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  Polar red-emitting rhodamine dyes with reactive groups: Synthesis, photophysical properties, and two-color STED nanoscopy applications.

Kolmakov, K., Wurm, C. A., Meineke, D. N. H., Göttfert, F., Boyarskiy, V. P., Belov, V. N., et al. (2013). Polar red-emitting rhodamine dyes with reactive groups: Synthesis, photophysical properties, and two-color STED nanoscopy applications. Chemistry, 20(1), 146-157. doi:10.1002/chem.201303433.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0014-F528-A Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0027-C86B-9
Genre: Journal Article

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 Creators:
Kolmakov, K.1, Author              
Wurm, C. A.1, Author              
Meineke, D. N. H.1, Author              
Göttfert, F.1, Author              
Boyarskiy, V. P., Author
Belov, V. N.1, Author              
Hell, S. W.1, Author              
Affiliations:
1Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society, ou_578627              

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Free keywords: bioconjugation; chromophores; click chemistry; fluorescent probes; rhodamines
 Abstract: The synthesis, reactivity, and photophysical properties of new rhodamines with intense red fluorescence, two polar residues (hydroxyls, primary phosphates, or sulfonic acid groups), and improved hydrolytic stability of the amino-reactive sites (NHS esters or mixed N-succinimidyl carbonates) are reported. All fluorophores contain an N-alkyl-1,2-dihydro-2,2,4-trimethylquinoline fragment, and most of them bear a fully substituted tetrafluoro phenyl ring with a secondary carboxamide group. The absorption and emission maxima in water are in the range of 635–639 and 655–659 nm, respectively. A vastly simplified approach to red-emitting rhodamines with two phosphate groups that are compatible with diverse functional linkers was developed. As an example, a phosphorylated dye with an azide residue was prepared and was used in a click reaction with a strained alkyne bearing an N-hydroxysuccinimid (NHS) ester group. This method bypasses the undesired activation of phosphate groups, and gives an amphiphilic amino-reactive dye, the solubility and distribution of which between aqueous and organic phases can be controlled by varying the pH. The presence of two hydroxyl groups and a phenyl ring with two carboxyl residues in the dyes with another substitution pattern is sufficient for providing the hydrophilic properties. Selective formation of a mono-N-hydroxysuccinimidyl ester from 5-carboxy isomer of this rhodamine is reported. The fluorescence quantum yields varied from 58 to 92 % for free fluorophores, and amounted to 18–64 % for antibody conjugates in aqueous buffers. The brightness and photostability of these fluorophores facilitated two-color stimulated emission depletion (STED) fluorescence nanoscopy of biological samples with high contrast and minimal background. Selecting a pair of fluorophores with absorption/emission bands at 579/609 and 635/655 nm enabled two-color channels with low cross-talk and negligible background at approximately 40 nm resolution.

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Language(s): eng - English
 Dates: 2013-12-11
 Publication Status: Published online
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 Rev. Method: Peer
 Identifiers: DOI: 10.1002/chem.201303433
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Title: Chemistry
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Source Genre: Journal
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Pages: - Volume / Issue: 20 (1) Sequence Number: - Start / End Page: 146 - 157 Identifier: ISSN: 0947-6539