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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路路路 蟺, O-H路路路O and C-H路路路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

(a) Molecular structures of complex 2, hydrogen atoms are omitted for clarity (Thermal ellipsoids are shown at 50% probability level.); (b) View showing the 3鈥揇 structure of complex 2; (c) The independent units A and B appear in pair connecting the infinite chain.
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pone.0130922.g005: (a) Molecular structures of complex 2, hydrogen atoms are omitted for clarity (Thermal ellipsoids are shown at 50% probability level.); (b) View showing the 3鈥揇 structure of complex 2; (c) The independent units A and B appear in pair connecting the infinite chain.

Mentions: Complex 2 crystallizes in space group P-1 and includes two crystallographically independent binuclear zinc molecules (denoted A and B, respectively) (Fig 5a). The two binuclear zinc molecules are isostructural and only molecule A is described representatively. In molecule A, the Zn1 center is five-coordinated with the ZnNO4 donor set in a distorted trigonal bipyramidal geometry (蟿 = 0.685). The equatorial plane are occupied by one imine nitrogen atom (N1) and two carboxylate oxygen atoms (O4, O5) from two bis(monodentate) bridging carboxylate groups, while one phenolic oxygen atom (O1) and one protonated alkoxo oxygen atom (O10) are positioned at the apical positions with the O1鈥揨n1鈥揙10 angle of 165.1(4掳. The deviation of Zn1 center from the least-squares plane defined by the three equatorial donor atoms is 0.1686(64) 脜 in A (while 0.9793(73) 脜 for Zn4 ion in B).


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)

(a) Molecular structures of complex 2, hydrogen atoms are omitted for clarity (Thermal ellipsoids are shown at 50% probability level.); (b) View showing the 3鈥揇 structure of complex 2; (c) The independent units A and B appear in pair connecting the infinite chain.
© Copyright Policy
Related In: Results  -  Collection

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

pone.0130922.g005: (a) Molecular structures of complex 2, hydrogen atoms are omitted for clarity (Thermal ellipsoids are shown at 50% probability level.); (b) View showing the 3鈥揇 structure of complex 2; (c) The independent units A and B appear in pair connecting the infinite chain.
Mentions: Complex 2 crystallizes in space group P-1 and includes two crystallographically independent binuclear zinc molecules (denoted A and B, respectively) (Fig 5a). The two binuclear zinc molecules are isostructural and only molecule A is described representatively. In molecule A, the Zn1 center is five-coordinated with the ZnNO4 donor set in a distorted trigonal bipyramidal geometry (蟿 = 0.685). The equatorial plane are occupied by one imine nitrogen atom (N1) and two carboxylate oxygen atoms (O4, O5) from two bis(monodentate) bridging carboxylate groups, while one phenolic oxygen atom (O1) and one protonated alkoxo oxygen atom (O10) are positioned at the apical positions with the O1鈥揨n1鈥揙10 angle of 165.1(4掳. The deviation of Zn1 center from the least-squares plane defined by the three equatorial donor atoms is 0.1686(64) 脜 in A (while 0.9793(73) 脜 for Zn4 ion in B).

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路路路 蟺, O-H路路路O and C-H路路路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