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Merck

C2997

Sigma-Aldrich

Cytosporone B

≥98% (HPLC), powder, nuclear receptor Nur77 agonist

Sinónimos:

3,5-Dihydroxy-2-(1-oxooctyl)benzeneacetic acid ethyl ester, Csn-B, Csn-B; 3,5-Dihydroxy-2-(1-oxooctyl)-benzeneacetic acid, ethyl ester

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About This Item

Fórmula empírica (notación de Hill):
C18H26O5
Número de CAS:
Peso molecular:
322.40
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77

Nombre del producto

Cytosporone B, ≥98% (HPLC)

Nivel de calidad

Ensayo

≥98% (HPLC)

Formulario

powder

color

white to off-white

solubilidad

DMSO: >20 mg/mL

temp. de almacenamiento

−20°C

cadena SMILES

CCCCCCCC(=O)c1c(O)cc(O)cc1CC(=O)OCC

InChI

1S/C18H26O5/c1-3-5-6-7-8-9-15(20)18-13(11-17(22)23-4-2)10-14(19)12-16(18)21/h10,12,19,21H,3-9,11H2,1-2H3

Clave InChI

UVVWQQKSNZLUQA-UHFFFAOYSA-N

Aplicación

Cytosporone B has been used:
  • as a positive control and NR4A1 agonist in NR4A1 reporter gene assay
  • for Nr4a1 activation
  • to treat OVX mice and study its effect on migration of osteoclast precursor

Acciones bioquímicas o fisiológicas

Cytosporone B (Csn-B) is the first naturally occurring agonist for nuclear orphan receptor Nur77.
Cytosporone B (Csn-B) is the first naturally occurring agonist for nuclear orphan receptor Nur77. It binds with high affinity (IC50=0.278 nM) to the ligand-binding domain of Nur77 and stimulates Nur77-dependent activities.

Nur77 is a nuclear receptor/transcription factor. A physiological ligand for Nur77 is as yet unknown, but there is increasing interest in Nur77 because of its known activities. Translocation of Nur77 from the nucleus to mitochondria initiates cell apoptosis, making it a potential target for cancer treatment. Nur77 is also involved in glucose homeostasis; it induces genes involved in gluconeogenesis. Csn-B physically binds to Nur77 and activates its transactivational activity and translocation to mitochondria to induce apoptosis. It inhibits cancer cell proliferation and tumor growth.
Cytosporone B is a fungal metabolite closely related to phomposin C. It is the first known agonist for the nuclear orphan receptor Nur77. It binds with high affinity (IC50 = 0.278 nM) to the ligand-binding domain of Nur77 and stimulates Nur77-dependent activities.

Nur77 is a nuclear receptor/transcription factor with no known physiological ligand, but there is increasing interest in Nur77 because of its known activities. Translocation of Nur77 from the nucleus to mitochondria initiates apoptosis, making it a potential target for cancer chemotherapy. Nur77 also induces genes involved in gluconeogenesis. Csn-B activates the Nur77 translocation to mitochondria to induce apoptosis, inhibiting cancer cell proliferation and tumor growth.

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Acute Tox. 4 Oral

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Benoit Egarnes et al.
PloS one, 12(10), e0186639-e0186639 (2017-10-21)
The transcription factor NR4A1 has emerged as a pivotal regulator of the inflammatory response and immune homeostasis. Although contribution of NR4A1 in the innate immune response has been demonstrated, its role in host defense against viral infection remains to be
Myeloid receptor CD36 is required for early phagocytosis of myocardial infarcts and induction of Nr4a1-dependent mechanisms of cardiac repair
Dehn S and Thorp EB
Faseb Journal, 254-264 (2017)
Shirley Dehn et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 32(1), 254-264 (2017-09-02)
Phagocytosis after myocardial infarction (MI) is a prerequisite to cardiac repair. Recruited monocytes clear necrotic cardiomyocytes and differentiate into cardiac macrophages. Some studies have linked apoptotic cell receptors on cardiac macrophages to tissue repair; however, the contribution of precursor monocyte
NR4A1 Regulates Motility of Osteoclast Precursors and Serves as Target for the Modulation of Systemic Bone Turnover
Scholtysek C, et al.
Journal of Bone and Mineral Research, 33(11), 2035-2047 (2018)
Aravind T Reddy et al.
PloS one, 15(2), e0229256-e0229256 (2020-02-23)
Cigarette smoke (CS) contains multiple gaseous and particulate materials that can cause lung inflammation, and smoking is the major cause of chronic obstructive pulmonary disease (COPD). We sought to determine the mechanisms of how CS triggers lung inflammation. Nur77, a

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