24:
324:(median inhibitory concentration = 0.14 nM), exhibits antiangiogenic activity, and has efficacy against several cancer cell lines. Its reported anticancer mechanism is that it acts as a
401:
Son BW, Jensen PR, Kauffman CA, Fenical W (May 1999). "New cytotoxic epidithiodioxopiperazines related to verticillin A from a marine isolate of the fungus
Penicillium".
328:. Dozens of semi-synthetic anticancer compounds have been made from dideoxyverticillin A. Dimeric derivatives are reported to have better anticancer activity.
659:
428:
Figueroa M, Graf TN, Ayers S, Adcock AF, Kroll DJ, Yang J, Swanson SM, Munoz-Acuna U, de Blanco EJ, Agrawal R, Wani MC (November 2012).
619:
321:
480:
Borthwick AD (May 2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal
Chemistry, and Bioactive Natural Products".
325:
188:
362:"The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis"
335:
first total synthesis of (+)-11,11′-dideoxyverticillin A, the structure of which contains many sterically congested,
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343:-sensitive functionality, was biosynthetically inspired and achieved with high levels of chemical sophistication.
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664:
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36:
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430:"Cytotoxic epipolythiodioxopiperazine alkaloids from filamentous fungi of the Bionectriaceae"
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629:[11'-Deoxyverticillin A induces caspase-dependent cell apoptosis in PC3M cells].
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517:"Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids"
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294:, is a complex epipolythiodioxopiperazine initially isolated from the
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268:
Except where otherwise noted, data are given for materials in their
515:
Boyer N, Morrison KC, Kim J, Hergenrother PJ, Movassaghi M (2013).
340:
73:)-2,2′,3,3′-Tetramethyl-2,2′,3,3′,5a,5′a,6,6′-octahydro-11
339:
stereogenic centers as well as acid- and base-labile and
303:
sp. in 1999. It has also been found in the marine fungus
90:
11,11′-Dideoxyverticillin A; 11,11′-Dideoxyverticillin
625:
Shi Y, Zhang Y, Ni Y, Shi G, Yang H (January 2012).
569:"Total synthesis of (+)-11,11'-dideoxyverticillin A"
567:Kim J, Ashenhurst JA, Movassaghi M (April 2009).
360:Gardiner DM, Waring P, Howlett BJ (April 2005).
309:, and belongs to a class of naturally occurring
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316:Dideoxyverticillin A potently inhibits the
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627:"11-脱氧轮枝菌素A引起前列腺癌PC3M细胞Caspase依赖的凋亡"
620:MIT News - 11,11′-Dideoxyverticillin
167:
14:
81:-pyrroloindole]-1,1′,4,4′-tetrone
322:epidermal growth factor receptor
232:
226:
22:
292:(+)-11,11′-dideoxyverticillin A
272:(at 25 °C , 100 kPa).
660:Farnesyltransferase inhibitors
326:farnesyl transferase inhibitor
244:
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631:Sheng Wu Gong Cheng Xue Bao
686:
434:The Journal of Antibiotics
415:10.1080/10575639908048788
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585:10.1126/science.1170777
403:Natural Product Letters
379:10.1099/mic.0.27847-0
311:2,5-diketopiperazines
17:Dideoxyverticillin A
288:Dideoxyverticillin A
37:Preferred IUPAC name
262: g·mol
18:
536:10.1039/C3SC50174D
446:10.1038/ja.2012.69
276:Infobox references
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670:Diketopiperazines
579:(5924): 238–241.
494:10.1021/cr200398y
284:Chemical compound
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482:Chemical Reviews
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320:activity of the
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96:Identifiers
88:Other names
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300:Penicillium
208:Properties
654:Categories
347:References
337:contiguous
255:Molar mass
198:BDQ3M208XA
144:ChemSpider
113:12795-76-5
103:CAS Number
643:22667113
603:19359584
554:23914293
502:22575049
464:22968289
388:15817772
153:10477789
594:4238916
573:Science
545:3728915
455:3573876
178:3084126
165:PubChem
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260:664.83
124:ChEMBL
31:Names
520:(PDF)
341:redox
69:,11′a
61:,10′b
639:PMID
599:PMID
550:PMID
498:PMID
460:PMID
384:PMID
331:The
189:UNII
77:,11′
65:,11a
57:,10b
53:,5′a
589:PMC
581:doi
577:324
540:PMC
532:doi
490:doi
486:112
450:PMC
442:doi
411:doi
374:doi
370:151
313:.
168:CID
49:,5a
45:,3′
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245:S
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239:O
236:6
233:N
227:H
221:C
79:H
75:H
71:S
67:S
63:R
59:R
55:R
51:R
47:S
43:S
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