M6635

N-(2-Mercaptopropionyl)glycine

Name: <I>N</I>-(2-Mercaptopropionyl)glycine
Brand: SIGMA

Synonym(s):

Tiopronin

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About This Item

Linear Formula:

CH₃CH(SH)CONHCH₂COOH

CAS Number:

1953-02-2

Molecular Weight:

163.19

NACRES:

NA.26

PubChem Substance ID:

24897101

eCl@ss:

32160406

UNSPSC Code:

12352209

EC Number:

217-778-4

MDL number:

MFCD00004861

Beilstein/REAXYS Number:

1859822

Key Documents

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InChI key

YTGJWQPHMWSCST-UHFFFAOYSA-N

InChI

1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)

SMILES string

CC(S)C(=O)NCC(O)=O

assay

≥98% (TLC)

form

powder

color

white

mp

98-100 °C

application(s)

cell analysis
peptide synthesis

Quality Level

100

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Related Categories

Amino Acids

Amino Acids, Resins & Reagents for Peptide Synthesis

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Cell Culture Supplements & Reagents

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Show Differences

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This Item	G3267	648480	WH0007134M1
Sigma-Aldrich M6635 N-(2-Mercaptopropionyl)glycine	Sigma-Aldrich G3267 Glycine benzyl ester hydrochloride	Sigma-Aldrich 648480 Troponin I, Human Heart	Sigma-Aldrich WH0007134M1 Monoclonal Anti-TNNC1 antibody produced in mouse
form powder	form powder	form lyophilized	form buffered aqueous solution
assay ≥98% (TLC)	assay ≥98% (TLC)	assay ≥95% (SDS-PAGE)	assay -
mp 98-100 °C	mp -	mp -	mp -
Quality Level 100	Quality Level 200	Quality Level 100	Quality Level 100
color white	color white	color -	color -
application(s) cell analysis peptide synthesis	application(s) -	application(s) -	application(s) -

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[1]
to study the role of reactive oxygen species (ROS) at the reperfusion stage in in vivo isoflurane preconditioning-induced neuroprotection[2]
as a ROS inhibitor to study its effect on lysophosphatidylcholine (LPC)-induced inflammasome activation[3]

Biochem/physiol Actions

N-(2-Mercaptopropionyl)glycine (NMPG) is a thiol compound associated with autoimmune hypoglycemia.[4] 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.[5]

N-(2-Mercaptopropionyl)glycine is a free radical scavenger.

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Role of reactive oxygen species at reperfusion stage in isoflurane preconditioning-induced neuroprotection.

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

Pyritinol

Meyler's Side Effects of Drugs: The International Encyclopedia of Adverse Drug Reactions and Interactions, 2988-2989 (2006)

N-(2-Mercaptopropionyl)-glycine, a diffusible antioxidant, activates HIF-1 by inhibiting HIF prolyl hydroxylase-2: implication in amelioration of rat colitis by the antioxidant.

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

Mechanism of Emulsified Isoflurane Postconditioning-Induced Activation of the Nrf2-Antioxidant Response Element Signaling Pathway During Myocardial Ischemia-Reperfusion: The Relationship With Reactive Oxygen Species.

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

Collateral sensitivity of multidrug-resistant cells to the orphan drug tiopronin.

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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