Rhizoxin | CAS#90996-54-6 | mitosis inhibitor

MedKoo Cat#: 461305 | Name: Rhizoxin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rhizoxin is an antitumor drug prepared from the fungus Rhizopus chinensis. It is a macrocyclic lactone compound that binds to tubulin and inhibits microtubule assembly.

Chemical Structure

Rhizoxin

CAS#90996-54-6

Theoretical Analysis

MedKoo Cat#: 461305

Name: Rhizoxin

CAS#: 90996-54-6

Chemical Formula: C35H47NO9

Exact Mass: 625.3251

Molecular Weight: 625.75

Elemental Analysis: C, 67.18; H, 7.57; N, 2.24; O, 23.01

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Rhizoxin; WF-1360; WF 1360; WF1360;

IUPAC/Chemical Name

(1S,3S,5R,8S,10S,11R,13R,16R,17R,E)-10-hydroxy-8-((2S,3R,4E,6E,8E)-3-methoxy-4,8-dimethyl-9-(2-methyloxazol-4-yl)nona-4,6,8-trien-2-yl)-11,16-dimethyl-4,7,12,18-tetraoxatetracyclo[15.3.1.03,5.011,13]henicos-14-ene-6,19-dione

InChi Key

OWPCHSCAPHNHAV-QIPOKPRISA-N

InChi Code

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

SMILES Code

O=C(O[C@H]([C@@H]([C@@H](OC)/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)C)C[C@H](O)[C@@]2(C)O[C@]2([H])/C=C/[C@@H](C)[C@]3([H])O4)[C@]5([H])O[C@@]5([H])C[C@@](C3)([H])CC4=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 625.75 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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Biochim Biophys Acta. 1987 Dec 7;926(3):215-23. PubMed PMID: 3120782. 5: Sullivan AS, Prasad V, Roach MC, Takahashi M, Iwasaki S, Ludueña RF. Interaction of rhizoxin with bovine brain tubulin. Cancer Res. 1990 Jul 15;50(14):4277-80. PubMed PMID: 2364385. 6: Tokui T, Kuroiwa C, Tokui Y, Sasagawa K, Kawai K, Kobayashi T, Ikeda T, Komai T. Contribution of serum lipoproteins as carriers of antitumour agent RS-1541 (palmitoyl rhizoxin) in mice. Biopharm Drug Dispos. 1994 Mar;15(2):93-107. PubMed PMID: 8011970. 7: Takahashi M, Matsumoto S, Iwasaki S, Yahara I. Molecular basis for determining the sensitivity of eucaryotes to the antimitotic drug rhizoxin. Mol Gen Genet. 1990 Jul;222(2-3):169-75. PubMed PMID: 2274023. 8: Loper JE, Henkels MD, Rangel LI, Olcott MH, Walker FL, Bond KL, Kidarsa TA, Hesse CN, Sneh B, Stockwell VO, Taylor BJ. Rhizoxin analogs, orfamide A and chitinase production contribute to the toxicity of Pseudomonas protegens strain Pf-5 to Drosophila melanogaster. Environ Microbiol. 2016 Oct;18(10):3509-3521. doi: 10.1111/1462-2920.13369. Epub 2016 Jun 15. PubMed PMID: 27130686. 9: Loper JE, Henkels MD, Shaffer BT, Valeriote FA, Gross H. Isolation and identification of rhizoxin analogs from Pseudomonas fluorescens Pf-5 by using a genomic mining strategy. Appl Environ Microbiol. 2008 May;74(10):3085-93. doi: 10.1128/AEM.02848-07. Epub 2008 Mar 14. PubMed PMID: 18344330; PubMed Central PMCID: PMC2394923. 10: Takahashi M, Kobayashi H, Iwasaki S. Rhizoxin resistant mutants with an altered beta-tubulin gene in Aspergillus nidulans. Mol Gen Genet. 1989 Dec;220(1):53-9. PubMed PMID: 2691873. 11: Bissett D, Graham MA, Setanoians A, Chadwick GA, Wilson P, Koier I, Henrar R, Schwartsmann G, Cassidy J, Kaye SB, et al. Phase I and pharmacokinetic study of rhizoxin. Cancer Res. 1992 May 15;52(10):2894-8. PubMed PMID: 1581905. 12: Scherlach K, Brendel N, Ishida K, Dahse HM, Hertweck C. Photochemical oxazole-nitrile conversion downstream of rhizoxin biosynthesis and its impact on antimitotic activity. Org Biomol Chem. 2012 Aug 14;10(30):5756-9. doi: 10.1039/c2ob25250c. Epub 2012 Mar 27. PubMed PMID: 22453231. 13: Graham MA, Bissett D, Setanoians A, Hamilton T, Kerr DJ, Henrar R, Kaye SB. Preclinical and phase I studies with rhizoxin to apply a pharmacokinetically guided dose-escalation scheme. J Natl Cancer Inst. 1992 Apr 1;84(7):494-500. PubMed PMID: 1545439. 14: Tokui T, Maeda N, Kuroiwa C, Sasagawa K, Inoue T, Kawai K, Ikeda T, Komai T. Tumor selective effect of RS-1541 (palmitoyl-rhizoxin) in M5076 sarcoma and host tissues in vivo. Pharm Res. 1995 Mar;12(3):370-5. PubMed PMID: 7617523. 15: Arioka H, Nishio K, Heike Y, Abe S, Saijo N. In vitro and in vivo modulation by rhizoxin of non-P-glycoprotein-mediated vindesine resistance. J Cancer Res Clin Oncol. 1997;123(4):195-200. PubMed PMID: 9177491. 16: Scherlach K, Partida-Martinez LP, Dahse HM, Hertweck C. Antimitotic rhizoxin derivatives from a cultured bacterial endosymbiont of the rice pathogenic fungus Rhizopus microsporus. J Am Chem Soc. 2006 Sep 6;128(35):11529-36. PubMed PMID: 16939276. 17: Tsuruo T, Oh-hara T, Iida H, Tsukagoshi S, Sato Z, Matsuda I, Iwasaki S, Okuda S, Shimizu F, Sasagawa K, et al. Rhizoxin, a macrocyclic lactone antibiotic, as a new antitumor agent against human and murine tumor cells and their vincristine-resistant sublines. Cancer Res. 1986 Jan;46(1):381-5. PubMed PMID: 3753552. 18: Takahashi M, Iwasaki S, Kobayashi H, Okuda S, Murai T, Sato Y, Haraguchi-Hiraoka T, Nagano H. Studies on macrocyclic lactone antibiotics. XI. Anti-mitotic and anti-tubulin activity of new antitumor antibiotics, rhizoxin and its homologues. J Antibiot (Tokyo). 1987 Jan;40(1):66-72. Erratum in: J Antibiot (Tokyo) 1987 Apr;40(4):following 565. PubMed PMID: 3606749. 19: Tolcher AW, Aylesworth C, Rizzo J, Izbicka E, Campbell E, Kuhn J, Weiss G, Von Hoff DD, Rowinsky EK. 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