Crystal Structure, Cytotoxicity and Interaction with DNA of Zinc (II) Complexes with o-Vanillin Schiff Base Ligands

• Published in: PloS one 2015-06, Vol.10 (6), p.e0130922
• Main Authors: Niu, Mei-Ju, Li, Zhen, Chang, Guo-Liang, Kong, Xiang-Jin, Hong, Min, Zhang, Qing-fu
• Format: Article
• Language: English
• Subjects: 1,3-Propanediol; Analysis; Benzaldehydes - chemistry; Benzaldehydes - pharmacology; Calf thymus; Cancer; Chemical engineering; Chemistry; Chirality; Circular dichroism; Cobalt; Coordination compounds; Crystal structure; Crystallography; Crystallography, X-Ray; Cytotoxicity; Cytotoxins - chemistry; Cytotoxins - pharmacology; Deoxyribonucleic acid; Dichroism; Dimethylformamide; DNA; DNA - chemistry; Double-stranded; Fluorescence; Fluorescence spectroscopy; Genetic research; Handedness; HL-60 Cells; Humans; Hydrogen; Hydrogen bonding; Imines; Infrared radiation; K562 Cells; Laboratories; Leukemia; Ligands; Molecular chains; Propanol; Propylene Glycols - chemistry; Propylene Glycols - pharmacology; Schiff bases; Schiff Bases - chemistry; Schiff Bases - pharmacology; Single crystals; Spectroscopy; Structural analysis; Toxicity; Vanillin; X-ray diffraction; Zinc
• ISSN: 1932-6203; 1932-6203
• DOI: 10.1371/journal.pone.0130922

Two new zinc complexes, Zn(HL1)2 (1) and [Zn2(H2L2)(OAc)2]2 (2) [H2L1 = Schiff base derived from o-vanillin and (R)-(+)-2-amino-3-phenyl-1-propanol, H3L2 = Schiff base derived from o-vanillin and 2-amino-2-ethyl-1,3-propanediol], have been synthesized and characterized by single crystal X-ray diffraction, elemental analyses, TG analyses, solid fluorescence, IR, UV-Vis and circular dichroism spectra. The structural analysis shows that complex 1 has a right-handed double helical chain along the crystallographic b axis. A homochiral 3D supramolecular architecture has been further constructed by intermolecular C-H··· π, O-H···O and C-H···O interactions. Complex 2 includes two crystallographically independent binuclear zinc molecules. The two binuclear zinc molecules are isostructural. The 2-D sheet supramolecular structure was formed by intermolecular hydrogen bonding interaction. The fluorescence of ligands and complexes in DMF at room temperature are studied. The interactions of two complexes with calf thymus DNA (CT-DNA) are investigated using UV-Vis, CD and fluorescence spectroscopy. The results show that complex 1 exhibits higher interaction with CT-DNA than complex 2. In addition, in vitro cytotoxicity of the complexes towards four kinds of cancerous cell lines (A549, HeLa, HL-60 and K562) were assayed by the MTT method. Investigations on the structures indicated that the chirality and nuclearity of zinc complexes play an important role on cytotoxic activity.