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Boron Dipyrromethene (BODIPY) Dyes and Their Derivatives

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 April 2024) | Viewed by 864

Special Issue Editor


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Guest Editor
Chair and Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Rokietnicka Street 3, 60-806 Poznan, Poland
Interests: anticancer; antimicrobial; BODIPY; organic synthesis; organometallic chemistry; photochemistry; photodynamic therapy; porphyrinoids

Special Issue Information

Dear Colleagues,

Boron-dipyrromethene derivatives (BODIPY), described for the first time in 1968, are tricyclic pyrrole-based complexes with boron as the central atom. BODIPYs are known for their interesting optical properties and versatile structures that can be easily modified, leading to a wide range of photophysical properties. Since their discovery, BODIPY dyes have found numerous applications in various fields, especially in diagnostic imaging, DNA and protein labeling, chemical detection, and photovoltaics. Proper modification of the BODIPY structure also provides several attractive properties for potential use as effective photosensitizers in photodynamic anticancer and antimicrobial treatments. These chromophores were also used to obtain different materials and nanoparticles. Such combinations were utilized to prepare various sensors and catalysts, as well as for imaging and therapeutic purposes.

This Special Issue aims to provide insight into the development of BODIPY dyes and their derivatives. Original research papers and comprehensive reviews concerning these special chromophores' preparation, properties, and applications are welcomed.

Dr. Jarosław Piskorz
Guest Editor

Manuscript Submission Information

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Keywords

  • BODIPY
  • organoboron compounds
  • catalysis
  • imaging agents
  • organic synthesis
  • photochemistry
  • photovoltaics
  • photosensitizers

Published Papers (1 paper)

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Research

18 pages, 5314 KiB  
Article
Designing Antitrypanosomal and Antileishmanial BODIPY Derivatives: A Computational and In Vitro Assessment
by Raquel C. R. Gonçalves, Filipe Teixeira, Pablo Peñalver, Susana P. G. Costa, Juan C. Morales and M. Manuela M. Raposo
Molecules 2024, 29(9), 2072; https://doi.org/10.3390/molecules29092072 - 30 Apr 2024
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Abstract
Leishmaniasis and Human African trypanosomiasis pose significant public health threats in resource-limited regions, accentuated by the drawbacks of the current antiprotozoal treatments and the lack of approved vaccines. Considering the demand for novel therapeutic drugs, a series of BODIPY derivatives with several functionalizations [...] Read more.
Leishmaniasis and Human African trypanosomiasis pose significant public health threats in resource-limited regions, accentuated by the drawbacks of the current antiprotozoal treatments and the lack of approved vaccines. Considering the demand for novel therapeutic drugs, a series of BODIPY derivatives with several functionalizations at the meso, 2 and/or 6 positions of the core were synthesized and characterized. The in vitro activity against Trypanosoma brucei and Leishmania major parasites was carried out alongside a human healthy cell line (MRC-5) to establish selectivity indices (SIs). Notably, the meso-substituted BODIPY, with 1-dimethylaminonaphthalene (1b) and anthracene moiety (1c), were the most active against L. major, displaying IC50 = 4.84 and 5.41 μM, with a 16 and 18-fold selectivity over MRC-5 cells, respectively. In contrast, the mono-formylated analogues 2b and 2c exhibited the highest toxicity (IC50 = 2.84 and 6.17 μM, respectively) and selectivity (SI = 24 and 11, respectively) against T. brucei. Further insights on the activity of these compounds were gathered from molecular docking studies. The results suggest that these BODIPYs act as competitive inhibitors targeting the NADPH/NADP+ linkage site of the pteridine reductase (PR) enzyme. Additionally, these findings unveil a range of quasi-degenerate binding complexes formed between the PRs and the investigated BODIPY derivatives. These results suggest a potential correlation between the anti-parasitic activity and the presence of multiple configurations that block the same site of the enzyme. Full article
(This article belongs to the Special Issue Boron Dipyrromethene (BODIPY) Dyes and Their Derivatives)
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