ArticleBioorganic & medicinal chemistry2013
Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs.
Article in Bioorganic & medicinal chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Encapsulation of a Highly Acid-Stable Dicyano-Bodipy in Zr-Based Metal-Organic Frameworks with Increased Fluorescence Lifetime and Quantum Yield Within the Solid Solution Concept.Molecules (Basel, Switzerland) · 2025Article
- Efficient Synthesis of Core-Fluorinated BODIPY-3,5-Diamides.International journal of molecular sciences · 2025Article
- Synthesis and Photophysical Properties of β-Alkenyl-Substituted BODIPY Dyes by Indium(III)-Catalyzed Intermolecular Alkyne Hydroarylation.The Journal of organic chemistry · 2024Article
- Carborane-based BODIPY dyes: synthesis, structural analysis, photophysics and applications.Frontiers in chemistry · 2024Review
- Acid-Resistant BODIPY Amino Acids for Peptide-Based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets.Angewandte Chemie (International ed. in English) · 2023Article
- Acid-Resistant BODIPY Amino Acids for Peptide-Based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2023Article
- Targeting EGFR Overexpression at the Surface of Colorectal Cancer Cells by Exploiting Amidated BODIPY-Peptide Conjugates.Photochemistry and photobiology · 2020Article
- Synthesis of BODIPY-Peptide Conjugates for Fluorescence Labeling of EGFR Overexpressing Cells.Bioconjugate chemistry · 2017Article
- Synthesis and Spectroscopic Investigation of a Series of Push-Pull Boron Dipyrromethenes (BODIPYs).The Journal of organic chemistry · 2017Article
- Synthesis and regioselective functionalization of perhalogenated BODIPYs.Organic & biomolecular chemistry · 2016Article
- Synthesis and properties of a series of carboranyl-BODIPYs.Journal of organometallic chemistry · 2015Article
- Synthesis, spectroscopic, and in vitro investigations of 2,6-diiodo-BODIPYs with PDT and bioimaging applications.Journal of photochemistry and photobiology. B, Biology · 2015Article
- Functionalization of 3,5,8-trichlorinated BODIPY dyes.The Journal of organic chemistry · 2014Article
- Synthesis and transformations of 5-chloro-2,2'-dipyrrins and their boron complexes, 8-chloro-BODIPYs.Chemistry (Weinheim an der Bergstrasse, Germany) · 2014Article
Corrections and comments
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8 authors.
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Abstract
A series of twenty-two BODIPY compounds were synthesized, containing various meso-phenyl and meso-thienyl groups, and their spectroscopic and structural properties were investigated using both experimental and computational methods. Further functionalization of the BODIPY framework via iodination at the 2,6-pyrrolic positions was explored in order to determine the effect of these heavy atoms on the photophysical and cytotoxicity of the meso-aryl-BODIPYs. BODIPYs bearing meso-thienyl substituents showed the largest red-shifted absorptions and emissions and reduced fluorescence quantum yields. The phototoxicity of the BODIPYs in human carcinoma HEp2 cells depends on both the presence of iodines and the nature of the meso-aryl groups. Six of the eleven 2,6-diiodo-BODIPYs investigated showed at least a sevenfold enhancement in phototoxicity (IC50 = 3.5-28 μM at 1.5 J/cm(2)) compared with the non-iodinated BODIPYs, while the others showed no cytotoxicity, while their singlet oxygen quantum yields ranged from 0.02 to 0.76. Among the series investigated, BODIPYs 2a and 4a bearing electron-donating meso-dimethoxyphenyl substituents showed the highest phototoxicity and dark/phototoxicity ratio, and are therefore the most promising for application in PDT.
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