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Impact of 1,5-disubstituted tetrazole ring on chelating ability of delta-selective opioid peptide

Lodyga-Chruscinska, Elzbieta and Oldziej, Stanislaw and Micera, Giovanni and Sanna, Daniele and Chruscinskac, Longin and Olczak, Jacek and Zabrocki, Janusz (2004) Impact of 1,5-disubstituted tetrazole ring on chelating ability of delta-selective opioid peptide. Journal of Inorganic Biochemistry, Vol. 98 (3), p. 447-458. ISSN 0162-0134. Article.

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DOI: 10.1016/j.jinorgbio.2003.11.011

Abstract

Complex formation between Cu(II) and three tetrazole analogues of opioid peptide – deltorphin I has been investigated. In potentiometric and spectroscopic (UV–Vis, CD and EPR) studies have been established the thermodynamic stability, speciation and structure of Cu(II) complexes with Tyr-D -Ala-Phe-Asp-Val-Val-Gly-NH2 (L1), Tyr-Ψ(CN4)-Gly-Phe-Asp-Val-Val-Gly-NH2 (L2), Tyr-Gly-Ψ(CN4)-Phe-Asp-Val-Val-Gly-NH2 (L3) and Tyr-D -Ala-Ψ(CN4)-Phe-Asp-Val-Val-Gly-NH2 (L4). The site of the insertion of tetrazole moiety Ψ(CN4) into the peptide sequences has critical impact on their co-ordination ability. Comparison of the binding ability of the tetrazole analogues reveals that around physiological pH region the L3 and L4 are more effective ligands for copper(II) than L1 and L2. The peptide conformation changes achieved by Cu(II) co-ordination may be essential for binding of the tetrazole deltorphins at the opiate receptors.

Item Type:Article
ID Code:1428
Status:Published
Refereed:Yes
Uncontrolled Keywords:Opioid peptides, tetrazole analogues of deltorphin I, Cu(II) complexes
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Elsevier Science
ISSN:0162-0134
Deposited On:18 Aug 2009 10:05

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