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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.


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Solid–state emission spectra of complexes 1 and 2 at room temperature.
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pone.0130922.g006: Solid–state emission spectra of complexes 1 and 2 at room temperature.

Mentions: The photoluminescence (PL) property of the ligands and complexes are studied in the solid–state at room temperature as shown in Fig 6, S2 and S3 Figs. The free ligand H2L1 displays a luminescence with an emission maximum at 517 nm excited at 440 nm, and complex 1 shows a similar strong luminescence with emission maximum peaks at 502 nm (with λex = 440 nm). The complex 2 exhibits weak emission at 483 nm upon excitation at 352 nm, relative to that of the corresponding ligand H3L2 (λem = 514 nm, λex = 468 nm) and complex 1. These emissions are neither metal-to-ligand charge transfer (MLCT) nor ligand-to-metal transfer (LMCT) in nature since the full filled d10 configuration of Zn2+ ions, which can probably be assigned to the intraligand (π-π*) fluorescent emission of benzene [31]. Investigations on the photoluminescence (PL) property shows the intensity of complex 1 is better than complex 2, which is probably due to the differences of ligands and coordination environment around central Zn (II) ions [32]. Thus, the high luminescence efficiency in the blue light region and the thermally stability indicates the chiral complex 1 may be excellent candidate of stable blue fluorescent materials.


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)

Solid–state emission spectra of complexes 1 and 2 at room temperature.
© Copyright Policy
Related In: Results  -  Collection

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

pone.0130922.g006: Solid–state emission spectra of complexes 1 and 2 at room temperature.
Mentions: The photoluminescence (PL) property of the ligands and complexes are studied in the solid–state at room temperature as shown in Fig 6, S2 and S3 Figs. The free ligand H2L1 displays a luminescence with an emission maximum at 517 nm excited at 440 nm, and complex 1 shows a similar strong luminescence with emission maximum peaks at 502 nm (with λex = 440 nm). The complex 2 exhibits weak emission at 483 nm upon excitation at 352 nm, relative to that of the corresponding ligand H3L2 (λem = 514 nm, λex = 468 nm) and complex 1. These emissions are neither metal-to-ligand charge transfer (MLCT) nor ligand-to-metal transfer (LMCT) in nature since the full filled d10 configuration of Zn2+ ions, which can probably be assigned to the intraligand (π-π*) fluorescent emission of benzene [31]. Investigations on the photoluminescence (PL) property shows the intensity of complex 1 is better than complex 2, which is probably due to the differences of ligands and coordination environment around central Zn (II) ions [32]. Thus, the high luminescence efficiency in the blue light region and the thermally stability indicates the chiral complex 1 may be excellent candidate of stable blue fluorescent materials.

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