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SML2140

Sigma-Aldrich

TCS 401

≥98% (HPLC)

Sinónimos:

2-[(Carboxycarbonyl)amino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid hydrochloride, TCS-401, TCS401

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About This Item

Fórmula empírica (notación de Hill):
C10H10N2O5S · xHCl
Número de CAS:
243966-09-8
Peso molecular:
270.26 (free base basis)
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

0.1 M NaOH: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

[s]1c2c(c(c1NC(=O)C(=O)O)C(=O)O)CC[N+H2]C2.[Cl-]

InChI key

LQGCAMWQDSYOAY-UHFFFAOYSA-N

Biochem/physiol Actions

Selective inhibitor of protein-tyrosine phosphatase 1B (PTP1B); insulin receptor sensitizing agent.
TCS 401 is a selective inhibitor of protein-tyrosine phosphatase 1B (PTP1B), which plays a key role in the negative regulation of the insulin signaling pathway, contributing to insulin resistance. It exhibited Ki values of 290 nM for PTP1B, with greater than 100-fold or more selectivity compared to other phosphatases. Inhibition of PTP1B by TCS 401 has been shown to sensitize the insulin signaling pathway and increase dopamine release in response to insulin. TCS-401 has also been shown to promote endothelial cell motility and to induce differentiation of retinal pigment epithelial cells toward improved contractility and motility.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Steve C Fordahl et al.
ACS chemical neuroscience, 8(2), 290-299 (2016-12-15)
Systemically released insulin crosses the blood-brain barrier and binds to insulin receptors on several neural cell types, including dopaminergic neurons. Insulin has been shown to decrease dopamine neuron firing in the ventral tegmental area (VTA), but potentiate release and reuptake
L F Iversen et al.
The Journal of biological chemistry, 275(14), 10300-10307 (2000-04-01)
Several protein-tyrosine phosphatases (PTPs) have been proposed to act as negative regulators of insulin signaling. Recent studies have shown increased insulin sensitivity and resistance to obesity in PTP1B knockout mice, thus pointing to this enzyme as a potential drug target
Samuel Legeay et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 127, 110200-110200 (2020-05-18)
Diabetes notably increases the risk for endothelial dysfunction, a main precursor for microvascular complications. While endoplasmic reticulum stress (ERS) and protein tyrosine phosphatase 1B (PTP1B) have been associated with endothelial dysfunction in resistance vessels, whether these mechanisms also contribute to
Zhao-dong Du et al.
Molecular vision, 21, 523-531 (2015-05-23)
To determine whether protein tyrosine phosphatase 1B (PTP1B) is expressed in rat retinal pigment epithelium (RPE) cells, to evaluate whether inhibition of PTP1B contributes to initiation of RPE cells into an active state, and to investigate the signaling pathways involved

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