106740-09-4

Basic information

• Product Name: GYY 4137 Morpholine salt
• Synonyms: GYY 4137;(4-Methoxyphenyl)morpholino-phosphinodithioic acid compound with morpholine
• CAS NO: 106740-09-4
• Molecular Formula: C₄H₉NO*C₁₁H₁₆NO₂PS₂
• Molecular Weight: 376.474361
• Mol File: 106740-09-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 164-166℃
• Appearance: /
• CAS DataBase Reference: GYY 4137 Morpholine salt(CAS DataBase Reference)
• NIST Chemistry Reference: GYY 4137 Morpholine salt(106740-09-4)
• EPA Substance Registry System: GYY 4137 Morpholine salt(106740-09-4)

Safety Data

• Hazardous Substances Data: 106740-09-4(Hazardous Substances Data)

Usage

Description

GYY 4137 Morpholine salt, also known as a water-soluble, slow-releasing hydrogen sulfide (H2S) donor, is a compound that mimics the actions of hydrogen sulfide, a gaseous mediator with significant physiological effects in mammals. It possesses vasodilator and anti-hypertensive properties and is used in various medical applications due to its ability to inhibit the production of certain cytokines and reduce the expression of specific enzymes and molecules.

Uses

Used in Pharmaceutical Applications:
GYY 4137 Morpholine salt is used as a vasodilator and anti-hypertensive agent for the treatment of acute (L-NAME-induced) or chronic (spontaneously hypertensive) hypertension in rats. It helps in reducing blood pressure and improving blood flow.
Used in Endotoxic Shock Treatment:
GYY 4137 Morpholine salt is used as a protective agent against endotoxic shock in rats. It inhibits the production of tumor necrosis factor-α, interleukin (IL)-1β, and IL-6, and reduces NF-κB activation, iNOS and cyclooxygenase-2 expression, and NO and prostaglandin E2 generation.
Used in Research and Development:
GYY 4137 Morpholine salt is used as a research compound for studying the role of hydrogen sulfide in various physiological processes and its potential therapeutic applications in different medical conditions.
Used in Drug Development:
GYY 4137 Morpholine salt is used as a lead compound in the development of new drugs targeting hypertension, endotoxic shock, and other related conditions, due to its vasodilator and anti-inflammatory properties.

Upstream product

• 19172-47-5 Lawessons reagent 
• 110-91-8 morpholine 

Downstream Products

• 7783-06-4 hydrogen sulfide 

Relevant articles and documents

Investigating the generation of hydrogen sulfide from the phosphonamidodithioate slow-release donor GYY4137

A combination of NMR spectroscopy, mass spectrometry and chemical synthesis was used to elucidate the two-step hydrolytic decomposition pathway of the slow-release hydrogen sulfide (H2S) donor GYY4137 and the key decomposition product was also prepared by an independent synthetic route. The (dichloromethane-free) sodium salt of the phosphonamidodithioate GYY4137 was also produced as a pharmaceutically more acceptable salt. In contrast with GYY4137 and its sodium salt, the decomposition product did not generate H2S or exert cytoprotective or anti-inflammatory effects in oxidatively stressed human Jurkat T-cells and LPS-treated murine RAW264.7 macrophages. The decomposition product represents a useful control compound for determining the biological and pharmacological effects of H2S generated from GYY4137.

Discovery of New H2S Releasing Phosphordithioates and 2,3-Dihydro-2-phenyl-2-sulfanylenebenzo[d][1,3,2]oxazaphospholes with Improved Antiproliferative Activity

Hydrogen sulfide (H2S) is now recognized as a physiologically important gasotransmitter. Compounds which release H2S slowly are sought after for their potential in therapy. Herein the synthesis of a series of phosphordithioates based on 1 (GYY4137) are described. Their H2S release profiles are characterized using 2,6-dansyl azide (2), an H2S specific fluorescent probe. Most compounds have anticancer activity in several solid tumor cell lines and are less toxic in a normal human lung fibroblast, WI38. A preferred compound, 14, with 10-fold greater anticancer activity than 1, was shown to release H2S in MCF7 cells using a cell active probe, 21. Both permeability and intracellular pH (pHi) were found to be significantly improved for 14 compared to 1. Furthermore, 14 was also negative in the AMES test for genotoxicity. Cyclization of these initial structures gave a series of 2,3-dihydro-2-phenyl-2-sulfanylenebenzo[d][1,3,2]oxazaphospholes, of which the simplest member, compound 22 (FW1256), was significantly more potent in cells. The improved therapeutic window of 22 in WI38 cells was compared with three other cell types. Potency of 22 was superior to 1 in MCF7 tumor spheroids and the mechanism of cell death was shown to be via apoptosis with an increase in cleaved PARP and activated caspase-7. Evidence of H2S release in cells is also presented. This work provides a "toolbox" of slow-release H2S donors useful for studies of H2S in biology and as potential therapeutics in cancer, inflammation, and cardiovascular disease. (Chemical Equation Presented).