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Hydrosolubilization of BODIPY for optical labelling of biomolecules
Bartoň, Jan ; Kotek, Jan (advisor) ; Vrábel, Milan (referee)
1 Abstract This work aims at showing synthesis and potential use of water-soluble fluorescent probes based on BODIPY. The preparation of probes containing bioorthogonal mono- and heterobifunctional functional groups was demonstrated. Ground work was done at the optimisation of reliable, scalable and fast sulfonation of BODIPY in 2,6-positions. A protocol for handling sulfonated BODIPY has been established; especially for the exchange of counterions. In counterion se- lection, their relation to synthetic pathway and biocompatibility were taken into consideration. The second part of the work shows series of water-soluble fluorescent probes, into which can be easily introduced bioactive or bioorthogonal functional groups. This can be used for click chemistry in connection with turn off/on probes or fluorescent sensing of molecules or ions. All this can be done in aqueous solution without organic solvents, which is relevant for biochemical, analytical and imaging applications. Keywords BODIPY, bifunctional, water-soluble, fluorescent probe, solubilization, biocompa- tible probes, bioorthogonal reaction, BODIPY sulfonation
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Bifunctional BODIPY for optical labelling of biomolecules
Bartoň, Jan ; Kotek, Jan (advisor) ; Henke, Petr (referee)
The water-soluble derivate of BODIPY was prepared, which will be further modified in order to prepare bioorthogonal bifunctional BODIPY. Target application of this derivate is fluorescent probe for labelling of biomolecules. Main goals of this thesis were optimalization of synthesis of BODIPY core and sulfonation to positions 2,6. It was found out that sodium salt of sulfonated BODIPY shows good solublility in water and methanol, but it is poorly soluble in less polar solvents. Based on these findings DIPEA salt of sulfonated BODIPY was prepared, which shows outstanding range of solubility from water to dichlormethane. These findings will be used for synthesis of bifunctional water- soluble BODIPY. Further, the potential of Pd-BODIPY complex for detection of CO was reasserted which will be further investigated. Keywords BODIPY, bifunctional, water-soluble, fluorescent probe, fluorescence, protein labelling, solubilization
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