Literature

Abstract

Analogues of the δ opioid antagonist peptide TIPP (H-Tyr-Tic-Phe-Phe-OH; Tic=1,2,3,4-tetrahydroisoquinoline3-carboxylic acid) containing various 4'-[N-(alkyl or aralkyl)carboxamido]phenylalanine analogues in place of Tyr(1) were synthesized. The compounds showed subnanomolar or low nanomolar δ opioid receptor binding affinity and various efficacy at the δ receptor (antagonism, partial agonism, full agonism) in the [(35)S]GTPγS binding assay. Two analogues, [1-Ncp(1)]TIPP (1-Ncp=4'-[N-(2-(naphthalene-1-yl)ethyl)carboxamido]phenylalanine) and [2-Ncp(1)]TIPP (2-Ncp=4'-[N-(2-(naphthalene-2-yl)ethyl)carboxamido]phenylalanine), were identified as potent and selective δ opioid agonists.

DOI： 10.1016/j.bmcl.2012.01.063

Novel TIPP (H-Tyr-Tic-Phe-Phe-OH) analogues displaying a wide range of efficacies at the δ opioid receptor. Discovery of two highly potent and selective δ opioid agonists

Bioorganic & Medicinal Chemistry Letters 2012.0

TIPP[.psi.]: a highly potent and stable pseudopeptide .delta. opioid receptor antagonist with extraordinary .delta. selectivity

Journal of Medicinal Chemistry 1993.0

N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile

Bioorganic & Medicinal Chemistry Letters 2013.0

The Opioid μ Agonist/δ Antagonist DIPP-NH<sub>2</sub>[Ψ] Produces a Potent Analgesic Effect, No Physical Dependence, and Less Tolerance than Morphine in Rats

Journal of Medicinal Chemistry 1999.0

N,N-Diethyl-4-[(3-hydroxyphenyl)(piperidin-4-yl)amino] benzamide derivatives: The development of diaryl amino piperidines as potent δ opioid receptor agonists with in vivo anti-nociceptive activity in rodent models

Bioorganic & Medicinal Chemistry Letters 2009.0

Cyclic Enkephalin Analogues with Exceptional Potency and Selectivity for δ-Opioid Receptors