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Merck

P0020

Sigma-Aldrich

Pristimerin

Sinónimos:

(9b,13a,14b,20a)-3-Hydroxy-9,13-dimethyl-2-oxo-24,25,26 -trinoroleana-1(10),3,5,7-tertraen-29-oic acid methyl ester, Celastrol methyl ester

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About This Item

Fórmula empírica (notación de Hill):
C30H40O4
Número de CAS:
Peso molecular:
464.64
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77

Ensayo

≥98% (HPLC)

Nivel de calidad

Formulario

powder

condiciones de almacenamiento

protect from light

color

orange

solubilidad

DMSO: ≥5 mg/mL

temp. de almacenamiento

−20°C

cadena SMILES

COC(=O)[C@]1(C)CC[C@]2(C)CC[C@]3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5[C@]4(C)CC[C@@]3(C)C2C1

InChI

1S/C30H40O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h8-9,16,23,32H,10-15,17H2,1-7H3/t23-,26-,27-,28+,29-,30+/m1/s1

Clave InChI

JFACETXYABVHFD-WXPPGMDDSA-N

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Aplicación

Pristimerin has been used as an anti-tumor agent to study its effects on conditionally reprogrammed patient-derived lung adenocarcinoma cells (CRLCs). It has also been used as an anti-tumor agent to study its effects on conditionally reprogrammed patient derived-primary hepatocellular carcinoma cells (CRHCs).

Acciones bioquímicas o fisiológicas

More active than euphol against MGL, better activity with rat neurons, but less selective relative to similar enzymes.
More active than euphol against MGL, better activity with rat neurons, but less selective relative to similar enzymes. First MGL inhibitor to act reversibly, several others covalently bind to cysteine residues. Other studies involve multiply mylome, pristimerin inhibits NF-κB activation via inhibition of IKK-α or IKK-β. It is the methyl ester of celastrol (C0869).
Pristimerin is a quinone methide triterpenoid found abundantly in Celastraceae and Hippocrateaceae families. It shows anti-inflammatory, anti-malarial, anti-bacterial, and insecticidal properties. Pristimerin exhibits anti-cancer and anti-proliferative activity by affecting vasculogenesis, apoptosis, autophagy, migration, and invasion of tumor cells. It has been studied to exhibit therapeutic effects against leukemia, glioma, breast cancer, prostate cancer, oral cancer, and lung cancer.

Características y beneficios

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Código de clase de almacenamiento

11 - Combustible Solids

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Tsugiya Murayama et al.
Antiviral chemistry & chemotherapy, 18(3), 133-139 (2007-07-14)
We examined the anticytomegalovirus properties of four compounds: pristimerin, the pristimerin analogue, lupeol and 2-acetylphenol-1-beta-D-glucopyranosyl (1 --> 6)-beta-D-xylpyranoside (acetophenol glycoside), isolated from Maytenus heterophylla, a Kenyan medicinal plant. The effects were studied on human cytomegalovirus (HCMV) replication in the human
Jin Sun Lee et al.
Biological & pharmaceutical bulletin, 36(2), 316-325 (2013-02-02)
Pristimerin is a naturally occurring triterpenoid that causes cytotoxicity in several cancer cell lines. However, the mechanism of action for the cytotoxic effect of pristimerin has not been unexplored. The purpose of this study was to investigate the effect of
Yongwei Wang et al.
PloS one, 7(8), e43826-e43826 (2012-09-07)
Despite rapid advances in chemotherapy and surgical resection strategies, pancreatic cancer remains the fourth leading cause of cancer related deaths in the United States with a 5-year survival rate of less than 5%. Therefore, novel therapeutic agents for the prevention
Jia-Jun Li et al.
Frontiers in pharmacology, 10, 746-746 (2019-07-30)
As a quinonemethide triterpenoid extracted from species of the Celastraceae and Hippocrateaceae, pristimerin has been shown potent anti-cancer effects. Specifically, it was found that pristimerin can affect many tumor-related processes, such as apoptosis, autophagy, migration and invasion, vasculogenesis, and drug
Du-Qiang Luo et al.
Pest management science, 61(1), 85-90 (2004-12-14)
Pristimerin and celastrol isolated from the roots of Celastrus hypoleucus (Oliv) Warb f argutior Loes exhibited inhibitory effects against diverse phytopathogenic fungi. Pristimerin and celastrol were found to inhibit the mycelial growth of Rhizoctonia solani Kuhn and Glomerella cingulata (Stonem)

Artículos

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