title: Effects of copper ions on DNA binding and cytotoxic activity of a chiral salicylidene Schiff base.
abstract: A chiral Schiff base HL N-(5-bromo-salicylaldehyde)dehydroabietylamine (1) and its chiral dinuclear copper complex [Cu2L4]·4DMF (2) have been synthesized and fully characterized. The interactions of 1 and 2 with salmon sperm DNA have been investigated by viscosity measurements, UV, fluorescence and circular dichroism (CD) spectroscopic techniques. Absorption spectral (Kb=3.30 × 10(5)M(-)(1) (1), 6.63 × 10(5)M(-)(1)(2)), emission spectral (Ksv=7.58 × 10(3)M(-)(1) (1), 1.52 × 10(4)M(-)(1) (2)), and viscosity measurements reveal that 1 and 2 interact with DNA through intercalation and 2 exhibits a higher DNA binding ability. In addition, CD study indicates 2 cause a more evident perturbation on the base stacking and helicity of B-DNA upon binding to it. In fluorimetric studies, the enthalpy (ΔH>0) and entropy (ΔS>0) changes of the reactions between the compounds with DNA demonstrate hydrophobic interactions. 1 and 2 were also screened for their cytotoxic ability and 2 demonstrates higher growth inhibition of the selected cancer cells at concentration of 50 μM, this result is identical with their DNA binding ability order. All the experimental results show that the involvement of Cu (II) centers has some interesting effect on DNA binding ability and cytotoxicity of the chiral Schiff base.
authors.affiliation: College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China; Coordination Chemistry Institute, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, China. Electronic address: hgfbl@njfu.edu.cn.
authors.forename: Bao-Li
authors.initials: BL
authors.lastname: Fei
authors.affiliation: College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.
authors.forename: Wu-Shuang
authors.initials: WS
authors.lastname: Xu
authors.affiliation: College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.
authors.forename: Hui-Wen
authors.initials: HW
authors.lastname: Tao
authors.affiliation: College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.
authors.forename: Wen
authors.initials: W
authors.lastname: Li
authors.affiliation: College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: College of Science, Nanjing Forestry University, Nanjing 210037, China.
authors.forename: Jian-Ying
authors.initials: JY
authors.lastname: Long
authors.affiliation: College of Science, Nanjing Forestry University, Nanjing 210037, China.
authors.forename: Qing-Bo
authors.initials: QB
authors.lastname: Liu
authors.affiliation: College of Science, Nanjing Forestry University, Nanjing 210037, China.
authors.forename: Bing
authors.initials: B
authors.lastname: Xia
authors.affiliation: Coordination Chemistry Institute, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, China.
authors.forename: Wei-Yin
authors.initials: WY
authors.lastname: Sun
mesh_terms: D045784:Abietanes / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity*; D017209:Apoptosis / Q000187:drug effects*; D045744:Cell Line, Tumor; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D006367:HeLa Cells; D056945:Hep G2 Cells; D006801:Humans; D007477:Ions / Q000737:chemistry; D061986:MCF-7 Cells; D008968:Molecular Conformation; D012545:Schiff Bases / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity*; D013237:Stereoisomerism; D013816:Thermodynamics; D014783:Viscosity
chemical_list: D045784:Abietanes; D056831:Coordination Complexes; D007477:Ions; D012545:Schiff Bases; D003300:Copper; D004247:DNA
keywords: Chiral; Cytotoxicity; DNA; Dehydroabietylamine Schiff base; Dinuclear copper complex