MedKoo Cat#: 341327 | Name: Disermolide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Disermolide, also known as Discodermolide or (+)-Discodermolide is a polyketide natural product found to stabilize microtubules. (+)-discodermolide was isolated by Gunasekera and his co-workers at the Harbor Branch Oceanographic Institute from the deep-sea sponge Discodermia dissoluta in 1990. Disermolide was found to be a potent inhibitor of tumor cell growth in several MDR cancer cell lines. (+)-discodermolide also shows some unique characters, including a linear backbone structure, immunosuppressive properties both in vitro and in vivo, potent induction of an accelerated senescence phenotype, and synergistic antiproliferative activity in combination with paclitaxel.

Chemical Structure

Disermolide
Disermolide
CAS#127943-53-7

Theoretical Analysis

MedKoo Cat#: 341327

Name: Disermolide

CAS#: 127943-53-7

Chemical Formula: C33H55NO8

Exact Mass: 593.3928

Molecular Weight: 593.80

Elemental Analysis: C, 66.75; H, 9.34; N, 2.36; O, 21.55

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Disermolide; XAA 296; XAA-296; XAA296.
IUPAC/Chemical Name
2H-Pyran-2-one, 6-(14-((aminocarbonyl)oxy)-2,6,12-trihydroxy-5,7,9,11,13,15-hexamethyl-3,8,16,18-nonadecatetraenyl)tetrahydro-4-hydroxy-3,5-dimethyl-, (3S-(3alpha,4beta,5beta,6alpha(2R*,3Z,5R*,6R*,7S*,8Z,11R*,12S*,13S*,14S*,15R*,16E)))-
InChi Key
AADVCYNFEREWOS-ZKGNTLCTSA-N
InChi Code
InChI=1S/C33H55NO8/c1-10-11-12-20(4)31(42-33(34)40)24(8)29(37)22(6)16-18(2)15-21(5)28(36)19(3)13-14-26(35)17-27-23(7)30(38)25(9)32(39)41-27/h10-15,19-31,35-38H,1,16-17H2,2-9H3,(H2,34,40)/b12-11+,14-13-,18-15-/t19?,20-,21+,22-,23+,24+,25-,26+,27+,28?,29+,30+,31+/m0/s1
SMILES Code
O=C1[C@@H](C)[C@H](O)[C@H](C)[C@@H](C[C@H](O)/C=C\C(C)C(O)[C@H](C)/C=C(C)\C[C@H](C)[C@@H](O)[C@@H](C)[C@H](OC(N)=O)[C@@H](C)/C=C/C=C)O1
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
>2 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
More Info
Discodermolide was recognized as one of the most potent natural promoters of tubulin assembly. A large number of efforts toward the total synthesis of (+)-discodermolide were directed by its interesting biological activities and extreme scarcity of natural sources (0.002% w/w from frozen marine sponge). The compound supply necessary for complete clinical trials cannot be met by harvesting, isolation, and purification. As of 2005, attempts at synthesis or semi-synthesis by fermentation have proven unsuccessful. As a result, all discodermolide used in preclinical studies and clinical trials has come from large-scale total synthesis.

Preparing Stock Solutions

The following data is based on the product molecular weight 593.80 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Terwilliger DW, Trauner D. Selective Synthesis of Divergolide I. J Am Chem Soc. 2018 Feb 28;140(8):2748-2751. doi: 10.1021/jacs.7b13092. Epub 2018 Feb 15. PubMed PMID: 29376358. 2: Ding L, Franke J, Hertweck C. Divergolide congeners illuminate alternative reaction channels for ansamycin diversification. Org Biomol Chem. 2015 Feb 14;13(6):1618-23. doi: 10.1039/c4ob02244k. PubMed PMID: 25464499. 3: Xu Z, Baunach M, Ding L, Peng H, Franke J, Hertweck C. Biosynthetic code for divergolide assembly in a bacterial mangrove endophyte. Chembiochem. 2014 Jun 16;15(9):1274-9. doi: 10.1002/cbic.201402071. Epub 2014 May 27. PubMed PMID: 24867126. 4: Li SR, Zhao GS, Sun MW, He HG, Wang HX, Li YY, Lu CH, Shen YM. Identification and characterization of the biosynthetic gene cluster of divergolides from Streptomyces sp. W112. Gene. 2014 Jul 1;544(1):93-9. doi: 10.1016/j.gene.2014.04.052. Epub 2014 Apr 24. PubMed PMID: 24768719. 5: Nawrat CC, Kitson RR, Moody CJ. Toward the total synthesis of hygrocin B and divergolide C: construction of the naphthoquinone-azepinone core. Org Lett. 2014 Apr 4;16(7):1896-9. doi: 10.1021/ol5003847. Epub 2014 Mar 25. PubMed PMID: 24661134. 6: Rasapalli S, Jarugumilli G, Yarrapothu GR, Golen JA, Rheingold AL. Studies toward total synthesis of divergolides C and D. Org Lett. 2013 Apr 5;15(7):1736-9. doi: 10.1021/ol400528g. Epub 2013 Mar 25. PubMed PMID: 23527658.