Latent Fluorophore Based on the Trimethyl Lock

• Published in: Journal of the American Chemical Society 2005-02, Vol.127 (6), p.1652-1653
• Main Authors: Chandran, Sunil S, Dickson, Kimberly A, Raines, Ronald T
• Format: Article
• Language: English
• Subjects: Analytical, structural and metabolic biochemistry; Biological and medical sciences; Coumaric Acids - chemical synthesis; Coumaric Acids - chemistry; Coumaric Acids - pharmacokinetics; Fluoresceins - chemistry; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Fluorescent Dyes - pharmacokinetics; Fundamental and applied biological sciences. Psychology; HeLa Cells; Humans; Inorganic compounds; Other biological molecules; Prodrugs - chemical synthesis; Prodrugs - chemistry; Prodrugs - pharmacokinetics; Rhodamines - chemical synthesis; Rhodamines - chemistry; Rhodamines - pharmacokinetics; Spectrometry, Fluorescence - methods
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja043736v

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.