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Synthesis, DNA-binding study, and antioxidant activity of 14-aryl-14H-dibenzo[a,j]xanthene derivatives

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Abstract

A simple and efficient one-pot method for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives using Ni(ClO4)2·6H2O as a catalyst is described. DNA-binding properties of 14-aryl-14H-dibenzo[a,j]xanthene derivatives 1a, 1j, 1l, 1m, and 1n were investigated using calf thymus DNA by electronic absorption spectroscopy and fluorescence spectroscopy. Binding constant (K b) with DNA was calculated from the absorption measurements. The spectral changes observed such as hypochromicity, red shift, and isosbestic point are consistent with the intercalation mode of binding of the chromophore into the stack DNA base pairs. Among the five, compound 1n with strong electron donating substituents on the phenyl ring shows better intercalative binding with DNA. Investigations of antioxidant properties show that the dibenzo[a,j]xanthene 1m with –OH group substitution has high radical scavenging properties against DPPH and ABTS+.

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Acknowledgments

AI, KA and KMP are thankful to the Defence Research Development Organisation (DRDO), New Delhi for financial support (ERIP/ER/0900377/M/01/1245, dt 23.05.2008). We thank DST-FISR for use of the NMR and XRD facility at the School of Chemistry, Bharathidasan University, Tiruchirappalli-620024, INDIA.

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Authors and Affiliations

  1. School of Chemistry, Bharathidasan University, Tiruchirappalli, 620024, India

    Andivelu Ilangovan, Karnambaram Anandhan, Pakkiri Vijayakumar & Rajalingam Renganathan

  2. Defence R&D Establishment, Jhansi Road, Gwalior, 474002, Madhya Pradesh, India

    Kaushik Mahabir Prasad

  3. Department of Environmental Biotechnology, Bharathidasan University, Tiruchirappalli, 620024, India

    Devanesan Arul Ananth & Thilagar Sivasudha

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  1. Andivelu Ilangovan
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  2. Karnambaram Anandhan
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  3. Kaushik Mahabir Prasad
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  4. Pakkiri Vijayakumar
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  5. Rajalingam Renganathan
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  7. Thilagar Sivasudha
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Correspondence to Andivelu Ilangovan.

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Ilangovan, A., Anandhan, K., Prasad, K.M. et al. Synthesis, DNA-binding study, and antioxidant activity of 14-aryl-14H-dibenzo[a,j]xanthene derivatives. Med Chem Res 24, 344–355 (2015). https://doi.org/10.1007/s00044-014-1124-8

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