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C8499

Sigma-Aldrich

Cucurbitacin B hydrate

≥97% (HPLC)

Sinonimo/i:

(2β,9β,10α,16α,23E)-25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-19-Norlanosta-5,23-diene-3,11,22-trione

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About This Item

Formula empirica (notazione di Hill):
C32H46O8 · xH2O
Numero CAS:
Peso molecolare:
558.70 (anhydrous basis)
Numero MDL:
Codice UNSPSC:
12352200
ID PubChem:
NACRES:
NA.77

Livello qualitativo

Saggio

≥97% (HPLC)

Forma fisica

powder

Colore

white to beige

Solubilità

DMSO: 10 mg/mL, clear

Temperatura di conservazione

2-8°C

Stringa SMILE

CC1(C)C([C@@H](O)C[C@]2([H])C1=CC[C@]([C@@](C[C@@H](O)[C@]3([H])[C@@](C)(O)C(/C=C/C(C)(C)OC(C)=O)=O)(C)[C@]3(C)C4)([H])[C@@]2(C)C4=O)=O

InChI

1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1
IXQKXEUSCPEQRD-DKRGWESNSA-N

Applicazioni

Cucurbitacin B hydrate has been used:
  • as a signal transducer and activator of transcription 3 (stat3) inhibitor to determine its effect on the expression of human lysosomal acid lipase (hLAL) in myeloid-derived suppressor cells (MDSCs).
  • as an ecdysone receptor (EcR) antagonist injection to lower the levels of 20-hydoxyecdysone (20E) signaling in butterflies.
  • to determine its effect on the cell viability of pancreatic cancer cell lines.

Azioni biochim/fisiol

Cucurbitacin B also exhibits anti-cancer activity by inhibiting telomerase and c-Myc in breast cancer. It also exhibits anti- artherosclerotic activity. Cucurbitacin B also possesses anti-inflammatory and anti-microbial activity.
Cucurbitacin B is a triterpenoid constituent of Cucurbitaceae plant species. Cucurbitacin B inhibits proliferation in a wide variety of tumor cell lines (IC50 15-30 nM) by inducing apoptosis and inducing cell cycle arrest at G2/M phase. Although the mechanism of action is unclear, Cucurbitacin B inhibits STAT 3 phosphorylation and expression levels and has been shown to block JAK2 activity. Curcubitacin B also inhibits the transcriptional activity of HIF1a and Nf-KB. Curcubitacin B is structurally similar to the JAK inhibitor Curcubitacin I.

Caratteristiche e vantaggi

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the JAKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pittogrammi

Skull and crossbones

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Acute Tox. 2 Oral

Codice della classe di stoccaggio

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


Certificati d'analisi (COA)

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PloS one, 8(2), e55732-e55732 (2013-02-09)
Cucurbitacin B (CuB) is one of the potential agents for long term anticancer chemoprevention. Cumulative evidences has shown that cucurbitacin B provides potent cellular biological activities such as hepatoprotective, anti-inflammatory and antimicrobial effects, but the precise mechanism of this agent
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Drug delivery, 17(3), 114-122 (2010-02-13)
This study intended to prepare liver-targeting solid lipid nanoparticles (SLNs) with a hepatoprotective drug, cucurbitacin B (Cuc B), using a galactosylated lipid, N-hexadecyl lactobionamide (N-HLBA). The galactosyl-lipid N-HLBA was prepared via the lactone form intermediates of lactobionic acid and synthesized
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Cucurbitacins which are structurally diverse triterpenes found in the members of Cucurbitaceae and several other plant families possess immense pharmacological potential. This diverse group of compounds may prove to be important lead molecules for future research. Research focused on these

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