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Sulfonamides Are an Overlooked Class of Electron Donors in Luminogenic Luciferins and Fluorescent Dyes

preprint
submitted on 28.12.2018 and posted on 31.12.2018 by Deepak K. Sharma, Spencer T. Adams, Kate L. Liebmann, Adam Choi, Stephen Miller
Many fluorophores, and all bright light-emitting substrates for firefly luciferase, contain hydroxyl or amine electron donors. Here we show that sulfonamides can serve as replacements for these canonical groups. Unlike “caged” carboxamides, sulfonamide analogues enable bioluminescence, and sulfonamidyl luciferins, coumarins, rhodols, and rhodamines are fluorescent in water. Sulfonamide donors thus have previously unappreciated potential to expand the functional repertoire of luminescent molecules.

Funding

NIH EB013270

NIH DA039961

History

Email Address of Submitting Author

stephen.miller@umassmed.edu

Institution

University of Massachusetts Medical School

Country

USA

ORCID For Submitting Author

0000-0001-7154-7757

Declaration of Conflict of Interest

no conflict of interest

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