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Photoactivatable rhodamine spiroamides and diazoketones decorated with “universal hydrophilizer” or hydroxyl groups.

MPG-Autoren
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Nizamov,  S.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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Stoldt,  S.
Research Group of Mitochondrial Structure and Dynamics, MPI for biophysical chemistry, Max Planck Society;

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Mitronova,  G.
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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Bossi,  M. L.
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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Zitation

Roubinet, B., Bischoff, M., Nizamov, S., Yan, S., Geisler, C., Stoldt, S., et al. (2018). Photoactivatable rhodamine spiroamides and diazoketones decorated with “universal hydrophilizer” or hydroxyl groups. The Journal of Organic Chemistry, (in press). doi:10.1021/acs.joc.8b00756.


Zitierlink: https://hdl.handle.net/21.11116/0000-0001-479F-D
Zusammenfassung
Photoactivatable rhodamine spiroamides and spirocyclic diazoketones emerged recently as synthetic markers applicable in multicolor superresolution 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 superresolution 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.