Potentiometric and spectroscopic studies on copper(II) and zinc(II) complexes of peptides containing bis(imidazolyl) ligands

K. Várnagy, I. Sóvágó, Károly Ágoston, Zsuzsanna Likó, H. Süli-Vargha, Daniele Sanna, Giovanni Micera

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Abstract

Copper- and zinc-(II) complexes of various bis(imidazolyl) ligands have been studied by potentiometric, visible and EPR spectroscopic methods. The ligands included bis(imidazol-2-yl)methane (CH2R2), bis-(imidazol-2-yl)methylamine (R2CHNH2) and 3,3-[bis(imidazol-2-yl)]propionic acid (R2CHCH2CO2H) and peptides in which the bis(imidazolyl) groups are coupled at the C-terminus, MeCO-Pro-Leu-Gly-NHCHR2 and ButOCO-Pro-His-Gly-NHCHR2, or the N-terminus, R2CHCH2CO-Ile-Ala-Gly-OEt and R2CHCH2CO-Ile-His-Gly-OEt (where R = imidazol-2-yl). The data revealed that stable mono- and bis-(ligand) complexes are formed with all ligands and the imidazole nitrogens are the main metal binding sites. Tridentate co-ordination of R2CHNH2 was concluded to exist in the equimolar solutions of copper(II) and R2CHNH2, which results in the formation of a dinuclear mixed-hydroxo complex with imidazole bridging. Deprotonation of the co-ordinated water molecules was also observed around the physiological pH range in the zinc(II)-R2CHNH2complex. The involvement of the side-chain imidazole residues of the peptides ButOCO-Pro-His-Gly-NHCHR2 and especially R2CHCH2CO-Ile-His-Gly-OEt in co-ordination has also been demonstrated.

Original languageEnglish
Pages (from-to)2939-2945
Number of pages7
JournalJournal of the Chemical Society, Dalton Transactions
Issue number20
DOIs
Publication statusPublished - 1994

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Zinc
Copper
Ligands
Peptides
Deprotonation
Methane
Paramagnetic resonance
Nitrogen
Metals
Binding Sites
Molecules
Water
imidazole

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Potentiometric and spectroscopic studies on copper(II) and zinc(II) complexes of peptides containing bis(imidazolyl) ligands. / Várnagy, K.; Sóvágó, I.; Ágoston, Károly; Likó, Zsuzsanna; Süli-Vargha, H.; Sanna, Daniele; Micera, Giovanni.

In: Journal of the Chemical Society, Dalton Transactions, No. 20, 1994, p. 2939-2945.

Research output: Contribution to journalArticle

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abstract = "Copper- and zinc-(II) complexes of various bis(imidazolyl) ligands have been studied by potentiometric, visible and EPR spectroscopic methods. The ligands included bis(imidazol-2-yl)methane (CH2R2), bis-(imidazol-2-yl)methylamine (R2CHNH2) and 3,3-[bis(imidazol-2-yl)]propionic acid (R2CHCH2CO2H) and peptides in which the bis(imidazolyl) groups are coupled at the C-terminus, MeCO-Pro-Leu-Gly-NHCHR2 and ButOCO-Pro-His-Gly-NHCHR2, or the N-terminus, R2CHCH2CO-Ile-Ala-Gly-OEt and R2CHCH2CO-Ile-His-Gly-OEt (where R = imidazol-2-yl). The data revealed that stable mono- and bis-(ligand) complexes are formed with all ligands and the imidazole nitrogens are the main metal binding sites. Tridentate co-ordination of R2CHNH2 was concluded to exist in the equimolar solutions of copper(II) and R2CHNH2, which results in the formation of a dinuclear mixed-hydroxo complex with imidazole bridging. Deprotonation of the co-ordinated water molecules was also observed around the physiological pH range in the zinc(II)-R2CHNH2complex. The involvement of the side-chain imidazole residues of the peptides ButOCO-Pro-His-Gly-NHCHR2 and especially R2CHCH2CO-Ile-His-Gly-OEt in co-ordination has also been demonstrated.",
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T1 - Potentiometric and spectroscopic studies on copper(II) and zinc(II) complexes of peptides containing bis(imidazolyl) ligands

AU - Várnagy, K.

AU - Sóvágó, I.

AU - Ágoston, Károly

AU - Likó, Zsuzsanna

AU - Süli-Vargha, H.

AU - Sanna, Daniele

AU - Micera, Giovanni

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N2 - Copper- and zinc-(II) complexes of various bis(imidazolyl) ligands have been studied by potentiometric, visible and EPR spectroscopic methods. The ligands included bis(imidazol-2-yl)methane (CH2R2), bis-(imidazol-2-yl)methylamine (R2CHNH2) and 3,3-[bis(imidazol-2-yl)]propionic acid (R2CHCH2CO2H) and peptides in which the bis(imidazolyl) groups are coupled at the C-terminus, MeCO-Pro-Leu-Gly-NHCHR2 and ButOCO-Pro-His-Gly-NHCHR2, or the N-terminus, R2CHCH2CO-Ile-Ala-Gly-OEt and R2CHCH2CO-Ile-His-Gly-OEt (where R = imidazol-2-yl). The data revealed that stable mono- and bis-(ligand) complexes are formed with all ligands and the imidazole nitrogens are the main metal binding sites. Tridentate co-ordination of R2CHNH2 was concluded to exist in the equimolar solutions of copper(II) and R2CHNH2, which results in the formation of a dinuclear mixed-hydroxo complex with imidazole bridging. Deprotonation of the co-ordinated water molecules was also observed around the physiological pH range in the zinc(II)-R2CHNH2complex. The involvement of the side-chain imidazole residues of the peptides ButOCO-Pro-His-Gly-NHCHR2 and especially R2CHCH2CO-Ile-His-Gly-OEt in co-ordination has also been demonstrated.

AB - Copper- and zinc-(II) complexes of various bis(imidazolyl) ligands have been studied by potentiometric, visible and EPR spectroscopic methods. The ligands included bis(imidazol-2-yl)methane (CH2R2), bis-(imidazol-2-yl)methylamine (R2CHNH2) and 3,3-[bis(imidazol-2-yl)]propionic acid (R2CHCH2CO2H) and peptides in which the bis(imidazolyl) groups are coupled at the C-terminus, MeCO-Pro-Leu-Gly-NHCHR2 and ButOCO-Pro-His-Gly-NHCHR2, or the N-terminus, R2CHCH2CO-Ile-Ala-Gly-OEt and R2CHCH2CO-Ile-His-Gly-OEt (where R = imidazol-2-yl). The data revealed that stable mono- and bis-(ligand) complexes are formed with all ligands and the imidazole nitrogens are the main metal binding sites. Tridentate co-ordination of R2CHNH2 was concluded to exist in the equimolar solutions of copper(II) and R2CHNH2, which results in the formation of a dinuclear mixed-hydroxo complex with imidazole bridging. Deprotonation of the co-ordinated water molecules was also observed around the physiological pH range in the zinc(II)-R2CHNH2complex. The involvement of the side-chain imidazole residues of the peptides ButOCO-Pro-His-Gly-NHCHR2 and especially R2CHCH2CO-Ile-His-Gly-OEt in co-ordination has also been demonstrated.

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