2-Mercaptosuccinic acid (MS) is an important and versatile substance for diverse fields of applications of which the most significant are surveyed in this article. Biological, chemical, and physical properties of MS as well as the knowledge of its synthesis and microbial degradation are illustrated. In addition, exemplary structural analogs of the organic sulfur compound are commented. The key application of MS in nanotechnology is discussed in detail with particular emphasis on quantum dots (nanocrystals) and self-assembled monolayers in combination with gold or silver. Furthermore, some medical and pharmaceutical applications are given, inter alia in bioimaging, as a nanocarrier, and with regard to the antimicrobial activity of MS-silver and MS-gold nanoparticles. Moreover, biological and chemical applications of MS are exemplified: the thiol compound can serve as an inhibitor for glutathione peroxidase, or the toxicity of substances can be increased due to the presence of MS in the respective cells or tissues. In the field of cosmetics, MS is widely utilized as a reducing agent for numerous products as explained in this article. Additionally, the microbial utilization of MS as a carbon and energy source for growth is elucidated in-depth, providing insight into different catabolic mechanisms.
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http://dx.doi.org/10.1007/s00253-015-6605-2 | DOI Listing |
Biomacromolecules
November 2023
Center for Chemistry and Biomedicine, Department of Pharmaceutical Technology, Institute of Pharmacy, University of Innsbruck, Innrain 80-82, A-6020 Innsbruck, Austria.
This study aims to design an anionic, thiolated cellulose derivative and to evaluate its mucoadhesive and permeation-enhancing properties utilizing enoxaparin as a model drug. 2-Mercaptosuccinic acid-modified cellulose (cellulose-mercaptosuccinate) was synthesized by the reaction of cellulose with -acetylmercaptosuccinic anhydride. The chemical structure of the target compound was confirmed by FTIR and H NMR spectroscopy.
View Article and Find Full Text PDFChemistry
October 2021
Manchester Institute of Biotechnology, The University of Manchester, 131 Princess Street, Manchester, M1 7DN, UK.
Thiol dioxygenases are important enzymes for human health; they are involved in the detoxification and catabolism of toxic thiol-containing natural products such as cysteine. As such, these enzymes have relevance to the development of Alzheimer's and Parkinson's diseases in the brain. Recent crystal structure coordinates of cysteine and 3-mercaptopropionate dioxygenase (CDO and MDO) showed major differences in the second-coordination spheres of the two enzymes.
View Article and Find Full Text PDFColloids Surf B Biointerfaces
May 2017
Key Laboratory of Biomedical Polymers of Ministry of Education, Department of Chemistry, Wuhan University, Wuhan 430072, China.
In this paper, four different kinds of mercaptan acids modified amphiphilic copolymers mPEG-b-PATMC-g-SRCOOH (R=CH, CHCH, (CH) and CH(COOH)CH) were successfully synthesized by thiol-ene "click" reaction between pendent carbon-carbon double bonds of PEG-b-PATMC and thiol groups of thioglycolic acid, 3-mercaptopropionic acid, 11-mercaptoundecanoic acid or 2-mercaptosuccinic acid. DLS and TEM measurements showed that all the mPEG-b-PATMC-g-SRCOOH copolymers could self-assemble to form micelles which dispersed in spherical shape with nano-size before and after DOX loading. The positively-charged DOX could effectively load into copolymer micelles via synergistic hydrophobic and electrostatic interactions.
View Article and Find Full Text PDFJ Exp Nanosci
December 2016
Department of Biomedical Engineering, Key Laboratory of Biomedical Information Engineering of Ministry of Education, School of Life Science and Technology, Xi'an Jiaotong University, Xi'an , PR China.
Water-dispersible ultrasmall nanogolds (WDU AuNPs) and their dopamine-coated nanogolds (WDU AuNPs@DPAs) were prepared by a reduction method with sodium borohydride as a reducing agent and a stabilised agent of 2-mercaptosuccinic acid in aqueous solution. The effects of these nanoparticles on computed tomography (CT) imaging were evaluated. The size distributions and Zeta potential of the nanoparticles were measured with a Malvern size analyser, and nanoparticle morphology was observed by transmission electron microscopy.
View Article and Find Full Text PDFDalton Trans
December 2015
Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, Ontario, Canada K7L 3N6.
The reaction between nitroprusside (NP, [Fe(II)(CN)5NO](2-)) and organic thiolates (RS(-)) in aqueous solution has long been known to produce an unstable red intermediate thus often being referred to as the "red product" (RP) in the literature. While RP has always been formulated as [Fe(II)(CN)5N(O)SR](3-), it is rather difficult to study it in aqueous solution because it is not only unstable but also exhibits rapid ligand exchange. All previous studies of RP have relied on UV-vis, IR, kinetics measurements, and analysis of decomposed products.
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