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SMB00376

CDDO Methyl Ester

≥98% (HPLC)

Synonyme(s) :

2-Cyano-3,12-dioxo-oleana-1,9(11)-dien-28-oic acid methyl ester, Bardoxolone Methyl, CDDO-Me

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A propos de cet article

Formule empirique (notation de Hill) :
C32H43NO4
Numéro CAS:
218600-53-4
Poids moléculaire :
505.69
NACRES:
NA.25
PubChem Substance ID:
329824977
UNSPSC Code:
12352205
MDL number:
MFCD11983137
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Quality Level

200

assay

≥98% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

CC1(C)CC[C@]2(C(OC)=O)CC[C@@]([C@@]3([H])[C@]2([H])C1)(C)[C@]4(C)CC[C@@]5([H])C(C)(C)C(C(C#N)=C[C@]5(C)C4=CC3=O)=O

InChI

1S/C32H43NO4/c1-27(2)11-13-32(26(36)37-8)14-12-31(7)24(20(32)17-27)21(34)15-23-29(5)16-19(18-33)25(35)28(3,4)22(29)9-10-30(23,31)6/h15-16,20,22,24H,9-14,17H2,1-8H3/t20-,22-,24-,29-,30+,31+,32-/m0/s1

InChI key

WPTTVJLTNAWYAO-KPOXMGGZSA-N

Gene Information

human ... IKBKB(3551), KEAP1(9817), NFE2L2(4780), PPARG(5468)

General description

CDDO-Me is a synthetic triterpenoid compound with anti-inflammatory, anti-tumor and cytoprotective properties. It is derived from the natural product oleanic acid.

Application

CDDO Methyl Ester has been used to test its effect on hepatocyte membrane transporters (HMTs) regulation and mitigation of cholestasis in hepatic ischemia-reperfusion injury (IRI). It has also been used activator of NF E2 Related Factor 2 (NRF2) to study its role in preventing cell death in melanoma cells.

Biochem/physiol Actions

CDDO-Me inhibits inflammatory mediators including interleukin-6 (IL-6), IL-10, and IL-12. It enhances apoptosis induced by TNF and chemotherapeutic agents. CDDO-Me exhibits anti-proliferative activity in osteosarcoma cells and enhances the effectiveness of chemotherapeutic agents by inducing an intrinsic mitochondrial-dependent apoptotic pathway. It can be used as an adjuvant treatment for advanced and fatal form of prostate cancer.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Consulter la Bibliothèque de documents

Differential regulation of innate immune cytokine production through pharmacological activation of Nuclear Factor-Erythroid-2-Related Factor 2 (NRF2) in burn patient immune cells and monocytes.
Eitas T K, et al.
PLoS ONE, 12(9), e0184164-e0184164 (2017)
A synthetic triterpenoid, CDDO-Me, inhibits IKBα kinase and enhances apoptosis induced by TNF and chemotherapeutic agents through down-regulation of expression of nuclear factor KB?regulated gene products in human leukemic cells.
Shishodia S, et al.
Clinical Cancer Research, 12(6), 1828-1838 (2006)
The synthetic triterpenoid CDDO-methyl ester modulates microglial activities, inhibits TNF production, and provides dopaminergic neuroprotection
Tran T A, et al.
Journal of Neuroinflammation, 5(1), 1-1 (2008)
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Numéro d'article de commerce international

RéférenceGTIN
SMB00376-100MG04061833051979
SMB00376-10MG04061833051986