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Didesmethylrocaglamide

  Cat. No.:  DC32587   Featured
Chemical Structure
177262-30-5
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Field of application
Didesmethylrocaglamide is a naturally occurring 1H-cyclopenta[b]benzofuran lignans of the rocaglamide type isolated from three Aglaia species (Aglaia duperreana, A. oligophylla and A. spectabilis). Didesmethylrocaglamide inhibited cell growth in a similar concentration range as the well-known anticancer drug vinblastine sulfate. Didesmethylrocaglamide arrested MPNST cells at G2-M, increased the sub-G1 population, induced cleavage of caspases and PARP, and elevated the levels of the DNA-damage response marker γH2A.X, while decreasing the expression of AKT and ERK1/2, consistent with translation inhibition.
Chemicals PropertiesBiological activity COA & MSDSRelated productsDatasheet
Cas No.: 177262-30-5
Chemical Name: (1R,2R,3S,3aR,8bS)-2,3,3a,8b-Tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxamide
Synonyms: Didesmethylrocaglamide; DDR; rocaglamide-derivative.
SMILES: O=C([C@H]([C@H]1C2=CC=CC=C2)[C@@H](O)[C@]3(O)[C@@]1(C4=CC=C(OC)C=C4)OC5=CC(OC)=CC(OC)=C35)N
Formula: C27H27NO7
M.Wt: 477.51
Purity: >98%
Sotrage: 2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO
Description: Didesmethylrocaglamide, a derivative of Rocaglamide, is a potent eukaryotic initiation factor 4A (eIF4A) inhibitor. Didesmethylrocaglamide has potent growth-inhibitory activity with an IC50 of 5 nM. Didesmethylrocaglamide suppresses multiple growth-promoting signaling pathways and induces apoptosis in tumor cells. Antitumor activity[1].
Target: Eukaryotic initiation factor 4A (eIF4A)[1]
In Vitro: Didesmethylrocaglamide (5 nM, and 10 nM; 72 hours; MPNST cells) treatment arrests MPNST cells at G2-M, increases the sub-G1 population, induces cleavage of caspases and PARP, and elevates the levels of the DNA-damage response marker γH2A.X, while decreasing the expression of AKT and ERK1/2[1]. Didesmethylrocaglamide inhibits MPNST cell proliferation by inducing cell cycle arrest at G2/M and subsequently, cell death. Didesmethylrocaglamide-treated 697-R cells exhibits IC50 values is very similar to those of parental 697 cells (4 vs 3nM of IC50, respectively)[1]. Didesmethylrocaglamide induces apoptosis in both neurofibromatosis type 1 (NF1)-expressing and NF1-deficient MPNST cells, possibly subsequent to the activation of the DNA damage response. Didesmethylrocaglamide-treated sarcoma cells show decreased levels of multiple oncogenic kinases, including insulin-like growth factor-1 receptor[1]. Western Blot Analysis[1] Cell Line: Malignant peripheral nerve sheath tumors (MPNST) cells Concentration: 5 nM, and 10 nM Incubation Time: 72 hours Result: Induced cleavage of caspases and PARP, and elevated the levels of the DNA-damage response marker γH2A.X.
References: [1]. Long-Sheng Chang, et al. Targeting Protein Translation by Rocaglamide and Didesmethylrocaglamide to Treat MPNST and Other Sarcomas. Mol Cancer Ther. 2020 Mar;19(3):731-741.
MSDS
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