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Issue 18, 2019
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A H-bond strategy to develop acid-resistant photoswitchable rhodamine spirolactams for super-resolution single-molecule localization microscopy

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Abstract

Rhodamine spirolactam based photoswitches have been extensively applied in super-resolution single-molecule localization microscopy (SMLM). However, the ring-opening reactions of spirolactams are cross-sensitive to acid, limiting their photoswitch use to neutral pH conditions. In addition, the ring-closing reactions of spirolactams are environment-sensitive and slow (up to hours), virtually making rhodamine spirolactams caged fluorescent dyes instead of reversible photoswitches in SMLM. Herein, by introducing hydrogen bonds to stabilize spirolactams, we report a series of acid-resistant rhodamine spirolactams with accelerated ring-closing reactions from fluorescent xanthyliums to non-fluorescent spirolactams, endowing them with good photoswitchable properties even in acidic environments. By further substitution of 6-phenylethynyl naphthalimide on the spirolactam, we shifted the photoactivation wavelength into the visible region (>400 nm). Subsequently, we have successfully applied these dyes in labeling and imaging the cell surface of Bacillus subtilis at pH 4.5 using SMLM.

Graphical abstract: A H-bond strategy to develop acid-resistant photoswitchable rhodamine spirolactams for super-resolution single-molecule localization microscopy

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Publication details

The article was received on 15 Mar 2019, accepted on 04 Apr 2019 and first published on 04 Apr 2019


Article type: Edge Article
DOI: 10.1039/C9SC01284B
Chem. Sci., 2019,10, 4914-4922
  • Open access: Creative Commons BY-NC license
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    A H-bond strategy to develop acid-resistant photoswitchable rhodamine spirolactams for super-resolution single-molecule localization microscopy

    Q. Qi, W. Chi, Y. Li, Q. Qiao, J. Chen, L. Miao, Y. Zhang, J. Li, W. Ji, T. Xu, X. Liu, J. Yoon and Z. Xu, Chem. Sci., 2019, 10, 4914
    DOI: 10.1039/C9SC01284B

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