Fusarenon-X | CAS#23255-69-8 | mycotoxin | induces DNA strand breakage

MedKoo Cat#: 540145 | Name: Fusarenon-X

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Description:

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

Fusarenon-X is a mycotoxin found in Fusarium. It induces DNA strand breakage and decreases food intake.

Chemical Structure

Fusarenon-X

CAS#23255-69-8

Theoretical Analysis

MedKoo Cat#: 540145

Name: Fusarenon-X

CAS#: 23255-69-8

Chemical Formula: C17H22O8

Exact Mass: 354.1315

Molecular Weight: 354.35

Elemental Analysis: C, 57.62; H, 6.26; O, 36.12

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 1,650.00	2 Weeks

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Related CAS #

No Data

Synonym

Fusarenone X; Fusarenon-X; Fusarenon; 3-Acetylnivalenol; 4-acetyl Nivalenol; NSC 197211; NSC197211; NSC-197211;

IUPAC/Chemical Name

(2S,2'R,3'R,4'S,5'S,5a'R,6'R,9a'R)-3',6'-dihydroxy-5a'-(hydroxymethyl)-5',8'-dimethyl-7'-oxo-2',3',4',5',5a',6',7',9a'-octahydrospiro[oxirane-2,10'-[2,5]methanobenzo[b]oxepin]-4'-yl acetate

InChi Key

XGCUCFKWVIWWNW-JHLSVGAZSA-N

InChi Code

InChI=1S/C17H22O8/c1-7-4-9-16(5-18,12(22)10(7)20)15(3)13(24-8(2)19)11(21)14(25-9)17(15)6-23-17/h4,9,11-14,18,21-22H,5-6H2,1-3H3/t9-,11-,12+,13-,14-,15-,16-,17+/m1/s1

SMILES Code

C[C@]1([C@@]([C@H]2O)3CO)[C@H](OC(C)=O)[C@@H](O)[C@H]([C@@]14CO4)O[C@]3([H])C=C(C)C2=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

>2 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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 354.35 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

1: Sutjarit S, Poapolathep A. Fusarenon-X-induced apoptosis in the liver, kidney, and spleen of mice. J Toxicol Pathol. 2016 Jul;29(3):207-11. doi: 10.1293/tox.2015-0063. Epub 2016 Apr 24. PubMed PMID: 27559248; PubMed Central PMCID: PMC4958617. 2: Saengtienchai T, Poapolathep S, Isariyodom S, Ikenaka Y, Ishizuka M, Poapolathep A. Toxicokinetics and tissue depletion of Fusarenon-X and its metabolite nivalenol in piglets. Food Chem Toxicol. 2014 Apr;66:307-12. doi: 10.1016/j.fct.2014.01.053. Epub 2014 Feb 7. PubMed PMID: 24508584. 3: Aupanun S, Poapolathep S, Imsilp K, Prapong T, Poapolathep A. Oral exposure of fusarenon-X induced apoptosis in Peyer's patches, thymus, and spleen of mice. Res Vet Sci. 2015 Oct;102:217-22. doi: 10.1016/j.rvsc.2015.08.012. Epub 2015 Sep 1. PubMed PMID: 26412547. 4: Sutjarit S, Nakayama SM, Ikenaka Y, Ishizuka M, Banlunara W, Rerkamnuaychoke W, Kumagai S, Poapolathep A. Apoptosis and gene expression in the developing mouse brain of fusarenon-X-treated pregnant mice. Toxicol Lett. 2014 Aug 17;229(1):292-302. doi: 10.1016/j.toxlet.2014.06.843. Epub 2014 Jun 28. PubMed PMID: 24983900. 5: Wu W, Zhou HR, He K, Pan X, Sugita-Konishi Y, Watanabe M, Zhang H, Pestka JJ. Role of cholecystokinin in anorexia induction following oral exposure to the 8-ketotrichothecenes deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, fusarenon X, and nivalenol. Toxicol Sci. 2014 Apr;138(2):278-89. doi: 10.1093/toxsci/kft335. Epub 2014 Jan 2. PubMed PMID: 24385417; PubMed Central PMCID: PMC4246666. 6: Wu W, Bates MA, Bursian SJ, Link JE, Flannery BM, Sugita-Konishi Y, Watanabe M, Zhang H, Pestka JJ. Comparison of emetic potencies of the 8-ketotrichothecenes deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, fusarenon X, and nivalenol. Toxicol Sci. 2013 Jan;131(1):279-91. doi: 10.1093/toxsci/kfs286. Epub 2012 Sep 20. PubMed PMID: 22997060; PubMed Central PMCID: PMC3537132. 7: Wu W, Flannery BM, Sugita-Konishi Y, Watanabe M, Zhang H, Pestka JJ. Comparison of murine anorectic responses to the 8-ketotrichothecenes 3-acetyldeoxynivalenol, 15-acetyldeoxynivalenol, fusarenon X and nivalenol. Food Chem Toxicol. 2012 Jun;50(6):2056-61. doi: 10.1016/j.fct.2012.03.055. Epub 2012 Mar 22. PubMed PMID: 22465835. 8: Aupanun S, Phuektes P, Poapolathep S, Sutjarit S, Giorgi M, Poapolathep A. Apoptosis and gene expression in Jurkat human T cells and lymphoid tissues of fusarenon-X-treated mice. Toxicon. 2016 Dec 1;123:15-24. doi: 10.1016/j.toxicon.2016.10.012. Epub 2016 Oct 20. PubMed PMID: 27773736. 9: Matsuoka Y, Kubota K. Studies on mechanisms of diarrhea induced by fusarenon-X, a trichothecene mycotoxin from Fusarium species: fusarenon-X-induced diarrhea is not mediated by cyclic nucleotides. Toxicol Appl Pharmacol. 1987 Dec;91(3):326-32. PubMed PMID: 2827346. 10: Matsuoka Y, Kubota K. Studies on mechanisms of diarrhea induced by fusarenon-X, a trichothecene mycotoxin from Fusarium species; characteristics of increased intestinal absorption rate induced by fusarenon-X. J Pharmacobiodyn. 1982 Mar;5(3):193-9. PubMed PMID: 7097487. 11: Ito Y, Ohtsubo K, Saito M. Effects of fusarenon-X, a trichothecene produced by Fusarium nivale, on pregnant mice and their fetuses. Jpn J Exp Med. 1980 Jun;50(3):167-72. PubMed PMID: 7431674. 12: Masuda E, Takemoto T, Tatsuno T, Obara T. Immunosuppressive effect of a trichothecene mycotoxin, Fusarenon-X in mice. Immunology. 1982 Apr;45(4):743-9. PubMed PMID: 7200080; PubMed Central PMCID: PMC1555432. 13: Thust R, Kneist S, Hühne V. Genotoxicity of Fusarium mycotoxins (nivalenol, fusarenon-X, T-2 toxin, and zearalenone) in Chinese hamster V79-E cells in vitro. Arch Geschwulstforsch. 1983;53(1):9-15. PubMed PMID: 6222715. 14: Fusarenon X. IARC Monogr Eval Carcinog Risk Chem Hum. 1983 Jul;31:153-61. PubMed PMID: 6579003. 15: Matsuoka Y, Kubota K. Characteristics of inflammation induced by fusarenon-X, a trichothecene mycotoxin from Fusarium species. Toxicol Appl Pharmacol. 1987 Dec;91(3):333-40. PubMed PMID: 3424369. 16: Baldwin NC, Bycroft BW, Dewick PM, Gilbert J. Metabolic conversions of trichothecene mycotoxins: biotransformation of 3-acetyldeoxynivalenol into fusarenon-X. Z Naturforsch C. 1986 Sep-Oct;41(9-10):845-50. PubMed PMID: 2948328. 17: Masuda E, Takemoto T, Tatsuno T, Obara T. Induction of suppressor macrophages in mice by Fusarenon-X. Immunology. 1982 Dec;47(4):701-8. PubMed PMID: 6216202; PubMed Central PMCID: PMC1555572. 18: Fusarenon-X. IARC Monogr Eval Carcinog Risk Chem Man. 1976;11:169-73. Review. PubMed PMID: 791815. 19: Poapolathep A, Poapolathep S, Sugita-Konishi Y, Imsilp K, Tassanawat T, Sinthusing C, Itoh Y, Kumagai S. Fate of fusarenon-X in broilers and ducks. Poult Sci. 2008 Aug;87(8):1510-5. doi: 10.3382/ps.2008-00008. PubMed PMID: 18648042. 20: Morishita Y, Nagasawa K, Nakano N, Shiromizu K. Bacterial overgrowth in the jejunum of ICR mice and Wistar rats orally administered with a single lethal dose of fusarenon-X, a trichothecene mycotoxin. J Appl Bacteriol. 1989 Apr;66(4):263-70. PubMed PMID: 2546912.