M6635
N-(2-Mercaptopropionyl)glycine
Synonym(s):
Tiopronin
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About This Item
Linear Formula:
CH3CH(SH)CONHCH2COOH
CAS Number:
Molecular Weight:
163.19
Beilstein:
1859822
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
Assay
≥98% (TLC)
form
powder
color
white
mp
98-100 °C
application(s)
cell analysis
peptide synthesis
SMILES string
CC(S)C(=O)NCC(O)=O
InChI
1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)
InChI key
YTGJWQPHMWSCST-UHFFFAOYSA-N
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Application
N-(2-Mercaptopropionyl)glycine or Tiopronin has been used:
- in the preparation of polyethylenimine (PEI)-coated gold microparticles (PEI-gold) for biolistic delivery of nucleic acids
- to study the role of reactive oxygen species (ROS) at the reperfusion stage in in vivo isoflurane preconditioning-induced neuroprotection
- as a ROS inhibitor to study its effect on lysophosphatidylcholine (LPC)-induced inflammasome activation
Biochem/physiol Actions
N-(2-Mercaptopropionyl)glycine (NMPG) is a thiol compound associated with autoimmune hypoglycemia. It is a diffusible antioxidant and reduces the severity of colonic injury. NMPG also relieves myeloperoxidase activity and stimulates hypoxia-inducible factor-1 (HIF-1) - vascular endothelial growth factor (VEGF) pathway for ulcer healing.
N-(2-Mercaptopropionyl)glycine is a free radical scavenger.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Journal of cardiovascular pharmacology, 73(5), 265-271 (2019-05-15)
Emulsified isoflurane (EI) has been shown to alleviate myocardial ischemia-reperfusion (IR) injury. However, previous reports have not been focused on the underlying mechanism. We used models of IR injury in Langendorff-isolated rat hearts to determine the relationship between the mechanism
Lei Cui et al.
Nanomedicine : nanotechnology, biology, and medicine, 9(2), 264-273 (2012-06-13)
The present study characterized the in vitro biological response of a comprehensive set of cancer cell lines to gold nanoparticles (2.7 nm) coated with tiopronin (AuNPs-TP). Our findings suggest that upon entering cells, the AuNPs-TP are sequestered in vacuoles such
Self-assembled ultra-high aspect ratio silver nanochains.
Matthew J Shiers et al.
Advanced materials (Deerfield Beach, Fla.), 24(38), 5227-5235 (2012-08-07)
Xiaoqing Cai et al.
Analytical and bioanalytical chemistry, 401(3), 809-816 (2011-05-04)
Well-dispersed gold nanoparticles (NP) coated with tiopronin were synthesized by X-ray irradiation without reducing agents. High-resolution transmission electron microscopy shows that the average core diameters of the NPs can be systematically controlled by adjusting the tiopronin to Au mole ratio
Andrew S Goldsborough et al.
Journal of medicinal chemistry, 54(14), 4987-4997 (2011-06-11)
A major challenge in the treatment of cancer is multidrug resistance (MDR) that develops during chemotherapy. Here we demonstrate that tiopronin (1), a thiol-substituted N-propanoylglycine derivative, was selectively toxic to a series of cell lines expressing the drug efflux pump
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