210:
71:
316:
24:
233:
InChI=1S/C35H47NO9/c1-19(13-25-18-41-23(5)36-25)9-8-10-21(3)32(40-7)22(4)27-17-29(37)35(6)30(45-35)12-11-20(2)26-14-24(16-31(38)42-26)15-28-33(43-28)34(39)44-27/h8-13,18,20,22,24,26-30,32-33,37H,14-17H2,1-7H3/b9-8+,12-11+,19-13+,21-10+/t20-,22+,24+,26-,27+,28+,29+,30-,32+,33-,35-/m1/s1
494:
Tsuruo T, Oh-hara T, Iida H, Tsukagoshi S, Sato Z, Matsuda I, et al. (January 1986). "Rhizoxin, a macrocyclic lactone antibiotic, as a new antitumor agent against human and murine tumor cells and their vincristine-resistant sublines".
398:. It is one of a large group of rhizoxin-like compounds produced by the bacteria. The bacterial endosymbiont can be grown independently in culture. This may allow easy harvesting of rhizoxin and the related compounds avoiding total
603:
Scherlach K, Partida-Martinez LP, Dahse HM, Hertweck C (September 2006). "Antimitotic rhizoxin derivatives from a cultured bacterial endosymbiont of the rice pathogenic fungus
Rhizopus microsporus".
329:
522:
Ikubo S, Takigawa N, Ueoka H, Kiura K, Tabata M, Shibayama T, et al. (1999). "In vitro evaluation of antimicrotubule agents in human small-cell lung cancer cell lines".
249:
721:"Multicentre phase II pharmacological evaluation of rhizoxin. Eortc early clinical studies (ECSG)/pharmacology and molecular mechanisms (PAMM) groups"
675:"Studies on macrocyclic lactone antibiotics. XI. Anti-mitotic and anti-tubulin activity of new antitumor antibiotics, rhizoxin and its homologues"
224:
835:
549:
Partida-Martinez LP, Hertweck C (October 2005). "Pathogenic fungus harbours endosymbiotic bacteria for toxin production".
336:
386:
167:
770:"Studies on macrocyclic lactone antibiotics. VII. Structure of a phytotoxin "rhizoxin" produced by Rhizopus chinensis"
188:
674:
111:
443:
Rhizoxin has undergone clinical trials as an anti-cancer drug although it did not reach later stages of
558:
474:
369:
364:
205:
820:
719:
McLeod HL, Murray LS, Wanders J, Setanoians A, Graham MA, Pavlidis N, et al. (December 1996).
37:
582:
399:
638:
Mitchell, I.S.; et al. (2005). "A total synthesis of the antitumour macrolide rhizoxin D".
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426:
131:
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Iwasaki S, Kobayashi H, Furukawa J, Namikoshi M, Okuda S, Sato Z, et al. (April 1984).
740:
732:
686:
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612:
566:
272:
673:
Takahashi M, Iwasaki S, Kobayashi H, Okuda S, Murai T, Sato Y, et al. (January 1987).
176:
47:
434:
209:
562:
257:
O=C1C(C32O3)()C((C)/C=C/(O4)4(C)(O)C((C)(OC)/C(C)=C/C=C/C(C)=C/C5=COC(C)=N5)()OC2=O)()O1
91:
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736:
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453:. Related compounds to rhizoxin have improved biological activity (E.G
449:
423:
411:
143:
616:
651:
360:
102:
306:
Except where otherwise noted, data are given for materials in their
23:
356:
82:
70:
60:
433:
assembled microtubules. The function of rhizoxin is similar to
193:
324:
429:
inhibiting cell division. Additionally rhizoxin can
422:
formation. This, in turn, prevents formation of the
402:, although total chemical synthesis is possible.
155:
598:
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46:
8:
208:
130:
15:
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605:Journal of the American Chemical Society
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236:Key: OWPCHSCAPHNHAV-QIPOKPRISA-N
110:
90:
7:
146:
705:Erratum in J. Antibiot. (Tokyo).,
359:activity. It is isolated from the
14:
314:
22:
310:(at 25 °C , 100 kPa).
1:
387:Paraburkholderia rhizoxinica
300:625.749 g/mol
852:
787:10.7164/antibiotics.37.354
774:The Journal of Antibiotics
709:(4), following 565. (1987)
679:The Journal of Antibiotics
465:Rhizoxin is a 16-membered
725:British Journal of Cancer
692:10.7164/antibiotics.40.66
304:
265:
245:
220:
30:
21:
836:Microtubule inhibitors
469:ring connected to an
737:10.1038/bjc.1996.657
447:due to low activity
396:Rhizopus microsporus
370:rice seedling blight
365:Rhizopus microsporus
571:10.1038/nature03997
563:2005Natur.437..884P
524:Anticancer Research
18:
406:Cytotoxic function
400:chemical synthesis
337:Infobox references
16:
640:Org. Biomol. Chem
617:10.1021/ja062953o
418:cells disrupting
345:Chemical compound
343:
342:
189:CompTox Dashboard
72:Interactive image
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611:(35): 11529–36.
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355:agent with anti-
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646:(24): 4412–31.
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557:(7060): 884–8.
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497:Cancer Research
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473:ring by a long
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445:clinical trials
410:Rhizoxin binds
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731:(12): 1944–8.
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530:(5B): 3985–8.
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503:(1): 381–385.
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394:of the fungus
390:, a bacterial
382:biosynthesised
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780:(4): 354–62.
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685:(1): 66–72.
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431:depolymerise
412:beta tubulin
409:
395:
392:endosymbiont
385:
380:Rhizoxin is
379:
376:Biosynthesis
363:
348:
347:
112:ChEMBL379989
31:Identifiers
475:unsaturated
420:microtubule
353:antimitotic
266:Properties
92:CHEBI:72590
821:Macrolides
810:Categories
481:References
455:Mertansine
416:eukaryotic
296:Molar mass
177:C1V1Y784E4
123:ChemSpider
59:3D model (
48:90996-54-6
38:CAS Number
461:Structure
438:alkaloids
17:Rhizoxin
831:Polyenes
826:Epoxides
816:Oxazoles
660:16327903
625:16939276
579:16208371
536:10628341
349:Rhizoxin
157:11969567
132:10405026
796:6547134
755:8980394
746:2074819
701:3606749
587:4416437
559:Bibcode
509:3753552
477:chain.
471:oxazole
467:lactone
450:in vivo
427:spindle
424:mitotic
330:what is
328: (
290:
144:PubChem
794:
753:
743:
699:
658:
623:
585:
577:
551:Nature
534:
507:
361:fungus
351:is an
325:verify
322:
250:SMILES
103:ChEMBL
583:S2CID
436:Vinca
357:tumor
225:InChI
83:ChEBI
61:JSmol
792:PMID
751:PMID
697:PMID
656:PMID
621:PMID
575:PMID
532:PMID
505:PMID
457:) .
168:UNII
782:doi
741:PMC
733:doi
687:doi
648:doi
613:doi
609:128
567:doi
555:437
414:in
384:by
194:EPA
147:CID
812::
790:.
778:37
776:.
772:.
749:.
739:.
729:74
727:.
723:.
707:40
695:.
683:40
681:.
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595:^
581:.
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528:19
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440:.
372:.
286:NO
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280:35
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689::
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650::
644:3
627:.
615::
589:.
569::
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538:.
511:.
320:N
288:9
282:H
278:C
196:)
192:(
63:)
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