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Merck

238590

Cucurbitacin I, Cucumis sativus L.

A cell-permeable and irreversible bitter triterpenoid compound (NCI identifier: NSC 521777) that displays anti-proliferative and antitumor properties both in vitro and in vivo.

Synonym(s):

Cucurbitacin I, Cucumis sativus L., JSI-124, STAT3 Inhibitor XIV

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About This Item

Empirical Formula (Hill Notation):
C30H42O7
CAS Number:
2222-07-3
Molecular Weight:
514.65
MDL number:
MFCD00270073
UNSPSC Code:
12352200
NACRES:
NA.77

Product Name

Cucurbitacin I, Cucumis sativus L., A cell-permeable and irreversible bitter triterpenoid compound (NCI identifier: NSC 521777) that displays anti-proliferative and antitumor properties both in vitro and in vivo.

InChI

1S/C30H42O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+/t17-,19-,20+,23+,27+,28-,29+,30+/m1/s1

InChI key

NISPVUDLMHQFRQ-MKIKIEMVSA-N

description

RTECS - RC6200000

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

ethanol: 10 mg/mL
DMSO: 100 mg/mL

shipped in

ambient

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Cell permeable: yes
Primary Target
JAK/STAT3
Product does not compete with ATP.
Reversible: no
Target IC50: 500 nM suppressing STAT3 tyrosine phosphorylation in v-Src-transformed NIH 3T3 cells and human lung adenocarcinoma A549 cells

Disclaimer

Toxicity: Standard Handling (A)

General description

A cell-permeable and irreversible bitter triterpenoid compound (NCI identifier: NSC 521777) that exhibits anti-proliferative and anti-tumor properties both in vitro and in vivo. Acts as a potent and highly selective inhibitor of Janus kinase/Signal transducer and activator of transcription 3 (Jak/STAT3) signaling pathway. Reported to suppress STAT3 tyrosine phosphorylation in v-src-transformed NIH 3T3 cells and human lung adenocarcinoma A549 cells (IC50 = 500 nM), resulting in inhibition of STAT3 DNA-binding and STAT3-mediated gene transcription. Also shown to inhibit the growth of STAT3-transformed tumors in nude mice. Does not affect oncogenic pathways mediated by Ras, Akt1, ERK1/2, or JNK.

Other Notes

Blaskovich, M.A., et al. 2003. Cancer Res.63, 1270.

Packaging

Packaged under inert gas

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Basic calcium phosphate (BCP) crystal and interleukin 6 (IL-6) have been implicated in osteoarthritis (OA). We hypothesise that these two factors may be linked in a reciprocal amplification loop which leads to OA. Primary murine chondrocytes and human cartilage explants

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