Beauvericin
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MedKoo CAT#: 526437

CAS#: 26048-05-5

Description: Beauvericin is an antifungal, blocking multidrug efflux and inhibiting the global regulator TORC1 kinase, thereby activating the protein kinase CK2 and inhibiting the molecular chaperone Hsp90.

Chemical Structure

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Beauvericin
CAS# 26048-05-5
Instruction

Theoretical Analysis

MedKoo Cat#: 526437
Name: Beauvericin
CAS#: 26048-05-5
Chemical Formula: C45H57N3O9
Exact Mass: 783.41
Molecular Weight: 783.960
Elemental Analysis: C, 68.94; H, 7.33; N, 5.36; O, 18.37

Price and Availability

Size Price Availability Quantity
1mg USD 250 2 Weeks
5mg USD 450 2 Weeks
10mg USD 750 2 Weeks
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Synonym: Beauvericin

IUPAC/Chemical Name: (3S,6R,9S,12R,15S,18R)-3,9,15-Tribenzyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexaone

InChi Key: GYSCAQFHASJXRS-FFCOJMSVSA-N

InChi Code: InChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1

SMILES Code: O=C([C@H](CC1=CC=CC=C1)N(C)C([C@@H](C(C)C)OC([C@H](CC2=CC=CC=C2)N(C)C([C@@H](C(C)C)OC([C@H](CC3=CC=CC=C3)N4C)=O)=O)=O)=O)O[C@H](C(C)C)C4=O

Appearance: Solid powder

Purity: >95% (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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 783.96 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Escrivá L, Jennen D, Caiment F, Manyes L. Transcriptomic Study of the Toxic Mechanism Triggered by Beauvericin in Jurkat Cells. Toxicol Lett. 2017 Dec 1. pii: S0378-4274(17)31496-0. doi: 10.1016/j.toxlet.2017.11.035. [Epub ahead of print] PubMed PMID: 29203277.

2: Zhang J, Meng LL, Wei JJ, Fan P, Liu SS, Yuan WY, Zhao YX, Luo DQ. PTP1B Inhibitors from the Entomogenous Fungi Isaria fumosorosea. Molecules. 2017 Nov 24;22(12). pii: E2058. doi: 10.3390/molecules22122058. PubMed PMID: 29186763.

3: Beccari G, Colasante V, Tini F, Senatore MT, Prodi A, Sulyok M, Covarelli L. Causal agents of Fusarium head blight of durum wheat (Triticum durum Desf.) in central Italy and their in vitro biosynthesis of secondary metabolites. Food Microbiol. 2018 Apr;70:17-27. doi: 10.1016/j.fm.2017.08.016. Epub 2017 Aug 30. PubMed PMID: 29173624.

4: Steiniger C, Hoffmann S, Mainz A, Kaiser M, Voigt K, Meyer V, Süssmuth RD. Harnessing fungal nonribosomal cyclodepsipeptide synthetases for mechanistic insights and tailored engineering. Chem Sci. 2017 Nov 1;8(11):7834-7843. doi: 10.1039/c7sc03093b. Epub 2017 Sep 25. PubMed PMID: 29163920; PubMed Central PMCID: PMC5674221.

5: Sun Y, Wink M, Wang P, Lu H, Zhao H, Liu H, Wang S, Sun Y, Liang Z. Biological characteristics, bioactive components and antineoplastic properties of sporoderm-broken spores from wild Cordyceps cicadae. Phytomedicine. 2017 Dec 1;36:217-228. doi: 10.1016/j.phymed.2017.10.004. Epub 2017 Oct 6. PubMed PMID: 29157818.

6: Mallebrera B, Prosperini A, Font G, Ruiz MJ. In vitro mechanisms of Beauvericin toxicity: A review. Food Chem Toxicol. 2017 Dec 8;111:537-545. doi: 10.1016/j.fct.2017.11.019. [Epub ahead of print] Review. PubMed PMID: 29154952.

7: Niehaus EM, Rindermann L, Janevska S, Münsterkötter M, Güldener U, Tudzynski B. Analysis of the global regulator Lae1 uncovers a connection between Lae1 and the histone acetyltransferase HAT1 in Fusarium fujikuroi. Appl Microbiol Biotechnol. 2017 Oct 28. doi: 10.1007/s00253-017-8590-0. [Epub ahead of print] PubMed PMID: 29080998.

8: Niehaus EM, Kim HK, Münsterkötter M, Janevska S, Arndt B, Kalinina SA, Houterman PM, Ahn IP, Alberti I, Tonti S, Kim DW, Sieber CMK, Humpf HU, Yun SH, Güldener U, Tudzynski B. Comparative genomics of geographically distant Fusarium fujikuroi isolates revealed two distinct pathotypes correlating with secondary metabolite profiles. PLoS Pathog. 2017 Oct 26;13(10):e1006670. doi: 10.1371/journal.ppat.1006670. eCollection 2017 Oct. PubMed PMID: 29073267; PubMed Central PMCID: PMC5675463.

9: Tong Y, Liu M, Zhang Y, Liu X, Huang R, Song F, Dai H, Ren B, Sun N, Pei G, Bian J, Jia XM, Huang G, Zhou X, Li S, Zhang B, Fukuda T, Tomoda H, Ōmura S, Cannon RD, Calderone R, Zhang L. Beauvericin counteracted multi-drug resistant Candida albicans by blocking ABC transporters. Synth Syst Biotechnol. 2016 Oct 25;1(3):158-168. doi: 10.1016/j.synbio.2016.10.001. eCollection 2016 Sep. PubMed PMID: 29062940; PubMed Central PMCID: PMC5640798.

10: Heilos D, Rodríguez-Carrasco Y, Englinger B, Timelthaler G, van Schoonhoven S, Sulyok M, Boecker S, Süssmuth RD, Heffeter P, Lemmens-Gruber R, Dornetshuber-Fleiss R, Berger W. The Natural Fungal Metabolite Beauvericin Exerts Anticancer Activity In Vivo: A Pre-Clinical Pilot Study. Toxins (Basel). 2017 Aug 24;9(9). pii: E258. doi: 10.3390/toxins9090258. PubMed PMID: 28837057; PubMed Central PMCID: PMC5618191.

11: D'Amato A, Volpe R, Vaccaro MC, Terracciano S, Bruno I, Tosolini M, Tedesco C, Pierri G, Tecilla P, Costabile C, Della Sala G, Izzo I, De Riccardis F. Cyclic Peptoids as Mycotoxin Mimics: An Exploration of Their Structural and Biological Properties. J Org Chem. 2017 Sep 1;82(17):8848-8863. doi: 10.1021/acs.joc.7b00965. Epub 2017 Aug 17. PubMed PMID: 28763612.

12: Adedeji BS, Ezeokoli OT, Ezekiel CN, Obadina AO, Somorin YM, Sulyok M, Adeleke RA, Warth B, Nwangburuka CC, Omemu AM, Oyewole OB, Krska R. Bacterial species and mycotoxin contamination associated with locust bean, melon and their fermented products in south-western Nigeria. Int J Food Microbiol. 2017 Oct 3;258:73-80. doi: 10.1016/j.ijfoodmicro.2017.07.014. Epub 2017 Jul 25. PubMed PMID: 28759798.

13: Luz C, Saladino F, Luciano FB, Mañes J, Meca G. Occurrence, toxicity, bioaccessibility and mitigation strategies of beauvericin, a minor Fusarium mycotoxin. Food Chem Toxicol. 2017 Sep;107(Pt A):430-439. doi: 10.1016/j.fct.2017.07.032. Epub 2017 Jul 15. Review. PubMed PMID: 28720287.

14: Fraeyman S, Croubels S, Devreese M, Antonissen G. Emerging Fusarium and Alternaria Mycotoxins: Occurrence, Toxicity and Toxicokinetics. Toxins (Basel). 2017 Jul 18;9(7). pii: E228. doi: 10.3390/toxins9070228. Review. PubMed PMID: 28718805; PubMed Central PMCID: PMC5535175.

15: Yoo S, Kim MY, Cho JY. Beauvericin, a cyclic peptide, inhibits inflammatory responses in macrophages by inhibiting the NF-κB pathway. Korean J Physiol Pharmacol. 2017 Jul;21(4):449-456. doi: 10.4196/kjpp.2017.21.4.449. Epub 2017 Jun 26. PubMed PMID: 28706459; PubMed Central PMCID: PMC5507784.

16: Gálvez L, Urbaniak M, Waśkiewicz A, Stępień Ł, Palmero D. Fusarium proliferatum - Causal agent of garlic bulb rot in Spain: Genetic variability and mycotoxin production. Food Microbiol. 2017 Oct;67:41-48. doi: 10.1016/j.fm.2017.05.006. Epub 2017 May 16. PubMed PMID: 28648292.

17: Stanciu O, Juan C, Miere D, Loghin F, Mañes J. Presence of Enniatins and Beauvericin in Romanian Wheat Samples: From Raw Material to Products for Direct Human Consumption. Toxins (Basel). 2017 Jun 12;9(6). pii: E189. doi: 10.3390/toxins9060189. PubMed PMID: 28604626; PubMed Central PMCID: PMC5488039.

18: Yu D, Xu F, Zhang S, Zhan J. Decoding and reprogramming fungal iterative nonribosomal peptide synthetases. Nat Commun. 2017 May 23;8:15349. doi: 10.1038/ncomms15349. PubMed PMID: 28534477; PubMed Central PMCID: PMC5457498.

19: Mallebrera B, Maietti A, Tedeschi P, Font G, Ruiz MJ, Brandolini V. Antioxidant capacity of trans-resveratrol dietary supplements alone or combined with the mycotoxin beauvericin. Food Chem Toxicol. 2017 Jul;105:315-318. doi: 10.1016/j.fct.2017.04.027. Epub 2017 Apr 25. PubMed PMID: 28450129.

20: Oyedele OA, Ezekiel CN, Sulyok M, Adetunji MC, Warth B, Atanda OO, Krska R. Mycotoxin risk assessment for consumers of groundnut in domestic markets in Nigeria. Int J Food Microbiol. 2017 Jun 19;251:24-32. doi: 10.1016/j.ijfoodmicro.2017.03.020. Epub 2017 Mar 28. PubMed PMID: 28380344.