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Rhodamines with a chloronicotinic acid fragment for live cell superresolution STED microscopy

MPS-Authors
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Stoldt,  S.
Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society;

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Khan,  T. A.
Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society;

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Belov,  V. N.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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Hell,  S. W.
Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society;

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Citation

Grimm, F., Rehman, J., Stoldt, S., Khan, T. A., Schlötel, J. G., Nizamov, S., et al. (2021). Rhodamines with a chloronicotinic acid fragment for live cell superresolution STED microscopy. Chemistry - A European Journal, 27(19), 6070-6076. doi:10.1002/chem.202005134.


Cite as: http://hdl.handle.net/21.11116/0000-0009-6EA5-2
Abstract
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.