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M2449

Sigma-Aldrich

MB-3

≥95% (HPLC)

Sinónimos:

γ-butyrolactone, Butyrolactone 3, (2R,3S)-rel-4-Methylene-5-oxo-2-propyltetrahydrofuran-3-carboxylic acid

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About This Item

Fórmula empírica (notación de Hill):
C9H12O4
Peso molecular:
184.19
MDL number:
MFCD08702690
UNSPSC Code:
12352200
PubChem Substance ID:
329817942
NACRES:
NA.77

assay

≥95% (HPLC)

form

powder

color

white to off-white

solubility

H2O: ≥10 mg/mL
DMSO: ≥20 mg/mL

storage temp.

−20°C

SMILES string

CCC[C@H]1OC(=O)C(=C)[C@@H]1C(O)=O

InChI

1S/C9H12O4/c1-3-4-6-7(8(10)11)5(2)9(12)13-6/h6-7H,2-4H2,1H3,(H,10,11)/t6-,7+/m1/s1

InChI key

SRQUTZJZABSZRQ-RQJHMYQMSA-N

Application

MB-3 has been used as a general control non-repressible 5 (GCN5) inhibitor:
  • to study its effects on lamin A/C-associated pY19-Cav-2-mediated histone H3 acetylations
  • to analyze its effects on the growth of Arabidopsis thaliana seedlings
  • to study its effects on craniofacial chondrocyte maturation

Biochem/physiol Actions

MB-3 can modify the gene expression in murine embryonic stem cells as well as yeast. It hinders the acetyltransferase activity of general control non-repressible 5 (GCN5) by binding to acetyl CoA pocket present in GCN5.
MB-3 is a Gcn5 HAT (Histone Acetyltransferase) inhibitor; anti-inflammatory, anti-carcinogenic.

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

nwg

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Hong-Bin Cai et al.
Journal of Alzheimer's disease : JAD, 77(1), 75-84 (2020-04-21)
The connection between diabetes and Alzheimer's disease (AD) is not fully determined. Hyperphosphorylation of tau protein is mediated by binding and stabilization of truncated p25 with cyclin-dependent kinase-5 (CDK5) in AD. We recently showed that diabetes-associated hyperglycemia increased the CDK5
Naomi Moris et al.
Stem cells (Dayton, Ohio), 36(12), 1828-1838 (2018-10-03)
Cell fate transitions in mammalian stem cell systems have often been associated with transcriptional heterogeneity; however, existing data have failed to establish a functional or mechanistic link between the two phenomena. Experiments in unicellular organisms support the notion that transcriptional
Hao Xu et al.
Scientific reports, 10(1), 1817-1817 (2020-02-06)
Mesenchymal stem cells (MSCs) specifically differentiate into cardiomyocytes as a potential way to reverse myocardial injury diseases, and uncovering this differentiation mechanism is immensely important. We have previously shown that histone acetylation/methylation and DNA methylation are involved in MSC differentiation
M Semer et al.
Nature chemical biology, 15(10), 992-1000 (2019-09-19)
Post-translational modifications of histone variant H2A.Z accompany gene transactivation, but its modifying enzymes still remain elusive. Here, we reveal a hitherto unknown function of human KAT2A (GCN5) as a histone acetyltransferase (HAT) of H2A.Z at the promoters of a set
Michael Tscherner et al.
Microorganisms, 7(7) (2019-07-18)
Candida species represent one of the most frequent causes of hospital-acquired infections in immunocompromised patient cohorts. Due to a very limited set of antifungals available and an increasing prevalence of drug resistance, the discovery of novel antifungal targets is essential.
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