Research into 1,8-napthalimide derivatives has grown in recent years due to their cell-permeable nature and ability to target certain cellular locations. 4-hydroxy-1,8-napthalimide fluorophores in particular have gained popularity because of their excellent photostability, high quantum yields and large Stokes shifts. Furthermore, esterification of the hydroxyl group results in hypsochromic shift of the emission maxima, which is advantageous in the design of ratiometric probes. Our lab has developed a screen for esterase activity based on acyloxymethyl ether analogues of 4-hydroxy-<i>N</i>-propyl-1,8-napthalimide. The fluorophore is synthesized from inexpensive reagents and converted to the chloromethyl ether, from which a library of acyloxymethyl ether derivatives are created using commercially-available carboxylic acids. These compounds are easily obtained under mild conditions and possess excellent stability against spontaneous hydrolysis, along with a set of photophysical characteristics that make them useful probes for both fluorescence and UV/visible spectroscopy.

Development of 4-hydroxy-<i>N</i>-propyl-1,8-napthalimide acyloxymethyl ethers for characterization of esterase activity

255th National Meeting (2018)

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Development of 4-hydroxy-N-propyl-1,8-napthalimide acyloxymethyl ethers for characterization of esterase activity