The development of fluorescent probes is an active area of research. Of particular interest are reactivity-based probes. The chemical synthesis for reactivity-based, fluorescein-type probes installs a fluorescent masking group on an oxygen atom to convert a fluorescent molecule to a non-fluorescent molecule. We had previously synthesized Pittsburgh Green, a fluorescent molecule by substituting carboxy group on the benzene ring of 2,7-dichlorofluorescein with a hydroxymethyl group which was beneficial to enhance the cell permeability and leverage the dynamics of spirocyclization. Here, we report the one-step masking of Pittsburgh Green to its mono-alkylated or esterified compounds. Unlike previous syntheses, this strategy tolerates a broader range of functional groups as masking groups. We also demonstrate the advantage of mono-alkylation over di-alkylation for metal detection.The new and simple protocol is applied to synthesize Pittsburgh Green derivatives with various enzyme-responsive masking groups that were inaccessible by previous methods.

Mono-O-functionalizations of Pittsburgh Green and their applications

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ACS Fall 2022

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