Latent fluorophore based on the trimethyl lock.
Fluorescent molecules are essential for basic research in the biological sciences and have numerous practical applications. Herein is described the synthesis and use of a new class of latent fluorophores based on a novel design element, the trimethyl lock, that confers distinct advantages over extant fluorophores and pro-fluorophores. A diacetyl version of the latent fluorophore is stable in a biological environment, but rapidly yields rhodamine 110 upon acetyl-group hydrolysis by pig liver esterase or endogenous esterases in the cytosol and lysosomes of human cells. This design element is general and, hence, provides access to an ensemble of useful latent fluorophores.
Chandran
Sunil S
SS
Departments of Biochemistry and Chemistry, University of Wisconsin, Madison, WI 53706, USA.
Dickson
Kimberly A
KA
Raines
Ronald T
RT
D003373:Coumaric Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics; D005452:Fluoresceins / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics; D006367:HeLa Cells; D006801:Humans; D011355:Prodrugs / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics; D012235:Rhodamines / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics; D013050:Spectrometry, Fluorescence / Q000379:methods
D003373:Coumaric Acids; D005452:Fluoresceins; D005456:Fluorescent Dyes; D011355:Prodrugs; D012235:Rhodamines; C049025:rhodamine 110; C018506:diacetylfluorescein