Exocyclically metallated tetrapyridinoporphyrazine as a potential photosensitizer for photodynamic therapy

0522841 - ÚMG 2020 RIV GB eng J - Journal Article
Schneider, L. - Larocca, M. - Wu, W. - Babu, V. - Padrutt, R. - Slyshkina, E. - Koenig, Ch. - Ferrari, Stefano - Spingler, B.
Exocyclically metallated tetrapyridinoporphyrazine as a potential photosensitizer for photodynamic therapy.
Photochemical & Photobiological Sciences. Roč. 18, č. 11 (2019), s. 2792-2803. ISSN 1474-905X. E-ISSN 1474-9092
R&D Projects: GA ČR GA17-02080S
Institutional support: RVO:68378050
Keywords : singlet oxygen * cancer-cells * zn-ii * tetra-2,3-pyrazinoporphyrazines * dna * tetra(3,4-pyrido)porphyrazines * phthalocyanines * porphyrazines * mg-ii(h2o) * complexes
OECD category: Pharmacology and pharmacy
Impact factor: 2.831, year: 2019
Method of publishing: Open access
https://pubs.rsc.org/en/content/articlelanding/2019/PP/C9PP00336C#!divAbstract

We report the first exocyclically metallated tetrapyridinoporphyrazine, [tetrakis-(trans-Pt(NH3)(2)Cl)-tetra(3,4-pyrido)porphyrazine-zinc(ii)](NO3)(4) (4), synthesized in a multistep synthesis starting from 3,4-pyridinedicarbonitrile (1). The synthetic procedure involved a platination reaction of the intermediate tetra(3,4-pyrido)porphyrazine-zinc(ii) (2), whereby the zinc(ii) enhanced the solubility of the intermediate enabling the platination reaction. A similar approach to synthesize [tetrakis-(trans-Pt(NH3)(2)Cl)-tetra(3,4-pyrido)porphyrazine](NO3)(4) (5) failed due to the unsuitable solubility properties of the intermediate tetra(3,4-pyrido)porphyrazine (3). The final product 4 and the intermediates were characterized, the photochemical and photophysical properties were determined and the photocytotoxicities were investigated. We demonstrate that the platinated tetra-pyridinoporphyrazine 4 is a potential photosensitizer for photodynamic therapy (PDT).
Permanent Link: http://hdl.handle.net/11104/0307263