydrophobic residues resulted in compounds that retained low nanomolar activities at both μ and δ opioid receptors, while ring contraction by incorporation of diaminobutyric acid in position 2 resulted in a more pronounced decrease in potency at both receptors for the ψ[CH2NH] pseudopeptide as compared to the all amide parent.

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Synthesis and biological activities of YkFA analogues: Effects of position 4 substitutions and altered ring size on in vitro opioid activity

Abstract

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