Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 19, Pages 6070-6076Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202005134
Keywords
dyes; pigments; fluorescence; fluorescent probes; scanning probe microscopy
Categories
Funding
- Bundesministerium fur Bildung und Foschung [13N14120, 13N14122]
- Projekt DEAL
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In this study, new rhodamine dyes were successfully synthesized through a series of reactions, and conjugates of these dyes with small molecules were used for specific labeling of organelles and components of the cytoskeleton in living cells. These dyes were also combined with fluorescent probes such as 610CP and SiR, and applied in two-color STED microscopy.
Formylation of 2,6-dichloro-5-R-nicotinic acids at C-4 followed by condensation with 3-hydroxy-N,N-dimethylaniline gave analogs of the popular TAMRA fluorescent dye with a 2,6-dichloro-5-R-nicotinic acid residues (R=H, F). The following reaction with thioglycolic acid is selective, involves only one chlorine atom at the carbon between pyridine nitrogen and the carboxylic acid group and affords new rhodamine dyes absorbing at 564/ 573 nm and emitting at 584/ 597 nm (R=H/ F, in aq. PBS). Conjugates of the dyes with small molecules provided specific labeling (covalent and non-covalent) of organelles as well as of components of the cytoskeleton in living cells and were combined with fluorescent probes prepared from 610CP and SiR dyes and applied in two-color STED microscopy with a 775 nm STED laser.
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