The species- and site-specific acid-base properties of biological thiols and their homodisulfides

Arash Mirzahosseini, Béla Noszál

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Cysteamine, cysteine, homocysteine, their homodisulfides and 9 related compounds were studied by 1H NMR-pH titrations and case-tailored evaluation methods. The resulting acid-base properties are quantified in terms of 33 macroscopic and 62 microscopic protonation constants and the concomitant 16 interactivity parameters, providing thus the first complete microspeciation of this vitally important family of biomolecules. The species- and site-specific basicities are interpreted by means of inductive and hydrogen-bonding effects through various intra- and intermolecular comparisons. The pH-dependent distribution of the microspecies is depicted. The thiolate basicities determined this way provide exclusive means for the prediction of thiolate oxidizabilities, a key parameter to understand and influence oxidative stress at the molecular level.

Original languageEnglish
Pages (from-to)184-192
Number of pages9
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume95
DOIs
Publication statusPublished - Jul 1 2014

Keywords

  • Disulfide
  • Microspeciation
  • Oxidizability
  • PK
  • Thiol

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmaceutical Science
  • Drug Discovery
  • Spectroscopy
  • Clinical Biochemistry

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