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. Author manuscript; available in PMC: 2023 Feb 9.
Published in final edited form as: Chem Rev. 2021 Dec 14;122(3):3336–3413. doi: 10.1021/acs.chemrev.1c00729

Figure 36.

Figure 36.

Labeling and imaging trehalose mycolates in mycobacteria using fluorescent trehalose derivatives. (A) Synthesis of FITC-Tre (93). Cbz, carbobenzyloxy; TMSOTf, trimethylsilyl triflate. (B) M. tuberculosis expressing red fluorescent protein (RFP) was incubated in the presence of 100 μM FITC-Tre (93), fixed, and imaged by fluorescence microscopy. Left, FITC channel; right, merge of FITC and RFP channels. (C) J774 macrophages were infected with M. tuberculosis, treated with 200 μM FITC-Tre (93), fixed, and imaged by fluorescence microscopy. Scale bars, 5 μm. Images in (B) and (C) were reproduced with permission from ref 264. Copyright 2011 Springer Nature. (D) M. smegmatis was incubated for varying durations with 100 μM 6-TMR-Tre, fixed, and imaged by structured illumination microscopy. Scale bars, 2 μm. Reproduced with permission from ref 301. Copyright 2018 Wiley-VCH. (E) M. smegmatis (Ms) and C. glutamicum (Cg) were incubated with 100 μM fluorogenic DMN-Tre (98) or 100 μM non-fluorogenic 6-FlTre (97) and directly imaged by fluorescence microscopy without washing. Scale bars, 5 μm. Reproduced with permission from ref 266. Copyright 2018 The American Association for the Advancement of Science.