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meso-Mono-[4-(1,4,7-triazacyclononanyl)]-tri(phenyl)]porphyrin and the respective zinc(ii)-complex: complete characterization and biomolecules binding abilities

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Abstract

We aimed to synthesize a new series of triazacyclononanyl-porphyrins (4 and 5) with the potential ability to bind DNA. For this, the free-base porphyrin 4 and the corresponding Zn(ii)-complex 5 were synthesized by the Schiff base formation reaction. The binding ability of the porphyrin derivatives 4 and 5 with DNA from calf-thymus was studied by UV-vis and emission spectroscopy. Detailed analysis of the results suggests that the interaction of these systems most probably occurs through π-stacking and secondary hydrogen interaction surface binding with ct-DNA. Moreover, we also demonstrate the substantial ability of porphyrins 4 and 5 to generate 1O2 and to photocleave plasmid DNA after irradiation.

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Authors and Affiliations

  1. Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC 88040-900, Brazil

    Bruna L. Auras, Ademir Neves & Bernardo A. Iglesias

  2. Centro de Biologia Molecular Estrutural, Universidade Federal de Santa Catarina, Florianópolis, SC 88040-900, Brazil

    Vanessa A. Oliveira & Hernán Terenzi

  3. Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS 97105-900, Brazil

    Bernardo A. Iglesias

Authors
  1. Bruna L. Auras
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  2. Vanessa A. Oliveira
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  3. Hernán Terenzi
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  4. Ademir Neves
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  5. Bernardo A. Iglesias
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Correspondence to Bernardo A. Iglesias.

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Auras, B.L., Oliveira, V.A., Terenzi, H. et al. meso-Mono-[4-(1,4,7-triazacyclononanyl)]-tri(phenyl)]porphyrin and the respective zinc(ii)-complex: complete characterization and biomolecules binding abilities. Photochem Photobiol Sci 15, 564–579 (2016). https://doi.org/10.1039/c6pp00016a

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