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SML0122

Sigma-Aldrich

Pit-1

≥98% (HPLC)

Synonym(s):

N-[[(3-Chloro-2-hydroxy-5-nitrophenyl)amino]thioxomethyl]-benzamide

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About This Item

Empirical Formula (Hill Notation):
C14H10ClN3O4S
CAS Number:
53501-41-0
Molecular Weight:
351.76
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥14 mg/mL

storage temp.

2-8°C

InChI

1S/C14H10ClN3O4S/c15-10-6-9(18(21)22)7-11(12(10)19)16-14(23)17-13(20)8-4-2-1-3-5-8/h1-7,19H,(H2,16,17,20,23)

InChI key

RIGXBXPAOGDDIG-UHFFFAOYSA-N

Application

Pit-1 may be used in PIP3-mediated cell signaling studies.

Biochem/physiol Actions

Pit-1 is a small-molecule phosphatidylinositol-3,4,5-trisphosphate (PIP3) antagonist that binds and blocks the pleckstrin domain. It shows inhibitory effects on tumor angiogenesis and metastasis by interfering with the activation of Akt.
PIT-1 represents a new class of molecules referred to as PITenins, or PITs. PITs inhibit the binding of PIP3 to the PH domains of several target proteins, including Akt and PDK1, without affecting interactions against PIP2-selective PH domains. PIT-1 inhibits PI3K-PKD-1-Akt dependent phosphorylation in cell based assays, including the phosphorylation of Akt-1, 2 and 3.
PIT-1 is a PIP3-PH domain antagonist

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the PKB/Akt page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H302,H400

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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B Miao et al.
Oncogene, 31(39), 4317-4332 (2011-12-20)
We have reported previously the development of small-molecule phosphatidylinositol-3,4,5-trisphosphate (PIP3) antagonists (PITs) that block pleckstrin homology (PH) domain interaction, including activation of Akt, and show anti-tumor potential. Here we show that the same molecules inhibit growth factor-induced actin remodeling, lamellipodia
Benchun Miao et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(46), 20126-20131 (2010-11-03)
The PI3-kinase (PI3K) pathway regulates many cellular processes, especially cell metabolism, cell survival, and apoptosis. Phosphatidylinositol-3,4,5-trisphosphate (PIP3), the product of PI3K activity and a key signaling molecule, acts by recruiting pleckstrin-homology (PH) domain-containing proteins to cell membranes. Here, we describe

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