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

Org Lett. 2019 Mar 15;21(6):1641-1644. doi: 10.1021/acs.orglett.9b00173. Epub 2019 Mar 5.

Abstract

Many fluorophores, and all bright light-emitting substrates for firefly luciferase, contain hydroxyl or amine electron donors. Sulfonamides were found to be capable of serving as replacements for these canonical groups. Unlike "caged" carboxamides, sulfonamide donors enable bioluminescence, and sulfonamidyl luciferins, coumarins, rhodols, and rhodamines are fluorescent in water.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Coumarins / chemistry*
  • Electrons
  • Fluorescent Dyes / chemistry*
  • Luciferases, Firefly / chemistry*
  • Molecular Structure
  • Rhodamines / chemistry*
  • Sulfonamides / chemistry*
  • Water

Substances

  • Coumarins
  • Fluorescent Dyes
  • Rhodamines
  • Sulfonamides
  • Water
  • Luciferases, Firefly