In this study, BODIPY compounds (2, 3, 5 and 6) bearing 3,4-bis(3-pyridin-3-ylpropoxy)benzyl, 4-(3-pyridin-3-ylpropoxy)benzyl groups were synthesized for the first time and further functionalized in a Knoevenagel condensation reaction with 3,4-bis(3-pyridin-3-ylpropoxy)benzaldehyde and 4-(3-pyridin-3-ylpropoxy)benzaldehyde. The water soluble derivatives of BODIPY compounds (3a and 6a) were synthesized by treating BODIPY compounds 3 and 6 with excess iodomethane in DMF. The photochemical properties and DNA binding modes of 3a and 6a were determined using ct-DNA by UV-Vis spectrophotometer and viscometer. DNA cleavage and topoisomerases inhibition properties were studied DNA using agarose gel electrophoresis. Their topoisomerase inhibition mechanisms were investigated at molecular level and correlations with the in vitro results were searched for using molecular docking method. In addition, cytotoxicity and phototoxicity of both compounds were performed on colorectal cancer cells (HCT-116) using MTT assay for 24 h. Annexin V-FITC/PI test was performed to determine the cell death mechanism of 6a induced by irradiation. Finally, 6a-loaded liposomes (LP6a) and PLGA nanoparticles (NP6a) were prepared and their cytotoxic and phototoxic effects were evaluated by MTT assay. The results claimed that 6a had great potential as photosensitizer agent for colorectal cancer owing to its photochemical, DNA interaction and phototoxic properties.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.ejmech.2019.111685 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Membrane-Active Singlet Oxygen Photogenerators as a Paradigm for Broad-Spectrum Antivirals: The Case of Halogenated (BOron)-DIPYrromethenes.
ACS Appl Mater Interfaces
January 2025
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, 117997 Moscow, Russia.
Enveloped viruses, such as flaviviruses and coronaviruses, are pathogens of significant medical concern that cause severe infections in humans. Some photosensitizers are known to possess virucidal activity against enveloped viruses, targeting their lipid bilayer. Here we report a series of halogenated difluoroboron-dipyrromethene (BODIPYs) photosensitizers with strong virus-inactivating activity.
View Article and Find Full Text PDFVisible-Light-Fueled Polymerizations for 3D Printing.
Acc Chem Res
January 2025
Department of Chemistry, The University of Texas at Austin, 105 East 24th Street, Austin, Texas 78712, United States.
ConspectusLight-driven polymerizations and their application in 3D printing have revolutionized manufacturing across diverse sectors, from healthcare to fine arts. Despite the popularized notion that with 3D printing "imagination is the only limit", we and others in the scientific community have identified fundamental hurdles that restrict our capabilities in this space. Herein, we describe the group's efforts in developing photochemical systems that respond to nontraditional colors of light to elicit the rapid, spatiotemporally controlled formation of plastics.
View Article and Find Full Text PDFSynthesis of BODIPYs using organoindium reagents and survey of their cytotoxicity and cell uptake on nervous system cells.
Bioorg Chem
December 2024
Universidade da Coruña, CICA - Centro Interdisciplinar de Química e Bioloxía and Departamento de Química, Facultad de Ciencias, Campus A Zapateira, 15071 A Coruña, Spain. Electronic address:
In this study, a series of BODIPY dyes were synthesized, containing various substituents at meso position. Further functionalization of the BODIPY framework at C2 and C2-C6 position(s) by palladium-catalysed cross-coupling reactions using organoindium reagents (RIn) was efficiently assessed, starting from C2(6)-halogenated BODIPYs, and their optical properties were measured. The cytotoxicity of BODIPY dyes on SH-SY5Y neuronal cells by MTT assay showed that those compounds bearing thien-2-yl and benzonitrile moieties at meso position, exhibited great efficiency in maintaining cell viability under all tested conditions (up to 50 µM for 24 h and 48 h).
View Article and Find Full Text PDFRecent advances in the development of enantiopure BODIPYs and some related enantiomeric compounds.
Chem Commun (Camb)
January 2025
Department of Chemistry, Khalifa University, SAN Campus, Abu Dhabi, United Arab Emirates.
Article Synopsis
- Small chiral organic dyes, especially chiral variants of boron dipyrromethene (BODIPY), are important for developing advanced smart chiroptical luminophores due to their outstanding photophysical properties.
- Recent research has focused on inducing chirality in achiral BODIPY by creating chiral centers at various positions, enhancing synthetic accessibility.
- The developments in chiral BODIPY have potential applications in fields such as photodynamic therapy, bio-imaging, optoelectronics, and more.
Plasmon-Enhanced Fluorescence Based on Gold Nanobipyramids with PEG-Controlled Distance for Near-Infrared and Visual Analysis of Amyloid-β Aggregation.
ACS Appl Mater Interfaces
January 2025
College of Food and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210023, PR China.
Article Synopsis
- The aging population is leading to a significant rise in Alzheimer's disease cases, making early detection crucial.
- Researchers developed a plasmon-enhanced fluorescence (PEF) sensor using gold nanobipyramids (Au NBPs) to visually detect amyloid-beta protein aggregation, a key marker for Alzheimer's.
- The sensor utilizes a near-infrared fluorescent substance for a highly sensitive detection method, which allows real-time monitoring of Aβ aggregation in human neuroblastoma cells, showing potential as an effective diagnostic tool for Alzheimer's disease.
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!