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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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(a) Right-handed twofold helical chain in 1 linked by intermolecular C–H···π interactions (red dotted line); (b) 3D supramolecular architecture construcated by C–H···π, O–H···O and C–H···O interactions.
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pone.0130922.g004: (a) Right-handed twofold helical chain in 1 linked by intermolecular C–H···π interactions (red dotted line); (b) 3D supramolecular architecture construcated by C–H···π, O–H···O and C–H···O interactions.

Mentions: As shown in Fig 4a, the mononuclear molecules of complex 1 are connected by intermolecular C–H···π weak interaction (C1–H1A···π#1, d[C1–H1A] = 0.93 Å, d[H1A···π#1] = 3.84 Å, d[C1···π#1] = 4.146 Å, ∠[C1–H1A···π#1] = 102.8°, symmetric operation code: #1, 1–x, y+1/2, 1–z) to generate a right-handed twofold helical chain along the b direction with a pitch about of 7.258 Å. In addition, the O–H···O interactions (O1–H1···O2#1, d[O1–H1] = 0.82 Å, d[H1–O2#2] = 2.01 Å, d[O1···O2#2] = 2.698(6) Å, ∠[O1–H1···O2#2] = 141.4°, and O6–H6···O1, d[O6–H6] = 0.82 Å, d[H6–O1] = 1.74 Å, d[O6···O1] = 2.559(7) Å, ∠[O6–H6···O1] = 174.4°) are observed in the helical chain, which are believed to consolidate the helical chain structure. Furthermore, the intermolecular C–H···O weak interactions (C13–H13···O6#1, d[C13–H13] = 0.93 Å, d[H13···O6#1] = 2.67 Å, d[C13···O6#1] = 3.573(8) Å, ∠[C13–H13···O6#1] = 163.1°; C26 –H26B···O4#2, d[C26–H26B] = 0.97 Å, d[H26B···O4#2] = 2.52 Å, d[C26···O4#2] = 3.434(7) Å, ∠[C26–H26B···O4#2] = 157.6°; symmetric operation codes: #1, 1-x, y+1/2, 1-z; #2, x, y+1, z) are found to help to construct a homochiral 3D supramolecular architecture (Fig 4b), all the C–H···π, O–H···O and C–H···O interactions observed in complex 1 could be considered as the key factor to transmit chiral information form single molecules to the homochiral 3D supramolecular architecture and yield the chiral crystals finally.


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) Right-handed twofold helical chain in 1 linked by intermolecular C–H···π interactions (red dotted line); (b) 3D supramolecular architecture construcated by C–H···π, O–H···O and C–H···O interactions.
© Copyright Policy
Related In: Results  -  Collection

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

pone.0130922.g004: (a) Right-handed twofold helical chain in 1 linked by intermolecular C–H···π interactions (red dotted line); (b) 3D supramolecular architecture construcated by C–H···π, O–H···O and C–H···O interactions.
Mentions: As shown in Fig 4a, the mononuclear molecules of complex 1 are connected by intermolecular C–H···π weak interaction (C1–H1A···π#1, d[C1–H1A] = 0.93 Å, d[H1A···π#1] = 3.84 Å, d[C1···π#1] = 4.146 Å, ∠[C1–H1A···π#1] = 102.8°, symmetric operation code: #1, 1–x, y+1/2, 1–z) to generate a right-handed twofold helical chain along the b direction with a pitch about of 7.258 Å. In addition, the O–H···O interactions (O1–H1···O2#1, d[O1–H1] = 0.82 Å, d[H1–O2#2] = 2.01 Å, d[O1···O2#2] = 2.698(6) Å, ∠[O1–H1···O2#2] = 141.4°, and O6–H6···O1, d[O6–H6] = 0.82 Å, d[H6–O1] = 1.74 Å, d[O6···O1] = 2.559(7) Å, ∠[O6–H6···O1] = 174.4°) are observed in the helical chain, which are believed to consolidate the helical chain structure. Furthermore, the intermolecular C–H···O weak interactions (C13–H13···O6#1, d[C13–H13] = 0.93 Å, d[H13···O6#1] = 2.67 Å, d[C13···O6#1] = 3.573(8) Å, ∠[C13–H13···O6#1] = 163.1°; C26 –H26B···O4#2, d[C26–H26B] = 0.97 Å, d[H26B···O4#2] = 2.52 Å, d[C26···O4#2] = 3.434(7) Å, ∠[C26–H26B···O4#2] = 157.6°; symmetric operation codes: #1, 1-x, y+1/2, 1-z; #2, x, y+1, z) are found to help to construct a homochiral 3D supramolecular architecture (Fig 4b), all the C–H···π, O–H···O and C–H···O interactions observed in complex 1 could be considered as the key factor to transmit chiral information form single molecules to the homochiral 3D supramolecular architecture and yield the chiral crystals finally.

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