Rasfonin
Product Code: AG-CN2-0173
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0173-C500 | 500 ug | £180.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-200
Documents
Further Information
Alternate Names/Synonyms:
(-)-Rasfonin; TT-1
Appearance:
Tan to brown viscous liquid (oily).
CAS:
303156-68-5
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS06
Handling Advice:
Protect from light and moisture.
Hazards:
H301
InChi:
InChI=1S/C25H38O6/c1-6-17(2)13-19(4)14-20(5)25-22(8-10-24(29)31-25)30-23(28)9-7-18(3)15-21(16-27)11-12-26/h6-10,15,19-22,25-27H,11-14,16H2,1-5H3/b9-7+,17-6+,18-15+/t19-,20-,21-,22?,25+/m0/s1
InChiKey:
OHRGHFXATDKGOV-MDKHPKFKSA-N
Long Description:
Chemical. CAS: 303156-68-5. Formula: C25H38O6. MW: 434.6. Isolated from Trichurus sp. Selective apoptosis inducer in ras-dependent cells. Autophagy (Akt-dependent), apoptosis and necroptosis inducer in renal cancer cell lines. Induces death of ras-mutated pancreatic tumor (Panc-1) cells in vitro and in vivo. Robust inhibitor of pancreatic cancers with the K-ras mutation. Reduced Sos1 expression and depressed Ras-MAPK activity.
MDL:
MFCD16876188
Molecular Formula:
C25H38O6
Molecular Weight:
434.6
Package Type:
Vial
PG:
III
Precautions:
P264, P301+P310+P330, P405, P501
Product Description:
Selective apoptosis inducer in ras-dependent cells. Autophagy (Akt-dependent), apoptosis and necroptosis inducer in renal cancer cell lines. Induces death of ras-mutated pancreatic tumor (Panc-1) cells in vitro and in vivo. Robust inhibitor of pancreatic cancers with the K-ras mutation. Reduced Sos1 expression and depressed Ras-MAPK activity.
Purity:
>95% (HPLC)
Signal Word:
Warning
SMILES:
O=C1O[C@@]([C@H](C[C@@H](C)C/C(C)=C/C)C)([H])C(OC(/C=C/C(C)=C/[C@@H](CO)CCO)=O)C=C1
Solubility Chemicals:
Soluble in ethanol, methanol or DMSO (all 1mg/ml).
Source / Host:
Isolated from Trichurus sp.
Transportation:
Non-hazardous
UN Nummer:
2811
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Rasfonin, a New Apoptosis Inducer in ras-dependent Cells from Talaromyces sp.: T. Tomikawa, et al.; J. Antibiot. 53, 848 (2000) | Total synthesis of TT-1 (rasfonin), an alpha-pyrone-containing natural product from a fungus Trichurus terrophilus: K. Akiyama, et al.; Tetrahedron 61, 1827 (2005) | Toward the Development of a General Chiral Auxiliary. Enantioselective Alkylation and a New Catalytic Asymmetric Addition of Silyloxyfurans: Application to a Total Synthesis of (-)-Rasfonin: R.K. Boeckman, et al.; JACS 128, 11032 (2006) | Rasfonin, a novel 2-pyrone derivative, induces ras-mutated Panc-1 pancreatic tumor cell death in nude mice: Z. Xiao, et al.; Cell Death Dis. 22, e1241 (2014) | Akt inhibition attenuates rasfonin-induced autophagy and apoptosis through the glycolytic pathway in renal cancer cells: Q. Lu, et al.; Cell Death Dis. 6, e2005 (2015) | Rasfonin promotes autophagy and apoptosis via upregulation of reactive oxygen species (ROS)/JNK pathway: W. Wang, et al.; Mycology 7, 64 (2016) | Fungal secondary metabolites rasfonin induces autophagy, apoptosis and necroptosis in renal cancer cell line: H. Sun, et al.; Mycology 7, 81 (2016)