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SML1540

Sigma-Aldrich

SBI-0206965

≥98% (HPLC)

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Synonym(s):
2-((5-Bromo-2-((3,4,5-trimethoxyphenyl)amino)pyrimidin-4-yl)oxy)-N-methylbenzamide
Empirical Formula (Hill Notation):
C21H21BrN4O5
CAS Number:
1884220-36-3
Molecular Weight:
489.32
UNSPSC Code:
12352200
PubChem Substance ID:
329825951
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

BrC1=C(OC2=C(C(NC)=O)C=CC=C2)N=C(NC3=CC(OC)=C(OC)C(OC)=C3)N=C1

InChI

1S/C21H21BrN4O5/c1-23-19(27)13-7-5-6-8-15(13)31-20-14(22)11-24-21(26-20)25-12-9-16(28-2)18(30-4)17(10-12)29-3/h5-11H,1-4H3,(H,23,27)(H,24,25,26)

InChI key

NEXGBSJERNQRSV-UHFFFAOYSA-N

Application

SBI-0206965 has been used to study its effect on the growth of cadmium-transformed prostate epithelial cells.

Biochem/physiol Actions

SBI-0206965 is a potent and selective inhibitor of the serine/threonine autophagy-initiating kinases ULK1 and ULK2 with selectivity for ULK1. SBI-0206965 has an IC50 value of 108 nM for ULK1, compared to 711nM for ULK2. Tumor cells require autophagy to remove misfolded proteins or damaged cellular organelles. SBI-0206965 was shown to suppress autophagy induced by mTOR inhibition. mTOR signaling is often hyperactive in many tumors and can drive proliferation, so mTOR inhibitors are being investigated as anticancer agents. However, mTOR inhibition also results in activation of the ULK1-dependent autophagy survival response, and most results with mTOR inhibitors have been at best cytostatic. SBI-0206965 synergizes with mTOR inhibition to induce apoptosis and cell death.
Since most of the tumor cells survive on autophagy mechanism, inhibition of autophagy inducers Unc-51 (serine/threonine-protein kinase)-like autophagy activating kinase (ULK1 and ULK2) might be useful in cancer therapy.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Venkatesh Kolluru et al.
Cancer letters, 408, 121-129 (2017-08-29)
Chronic exposure to cadmium is known to be a risk factor for human prostate cancer. Despite over-whelming evidence of cadmium causing carcinogenicity in humans, the specific underlying molecular mechanisms that govern metal-induced cellular transformation remain unclear. Acute exposure (up to
Structure and function of the ULK1 complex in autophagy.
Lin M G and James H H
Current Opinion in Cell Biology, 39, 61-68 (2016)
Séverine Olivier et al.
International journal of molecular sciences, 20(20) (2019-10-23)
The AMP-activated protein kinase (AMPK) is principally known as a major regulator of cellular energy status, but it has been recently shown to play a key structural role in cell-cell junctions. The aim of this study was to evaluate the
Prajna Paramita Naik et al.
Life sciences, 264, 118722-118722 (2020-11-09)
Secretory clusterin (sCLU) plays an important role in tumor development and cancer progression. However, the molecular mechanisms and physiological functions of sCLU in oral cancer is unclear. We examined the impact of sCLU-mediated autophagy in cell survival and apoptosis inhibition
Cansu Karabiyik et al.
STAR protocols, 2(4), 100926-100926 (2021-11-13)
The regulation of lipid kinases has remained elusive given the difficulties of assessing changes in lipid levels. Here, we describe the isolation of protein and lipid kinases to determine the regulation of lipid kinases in vitro. This can be followed
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