AdipoGen Life Sciences

Sipholenone A

CHF 175.00
In stock
AG-CN2-0507-C100100 µgCHF 175.00
More Information
Product Details
Synonyms NSC 378978
Product Type Chemical
Properties
Formula

C30H50O4

MW 474.7
CAS 78518-74-8
Source/Host Chemicals Isolated from marine sponge Siphonochalina siphonella.
Purity Chemicals ≥98% (HPLC)
Appearance White to off-white lyophilized powder.
Solubility Soluble in DMSO or 100% ethanol (25mg/ml).
InChi Key LKZQMXLIWZQEEU-KOGSSWOMSA-N
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
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
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.
Product References
  1. The sipholanes, a novel group of triterpenes from the marine sponge Siphonochalina siphonella: S. Carmely & Y. Kashman; J. Org. Chem. 48, 3517 (1983)
  2. New triterpenoids from the Red Sea sponge Siphonochalina siphonella: Y. Kashman, et al.; J. Nat. Prod. 64, 175 (2001)
  3. Biocatalysis of the anticancer sipholane triterpenoids: S. Jain, et al.; Planta Med. 73, 591 (2007)
  4. 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)
  5. Sipholane triterpenoids: chemistry, reversal of ABCB1/P-glycoprotein-mediated multidrug resistance, and pharmacophore modeling: S. Jain, et al.; J. Nat. Prod. 72, 1291 (2009)
  6. Esters of the marine-derived triterpene sipholenol A reverse P-GP-mediated drug resistance: Y. Zhang, et al.; Mar. Drugs 13, 2267 (2015)
  7. Potent antifouling metabolites from Red Sea organisms: S.S. Al-Lihaibi, et al.; Asian J. Chem. 27, 2252 (2015)
  8. 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)
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