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SMB00376

Sigma-Aldrich

CDDO Methyl Ester

≥98% (HPLC)

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C32H43NO4
Numero CAS:
218600-53-4
Peso molecolare:
505.69
Numero MDL:
MFCD11983137
Codice UNSPSC:
12352205
ID PubChem:
329824977
NACRES:
NA.25

Livello qualitativo

200

Saggio

≥98% (HPLC)

Forma fisica

powder

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Temperatura di conservazione

−20°C

Stringa SMILE

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
WPTTVJLTNAWYAO-KPOXMGGZSA-N

Informazioni sul gene

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

Categorie correlate

Descrizione generale

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

Applicazioni

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.

Azioni biochim/fisiol

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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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)
Timothy K Eitas et al.
PloS one, 12(9), e0184164-e0184164 (2017-09-09)
Burn patients suffer from immunological dysfunction for which there are currently no successful interventions. Similar to previous observations, we find that burn shock patients (≥15% Total Burn Surface Area (TBSA) injury) have elevated levels of the innate immune cytokines Interleukin-6
Laure Maneix et al.
Cancers, 13(4) (2021-03-07)
Multiple myeloma and its precursor plasma cell dyscrasias affect 3% of the elderly population in the US. Proteasome inhibitors are an essential part of several standard drug combinations used to treat this incurable cancer. These drugs interfere with the main
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