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. 2007 Jan 11;50(1):165-8.
doi: 10.1021/jm061268p.

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

Yeon Sun Lee  1 , Richard S Agnes, Peg Davis, Shou-wu Ma, Hamid Badghisi, Josephine Lai, Frank Porreca, Victor J Hruby
Affiliations

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

Yeon Sun Lee et al. J Med Chem. .

Abstract

Partially modified retro-inverso, retro, and inverso isomers of hydrazide linked bifunctional peptides were designed, synthesized, and evaluated for bioactivities at delta/mu 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 delta and mu 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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Figures

Figure 1
Figure 1
Structures of partially retro–inverso (3 and 4), retro (5 and 6), and inverso (7 and 8) modified bifunctional peptides.
See this image and copyright information in PMC

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