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

Niu MJ, Li Z, Chang GL, Kong XJ, Hong M, Zhang QF - PLoS ONE (2015)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong, 252059, China; Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, Liaocheng University, Liaocheng, Shandong, 252059, China.

ABSTRACT
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.

No MeSH data available.


Related in: MedlinePlus

CD-spectra of CT-DNA in the absence and presence of complexes 1 and 2, [DNA] = 100 μM, [VOL] = 0 and 40 μM, respectively.
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pone.0130922.g010: CD-spectra of CT-DNA in the absence and presence of complexes 1 and 2, [DNA] = 100 μM, [VOL] = 0 and 40 μM, respectively.

Mentions: CD spectroscopy is one of the most sensitive ways and used to elucidate the changes, the conformational variations of DNA upon interaction with small molecules (often organic ligands or metal complexes) in solution. The CD spectra of CT-DNA on the addition of complexes 1 and 2, exhibit significant perturbations both in negative and positive bands (shown in Fig 10). CD spectrum of CT-DNA exhibits a positive band at 274 nm (base stacking) and a negative band at 244 nm (helicity). The observed CD spectrum of CT DNA consists of a positive band at 274 nm due to base stacking and a negative band at 244 nm caused by helicity, which are characteristic of DNA in right-handed B-form. However, the positive and negative bands of complexes 1, 2 exhibited increase in intensity with a slight red-shift of the maximum which was attributed to partial insertion of planar aromatic chromophores in between the DNA base pairs causing stabilization of base stacking consequently [2]. The CD spectra also showed that the binding of the complex to CT-DNA does not lead to a significant change in the helix conformation of CT-DNA.


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

Niu MJ, Li Z, Chang GL, Kong XJ, Hong M, Zhang QF - PLoS ONE (2015)

CD-spectra of CT-DNA in the absence and presence of complexes 1 and 2, [DNA] = 100 μM, [VOL] = 0 and 40 μM, respectively.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4482705&req=5

pone.0130922.g010: CD-spectra of CT-DNA in the absence and presence of complexes 1 and 2, [DNA] = 100 μM, [VOL] = 0 and 40 μM, respectively.
Mentions: CD spectroscopy is one of the most sensitive ways and used to elucidate the changes, the conformational variations of DNA upon interaction with small molecules (often organic ligands or metal complexes) in solution. The CD spectra of CT-DNA on the addition of complexes 1 and 2, exhibit significant perturbations both in negative and positive bands (shown in Fig 10). CD spectrum of CT-DNA exhibits a positive band at 274 nm (base stacking) and a negative band at 244 nm (helicity). The observed CD spectrum of CT DNA consists of a positive band at 274 nm due to base stacking and a negative band at 244 nm caused by helicity, which are characteristic of DNA in right-handed B-form. However, the positive and negative bands of complexes 1, 2 exhibited increase in intensity with a slight red-shift of the maximum which was attributed to partial insertion of planar aromatic chromophores in between the DNA base pairs causing stabilization of base stacking consequently [2]. The CD spectra also showed that the binding of the complex to CT-DNA does not lead to a significant change in the helix conformation of CT-DNA.

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong, 252059, China; Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, Liaocheng University, Liaocheng, Shandong, 252059, China.

ABSTRACT
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.

No MeSH data available.


Related in: MedlinePlus