C2997
Cytosporone B
≥98% (HPLC), powder, nuclear receptor Nur77 agonist
Synonym(s):
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
Empirical Formula (Hill Notation):
C18H26O5
CAS Number:
Molecular Weight:
322.40
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
product name
Cytosporone B, ≥98% (HPLC)
Quality Level
Assay
≥98% (HPLC)
form
powder
color
white to off-white
solubility
DMSO: >20 mg/mL
storage temp.
−20°C
SMILES string
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
InChI key
UVVWQQKSNZLUQA-UHFFFAOYSA-N
Application
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
Biochem/physiol Actions
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.
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.
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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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)
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)
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
A C Kramer et al.
Leukemia, 31(11), 2479-2490 (2017-03-23)
T-cell acute lymphoblastic leukemia (T-ALL) is an aggressive hematopoietic neoplasm resulting from the malignant transformation of T-cell progenitors, and comprises ~15% and 25% of pediatric and adult ALL cases, respectively. It is well-established that activating NOTCH1 mutations are the major
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