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2004 | 51 | 1 | 93-106
Article title

Effect of tetrazole moiety on coordinating efficiency of deltorphin.

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EN
Abstracts
EN
A study of the effect of the tetrazole moiety, a cis-amide bond surrogate, on the Cu(II) coordinating properties of oligopeptides is reported. Insertion of the tetrazole moiety Ψ[CN4] into the peptide sequence of [D-Ala2]deltorphin I changes considerably the coordination ability of the peptide. Potentiometric and spectroscopic results show that if the tetrazole moiety is in a suitable position in the peptide chain, i.e. it follows the second residue, a stable CuL species involving 3N coordination is formed in the physiological pH range. The tetrazole Ψ[CN4] ring provides one of these nitrogens. The data indicate that Cu(II) ions are strongly trapped inside a bent peptide backbone. The peptide conformation changes achieved by Cu(II) coordination may be essential for the binding of tetrazole deltorphins at opiate receptors.
Publisher

Year
Volume
51
Issue
1
Pages
93-106
Physical description
Dates
published
2004
received
2003-10-31
revised
2004-02-03
accepted
2004-02-06
Contributors
  • Institute of General Food Chemistry, Technical University of Łódź, Łódź, Poland
  • Faculty of Chemistry, University of Gdańsk, Gdańsk, Poland
  • Department of Chemistry, University of Sassari, Sassari, Italy
author
  • Istituto C.N.R. Chim. Biomolecolare, Sassari, Italy
  • Faculty of Process and Environmental Engineering, Technical University of Łódź, Łódź, Poland
author
  • Institute of Organic Chemistry, Technical University of Łódź, Łódź, Poland
  • Institute of Organic Chemistry, Technical University of Łódź, Łódź, Poland
References
  • Allen FH, Kennar R, Taylor R. (1983) Systematic analysis of structural data as a research technique in organic chemistry. Acc Chem Res.; 16: 146-54.
  • Bal W, Kozłowski H, Kupryszewski G, Mackiewicz Z, Pettit LD, Robbins R. (1993) Complexes of Cu(II) with Asn-Ser-Phe- Arg-Tyr-NH2; an example of metal ion-promoted conformational organization which results in exceptionally high complex stability. J Inorg Biochem.; 52: 79-87.
  • Brasun J, Ciapetti P, Kozlowski H, Oldziej S, Taddei M, Valensin G, Gaggelli N. (2000) Chiral peptide nucleic acids having thymine and adenine in their side chain as specific ligands for Ni2+ and Cu2+ J Chem Soc Dalton Trans.; 2639-44.
  • Brasun J, Oldziej S, Taddei M, Kozlowski H. (2001) Impact of Cu(II) and Ni(II) on a structure of chiral peptide nucleic acids having four, six and eight thymines in a peptide side chain. J Inorg Biochem.; 85: 79-87.
  • Bryant SD, Attila M, Salvadori S, Guerrini R, Lazarus LH. (1994) Molecular dynamics conformations of deltorphin analogues advocate δ opiod binding site models. Pept Res.; 7: 175-84.
  • Chruscinska E, Dyba M, Micera G, Ambroziak W, Olczak J, Zabrocki J, Kozlowski H. (1997) Binding ability of Cu2+ ions by opiate-like fragments of bovine casein. J Inorg Biochem.; 66: 19-22.
  • Chruscinska E, Olczak J, Zabrocki J, Dyba M, Micera G, Sanna D, Kozlowski H. (1998) Specific interaction of bovine and human β-casomorphin-7 with Cu(II) ions. J Inorg Biochem.; 69: 91-5.
  • Chruscinska E, Micera G, Sanna D, Olczak J, Zabrocki J. (2001) A new class of peptide chelating agents towards copper(II) ions. Polyhedron.; 20: 1915-23.
  • Chruścińska E, Derdowska I, Kozlowski H, Lammek B, Łuczkowski M, Ołdziej S, Świątek-Kozłowska J. (2003) Unusual gain in the coordination ability of vasopressin-like peptides towards Cu2+ ions by insertion of the highly hydrophobic side chain. New J Chem.; 27: 251-6.
  • Daniele PG, Prenesti E, Ostacoli G. (1996) Ultraviolet-circular dichroism spectra for structural analysis of copper(II) complexes with aliphatic and aromatic ligands in aqueous solution. J Chem Soc Dalton Trans.; 3269-75.
  • Decock-Le Reverend B, Lebkiri A, Livera C, Pettit LD. (1986) A potentiometric and spectroscopic study of the interaction of Ala-Ala- Asp-Ala with Cu(II). Inorg Chim Acta.; 124: L19-22.
  • Decock-Le Reverend B, Adrianarijaona L, Livera C, Pettit LD, Steel I, Kozłowski H. (1986) A potentiometric and spectroscopic study of the interaction of the N terminal tetrapeptide fragment of fibrinopeptide A with CuII and NiII. J Chem Soc Dalton Trans.; 2221-6.
  • Dewar MJS, Zoebisch EG, Healy EF, Stewart JP. (1985) Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model. J Am Chem Soc.; 107: 3902-9.
  • Galey JF, Decock-Le Reverend B, Lebkiri A, Pettit LD, Pyburn SI, Kozłowski H. (1991) Specific interactions of the β-carboxylate group of the aspartic acid residue in oligopeptides containing one, two or three such residues with copper(II) ions. A potentiometric and spectroscopic study. J Chem Soc Dalton Trans.; 2281-7.
  • Gans P, Sabatini A, Vacca A. (1985) An improved general program for computation of formation constants from potentiometric data. J Chem Soc Dalton Trans.; 1195-200.
  • Gnonlonfoun N, El Mardi S, Lambs L, Berthon G. (1996) Copper(II) binary complex equilibria with [S]- and [R]-2-benzylaminomethylpyrrolidines under physiological conditions. Inorg Chim Acta.; 247: 175-81.
  • Hefford RJW, Pettit LD. (1981) Potentiometric and spectrophotometric study of the coordination compounds formed between cooper(II) and dipeptides containing tyrosine. J Chem Soc Dalton Trans.; 1331-5.
  • Irving H, Miles MG, Pettit LD. (1967) A study of some problems in determining the stoichiometric proton dissociation constants of complexes by potentiometic titrations using a glass electrode. Anal Chim Acta.; 38: 475-88.
  • Klamt A, Schurman G. (1993) COSMO - a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J Chem Soc Perkin Trans.; 2: 799-805.
  • Kowalik-Jankowska T, Jasionowski M, Łankiewicz L. (1999) Copper(II) complexation by pituitary adenylate cyclase activating polypeptide fragments. J Inorg Biochem.; 76: 63-70.
  • Kowalik-Jankowska T, LeŚniak W, Brasuń J, Stasiak M, Leplawy MT. (2000) Copper(II) complexes of deltakephalin and its analogues containing α-hydroxymethlyserine. Polyhedron.; 19: 241-5.
  • Kozłowski H, Micera G. (1995) Biological Fluids in Bioinorganic Chemistry. In Handbook of Metal-Ligand Interactions. Berthon G. ed, vol 1, pp 566-82. Marcel Dekker, New York.
  • Kozlowski H, Bal W, Dyba M, Kowalik-Jankowska T. (1999) Specific structure-stability relations in metallopeptides. Coord Chem Rev.; 184: 319-46.
  • Linder MC, Goode CA. (1991) Biochemistry of Copper. pp 220-31. Plenum Press, New York.
  • Livera C, Pettit LD, Bataille M, Krembel J, Bal W, Kozlowski H. (1988) Copper(II) complexes with some tetrapeptides containing the 'break-point' prolyl residue in the third position. J Chem Soc Dalton Trans.; 1357-60.
  • Lodyga-Chruscinska E, Micera G, Szajdzinska-Pietek E, Sanna D. (1998) Copper(II) complexes of opiate-like food peptides. J Agric Food Chem.; 46: 115-8.
  • Lodyga-Chruscinska E, Micera G, Sanna D, Olczak J, Zabrocki J, Kozlowski H, Chruscinski L. (1999) Effect of the tetrazole cis-amide bond surrogate on the complexing ability of some enkephalin analogues toward Cu(II) ions. J Inorg Biochem.; 76: 1-11.
  • Lodyga-Chruscinska E, Brzezinska-Blaszczyk E, Micera G, Sanna D, Kozlowski H, Olczak J, Zabrocki J, Olejnik AK. (2000) Can the 1,5-disubstituted tetrazole ring modify the co-ordination ability and biological activity of opiate-like peptides. J Inorg Biochem.; 78: 283-91.
  • Melchiorri PV, Falconieri-Erspamer G, Negri L, Corsi R, Barra D, Simmaco M, Kreil M. (1989) A family of naturally occurring peptides with high affinity and selectivity for δ opioid binding sites. Proc Natl Acad Sci U S A.; 86: 5188-92.
  • MOPAC 2002 (2002) Fujitsu Ltd.
  • Pettit LD, Gregor JG, Kozlowski H. (1990) In Perspectives on Bioinorganic Chemistry. Hay RW, Dilworth JR, Nolan KB, eds, vol 1, pp 16-27. JAI Press, London.
  • Sigel H, Martin RB. (1982) Coordinating properties of the amide bond. Stability and structure of metal ion complexes of peptides and related ligands. Chem Rev.; 82: 385-426.
  • Sovago I. (1990) Metal complexes of peptides and their derivatives. In Biocoordination Chemistry: Coordination Equilibria in Biologically Active Systems. Burger K, ed, pp 135-184. Ellis Horwood.
  • Woody RW. (1985) Circular Dichroism of peptides. In The Peptides. Hruby V ed, vol 7, pp 16-114. Academic Press, New York.
  • Voityuk AA, Rosch J. (2000) AM1/d parameters for molybdenum. J Phys Chem.; 104: 4089-94.
  • Zabrocki J, Smith GD, Dunbar J, Jijima H, Marshall GR. (1988) Conformational mimicry. 1. 1,5-Disubstituted tetrazole ring as a surrogate for the cis amide bond. J Am Chem Soc.; 110: 5875-80.
Document Type
Publication order reference
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YADDA identifier
bwmeta1.element.bwnjournal-article-abpv51i1p93kz
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