Rhizoxin is biosynthesised by Paraburkholderia rhizoxinica, a bacterial endosymbiont of the fungus Rhizopus microsporus.[3] It is one of a large group of rhizoxin-like compounds produced by the bacteria.[4] The bacterial endosymbiont can be grown independently in culture. This may allow easy harvesting of rhizoxin and the related compounds avoiding total chemical synthesis, although total chemical synthesis is possible.[5]
Rhizoxin has undergone clinical trials as an anti-cancer drug[7] although it did not reach later stages of clinical trials due to low activity in vivo. Related compounds to rhizoxin may have improved biological activity.[4]
^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". Cancer Research. 46 (1): 381–385. PMID 3753552.
^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". Anticancer Research. 19 (5B): 3985–8. PMID 10628341.
^ abScherlach 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". Journal of the American Chemical Society. 128 (35): 11529–36. doi:10.1021/ja062953o. PMID 16939276.
^Mitchell, I.S.; et al. (2005). "A total synthesis of the antitumour macrolide rhizoxin D". Org. Biomol. Chem. 3 (24): 4412–31. doi:10.1039/b507570j. PMID 16327903.
^Takahashi M, Iwasaki S, Kobayashi H, Okuda S, Murai T, Sato Y, et al. (January 1987). "Studies on macrocyclic lactone antibiotics. XI. Anti-mitotic and anti-tubulin activity of new antitumor antibiotics, rhizoxin and its homologues". The Journal of Antibiotics. 40 (1): 66–72. doi:10.7164/antibiotics.40.66. PMID 3606749.Erratum in J. Antibiot. (Tokyo)., 40 (4), following 565. (1987)
^McLeod HL, Murray LS, Wanders J, Setanoians A, Graham MA, Pavlidis N, et al. (December 1996). "Multicentre phase II pharmacological evaluation of rhizoxin. Eortc early clinical studies (ECSG)/pharmacology and molecular mechanisms (PAMM) groups". British Journal of Cancer. 74 (12): 1944–8. doi:10.1038/bjc.1996.657. PMC2074819. PMID 8980394.
^Iwasaki S, Kobayashi H, Furukawa J, Namikoshi M, Okuda S, Sato Z, et al. (April 1984). "Studies on macrocyclic lactone antibiotics. VII. Structure of a phytotoxin "rhizoxin" produced by Rhizopus chinensis". The Journal of Antibiotics. 37 (4): 354–62. doi:10.7164/antibiotics.37.354. PMID 6547134.
March 14, 2024
rhizoxin, antimitotic, agent, with, anti, tumor, activity, isolated, from, pathogenic, plant, fungus, rhizopus, microsporus, which, causes, rice, seedling, blight, identifierscas, number, 90996, model, jsmol, interactive, imagechebi, chebi, 72590chembl, chembl. Rhizoxin is an antimitotic agent with anti tumor activity 1 2 It is isolated from a pathogenic plant fungus Rhizopus microsporus which causes rice seedling blight Rhizoxin IdentifiersCAS Number 90996 54 6 Y3D model JSmol Interactive imageChEBI CHEBI 72590ChEMBL ChEMBL379989 NChemSpider 10405026PubChem CID 11969567UNII C1V1Y784E4 YCompTox Dashboard EPA DTXSID20897515InChI 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 s1Key OWPCHSCAPHNHAV QIPOKPRISA NSMILES O C1C C C C H 3 C H 2O3 H C C C H C C C C H O4 C 4 C C H O C C C H C C H OC C C C C C C C C C5 COC C N5 H OC2 O H O1PropertiesChemical formula C35H47NO9Molar mass 625 749 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Biosynthesis 2 Cytotoxic function 3 Structure 4 ReferencesBiosynthesis editRhizoxin is biosynthesised by Paraburkholderia rhizoxinica a bacterial endosymbiont of the fungus Rhizopus microsporus 3 It is one of a large group of rhizoxin like compounds produced by the bacteria 4 The bacterial endosymbiont can be grown independently in culture This may allow easy harvesting of rhizoxin and the related compounds avoiding total chemical synthesis although total chemical synthesis is possible 5 Cytotoxic function editRhizoxin binds beta tubulin in eukaryotic cells disrupting microtubule formation This in turn prevents formation of the mitotic spindle inhibiting cell division Additionally rhizoxin can depolymerise assembled microtubules 6 The function of rhizoxin is similar to Vinca alkaloids Rhizoxin has undergone clinical trials as an anti cancer drug 7 although it did not reach later stages of clinical trials due to low activity in vivo Related compounds to rhizoxin may have improved biological activity 4 Structure editRhizoxin is a 16 membered lactone ring connected to an oxazole ring by a long unsaturated chain 8 References edit 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 Cancer Research 46 1 381 385 PMID 3753552 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 Anticancer Research 19 5B 3985 8 PMID 10628341 Partida Martinez LP Hertweck C October 2005 Pathogenic fungus harbours endosymbiotic bacteria for toxin production Nature 437 7060 884 8 Bibcode 2005Natur 437 884P doi 10 1038 nature03997 PMID 16208371 S2CID 4416437 a b 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 Journal of the American Chemical Society 128 35 11529 36 doi 10 1021 ja062953o PMID 16939276 Mitchell I S et al 2005 A total synthesis of the antitumour macrolide rhizoxin D Org Biomol Chem 3 24 4412 31 doi 10 1039 b507570j PMID 16327903 Takahashi M Iwasaki S Kobayashi H Okuda S Murai T Sato Y et al January 1987 Studies on macrocyclic lactone antibiotics XI Anti mitotic and anti tubulin activity of new antitumor antibiotics rhizoxin and its homologues The Journal of Antibiotics 40 1 66 72 doi 10 7164 antibiotics 40 66 PMID 3606749 Erratum in J Antibiot Tokyo 40 4 following 565 1987 McLeod HL Murray LS Wanders J Setanoians A Graham MA Pavlidis N et al December 1996 Multicentre phase II pharmacological evaluation of rhizoxin Eortc early clinical studies ECSG pharmacology and molecular mechanisms PAMM groups British Journal of Cancer 74 12 1944 8 doi 10 1038 bjc 1996 657 PMC 2074819 PMID 8980394 Iwasaki S Kobayashi H Furukawa J Namikoshi M Okuda S Sato Z et al April 1984 Studies on macrocyclic lactone antibiotics VII Structure of a phytotoxin rhizoxin produced by Rhizopus chinensis The Journal of Antibiotics 37 4 354 62 doi 10 7164 antibiotics 37 354 PMID 6547134 Retrieved from https en wikipedia org w index php title Rhizoxin amp oldid 1209236175, wikipedia, wiki, book, books, library,
