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Didesmethylrocaglamide is one of three Aglaia species (Aglaia duperreana, A. oligophylla, and A. spectabilis) that naturally produce this rocaglamide type of 1H-cyclopenta[b]benzofuran lignans. Similar concentration ranges of the well-known anticancer medication vinblastine sulfate and didesmethylrocaglamide both inhibited cell growth. Didesmethylrocaglamide reduced the expression of AKT and ERK1/2, consistent with translation inhibition, while arresting MPNST cells at G2-M, increasing the sub-G1 population, inducing caspase and PARP cleavage, and elevating the levels of the DNA-damage response marker γH2A.X
Targets |
Eukaryotic initiation factor 4A (eIF4A)
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ln Vitro |
Didesmethylrocaglamide (5 nM and 10 nM; 72 hours; MPNST cells) treatment arrests MPNST cells at G2-M, increases the sub-G1 population, induces caspase and PARP cleavage, and elevates DNA-damage response marker γH2A.X levels while lowering the expression of AKT and ERK1/2[1].
Didesmethylrocaglamide causes cell cycle arrest at G2/M, which leads to cell death, and thereby reduces MPNST cell proliferation. 697-R cells treated with didesmethylrocaglamide display IC50 values that are remarkably similar to those of parental 697 cells (4 vs. 3nM, respectively)[1]. Didesmethylrocaglamide triggers apoptosis in MPNST cells with and without neurofibromatosis type 1 (NF1), possibly as a result of the DNA damage response. Insulin-like growth factor-1 receptor is just one of the oncogenic kinases that are reduced in didesmethylrocaglamide-treated sarcoma cells[1]. |
References |
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Molecular Formula |
C27H27NO7
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Molecular Weight |
477.513
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Exact Mass |
477.18
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Elemental Analysis |
C, 67.91; H, 5.70; N, 2.93; O, 23.45
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CAS # |
177262-30-5
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Related CAS # |
Rocaglamide;84573-16-0
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Appearance |
Solid powder
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SMILES |
COC1=CC=C(C=C1)[C@]23[C@@H]([C@H]([C@H]([C@]2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)N)C5=CC=CC=C5
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InChi Key |
RMNPQEWLGQURNX-PXIJUOARSA-N
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InChi Code |
InChI=1S/C27H27NO7/c1-32-17-11-9-16(10-12-17)27-22(15-7-5-4-6-8-15)21(25(28)30)24(29)26(27,31)23-19(34-3)13-18(33-2)14-20(23)35-27/h4-14,21-22,24,29,31H,1-3H3,(H2,28,30)/t21-,22-,24-,26+,27+/m1/s1
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Chemical Name |
(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
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Synonyms |
Didesmethylrocaglamide; rocaglamide-derivative; DDR
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HS Tariff Code |
2934.99.9001
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
DMSO: ~100 mg/mL (~209.4 mM)
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Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (5.24 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 2.0942 mL | 10.4710 mL | 20.9420 mL | |
5 mM | 0.4188 mL | 2.0942 mL | 4.1884 mL | |
10 mM | 0.2094 mL | 1.0471 mL | 2.0942 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Identification of didesmethylrocaglamide and rocaglamide with potent growth-inhibitory activity comparable to silvestrol. Mol Cancer Ther . 2020 Mar;19(3):731-741. td> |