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F8807

Sigma-Aldrich

FM19G11

≥98% (HPLC)

Synonym(s):

3-[(2,4-Dinitrobenzoyl)amino]-benzoic acid 2-(4-methylphenyl)-2-oxoethyl ester, [2-oxo-2-(p-tolyl)ethyl] 3-[(2,4-dinitrobenzoyl)amino]benzoate

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About This Item

Empirical Formula (Hill Notation):
C23H17N3O8
CAS Number:
329932-55-0
Molecular Weight:
463.40
MDL number:
MFCD01174289
UNSPSC Code:
12352200
PubChem Substance ID:
329799774
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

off-white to light brown

solubility

DMSO: ≥40 mg/mL

storage temp.

2-8°C

SMILES string

Cc1ccc(cc1)C(=O)COC(=O)c2cccc(NC(=O)c3ccc(cc3[N+]([O-])=O)[N+]([O-])=O)c2

InChI

1S/C23H17N3O8/c1-14-5-7-15(8-6-14)21(27)13-34-23(29)16-3-2-4-17(11-16)24-22(28)19-10-9-18(25(30)31)12-20(19)26(32)33/h2-12H,13H2,1H3,(H,24,28)

InChI key

XVUOIWIIQVGWAJ-UHFFFAOYSA-N

Application

FM19G11 has been used as ahypoxia-inducible factor-1α (HIF- 1α):
  • to study the effects ofFM19G11-loaded gold nanoparticles (NPs) on self-renewal and proliferation of ependymal stem progenitor cells (epSPCs) of mice
  • to study its effects on the O6-methylguanine DNA-methyltransferase (MGMT) expression in glioblastoma (GBM) cells
  • to study its effects on microphthalmia-associated transcription factor (MITF) expression in melanoma cell line

Biochem/physiol Actions

FM19G11 is an inhibitor of Hypoxia Inducible Factors α (HIFα), reported to affect self-renewal and differentiation of stem cells. Hypoxia-inducible factors (HIFs) are transcription factors that respond to changes in available oxygen in the cellular environment. Among other functions (like angiogenesis), HIFα proteins affect the self-renewal and the differentiation processes of stem cells. FM19G11 inhibits the HIFα proteins that repress the target genes of the two α subunits, in various tumor cell lines as well as in adult and embryonic stem cell (ESC) models.

Storage Class Code

11 - Combustible Solids

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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Sung Ji Choi et al.
PloS one, 8(3), e58662-e58662 (2013-03-23)
Although both glucose deprivation and hypoxia have been reported to promote cascades of biological alterations that lead to induction of inflammatory mediators, we hypothesized that glucose deprivation and hypoxia might show neutral, synergistic or antagonistic effects to each other on
Stefania Marcuzzo et al.
Cells, 8(3) (2019-03-27)
Amyotrophic lateral sclerosis (ALS) is a progressive neurodegenerative disease affecting motor neurons. In ALS mice, neurodegeneration is associated with the proliferative restorative attempts of ependymal stem progenitor cells (epSPCs) that normally lie in a quiescent in the spinal cord. Thus
UV-protection timer controls linkage between stress and pigmentation skin protection systems
Malcov B, et al.
Molecular Cell, 72(3), 444-456 (2018)
Eisuke Ueshima et al.
Liver cancer, 9(1), 63-72 (2020-02-20)
The underlying mechanism involved in the recurrence of hepatoma after hepatic arterial embolization (HAE) is not adequately examined. An immunosuppressive cytokine, transforming growth factor β1 (TGF-β1), can lead to tumor progression and is affected by hypoxia in various cancers. The
Chao-Guo You et al.
Cancer medicine (2018-05-16)
FM19G11 is a small molecular agent that inhibits hypoxia-inducible factor-1-alpha (HIF-1α) and other signaling pathways. In this study, we characterized the modulating effects of FM19G11 on O6 -methylguanine DNA-methyltransferase (MGMT), the main regulator of temozolomide (TMZ) resistance in glioblastomas. This
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