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M6635

Sigma-Aldrich

N-(2-Mercaptopropionyl)glycine

Sinónimos:

Tiopronin

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About This Item

Fórmula lineal:
CH3CH(SH)CONHCH2COOH
Número de CAS:
1953-02-2
Peso molecular:
163.19
Beilstein/REAXYS Number:
1859822
EC Number:
217-778-4
MDL number:
MFCD00004861
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24897101
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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Soohwan Yum et al.
Biochemical and biophysical research communications, 443(3), 1008-1013 (2013-12-24)
We investigated anti-colitic effects of N-(2-mercaptopropionyl)-glycine (NMPG), a diffusible antioxidant, in TNBS-induced rat colitis model and a potential molecular mechanism underlying the pharmacologic effect of the antioxidant. NMPG alleviated colonic injury and effectively lowered myeloperoxidase activity. Moreover, NMPG substantially attenuated
Wei Chen et al.
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
Pyritinol
Meyler's Side Effects of Drugs: The International Encyclopedia of Adverse Drug Reactions and Interactions, 2988-2989 (2006)
Sang Hyun Lee et al.
Brain research, 1723, 146405-146405 (2019-08-28)
In this in vivo and in vitro study, we aimed to investigate whether isoflurane preconditioning-induced neuronal protection is mediated by reactive oxygen species (ROS) signaling at the reperfusion stage. In the in vivo study, Sprague-Dawley rats were subjected to middle
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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