The mycobacterial cell envelope has a unique mycolic acid-rich layer that is very hydrophobic. These mycolic acids are esterified to carbohydrates such as trehalose to form trehalose mono- and dimycolate and arabinogalactan to form arabinogalactan-linked mycolate. Several labs have taken advantage of the trehalose-mediated biosynthesis of these glycolipids as well as membrane hydrophobicity to develop detectable trehalose analogs that have shown promise as mycobacterial-specific detection reagents. These reagents include recently reported solvatochromic and FRET-based fluorogenic probes that are turned on upon metabolic incorporation into live mycobacteria. Though these reagents have proved useful in mycobacteria research, they all have absorption/emission wavelength in the blue/green region, limiting their applications. To address this limitation, we have developed and evaluated a far-red shifted trehalose-based fluorogenic probe bearing a molecular rotor fluorophore that is turned on upon metabolic incorporation into the mycobacterial outer membrane layer. This probe enabled rapid, no-wash fluorescence detection of live mycobacteria, which could be helpful for sensitive mycobacteria-specific detection for tuberculosis research and diagnosis.

Far-red molecular rotor-based fluorogenic trehalose probes for the detection of live mycobacteria

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ACS Fall 2022

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