Partial retro-inverso, retro, and inverso modifications of hydrazide linked bifunctional peptides for opioid and cholecystokinin (CCK) receptors

Sun Lee Yeon; Richard S. Agnes; Peg Davis; Shou Wu Ma; Hamid Badghisi; Josephine Lai; Frank Porreca; Victor J. Hruby

doi:10.1021/jm061268p

Partial retro-inverso, retro, and inverso modifications of hydrazide linked bifunctional peptides for opioid and cholecystokinin (CCK) receptors

Sun Lee Yeon
, Richard S. Agnes
, Peg Davis
, Shou Wu Ma
, Hamid Badghisi
, Josephine Lai
, Frank Porreca
, Victor J. Hruby

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

29 Scopus citations

Abstract

Partially modified retro-inverso, retro, and inverso isomers of hydrazide linked bifunctional peptides were designed, synthesized, and evaluated for bioactivities at δ/μ opioid receptors and CCK-1/CCK-2 receptors. All modifications of the CCK pharmacophore moiety affected bioactivities for the CCK-1 and CCK-2 receptors (up to 180-fold increase in the binding affinity with higher selectivity) and for the δ and μ opioid receptors. The results indicate that the opioid and CCK pharmacophores in one molecule interact with each other to induce topographical changes for both pharmacophores.

Original language	English (US)
Pages (from-to)	165-168
Number of pages	4
Journal	Journal of Medicinal Chemistry
Volume	50
Issue number	1
DOIs	https://doi.org/10.1021/jm061268p
State	Published - Jan 1 2007

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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10.1021/jm061268p

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abstract = "Partially modified retro-inverso, retro, and inverso isomers of hydrazide linked bifunctional peptides were designed, synthesized, and evaluated for bioactivities at δ/μ opioid receptors and CCK-1/CCK-2 receptors. All modifications of the CCK pharmacophore moiety affected bioactivities for the CCK-1 and CCK-2 receptors (up to 180-fold increase in the binding affinity with higher selectivity) and for the δ and μ opioid receptors. The results indicate that the opioid and CCK pharmacophores in one molecule interact with each other to induce topographical changes for both pharmacophores.",

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T1 - Partial retro-inverso, retro, and inverso modifications of hydrazide linked bifunctional peptides for opioid and cholecystokinin (CCK) receptors

AU - Yeon, Sun Lee

AU - Agnes, Richard S.

AU - Davis, Peg

AU - Ma, Shou Wu

AU - Badghisi, Hamid

AU - Lai, Josephine

AU - Porreca, Frank

AU - Hruby, Victor J.

PY - 2007/1/1

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N2 - Partially modified retro-inverso, retro, and inverso isomers of hydrazide linked bifunctional peptides were designed, synthesized, and evaluated for bioactivities at δ/μ opioid receptors and CCK-1/CCK-2 receptors. All modifications of the CCK pharmacophore moiety affected bioactivities for the CCK-1 and CCK-2 receptors (up to 180-fold increase in the binding affinity with higher selectivity) and for the δ and μ opioid receptors. The results indicate that the opioid and CCK pharmacophores in one molecule interact with each other to induce topographical changes for both pharmacophores.

AB - Partially modified retro-inverso, retro, and inverso isomers of hydrazide linked bifunctional peptides were designed, synthesized, and evaluated for bioactivities at δ/μ opioid receptors and CCK-1/CCK-2 receptors. All modifications of the CCK pharmacophore moiety affected bioactivities for the CCK-1 and CCK-2 receptors (up to 180-fold increase in the binding affinity with higher selectivity) and for the δ and μ opioid receptors. The results indicate that the opioid and CCK pharmacophores in one molecule interact with each other to induce topographical changes for both pharmacophores.

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Partial retro-inverso, retro, and inverso modifications of hydrazide linked bifunctional peptides for opioid and cholecystokinin (CCK) receptors

Abstract

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