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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Oral anticoagulants are vital tools in preventing and treating blood clotting disorders. This diverse class of medications can be categorized as vitamin K antagonists, exemplified by warfarin, and direct thrombin inhibitors (DTIs), such as dabigatran, as well as factor Xa inhibitors, including rivaroxaban.
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Hemostasis is a crucial process that prevents excessive blood loss from damaged blood vessels. It involves various mechanisms such as vasoconstriction, platelet adhesion and activation, and fibrin formation. The importance of each mechanism depends on the type of vessel injury. In contrast, thrombosis is the abnormal formation of a blood clot within the blood vessels, leading to potential complications if the clot obstructs blood flow. Thrombosis can be caused by increased coagulability of the...
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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

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S-nitrosothiols as selective antithrombotic agents - possible mechanisms.

M P Gordge1, F Xiao

  • 1Department of Biomedical Science, University of Westminster, London, UK. m.p.gordge@wmin.ac.uk

British Journal of Pharmacology
|March 18, 2010
PubMed
Summary

S-nitrosothiols show promise as antithrombotic agents due to their platelet inhibitory effects. Novel pathways and cell surface interactions may explain their selective action and potential for treating thrombosis.

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Area of Science:

  • Biochemistry
  • Pharmacology
  • Hematology

Background:

  • S-nitrosothiols (RSNOs) are investigated for clinical applications, particularly as antithrombotic agents.
  • RSNOs exhibit platelet inhibitory effects, suggesting potential therapeutic benefits in thrombosis.
  • The precise mechanism underlying RSNOs' platelet selectivity remains unclear.

Purpose of the Study:

  • To elucidate the mechanisms of nitric oxide (NO) delivery from RSNOs into cells.
  • To explore the role of different cellular pathways in mediating RSNO effects.
  • To identify novel antithrombotic actions of RSNOs.

Main Methods:

  • Investigated denitrosation by cell surface enzymes.
  • Examined the transport of S-nitrosocysteine via the amino acid transporter system-L (L-AT).
  • Assessed the regulation of cell surface targets involved in thrombosis by RSNOs.

Main Results:

  • Identified cell surface enzyme denitrosation and L-AT as key pathways for NO signaling from RSNOs.
  • Observed differences in these pathways between platelets and vascular cells, potentially explaining platelet selectivity.
  • Found that RSNOs regulate exofacial targets like protein disulphide isomerase, integrins, and tissue factor.

Conclusions:

  • Cellular uptake and denitrosation pathways contribute to the antithrombotic effects of S-nitrosothiols.
  • Differences in these pathways may underlie the observed platelet selectivity of RSNOs.
  • RSNOs may offer novel antithrombotic strategies by targeting cell surface proteins, potentially without requiring intracellular NO delivery.