Sipholenone A
Product Code: AG-CN2-0507
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0507-C100 | 100 ug | £140.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
NSC 378978
Appearance:
White to off-white lyophilized powder.
CAS:
78518-74-8
EClass:
32160000
Form (Short):
solid
Handling Advice:
Keep cool and dry.
InChi:
InChI=1S/C30H50O4/c1-19-9-10-22-21(13-17-29(22,7)32)26(2,3)20(19)11-12-23-28(6)16-14-24(31)27(4,5)34-25(28)15-18-30(23,8)33/h9,20-23,25,32-33H,10-18H2,1-8H3/t20-,21+,22+,23+,25+,28+,29+,30-/m0/s1
InChiKey:
LKZQMXLIWZQEEU-KOGSSWOMSA-N
Long Description:
Chemical. CAS: 78518-74-8. Formula: C30H50O4. MW: 474.7. Isolated from marine sponge Siphonochalina siphonella. Efficient inhibitor of P-glycoprotein (Pgp, MDR-1) function through direct interactions. By inhibiting MDR-1, active compounds remain in the cytoplasm longer and allowing them to be more effective within the cell. Reversing agent for the treatment of multidrug resistance (MDR) in Pgp-overexpressing tumors. Potentiates the cytotoxicity of established P-gp substrates such as colchicine, vinblastine and paclitaxel. Antiproliferative, antiangiogenic and cytotoxic compound. Moderate antifouling compound.
MDL:
N/A
Molecular Formula:
C30H50O4
Molecular Weight:
474.7
Package Type:
Vial
Product Description:
Efficient inhibitor of P-glycoprotein (Pgp, MDR-1) function through direct interactions. By inhibiting MDR-1, active compounds remain in the cytoplasm longer and allowing them to be more effective within the cell. Reversing agent for the treatment of multidrug resistance (MDR) in Pgp-overexpressing tumors. Potentiates the cytotoxicity of established Pgp substrates such as colchicine, vinblastine and paclitaxel. Antiproliferative, antiangiogenic and cytotoxic compound. Moderate antifouling compound.
Purity:
>98% (HPLC)
SMILES:
CC(O1)(C)C(CC[C@@]2(C)[C@@]1([H])CC[C@@](O)(C)[C@@H]2CC[C@@H]3C(C)(C)[C@@](CC[C@@]4(C)O)([H])[C@@]4([H])CC=C3C)=O
Solubility Chemicals:
Soluble in DMSO or 100% ethanol (25mg/ml).
Source / Host:
Isolated from marine sponge Siphonochalina siphonella.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
The sipholanes, a novel group of triterpenes from the marine sponge Siphonochalina siphonella: S. Carmely & Y. Kashman; J. Org. Chem. 48, 3517 (1983) | New triterpenoids from the Red Sea sponge Siphonochalina siphonella: Y. Kashman, et al.; J. Nat. Prod. 64, 175 (2001) | Biocatalysis of the anticancer sipholane triterpenoids: S. Jain, et al.; Planta Med. 73, 591 (2007) | Sipholenol A, a marine-derived sipholane triterpene, potently reverses P-glycoprotein (ABCB1)-mediated multidrug resistance in cancer cells: Z. Shi, et al.; Cancer Sci. 98, 1373 (2007) | Sipholane triterpenoids: chemistry, reversal of ABCB1/P-glycoprotein-mediated multidrug resistance, and pharmacophore modeling: S. Jain, et al.; J. Nat. Prod. 72, 1291 (2009) | Esters of the marine-derived triterpene sipholenol A reverse P-GP-mediated drug resistance: Y. Zhang, et al.; Mar. Drugs 13, 2267 (2015) | Potent antifouling metabolites from Red Sea organisms: S.S. Al-Lihaibi, et al.; Asian J. Chem. 27, 2252 (2015) | Antiproliferative effects of triterpenoidal derivatives, obtained from the marine sponge Siphonochalina sp. on human hepatic and colorectal cancer cells: A. Abdel-Lateff, et al.; Z. Naturforsch. C. 71, 29 (2016)