Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
7.4
4.2
Journals
Molecules
Special Issues
Boron Dipyrromethene (BODIPY) Dyes and Their Derivatives
molecules-logo
Submit to Molecules Review for Molecules Propose a Special Issue

Journal Menu

► Journal Menu

Journal Browser

► Journal Browser
share announcement

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 (28 February 2025) | Viewed by 8260

Special Issue Editor

Dr. Jarosław Piskorz

E-Mail Website
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

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

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

Benefits of Publishing in a Special Issue

  • Ease of navigation: Grouping papers by topic helps scholars navigate broad scope journals more efficiently.
  • Greater discoverability: Special Issues support the reach and impact of scientific research. Articles in Special Issues are more discoverable and cited more frequently.
  • Expansion of research network: Special Issues facilitate connections among authors, fostering scientific collaborations.
  • External promotion: Articles in Special Issues are often promoted through the journal's social media, increasing their visibility.
  • e-Book format: Special Issues with more than 10 articles can be published as dedicated e-books, ensuring wide and rapid dissemination.

Further information on MDPI's Special Issue policies can be found here.

Published Papers (4 papers)

Download All Papers
Order results
Result details
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:

Research

Jump to: Review

19 pages, 3472 KiB  
Article
Liposomal Formulations of Novel BODIPY Dimers as Promising Photosensitizers for Antibacterial and Anticancer Treatment
by Weronika Porolnik, Magdalena Ratajczak, Aleksandra Mackowiak, Marek Murias, Malgorzata Kucinska and Jaroslaw Piskorz
Molecules 2024, 29(22), 5304; https://doi.org/10.3390/molecules29225304 - 10 Nov 2024
Cited by 1 | Viewed by 1570
Abstract
Synthesis, photochemical properties, liposomal encapsulation, and in vitro photodynamic activity studies of novel BODIPY dimer connected at meso-meso positions and its brominated and iodinated analogs were described. UV-Vis measurements indicated that the dimeric structure of obtained BODIPYs did not significantly influence the positions [...] Read more.
Synthesis, photochemical properties, liposomal encapsulation, and in vitro photodynamic activity studies of novel BODIPY dimer connected at meso-meso positions and its brominated and iodinated analogs were described. UV-Vis measurements indicated that the dimeric structure of obtained BODIPYs did not significantly influence the positions of the absorption maxima. Emission properties and singlet oxygen generation studies revealed a strong heavy atom effect of brominated and iodinated BODIPY dimers, manifested by fluorescence intensity reduction and increased singlet oxygen generation ability compared to analog without halogen atoms. For the in vitro photodynamic activity studies, dimers were incorporated into two different types of liposomes: positively charged DOTAP:POPC and negatively charged POPG:POPC. The photoinactivation studies revealed high activity of brominated and iodinated dimers incorporated into DOTAP:POPC liposomes on both Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli. Anticancer studies on human breast adenocarcinoma MDA-MB-231 and human ovarian carcinoma A2780 cells revealed that DOTAP:POPC liposomes containing brominated and iodinated dimers were active even at low nanomolar concentrations. In addition, they were more active against MDA-MB-231 cells than A2780 cells, which is particularly important since the MDA-MB-231 cell line represents triple-negative breast cancer, which has limited therapeutic options. Full article
(This article belongs to the Special Issue Boron Dipyrromethene (BODIPY) Dyes and Their Derivatives)
►▼ Show Figures

Graphical abstract

12 pages, 2733 KiB  
Article
A New BODIPY-Based Receptor for the Fluorescent Sensing of Catecholamines
by Roberta Puglisi, Alessia Cavallaro, Andrea Pappalardo, Manuel Petroselli, Rossella Santonocito and Giuseppe Trusso Sfrazzetto
Molecules 2024, 29(15), 3714; https://doi.org/10.3390/molecules29153714 - 5 Aug 2024
Cited by 2 | Viewed by 1466
Abstract
The human body synthesizes catecholamine neurotransmitters, such as dopamine and noradrenaline. Monitoring the levels of these molecules is crucial for the prevention of important diseases, such as Alzheimer’s, schizophrenia, Parkinson’s, Huntington’s, attention-deficit hyperactivity disorder, and paragangliomas. Here, we have synthesized, characterized, and functionalized [...] Read more.
The human body synthesizes catecholamine neurotransmitters, such as dopamine and noradrenaline. Monitoring the levels of these molecules is crucial for the prevention of important diseases, such as Alzheimer’s, schizophrenia, Parkinson’s, Huntington’s, attention-deficit hyperactivity disorder, and paragangliomas. Here, we have synthesized, characterized, and functionalized the BODIPY core with picolylamine (BDPy-pico) in order to create a sensor capable of detecting these biomarkers. The sensing properties of the BDPy-pico probe in solution were studied using fluorescence titrations and supported by DFT studies. Catecholamine sensing was also performed in the solid state by a simple strip test, using an optical fiber as the detector of emissions. In addition, the selectivity and recovery of the sensor were assessed, suggesting the possibility of using this receptor to detect dopamine and norepinephrine in human saliva. Full article
(This article belongs to the Special Issue Boron Dipyrromethene (BODIPY) Dyes and Their Derivatives)
►▼ Show Figures

Graphical abstract

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
Cited by 3 | Viewed by 1493
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)
►▼ Show Figures

Graphical abstract

Review

Jump to: Research

24 pages, 3807 KiB  
Review
BODIPY Compounds Substituted on Boron
by Marko Bogomolec, Mladena Glavaš and Irena Škorić
Molecules 2024, 29(21), 5157; https://doi.org/10.3390/molecules29215157 - 31 Oct 2024
Cited by 1 | Viewed by 2085
Abstract
BODIPY compounds are important organic dyes with exceptional spectral and photophysical properties and numerous applications in different scientific fields. Their widespread applications have flourished due to their easy structural modifications, which enable the preparation of different molecular structures with tunable spectral and photophysical [...] Read more.
BODIPY compounds are important organic dyes with exceptional spectral and photophysical properties and numerous applications in different scientific fields. Their widespread applications have flourished due to their easy structural modifications, which enable the preparation of different molecular structures with tunable spectral and photophysical properties. To date, researchers have mostly devoted their efforts to modifying BODIPY meso-position or pyrrole rings, whereas the substitution of fluorine atoms remains largely unexplored. However, chemistry of the boron atom is possible, and it enables tuning of the photophysical properties of the dyes, without tackling their spectral properties. Furthermore, modifications of boron affect the solubility and aggregation propensity of the molecules. This review article highlights methods for the preparation of 4-substituted compounds and the most important reactions on the boron of the BODIPY dyes. They were divided into reactions promoted by Lewis acid (AlCl3 or BCl3), or bases such as alkoxides and organometallic reagents. By using these two methodologies, it is possible to cleave B–F bonds and substitute them with B–C, B–N, or B–O bonds from different nucleophiles. A special emphasis in this review is given to still underdeveloped photochemical reactions of the boron atom of BODIPY dyes. These reactions have the potential to be used in the development of a new line of BODIPY photo-cleavable protective groups (also known as photocages) with bio-medicinal and photo-pharmacological applications, such as drug delivery. Full article
(This article belongs to the Special Issue Boron Dipyrromethene (BODIPY) Dyes and Their Derivatives)
►▼ Show Figures

Graphical abstract

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying articles 1-4
Back to TopTop