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Synthesis, CMC determination and nucleic acid-binding interaction of a surfactant copper(II) complex containing amino acid–Schiff base ligand:[Cu(sal-ala)(bpy)(DA)]

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Abstract

The surfactant copper(II) complex, [Cu(sal-ala)(bpy)(DA)] (sal-ala = amino acid Schiff base, bpy = 2,2′-bipyridyl, DA = dodecylamine) has been synthesized and characterized by elemental analysis, UV–Vis, IR and EPR spectra. The critical micelle concentration (CMC) values of this surfactant copper(II) complex in aqueous solution was 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 (Δ\(G_{\text{m}}^0\), Δ\(H_{\text{m}}^0\) and Δ\(S_{\text{m}}^0\)). Absorption, fluorescence, cyclic voltammetry, circular dichroism spectroscopy and viscosity experiments have been carried to study the interaction of this surfactant complex with nucleic acids. The results suggest that the complex could bind to nucleic acids by intercalation via salicylidene aromatic chromophore into the base pairs of CT DNA. The long aliphatic chain of the surfactant complex increases the hydrophobic interaction between the complex and nucleic acid. The surfactant copper(II) complex was screened for their antibacterial and antifungal activities against various microorganisms. The results were compared with the standard drugs, amikacin (antibacterial) and ketokonazole (antifungal).

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Acknowledgments

We are grateful to the UGC-COSIST and DST-FIST programmes of the Department of Chemistry, Bharathidasan University, and UGC-RFSMS fellowship to one of the authors, K. Nagaraj, by Bharathidasan University. Financial assistance from the CSIR (Grant No. 01(2461)/11/EMR-II), DST (Grant No. SR/S1/IC-13/2009) and UGC (Grant No. 41-223/2012(SR) sanctioned to S. Arunachalam are also gratefully acknowledged.

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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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Fig.S1. EPR spectrum of [Cu(sal-ala)(bpy)(DA)] at LNT (liquid nitrogen temperature)

Fig.S2. Emission spectra of EB bound to CT DNA: (A). in the absence of the surfactant copper(II) complex (dotted line) and in the presence of the complex (solid line). {Insets: Plot of [complex]/[DNA] vs I/Io}. [DNA] = 1 × 10−4 M; [complex] = 1.5 × 10−4 M; (B). Emission spectra of EB bound to RNA: in the absence of the complex (dotted line) and in the presence of the complex. {Insets: Plot of [complex]/[RNA] vs I/Io}. [RNA] = 1 × 10−4 M; [complex] = 4 × 10−5 M.

Fig.S3. (A). CV spectra of [Cu(sal-ala)(bpy)(DA)] in the absence (black line) and in the presence (red line) of CT DNA. {Inset: Plot of v1/2 (mV/s) vs. current(µA)}. [complex] = 1 × 10−3 M; [DNA] = 0–2.68 × 10−5 M; (B). In the absence (dotted line) and in the presence (solid line) of RNA. [complex] = 1 × 10−3 M; [RNA] = 0–2.68 × 10−5 M.

Fig.S4. Circular dichroism spectra in the absence (dotted line) and in the presence of surfactant metal complex [Cu(sal-ala)(bpy)(DA)]. [complex] = 1 × 10−5M; [DNA] = 1 × 10−4 M.

Fig.S5. Effects of increasing amounts of complex [Cu(sal-ala)(bpy)(DA)] (•) and complex [Cu(sal-ala)(bpy)(H2O)] (■) on the relative viscosities of calf thymus DNA at 29.0 (±0.1) °C.

Fig. S6. Effects of increasing amounts of complex [Cu(sal-ala)(bpy)(DA)] presence (•) and complex [Cu(sal-ala)(bpy)(H2O)] (■) on the relative viscosities of calf thymus RNA at 29.0 (±0.1) °C.

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Nagaraj, K., Sakthinathan, S. & Arunachalam, S. Synthesis, CMC determination and nucleic acid-binding interaction of a surfactant copper(II) complex containing amino acid–Schiff base ligand:[Cu(sal-ala)(bpy)(DA)]. J IRAN CHEM SOC 12, 267–275 (2015). https://doi.org/10.1007/s13738-014-0481-z

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