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Synthesis, CMC Determination, Antimicrobial Activity and Nucleic Acid Binding of A Surfactant Copper(II) Complex Containing Phenanthroline and Alanine Schiff-Base

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Abstract

A new water-soluble surfactant copper(II) complex [Cu(sal-ala)(phen)(DA)] (sal-ala = salicylalanine, phen = 1,10-phenanthroline, DA = dodecylamine), has been synthesized and characterized by physico-chemical and spectroscopic methods. The critical micelle concentration (CMC) values of this surfactant–copper(II) complex in aqueous solution were obtained from conductance measurements. Specific conductivity data (at 303, 308, 313. 318 and 323 K) served for the evaluation of the temperature-dependent CMC and the thermodynamics of micellization (ΔG0m, ΔH0m and ΔS0m). The interaction of this complex with nucleic acids (DNA and RNA) has been explored by using electronic absorption spectral titration, competitive binding experiment, cyclic voltammetry, circular dichroism (CD) spectra, and viscosity measurements. Electronic absorption studies have revealed that the complex can bind to nucleic acids by the intercalative binding mode which has been verified by viscosity measurements. The DNA binding constants have also been calculated (Kb = 1.2 × 105 M−1 for DNA and Kb = 1.6 × 105 M−1 for RNA). Competitive binding study with ethidium bromide (EB) showed that the complex exhibits the ability to displace the DNA-bound-EB indicating that the complex binds to DNA in strong competition with EB for the intercalative binding site. The presence of hydrophobic ligands, alanine Schiff-base, phenanthroline and long aliphatic chain amine in the complex were responsible for this strong intercalative binding. The surfactant–copper (II) complex was screened for its antibacterial and antifungal activities against various microorganisms. The results were compared with the standard drugs, amikacin(antibacterial) and ketokonazole(antifungal).

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Authors and Affiliations

  1. School of Chemistry, Bharathidasan University, Trichirappalli, 620024, Tamilnadu, India

    Karuppiah Nagaraj, Subramanian Sakthinathan & Sankaralingam Arunachalam

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  1. Karuppiah Nagaraj
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  2. Subramanian Sakthinathan
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  3. Sankaralingam Arunachalam
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Correspondence to Sankaralingam Arunachalam.

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Nagaraj, K., Sakthinathan, S. & Arunachalam, S. Synthesis, CMC Determination, Antimicrobial Activity and Nucleic Acid Binding of A Surfactant Copper(II) Complex Containing Phenanthroline and Alanine Schiff-Base. J Fluoresc 24, 589–598 (2014). https://doi.org/10.1007/s10895-013-1332-5

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  • DOI: https://doi.org/10.1007/s10895-013-1332-5

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