Issue 29, 2023

Synthesis and in vitro photodynamic activity of aza-BODIPY-based photosensitizers

Abstract

Aza-BODIPY dyes have recently come to attention owing to their excellent chemical and photophysical properties. In particular, their absorption and emission maxima can efficiently be shifted to the red or even to the NIR spectral region. On this basis, aza-BODIPY derivatives are widely investigated as fluorescent probes or phototherapeutic agents. Here we report the synthesis of a set of novel aza-BODIPY derivatives as potential photosensitizers for use in photodynamic therapy. Triazolyl derivatives were obtained via Cu(I)-catalyzed azide–alkyne cycloaddition as the key step. In vitro photodynamic activities of the newly synthesized compounds were evaluated on the A431 human epidermoid carcinoma cell line. Structural differences influenced the light-induced toxicity of the test compounds markedly. Compared to the initial tetraphenyl aza-BODIPY derivative, the compound bearing two hydrophilic triethylene glycol side chains showed substantial, more than 250-fold, photodynamic activity with no dark toxicity. Our newly synthesized aza-BODIPY derivative, acting in the nanomolar range, might serve as a promising candidate for the design of more active and selective photosensitizers.

Graphical abstract: Synthesis and in vitro photodynamic activity of aza-BODIPY-based photosensitizers

Supplementary files

Article information

Article type
Paper
Submitted
05 May 2023
Accepted
05 Jul 2023
First published
12 Jul 2023
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2023,21, 6018-6027

Synthesis and in vitro photodynamic activity of aza-BODIPY-based photosensitizers

T. Hlogyik, R. Laczkó-Rigó, É. Bakos, M. Poór, Z. Kele, C. Özvegy-Laczka and E. Mernyák, Org. Biomol. Chem., 2023, 21, 6018 DOI: 10.1039/D3OB00699A

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements