Possibilities and pitfalls in quantifying the extent of cysteine sulfenic acid modification of specific proteins within complex biofluids

BMC Biochem. 2010 Jul 1:11:25. doi: 10.1186/1471-2091-11-25.

Abstract

Background: Cysteine sulfenic acid (Cys-SOH) plays important roles in the redox regulation of numerous proteins. As a relatively unstable posttranslational protein modification it is difficult to quantify the degree to which any particular protein is modified by Cys-SOH within a complex biological environment. The goal of these studies was to move a step beyond detection and into the relative quantification of Cys-SOH within specific proteins found in a complex biological setting--namely, human plasma.

Results: This report describes the possibilities and limitations of performing such analyses based on the use of thionitrobenzoic acid and dimedone-based probes which are commonly employed to trap Cys-SOH. Results obtained by electrospray ionization-based mass spectrometric immunoassay reveal the optimal type of probe for such analyses as well as the reproducible relative quantification of Cys-SOH within albumin and transthyretin extracted from human plasma--the latter as a protein previously unknown to be modified by Cys-SOH.

Conclusions: The relative quantification of Cys-SOH within specific proteins in a complex biological setting can be accomplished, but several analytical precautions related to trapping, detecting, and quantifying Cys-SOH must be taken into account prior to pursuing its study in such matrices.

Publication types

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

MeSH terms

  • Cyclohexanones / chemistry
  • Cysteine / analogs & derivatives*
  • Cysteine / chemistry
  • Cysteine / metabolism
  • Humans
  • Nitrobenzoates / chemistry
  • Oxidation-Reduction
  • Prealbumin / chemistry*
  • Serum Albumin / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Sulfenic Acids / chemistry
  • Sulfenic Acids / metabolism*
  • Sulfhydryl Compounds / chemistry

Substances

  • Cyclohexanones
  • Nitrobenzoates
  • Prealbumin
  • Serum Albumin
  • Sulfenic Acids
  • Sulfhydryl Compounds
  • thionitrobenzoic acid
  • dimedone
  • cysteinesulfenic acid
  • Cysteine