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Preparation of NIR absorbing axial substituted tin(IV) porphyrins and their photocytotoxic properties

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Abstract

Sn(IV) porphyrins ([Sn(IV)TTP(3PyO)2] (5) and [Sn(IV)TPP(3PyO)2] (6) [tetrathienylporphyrin (TTP), tetraphenylporphyrin (TPP), and pyridyloxy (PyO)]) were prepared and characterized and their photocytotoxicity upon irradiation with 625 nm light has been studied. The presence of the 3PyO axial ligands was found to limit the aggregation and enhance the solubility of 5 and 6 in DMF/H2O (1 : 1). The photophysical properties and photodynamic therapy (PDT) activity of the meso-2-thienyl and meso-phenyl-substituted Sn(IV) porphyrins are compared. 5 and 6 were found to be photocytotoxic in MCF-7 cancer cells when irradiated with a Thorlabs M625L3 LED at 625 nm but remained nontoxic in the dark. The PDT activity of Sn(IV) meso-tetra-2-thienylporphyrin 5 was found to be significantly enhanced relative to its analogous tetraphenylporphyrin 6. There is a marked red-shift of the Q00 band of 5 into the therapeutic window due to the meso-2-thienyl rings, and 5 has an unusually high singlet oxygen quantum yield value of 0.83 in DMF. The results demonstrate that readily synthesized axially ligated Sn(IV) meso-arylporphyrins are potentially suitable for use as singlet oxygen photosensitizers in biomedical applications and merit further in depth investigation in this context.

Graphical abstract: Preparation of NIR absorbing axial substituted tin(iv) porphyrins and their photocytotoxic properties

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Publication details

The article was received on 26 Jul 2018, accepted on 18 Oct 2018 and first published on 19 Oct 2018


Article type: Research Article
DOI: 10.1039/C8MD00373D
Citation: Med. Chem. Commun., 2018, Advance Article
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    Preparation of NIR absorbing axial substituted tin(IV) porphyrins and their photocytotoxic properties

    B. Babu, E. Amuhaya, D. Oluwole, E. Prinsloo, J. Mack and T. Nyokong, Med. Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8MD00373D

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