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

Arash Mirzahosseini, B. Noszál

Research output: Contribution to journalArticle

10 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 2014

Fingerprint

Alkalinity
Sulfhydryl Compounds
Cysteamine
Acids
Oxidative stress
Protonation
Biomolecules
Homocysteine
Hydrogen Bonding
Titration
Cysteine
Hydrogen bonds
Oxidative Stress
Nuclear magnetic resonance
Proton Magnetic Resonance Spectroscopy

Keywords

  • Disulfide
  • Microspeciation
  • Oxidizability
  • PK
  • Thiol

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Spectroscopy
  • Clinical Biochemistry
  • Medicine(all)

Cite this

The species- and site-specific acid-base properties of biological thiols and their homodisulfides. / Mirzahosseini, Arash; Noszál, B.

In: Journal of Pharmaceutical and Biomedical Analysis, Vol. 95, 07.2014, p. 184-192.

Research output: Contribution to journalArticle

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