6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid mimics active conformation of tyrosine in opioid peptides

Emanuela Sperlinga; Piotr Kosson; Zofia Urbanczyk-Lipkowska; Giuseppe Ronsisvalle; Daniel B Carr; Andrzej W Lipkowski

doi:10.1016/j.bmcl.2005.03.075

6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid mimics active conformation of tyrosine in opioid peptides

Bioorg Med Chem Lett. 2005 May 16;15(10):2467-9. doi: 10.1016/j.bmcl.2005.03.075.

Authors

Emanuela Sperlinga¹, Piotr Kosson, Zofia Urbanczyk-Lipkowska, Giuseppe Ronsisvalle, Daniel B Carr, Andrzej W Lipkowski

Affiliation

¹ Department of Pharmaceutical Sciences, University of Catania, Catania 95125, Italy.

PMID: 15863298
DOI: 10.1016/j.bmcl.2005.03.075

Abstract

6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (6Htc) has been proposed as a rigid mimic of tyrosine conformation in opioid ligand-receptor complex. The significant receptor binding to mu and delta opioid receptors of respective analogues of deltorphin, dermorphin, and endomorphin with D,L-6Htc prove initial prediction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carboxylic Acids / chemistry*
Crystallography, X-Ray
Isoquinolines / chemistry*
Molecular Structure
Opioid Peptides / chemistry*
Receptors, Opioid / chemistry
Tyrosine / chemistry*

Substances

Carboxylic Acids
Isoquinolines
Opioid Peptides
Receptors, Opioid
Tyrosine