Photoactivatable Rhodamine Spiroamides and Diazoketones Decorated with 'Universal Hydrophilizer' or Hydroxyl Groups
| Autor: | Mariano L. Bossi, Matthias Bischoff, Vladimir N. Belov, Benoît Roubinet, Stefan Stoldt, Stefan W. Hell, Shamil Nizamov, Gyuzel Yu. Mitronova, Claudia Geisler, Sergey Yan |
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| Rok vydání: | 2018 |
| Předmět: |
0301 basic medicine
Allylic rearrangement Aqueous solution Dipeptide 010405 organic chemistry Organic Chemistry Adhesion 01 natural sciences Combinatorial chemistry 0104 chemical sciences Hydroxylation Rhodamine 03 medical and health sciences chemistry.chemical_compound 030104 developmental biology chemistry Reactivity (chemistry) Solubility |
| Zdroj: | The Journal of Organic Chemistry |
| ISSN: | 1520-6904 |
| Popis: | Photoactivatable rhodamine spiroamides and spirocyclic diazoketones emerged recently as synthetic markers applicable in multicolor super-resolution microscopy. However, their applicability in single molecule localization microscopy (SMLM) is often limited by aggregation, unspecific adhesion, and low reactivity caused by insufficient solubility and precipitation from aqueous solutions. We report here two synthetic modifications increasing the polarity of compact polycyclic and hydrophobic labels decorated with a reactive group: attachment of 3-sulfo-l-alanyl-beta-alanine dipeptide (a "universal hydrophilizer") or allylic hydroxylation in photosensitive rhodamine diazoketones (and spiroamides). The super-resolution images of tubulin and keratin filaments in fixed and living cells exemplify the performance of "blinking" spiroamides derived from N, N, N', N'-tetramethyl rhodamine. |
| Databáze: | OpenAIRE |
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