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Exocyclically metallated tetrapyridinoporphyrazine as a potential photosensitizer for photodynamic therapy


Schneider, Lukas; Larocca, Michele; Wu, Wenyu; Babu, Vipin; Padrutt, Roxane; Slyshkina, Ekaterina; König, Christiane; Ferrari, Stefano; Spingler, Bernhard (2019). Exocyclically metallated tetrapyridinoporphyrazine as a potential photosensitizer for photodynamic therapy. Photochemical & Photobiological Sciences, 18(11):2792-2803.

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).

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).

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Physical and Theoretical Chemistry
Language:English
Date:11 October 2019
Deposited On:20 Dec 2019 15:13
Last Modified:22 Dec 2019 07:02
Publisher:Royal Society of Chemistry
ISSN:1474-905X
OA Status:Closed
Publisher DOI:https://doi.org/10.1039/c9pp00336c
Project Information:
  • : FunderSNSF
  • : Grant ID205321_159976
  • : Project TitleChemo- and Phototoxic Conjugates: On the Way to a More Efficient Photodynamic Therapy

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