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{{chembox |
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| verifiedrevid = 411788555 |
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| ImageFile = Rhizoxin.png |
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| ImageFile = Rhizoxin.png |
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| ImageSize = 250px |
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| ImageSize = 250px |
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| IUPACName = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 90996-54-6 |
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| PubChem = 11969567 |
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| CASNo = 90996-54-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = 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 |
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| UNII = C1V1Y784E4 |
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| PubChem = 11969567 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 379989 |
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| ChEBI = 72590 |
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| ChemSpiderID = 10405026 |
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| SMILES = 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 |
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| StdInChI = 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 |
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| StdInChIKey = OWPCHSCAPHNHAV-QIPOKPRISA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>35</sub>H<sub>47</sub>NO<sub>9</sub> |
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| Formula = C<sub>35</sub>H<sub>47</sub>NO<sub>9</sub> |
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| MolarMass = 625.749 g/mol |
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| MolarMass = 625.749 g/mol |
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| Section3 = {{Chembox Hazards |
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'''Rhizoxin''' is an ] agent with anti-] activity.<ref>{{cite journal | author = Tsuro, T., ''et al.'' | title = Rhizoxin, a macrocyclic lactone antibiotic, as a new antitumor agent against human and murine tumor cells and their vincristine resistant sublines | journal = Cancer Res. | volume = 46 | pages = 381–385 | year = 1986 | pmid = 3753552 | issue = 1}}</ref><ref>{{cite journal | author = Ikubo, S., ''et al.'', | title = In vitro evaluation of antimicrotubule agents in human small-cell lung cancer cell lines | journal = Anticancer Res. | volume = 19 | pages = 3985–3988 year = 1999 | pmid=10628341}}</ref> It is isolated from a ]ic plant ] (''] microsporus'') which causes rice seedling blight. |
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'''Rhizoxin''' is an ] agent with anti-] activity.<ref name="pmid3753552">{{cite journal | vauthors = Tsuruo T, Oh-hara T, Iida H, Tsukagoshi S, Sato Z, Matsuda I, Iwasaki S, Okuda S, Shimizu F, Sasagawa K|display-authors = 6 | title = Rhizoxin, a macrocyclic lactone antibiotic, as a new antitumor agent against human and murine tumor cells and their vincristine-resistant sublines | journal = Cancer Research | volume = 46 | issue = 1 | pages = 381–385 | date = January 1986 | pmid = 3753552 }}</ref><ref name="pmid10628341">{{cite journal | vauthors = Ikubo S, Takigawa N, Ueoka H, Kiura K, Tabata M, Shibayama T, Chikamori M, Aoe K, Matsushita A, Harada M |display-authors = 6| title = In vitro evaluation of antimicrotubule agents in human small-cell lung cancer cell lines | journal = Anticancer Research | volume = 19 | issue = 5B | pages = 3985–8 | date = 1999 | pmid = 10628341 | doi = | url = }}</ref> It is isolated from the ] '']'' which causes ]. |
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==Biosynthesis== |
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==Biosynthesis== |
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Rhizoxin is ]ed by ''] rhizoxinica'', a bacterial ] of the fungus ''Rhizopus microsporus''.<ref>{{cite journal | author = Laila, P. & Hertweck, C. | title = Pathogenic fungus harbours endosymbiotic bacteria for toxin production | journal = Nature | volume = 437 | pages = 884–888 | year = 2005 | doi = 10.1038/nature03997 | pmid = 16208371 | issue = 7060}}</ref> It is one of a large group of rhizoxin-like compounds produced by the bacteria.<ref name="manycompounds">{{cite journal | author = Scherlach, K., Partida-Martinez, L.P., Dahse, H.M. & Hertweck, C. | title = Antimitotic Rhizoxin Derivatives from a Cultured Bacterial Endosymbiont of the Rice Pathogenic Fungus ''Rhizopus microsporus'' | journal = J. Am. Chem. Soc. | volume = 128 | pages = 11529–11536 | year = 2006 | doi = 10.1021/ja062953o | pmid = 16939276 | issue = 35}}</ref> The bacterial endosymbiont can be grown independently in culture. This may allow easy harvesting of rhizoxin and the related compounds avoiding total ], although total chemical synthesis is possible.<ref>{{cite journal | author = Mitchell, I.S., ''et al.'' | title = A total synthesis of the antitumour macrolide rhizoxin D | journal = Org. Biomol. Chem. | volume = 24 | pages = 4412–31 | year = 2005 | doi = 10.1039/b507570j | pmid = 16327903 | issue = 24}}</ref> |
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Rhizoxin is ]ed by '']'', a bacterial ] of the fungus ''Rhizopus microsporus''.<ref name="pmid16208371">{{cite journal | vauthors = Partida-Martinez LP, Hertweck C | title = Pathogenic fungus harbours endosymbiotic bacteria for toxin production | journal = Nature | volume = 437 | issue = 7060 | pages = 884–8 | date = October 2005 | pmid = 16208371 | doi = 10.1038/nature03997 | bibcode = 2005Natur.437..884P | s2cid = 4416437 }}</ref> It is one of a large group of rhizoxin-like compounds produced by the bacteria.<ref name="manycompounds">{{cite journal | vauthors = Scherlach K, Partida-Martinez LP, Dahse HM, Hertweck C | title = Antimitotic rhizoxin derivatives from a cultured bacterial endosymbiont of the rice pathogenic fungus Rhizopus microsporus | journal = Journal of the American Chemical Society | volume = 128 | issue = 35 | pages = 11529–36 | date = September 2006 | pmid = 16939276 | doi = 10.1021/ja062953o }}</ref> The bacterial endosymbiont can be grown independently in culture. This may allow easy harvesting of rhizoxin and the related compounds avoiding total ], although total chemical synthesis is possible.<ref>{{cite journal | author = Mitchell, I.S.| title = A total synthesis of the antitumour macrolide rhizoxin D | journal = Org. Biomol. Chem. | volume = 3 | pages = 4412–31 | year = 2005 | doi = 10.1039/b507570j | pmid = 16327903 | issue = 24|display-authors=etal}}</ref> |
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==Cytotoxic function== |
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==Cytotoxic function== |
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Rhizoxin binds ] in ] cells disrupting ] formation. This, in turn, prevents formation of the ] ] inhibiting cell division. Additionally rhizoxin can ] assembled microtubules.<ref>{{cite journal | author = Takahashi, M., ''et al.'' | title = Studies on macrocyclic lactone antibiotics. XI. Anti-mitotic and anti-tubulin activity of new antitumor antibiotics, rhizoxin and its homologues | journal = J. Antibiot. | volume = 40 | issue = 1 | pages = 66–72 | year = 1987 | pmid = 3606749}} Erratum in J. Antibiot. (Tokyo)., '''40''' (4), following 565. (1987).</ref> The function of rhizoxin is similar to ]. |
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Rhizoxin binds ] in ] cells disrupting ] formation. This, in turn, prevents formation of the ] ] inhibiting cell division. Additionally rhizoxin can ] assembled microtubules.<ref name="pmid3606749">{{cite journal | vauthors = Takahashi M, Iwasaki S, Kobayashi H, Okuda S, Murai T, Sato Y, Haraguchi-Hiraoka T, Nagano H |display-authors=6| title = Studies on macrocyclic lactone antibiotics. XI. Anti-mitotic and anti-tubulin activity of new antitumor antibiotics, rhizoxin and its homologues | journal = The Journal of Antibiotics | volume = 40 | issue = 1 | pages = 66–72 | date = January 1987 | pmid = 3606749 | doi = 10.7164/antibiotics.40.66 | doi-access = free| url = https://www.jstage.jst.go.jp/article/antibiotics1968/40/1/40_1_66/_pdf }}Erratum in J. Antibiot. (Tokyo)., '''40''' (4), following 565. (1987)</ref> The function of rhizoxin is similar to ]. |
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Rhizoxin has undergone clinical trials as an anti-cancer drug<ref>{{cite journal | author = McLeod, H.L., ''et al.'' | title = Multicentre phase II pharmacological evaluation of rhizoxin. Eortc early clinical studies (ECSG)/pharmacology and molecular mechanisms (PAMM) groups | journal = Br. J. Cancer. | volume = 74 | issue = 12 | pages = 1944–8 | year = 1996 | pmid = 8980394 | pmc = 2074819}}</ref> although, unfortunately, did not reach later stages of ]s due to low activity '']''. Related compounds to rhizoxin may have improved biological activity.<ref name="manycompounds" /> |
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Rhizoxin has undergone clinical trials as an anti-cancer drug<ref name="pmid8980394">{{cite journal | vauthors = McLeod HL, Murray LS, Wanders J, Setanoians A, Graham MA, Pavlidis N, Heinrich B, ten Bokkel Huinink WW, Wagener DJ, Aamdal S, Verweij J |display-authors = 6| title = Multicentre phase II pharmacological evaluation of rhizoxin. Eortc early clinical studies (ECSG)/pharmacology and molecular mechanisms (PAMM) groups | journal = British Journal of Cancer | volume = 74 | issue = 12 | pages = 1944–8 | date = December 1996 | pmid = 8980394 | pmc = 2074819 | doi = 10.1038/bjc.1996.657 }}</ref> although it did not reach later stages of ]s due to low activity '']''. Related compounds to rhizoxin have improved biological activity (E.G ]) .<ref name="manycompounds" /> |
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==Structure== |
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==Structure== |
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Rhizoxin is a 16-membered ] ring connected to an ] ring by a long ] chain.<ref>{{cite journal | author = Iwasaki, S., ''et al.'', | title = Studies on macrocyclic lactone antibiotics. VII. Structure of a phytotoxin "rhizoxin" produced by Rhizopus chinensis | journal = J. Antibiot. (Tokyo) | volume = 37 | issue = 4 | pages = 354–62 | year = 1984}}</ref> |
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Rhizoxin is a 16-membered ] ring connected to an ] ring by a long ] chain.<ref name="pmid6547134">{{cite journal | vauthors = Iwasaki S, Kobayashi H, Furukawa J, Namikoshi M, Okuda S, Sato Z, Matsuda I, Noda T|display-authors = 6 | title = Studies on macrocyclic lactone antibiotics. VII. Structure of a phytotoxin "rhizoxin" produced by Rhizopus chinensis | journal = The Journal of Antibiotics | volume = 37 | issue = 4 | pages = 354–62 | date = April 1984 | pmid = 6547134 | doi = 10.7164/antibiotics.37.354 | doi-access = free }}</ref> |
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==References== |
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==References== |
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