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

MPG-Autoren
http://pubman.mpdl.mpg.de/cone/persons/resource/persons118566

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons15877

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons36443

Mitronova,  G.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons14832

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons14883

Bossi,  M. L.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons15210

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: http://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.