Dideoxyverticillin A
Chemical compound
From Wikipedia, the free encyclopedia
Dideoxyverticillin A, also known as (+)-11,11′-dideoxyverticillin A, is a complex epipolythiodioxopiperazine[1] initially isolated from the marine fungus Penicillium sp. in 1999.[2] It has also been found in the marine fungus Bionectriaceae,[3] and belongs to a class of naturally occurring 2,5-diketopiperazines.[4]
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| Preferred IUPAC name
(3S,3′S,5aR,5′aR,10bR,10′bR,11aS,11′aS)-2,2′,3,3′-Tetramethyl-2,2′,3,3′,5a,5′a,6,6′-octahydro-11H,11′H-[10b,10′b-bi-3,11a-disulfanopyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole]-1,1′,4,4′-tetrone | |
| Other names
11,11′-Dideoxyverticillin A; 11,11′-Dideoxyverticillin | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
PubChem CID |
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| UNII | |
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| Properties | |
| C30H28N6O4S4 | |
| Molar mass | 664.83 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dideoxyverticillin A potently inhibits the tyrosine kinase activity of the epidermal growth factor receptor (median inhibitory concentration = 0.14 nM), exhibits antiangiogenic activity, and has efficacy against several cancer cell lines.[4] Its reported anticancer mechanism is that it acts as a farnesyl transferase inhibitor. Dozens of semi-synthetic anticancer compounds have been made from dideoxyverticillin A. Dimeric derivatives are reported to have better anticancer activity.[5]
The enantioselective first total synthesis of (+)-11,11′-dideoxyverticillin A, the structure of which contains many sterically congested, contiguous stereogenic centers as well as acid- and base-labile and redox-sensitive functionality, was biosynthetically inspired and achieved with high levels of chemical sophistication.[6]