A fluorogenic substrate for the continuous assaying of aryl sulfatases

Anal Biochem. 2005 May 1;340(1):80-8. doi: 10.1016/j.ab.2005.02.007.

Abstract

The most common fluorogenic substrate for assaying aryl sulfatases (ARSs) is 4-methylumbelliferyl sulfate (MUS). However, ARSs operate optimally at pH values that are less than the pK(a) (7.8) of the reaction product of MUS, 4-methylumbelliferone (4-MU). Thus, a major disadvantage of this assay is that it is usually run in a discontinuous mode due to the need for basification of the reaction mixture to achieve complete ionization of the phenolic products and maximum fluorescence. To circumvent this problem, 6,8-difluoro-4-methylumbelliferyl sulfate (DiFMUS) was prepared and examined as a substrate for ARSs. The product of the reaction is 6,8-difluoro-4-methylumbelliferone, a known coumarin with fluorescent properties equal to those of 4-MU, and has a pK(a) of 4.9. This allowed for the continuous assaying of human placental ARSs A, B, and C, which operate optimally between pH 5.0 and pH 7.0. Furthermore, DiFMUS exhibited a lower K(m) (up to 20-fold) for the ARSs than did MUS; for ARSA and ARSB, it exhibited a greater V(max) than did MUS. This substrate should have considerable utility for the continuous assay of ARS activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fluorescence
  • Humans
  • Hydrogen-Ion Concentration
  • Hydrolysis
  • Hymecromone / analogs & derivatives
  • Hymecromone / metabolism
  • Kinetics
  • Molecular Structure
  • Placenta / enzymology
  • Sulfatases / analysis*
  • Sulfatases / metabolism*

Substances

  • 6,8-difluoro-4-methylumbelliferyl sulfate
  • Hymecromone
  • Sulfatases