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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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Molecular structures of complex 1, hydrogen atoms are omitted for clarity (Thermal ellipsoids are shown at 50% probability level).
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pone.0130922.g003: Molecular structures of complex 1, hydrogen atoms are omitted for clarity (Thermal ellipsoids are shown at 50% probability level).

Mentions: Single crystal X-ray diffraction analysis reveals that complex 1 crystallizes in monoclinic space group P21, and consists of one Zn (II) ion and two chiral HL1- in the asymmetric unit. As shown in Fig 3, the central Zn (II) ion is four-coordinated by two deprotonated phenolic O atoms and two imino N atoms from two different chiral HL1- ligands, displaying a distorted tetrahedral geometry with six bond angles ranging from 95.97(15) to 129.70(19°. The Zn–O and Zn–N bond distances are in the normal range of Zn-Schiff base complexes [30]. The two chiral HL1- ligands in complex 1 are both mono-deprotonated, namely, only the phenolic–OH group is deprotonated, which is consistent with the IR spectrum analysis (vide supra). Therefore, the two chiral HL1- ligands exhibit a bidentate N:O chelate mode to bind the central Zn (II) ions and form two stable six-member ring structures [C(1)–C(2)–C(3)–N(1)–O(4)–Zn(1); C(18)–C(19)–C(20)–N(2)–O(2)–Zn(1)], which are arranged in a closely perpendicular mode (the dihedral angle of C(1)–C(2)–C(3)–N(1)–O(4)–Zn(1) and C(18)–C(19)–C(20)–N(2)–O(2)–Zn(1) is about of 81.20°) between each other in order to satisfy the steric requirement of the two larger HL1- ligands. The detailed structural analysis shows that the configurations of the chiral carbon atoms [C(10) and C(27)] in complex 1 are (R)-modes, which suggests that no chiral inversion of the HL1- ligand has been observed and the chirality of the H2L1 free ligand has been successfully transferred into the Zn-complex.


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)

Molecular structures of complex 1, hydrogen atoms are omitted for clarity (Thermal ellipsoids are shown at 50% probability level).
© Copyright Policy
Related In: Results  -  Collection

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

pone.0130922.g003: Molecular structures of complex 1, hydrogen atoms are omitted for clarity (Thermal ellipsoids are shown at 50% probability level).
Mentions: Single crystal X-ray diffraction analysis reveals that complex 1 crystallizes in monoclinic space group P21, and consists of one Zn (II) ion and two chiral HL1- in the asymmetric unit. As shown in Fig 3, the central Zn (II) ion is four-coordinated by two deprotonated phenolic O atoms and two imino N atoms from two different chiral HL1- ligands, displaying a distorted tetrahedral geometry with six bond angles ranging from 95.97(15) to 129.70(19°. The Zn–O and Zn–N bond distances are in the normal range of Zn-Schiff base complexes [30]. The two chiral HL1- ligands in complex 1 are both mono-deprotonated, namely, only the phenolic–OH group is deprotonated, which is consistent with the IR spectrum analysis (vide supra). Therefore, the two chiral HL1- ligands exhibit a bidentate N:O chelate mode to bind the central Zn (II) ions and form two stable six-member ring structures [C(1)–C(2)–C(3)–N(1)–O(4)–Zn(1); C(18)–C(19)–C(20)–N(2)–O(2)–Zn(1)], which are arranged in a closely perpendicular mode (the dihedral angle of C(1)–C(2)–C(3)–N(1)–O(4)–Zn(1) and C(18)–C(19)–C(20)–N(2)–O(2)–Zn(1) is about of 81.20°) between each other in order to satisfy the steric requirement of the two larger HL1- ligands. The detailed structural analysis shows that the configurations of the chiral carbon atoms [C(10) and C(27)] in complex 1 are (R)-modes, which suggests that no chiral inversion of the HL1- ligand has been observed and the chirality of the H2L1 free ligand has been successfully transferred into the Zn-complex.

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