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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

Effects of complexes 1 and 2 on the fluorescent spectra of EB–DNA system (λex = 258 nm); CDNA = 30 μM; CEB = 3 μM; from 1 to 6 CVOL = 0, 15, 30, 60, 90, 120 μM, respectively; Inset: plot of I0/I vs r (r = CVOL/CDNA).
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pone.0130922.g008: Effects of complexes 1 and 2 on the fluorescent spectra of EB–DNA system (λex = 258 nm); CDNA = 30 μM; CEB = 3 μM; from 1 to 6 CVOL = 0, 15, 30, 60, 90, 120 μM, respectively; Inset: plot of I0/I vs r (r = CVOL/CDNA).

Mentions: The competitive binding experiments using metal complexes as quenchers could provide some information about the binding of the complexes to DNA. This displacement method serves as an indirect evidence to identify intercalative binding modes. In this work, we studied that the interaction of two Zn (II) complexes with DNA was evaluated by the EB–DNA adduct, which can be used to distinguish intercalating and non intercalating compounds [18]. Competitive binding of other intercalators leads to a loss of fluorescence because of depletion of the EB–DNA complexes. The emission spectra of EB–DNA system in the presence and absence of complex 1 and 2 are shown in Fig 8. Fluorescence emission intensity of DNA–EB system are remarkably quenched at 590 nm as the concentration of complexes increase stepwise, this maybe because Zn (II) complexes could replace of EB and binds to DNA in an intercalative mode in the strong degree. The plot of Io/I versus r [complex]/[DNA] is inserted. The Stern-Volmer quenching constant, Ksq, for the complexes 1 and 2 were 0.94, 0.75, respectively. These values are higher than those for some other complexes (Ksq = 0.73 and 0.52) [33], and the intensity of chiral complex 1 is better than achiral complex 2.


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)

Effects of complexes 1 and 2 on the fluorescent spectra of EB–DNA system (λex = 258 nm); CDNA = 30 μM; CEB = 3 μM; from 1 to 6 CVOL = 0, 15, 30, 60, 90, 120 μM, respectively; Inset: plot of I0/I vs r (r = CVOL/CDNA).
© Copyright Policy
Related In: Results  -  Collection

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

pone.0130922.g008: Effects of complexes 1 and 2 on the fluorescent spectra of EB–DNA system (λex = 258 nm); CDNA = 30 μM; CEB = 3 μM; from 1 to 6 CVOL = 0, 15, 30, 60, 90, 120 μM, respectively; Inset: plot of I0/I vs r (r = CVOL/CDNA).
Mentions: The competitive binding experiments using metal complexes as quenchers could provide some information about the binding of the complexes to DNA. This displacement method serves as an indirect evidence to identify intercalative binding modes. In this work, we studied that the interaction of two Zn (II) complexes with DNA was evaluated by the EB–DNA adduct, which can be used to distinguish intercalating and non intercalating compounds [18]. Competitive binding of other intercalators leads to a loss of fluorescence because of depletion of the EB–DNA complexes. The emission spectra of EB–DNA system in the presence and absence of complex 1 and 2 are shown in Fig 8. Fluorescence emission intensity of DNA–EB system are remarkably quenched at 590 nm as the concentration of complexes increase stepwise, this maybe because Zn (II) complexes could replace of EB and binds to DNA in an intercalative mode in the strong degree. The plot of Io/I versus r [complex]/[DNA] is inserted. The Stern-Volmer quenching constant, Ksq, for the complexes 1 and 2 were 0.94, 0.75, respectively. These values are higher than those for some other complexes (Ksq = 0.73 and 0.52) [33], and the intensity of chiral complex 1 is better than achiral complex 2.

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