Didesmethylrocaglamide
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MedKoo CAT#: 408096

CAS#: 177262-30-5

Description: 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.


Price and Availability

Size Price Shipping out time Quantity
5mg USD 395 2 Weeks
10mg USD 685 2 Weeks
50mg USD 1685 2 Weeks
100mg USD 2950 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-22. Prices are subject to change without notice.

Didesmethylrocaglamide is in stock.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 408096
Name: Didesmethylrocaglamide
CAS#: 177262-30-5
Chemical Formula: C27H27NO7
Exact Mass: 477.1788
Molecular Weight: 477.513
Elemental Analysis: C, 67.91; H, 5.70; N, 2.93; O, 23.45


Synonym: Didesmethylrocaglamide; DDR; rocaglamide-derivative.

IUPAC/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

InChi Key: RMNPQEWLGQURNX-PXIJUOARSA-N

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

SMILES Code: 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


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Chang LS, Oblinger JL, Burns SS, Huang J, Anderson LW, Hollingshead MG, Shen R, Pan L, Agarwal G, Ren Y, Roberts RD, O'Keefe BR, Kinghorn AD, Collins JM. Targeting Protein Translation by Rocaglamide and Didesmethylrocaglamide to Treat MPNST and Other Sarcomas. Mol Cancer Ther. 2020 Mar;19(3):731-741. doi: 10.1158/1535-7163.MCT-19-0809. Epub 2019 Dec 17. PMID: 31848295; PMCID: PMC7056570.

2: Bohnenstengel FI, Steube KG, Meyer C, Quentmeier H, Nugroho BW, Proksch P. 1H-cyclopenta[b]benzofuran lignans from Aglaia species inhibit cell proliferation and alter cell cycle distribution in human monocytic leukemia cell lines. Z Naturforsch C J Biosci. 1999 Dec;54(12):1075-83. doi: 10.1515/znc-1999-1212. PMID: 10685499.

3: Bohnenstengel FI, Steube KG, Meyer C, Nugroho BW, Hung PD, Kiet LC, Proksch P. Structure activity relationships of antiproliferative rocaglamide derivatives from Aglaia species (Meliaceae). Z Naturforsch C J Biosci. 1999 Jan- Feb;54(1-2):55-60. PMID: 10223787.