Photoactivatable Rhodamine Spiroamides and Diazoketones Decorated with "Universal Hydrophilizer" or Hydroxyl Groups

The Journal of Organic Chemistry
Benôit RoubinetStefan W Hell

Abstract

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.

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Citations

Sep 25, 2018·Angewandte Chemie·Chamari S WijesooriyaEmily A Smith
Dec 13, 2018·Organic & Biomolecular Chemistry·Eszter Kozma, Péter Kele
Jan 2, 2021·Chemical Science·Axel LoredoHan Xiao
Jun 2, 2021·Chemistry : a European Journal·Yang ZhangFrançisco M Raymo
Oct 29, 2020·The Journal of Organic Chemistry·Danijel GlavačMatija Gredičak
Dec 13, 2019·Journal of the American Chemical Society·Parker E DealEvan W Miller
Oct 27, 2018·Analytical Chemistry·Pieter E OomenAndrew G Ewing
Mar 10, 2020·Bioconjugate Chemistry·Yang Zhang, Françisco M Raymo
Nov 26, 2021·Chemistry, an Asian Journal·Stylianos PanagiotakisKonstantina Yannakopoulou
Dec 18, 2021·The Journal of Organic Chemistry·Heydar ShojaeiStefan W Hell

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