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The synthesis and investigation of photochemical, photophysical and biological properties of new lutetium, indium, and zinc phthalocyanines substituted with PEGME-2000 blocks

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Abstract

Zinc(II) (5), indium(III) (6), and lutetium(III) (7) phthalocyanines (Pcs) peripherally substituted with poly (ethylene glycol) (PEG) monomethyl ether 2000 (PEGME-2000) blocks were synthesized via Sonogashira coupling reaction with high yields and their photophysical, photochemical and photobiological properties were investigated. We elucidated the interactions of these compounds with calf thymus DNA and bovine serum albumin (BSA), and determined K(DNA) and K(BSA) binding constants at degrees of 105 and 106, respectively. Singlet oxygen quantum yields were found (Ф∆ = 0.44, 0.54, and 0.68 for 5, 6, and 7, respectively). Thermodynamic parameters, as well as thermal denaturation profile of double-stranded CT-DNA were examined to determine the type of binding mode. According to our experimental data, we report that PEGME-2000 favors the formation of binary complex between DNA, and phthalocyanine complexes. Therein, thermodynamic data suggest that this binding mode is indeed spontaneous under reported conditions, and rather non-specific. Additionally, Pcs 5, 6, and 7 substituted with PEGME-2000 blocks showed antimicrobial activity against Gram-positive and Gram-negative bacteria, as well as fungi (yeast), and Pc 5 had the highest antimicrobial activity among them, as revealed by disc diffusion assay results. In short, our results suggest that these compounds could be used for photodynamic therapy, they have both antibacterial and antifungal activity, and the binding ability of new phthalocyanines 5, 6, and 7 with BSA paves the way for their utilization as drug vehicle in blood plasma.

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Acknowledgements

This work was supported by Istanbul Technical University (BAP No: 39424, and 39556). We are thankful to Dr. Onur Alptürk for his technical support and Prof. Dr. Ayten Karataş for providing the bacterial strains.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science and Letters, Istanbul Technical University, Maslak, 34469, Istanbul, Turkey

    Canan Uslan, Yeşim Hepuzer Gürsel & B. Sebnem Sesalan

  2. Faculty of Engineering, Istanbul Kultur University, Atakoy Campus, Bakirkoy, 34156, Istanbul, Turkey

    Canan Uslan

  3. Department of Chemistry, Gebze Technical University, 41400, Gebze, Kocaeli, Turkey

    Baybars Köksoy & Mahmut Durmuş

  4. Department of Molecular Biology and Genetics, Faculty of Science and Letters, Istanbul Technical University, Maslak, 34469, Istanbul, Turkey

    Naciye Durmuş İşleyen, Yetkin Öztürk & Z. Petek Çakar

  5. Dr. Orhan Öcalgiray Molecular Biology, Biotechnology and Genetics Research Center (ITU-MOBGAM), Istanbul Technical University, Maslak, 34469, Istanbul, Turkey

    Naciye Durmuş İşleyen, Yetkin Öztürk & Z. Petek Çakar

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  1. Canan Uslan
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Uslan, C., Köksoy, B., Durmuş, M. et al. The synthesis and investigation of photochemical, photophysical and biological properties of new lutetium, indium, and zinc phthalocyanines substituted with PEGME-2000 blocks. J Biol Inorg Chem 24, 191–210 (2019). https://doi.org/10.1007/s00775-019-01638-5

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