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

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Schlagwörter: bioconjugation; chromophores; click chemistry; fluorescent probes; rhodamines
 Zusammenfassung: 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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Sprache(n): eng - English
 Datum: 2013-12-11
 Publikationsstatus: Online veröffentlicht
 Seiten: -
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: DOI: 10.1002/chem.201303433
 Art des Abschluß: -

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Titel: Chemistry
  Alternativer Titel :
Genre der Quelle: Zeitschrift
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Ort, Verlag, Ausgabe: -
Seiten: - Band / Heft: 20 (1) Artikelnummer: - Start- / Endseite: 146 - 157 Identifikator: ISSN: 0947-6539