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SML1143

Sigma-Aldrich

PTC-209

≥98% (HPLC)

Synonym(s):

N-(2,6-Dibromo-4-methoxyphenyl)-4-(2-methylimidazo[1,2-a]pyrimidin-3-yl)-2-thiazolamine

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About This Item

Empirical Formula (Hill Notation):
C17H13Br2N5OS
CAS Number:
315704-66-6
Molecular Weight:
495.19
MDL number:
MFCD02110649
UNSPSC Code:
12352200
PubChem Substance ID:
329825677
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to brown

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

BrC1=CC(OC)=CC(Br)=C1NC2=NC(C3=C(C)N=C4N3C=CC=N4)=CS2

InChI

1S/C17H13Br2N5OS/c1-9-15(24-5-3-4-20-16(24)21-9)13-8-26-17(22-13)23-14-11(18)6-10(25-2)7-12(14)19/h3-8H,1-2H3,(H,22,23)

InChI key

XVOOCQSWCCRVDY-UHFFFAOYSA-N

Application

PTC-209 has been used as a B lymphoma Mo-MLV insertion region 1 homolog (BMI1) inhibitor to study its effects on:
  • the cell viability of canine osteosarcoma (OSA) cell lines
  • lipidated microtubule-associated protein 1 light chain 3 (LC3B-II) and Sequestosome 1 (SQSTM1) protein levels in ovarian cancer (OvCa) cells
  • cardiac reprogramming efficiency in mouse embryonic fibroblasts (MEF)

Biochem/physiol Actions

PTC-209 inhibits the expression of the oncogene BMI-1 (B lymphoma Mo-MLV insertion region 1 homolog), which encodes a polycomb group RING finger protein involved in cell cycle. PTC-209 lowers the self-renewal properties of colorectal cancer-initiating cells (CICs) The compound inhibits tumor growth, and reduces the levels of CICs present in colon cancer tumor xenografts in mice.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk_germany

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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Inhibition of BMI1 induces autophagy-mediated necroptosis
Dey A, et al.
Autophagy, 12(4), 659-670 (2016)
Mohammad Alzrigat et al.
Oncotarget, 8(61), 103731-103743 (2017-12-22)
Multiple myeloma (MM) is a tumor of plasmablasts/plasma cells (PCs) characterized by the expansion of malignant PCs with complex genetic aberrations in the bone marrow (BM). Recent reports, by us and others, have highlighted the polycomb group (PcG) proteins as
Sami Al-Nadaf et al.
Veterinary and comparative oncology, 20(4), 871-880 (2022-07-15)
The BMI1 proto-oncogene, polycomb ring finger protein (BMI1) is a key component of the epigenetic polycomb repressor complex 1, and has been associated with aggressive behaviour and chemotherapeutic resistance in various malignances including human gliomas. Similar to humans, spontaneous canine
Anindya Dey et al.
Molecular cancer therapeutics, 17(1), 39-49 (2017-11-22)
BMI-1, also known as a stem cell factor, is frequently upregulated in several malignancies. Elevated expression of BMI-1 correlates with poor prognosis and is therefore considered a viable therapeutic target in a number of malignancies including ovarian cancer. Realizing the

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