Wavelength dependent photochemistry of BODIPY-phenols and their applications in fluorescent labeling of proteins
| Autor: | Nikola Basarić, Ivana Antol, Matej Cindrić, Katarina Zlatić, Lidija Uzelac, Branka Mihaljević, Marijeta Kralj |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Boron Compounds
biology Anti-Kasha photochemistry BODIPY Quinone methides Protein labelling Radical Organic Chemistry Basic Medical Sciences Photochemistry Biochemistry Quinone methide Fluorescence Photoexcitation chemistry.chemical_compound chemistry biology.protein Flash photolysis Molecule Physical and Theoretical Chemistry Bovine serum albumin |
| Zdroj: | Journal of Organic and Biomolecular Simulations |
| Popis: | A series of BODIPY dyes were synthesized, that were at the 3, or 3 and 5 positions, substituted by photochemically reactive quinone methide (QM) precursor moieties. Fluorescence properties of the molecules were investigated and we demonstrated that the molecules undergo wavelength dependent photochemistry. Photodeamination to deliver QMs takes place only upon excitation to higher excited singlet states, showing unusual anti-Kasha photochemical reactivity. The findings were corroborated by TD-DFT computations. Laser flash photolysis experiments could not reveal QMs due to the low efficiency of their formation, but enabled the detection of phenoxyl radicals. The applicability of the molecules for the fluorescent labeling of bovine serum albumin as a model protein upon photoexcitation at 350 nm was demonstrated. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|