Complexes of salicylaldehyde acylhydrazones: Cytotoxicity, QSAR and crystal structure of the sterically hindered t-butyl dimer

A series of acylhydrazones of salicylaldehyde and their transition metal complexes, predominantly copper(II), have been prepared and characterized. The crystal structure of the Cu(II) complex of the sterically hindered t-butyl derivative contains a phenolato bridged dimer with the ligand coordinated...

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Bibliographic Details
Published in:Journal of inorganic biochemistry 1998-12, Vol.72 (3), p.155-162
Main Authors: Koh, L.L, Kon, O.L, Loh, K.W, Long, Y.C, Ranford, J.D, Tan, A.L.C, Tjan, Y.Y
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Crystallography, X-Ray
Dimerization
Humans
Hydrazones - chemistry
Hydrazones - pharmacology
Structure-Activity Relationship
Tumor Cells, Cultured
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Summary:A series of acylhydrazones of salicylaldehyde and their transition metal complexes, predominantly copper(II), have been prepared and characterized. The crystal structure of the Cu(II) complex of the sterically hindered t-butyl derivative contains a phenolato bridged dimer with the ligand coordinated as a tridentate moiety. QSAR analyses of the cytotoxicity of the chelators and their Cu(II) complexes reveals that solubility is the dominant factor for activity. Compounds display a maximum with respect to lipophilicity, allowing optimization of the bioactivity for both the ligands and their complexes. Copper complexes are significantly more cytotoxic than the metal-free ligands and complexes of other metals: Cu > Ni > Zn=Mn > Fe=Cr > Co.
ISSN:0162-0134
1873-3344
DOI:10.1016/S0162-0134(98)10075-2