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Experimental and theoretical investigation of water-soluble silicon(IV) phthalocyanine and its interaction with bovine serum albumin

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Abstract

Photodynamic therapy (PDT) has drawn a great scientific attention to cancer treatment over the last decades. However, the bottleneck for the PDT is to find good photosensitizers (PSs) with greater water solubility, no aggregation, and fast discharge from the body. Therefore, there are still a big scientific desire for the synthesizing new rational PSs for treatment of cancer by PDT technique. In favor of improving the competence of PDT, an axially bis[4-(diphenylamino-1,1′-biphenyl-4-ol)] substituted silicon(IV) phthalocyanine (3) was converted to its water-soluble quaternized derivative (3Q). Their structures were fully characterized by single-crystal X-ray diffraction, elemental analysis, and different spectroscopic methods such as FT-IR, UV–Vis, MALDI-TOF, and 1H-NMR. The photophysical properties such as fluorescence quantum yields and lifetimes, and the photochemical properties such as singlet oxygen generation of both phthalocyanines were investigated. Ground and excited-state calculations were performed to explain the observed electronic absorption spectra. The addition of the 4-diphenylamino-1,1′-biphenyl-4-ol groups on the axially positions of the silicon(IV) phthalocyanine increased the singlet oxygen quantum yield from 0.15 to around 0.20. Especially quaternized compound 3Q showed high singlet oxygen quantum yield of 0.26 in water solution. In addition, a spectroscopic investigation of the binding behavior of the quaternized silicon (IV) phthalocyanine complex to bovine serum albumin (BSA) is also studied in this work, confirming the possible interaction. Further theoretical calculations were carried out to find out the plausible-binding regions of the BSA protein.

Graphic abstract

Axially bis[4-(diphenylamino-1,1′-biphenyl-4-ol)] substituted silicon(IV) phthalocyanine (3) was converted to its quaternized water soluble derivative (3Q). The photophysical properties such as fluorescence quantum yields and lifetimes, and the photochemical properties such as singlet oxygen generation of both phthalocyanines were investigated. In addition, a spectroscopic investigation of the binding behavior of the quaternized silicon (IV) phthalocyanine complex to bovine serum albumin (BSA) is also studied in this work, confirming the possible interaction. Further theoretical calculations were carried out to find out the plausible binding regions of the BSA protein.

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Acknowledgements

Khaoula Khezami would like to thank TUBITAK for the fellowship 2216, RESEARCH FELLOWSHIP PROGRAMME FOR INTERNATIONAL RESEARCHERS.

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Authors and Affiliations

  1. Department of Chemistry, Taibah University, P.O Box 344, Al-Madinah Al Munawrah, Saudi Arabia

    Shaya Y. Al-Raqa

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

    Khaoula Khezami, Esra N. Kaya, Abdulkadir Kocak & Mahmut Durmuş

  3. Faculty of Science of Bizert, University of Carthage, Tunis, Tunisia

    Khaoula Khezami

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  1. Shaya Y. Al-Raqa
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  2. Khaoula Khezami
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Correspondence to Mahmut Durmuş.

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Al-Raqa, S.Y., Khezami, K., Kaya, E.N. et al. Experimental and theoretical investigation of water-soluble silicon(IV) phthalocyanine and its interaction with bovine serum albumin. J Biol Inorg Chem 26, 235–247 (2021). https://doi.org/10.1007/s00775-021-01848-w

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  • DOI: https://doi.org/10.1007/s00775-021-01848-w

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