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

Qingkai Qi, Weijie Chi, Yuanyuan Li, Qinglong Qiao, Jie Chen, Lu Miao, Yi Zhang, Jin Li, Wei Ji, Tao Xu, Xiaogang Liu, Juyoung Yoon, Zhaochao Xu

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

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.

Original languageEnglish
Pages (from-to)4914-4922
Number of pages9
JournalChemical Science
Volume10
Issue number18
DOIs
StatePublished - 2019

Fingerprint

Dive into the research topics of 'A H-bond strategy to develop acid-resistant photoswitchable rhodamine spirolactams for super-resolution single-molecule localization microscopy'. Together they form a unique fingerprint.

Cite this