Syntheses and characterization of Cu2+, Ni2+ and Zn2+ binding capability of histidinehydroxamic acid derivatives

Edit Csapó, P. Buglyó, N. Nagy, M. Amélia Santos, Alma Corona, E. Farkas

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Two histidinehydroxamic acid derivatives (N-methyl-histidinehydroxamic acid, N-Me-Hisha and Z-histidinehydroxamic acid, Z-Hisha) have been synthesized and their complexation with Cu2+-, Ni2+- and Zn 2+-ions has been studied by using pH-potentiometric, UV-Vis, CD, 1H NMR, EPR and ESI-MS methods. Both of the two new derivatives contain one donor atom less compared to the histidinehydroxamic acid (Hisha). In the case of N-Me-Hisha the hydroxamate-N as donor is eliminated, while the coordination of the amino-N of Z-Hisha is not possible at all. With the ambidentate N-Me-Hisha, the histamine-type coordination mode is favoured if the metal ion is Ni2+ and the bis-[NH2,Nimid] complex is the most stable in this system. The mixed type, [NH 2,Nimid] + [O,O], coordination mode dominates in the Cu2+- N-Me-Hisha complexes, while different low stability mono-chelated linkage isomers are formed with Zn2+. With Z-Hisha (having poor water solubility) hydroxamate-type coordination mode predominates in low stability complexes in the Ni2+ and Zn2+ containing systems. Interestingly, the interaction with Cu2+ is very strong and results in the formation of a high stability 12-MC-4 type metallacrown with involvement of 5-membered and 7-membered chelates.

Original languageEnglish
Pages (from-to)3137-3145
Number of pages9
JournalPolyhedron
Volume29
Issue number16
DOIs
Publication statusPublished - Oct 29 2010

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Derivatives
acids
Acids
synthesis
histidinehydroxamic acid
histamines
Complexation
chelates
linkages
Isomers
Histamine
Metal ions
Paramagnetic resonance
metal ions
isomers
solubility
Solubility
Nuclear magnetic resonance
Ions
Atoms

Keywords

  • Cu-, Ni-, Zn-complexes
  • Histidinehydroxamic acid derivatives
  • Potential metalloenzyme inhibitors
  • Solution equilibrium

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Materials Chemistry
  • Physical and Theoretical Chemistry

Cite this

Syntheses and characterization of Cu2+, Ni2+ and Zn2+ binding capability of histidinehydroxamic acid derivatives. / Csapó, Edit; Buglyó, P.; Nagy, N.; Santos, M. Amélia; Corona, Alma; Farkas, E.

In: Polyhedron, Vol. 29, No. 16, 29.10.2010, p. 3137-3145.

Research output: Contribution to journalArticle

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N2 - Two histidinehydroxamic acid derivatives (N-methyl-histidinehydroxamic acid, N-Me-Hisha and Z-histidinehydroxamic acid, Z-Hisha) have been synthesized and their complexation with Cu2+-, Ni2+- and Zn 2+-ions has been studied by using pH-potentiometric, UV-Vis, CD, 1H NMR, EPR and ESI-MS methods. Both of the two new derivatives contain one donor atom less compared to the histidinehydroxamic acid (Hisha). In the case of N-Me-Hisha the hydroxamate-N as donor is eliminated, while the coordination of the amino-N of Z-Hisha is not possible at all. With the ambidentate N-Me-Hisha, the histamine-type coordination mode is favoured if the metal ion is Ni2+ and the bis-[NH2,Nimid] complex is the most stable in this system. The mixed type, [NH 2,Nimid] + [O,O], coordination mode dominates in the Cu2+- N-Me-Hisha complexes, while different low stability mono-chelated linkage isomers are formed with Zn2+. With Z-Hisha (having poor water solubility) hydroxamate-type coordination mode predominates in low stability complexes in the Ni2+ and Zn2+ containing systems. Interestingly, the interaction with Cu2+ is very strong and results in the formation of a high stability 12-MC-4 type metallacrown with involvement of 5-membered and 7-membered chelates.

AB - Two histidinehydroxamic acid derivatives (N-methyl-histidinehydroxamic acid, N-Me-Hisha and Z-histidinehydroxamic acid, Z-Hisha) have been synthesized and their complexation with Cu2+-, Ni2+- and Zn 2+-ions has been studied by using pH-potentiometric, UV-Vis, CD, 1H NMR, EPR and ESI-MS methods. Both of the two new derivatives contain one donor atom less compared to the histidinehydroxamic acid (Hisha). In the case of N-Me-Hisha the hydroxamate-N as donor is eliminated, while the coordination of the amino-N of Z-Hisha is not possible at all. With the ambidentate N-Me-Hisha, the histamine-type coordination mode is favoured if the metal ion is Ni2+ and the bis-[NH2,Nimid] complex is the most stable in this system. The mixed type, [NH 2,Nimid] + [O,O], coordination mode dominates in the Cu2+- N-Me-Hisha complexes, while different low stability mono-chelated linkage isomers are formed with Zn2+. With Z-Hisha (having poor water solubility) hydroxamate-type coordination mode predominates in low stability complexes in the Ni2+ and Zn2+ containing systems. Interestingly, the interaction with Cu2+ is very strong and results in the formation of a high stability 12-MC-4 type metallacrown with involvement of 5-membered and 7-membered chelates.

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