Issue 11, 2019
From the journal:

Photochemical & Photobiological Sciences

Exocyclically metallated tetrapyridinoporphyrazine as a potential photosensitizer for photodynamic therapy†

Lukas Schneider, ORCID logo a   Michele Larocca, ORCID logo a   Wenyu Wu,a   Vipin Babu, ORCID logo a   Roxane Padrutt, ORCID logo a   Ekaterina Slyshkina, ORCID logo a   Christiane König,b   Stefano Ferrari ORCID logo *bc  and  Bernhard Spingler ORCID logo *a  

* Corresponding authors

a Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland
E-mail: spingler@chem.uzh.ch
Web: http://www.chem.uzh.ch/en/research/groups/spingler.html
Fax: +4144 635 68 02
Tel: +41 44 635 46 56

b Institute of Molecular Cancer Research, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland
E-mail: sferrari@imcr.uzh.ch
Web: http://www.imcr.uzh.ch/research/Alumni-Ferrari.html
Fax: +4144 635 34 84
Tel: +41 44 635 34 71

c Institute of Molecular Genetics of the Czech Academy of Sciences, Videnska 1083, Prague, Czech Republic

Abstract

We report the first exocyclically metallated tetrapyridinoporphyrazine, [tetrakis-(trans-Pt(NH3)2Cl)-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)2Cl)-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).

Graphical abstract: Exocyclically metallated tetrapyridinoporphyrazine as a potential photosensitizer for photodynamic therapy

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Article information

DOI
https://doi.org/10.1039/C9PP00336C
Article type
Paper
Submitted
12 Aug 2019
Accepted
11 Oct 2019
First published
11 Oct 2019
This article is Open Access
Creative Commons BY-NC license

Photochem. Photobiol. Sci., 2019,18, 2792-2803

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Exocyclically metallated tetrapyridinoporphyrazine as a potential photosensitizer for photodynamic therapy

L. Schneider, M. Larocca, W. Wu, V. Babu, R. Padrutt, E. Slyshkina, C. König, S. Ferrari and B. Spingler, Photochem. Photobiol. Sci., 2019, 18, 2792 DOI: 10.1039/C9PP00336C

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