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

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, 83(12), 6466-6476. doi:10.1021/acs.joc.8b00756.

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Roubinet, B.1, Author           
Bischoff, M., Author
Nizamov, S.1, Author           
Yan, S., Author
Geisler, C., Author
Stoldt, S.2, Author           
Mitronova, G.1, Author           
Belov, V. N.1, Author                 
Bossi, M. L.1, Author           
Hell, S. W.1, Author                 
Affiliations:
1Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society, ou_578627              
2Research Group of Mitochondrial Structure and Dynamics, MPI for biophysical chemistry, Max Planck Society, ou_578566              

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 Abstract: 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.

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Language(s): eng - English
 Dates: 2018-05-112018-06-15
 Publication Status: Issued
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 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.joc.8b00756
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Title: The Journal of Organic Chemistry
Source Genre: Journal
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Pages: - Volume / Issue: 83 (12) Sequence Number: - Start / End Page: 6466 - 6476 Identifier: -