BEAUVERICIN

BEAUVERICIN Basic information
Product Name:BEAUVERICIN
Synonyms:Beauvericin, froM Beauveria bassiana;CYCLO-[D-ALPHA-HYDROXYISOVALERYL-L-N-METHYLPHENYLALANYL]3;CYCLO(-D-ALPHA-HYDROXYISOVALERYL-N-ME-PHE)3;BEAUVERICIN;cyclo(d-α-hydroxyisovaleryl-l-n-methyl-phe)3;BEAUVERFICIN;beauverin;beauverin bassiaua vuillemin
CAS:26048-05-5
MF:C45H57N3O9
MW:783.95
EINECS:
Product Categories:Antibiotic;Intermediates & Fine Chemicals;peptide;Peptides;Pharmaceuticals
Mol File:26048-05-5.mol
BEAUVERICIN Structure
BEAUVERICIN Chemical Properties
Melting point 93-94℃
Boiling point 975.6±65.0 °C(Predicted)
density 1.126±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility Soluble in DMSO (30 mg/ml)
pka-1.02±0.70(Predicted)
form neat
color White
Stability:Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChIKeyGYSCAQFHASJXRS-ABKJGVMTSA-N
Safety Information
WGK Germany 3
HS Code 29419090
MSDS Information
ProviderLanguage
SigmaAldrich English
BEAUVERICIN Usage And Synthesis
DescriptionBeauvericin (CAS 26048-05-5) induces apoptosis in A549 cancer cells.1 Disrupts mitochondrial volume regulation.2 Antifungal activity acting via inhibition of both multidrug efflux and TORC1 kinase.3 Crosses the blood-brain barrier in mice.4 Inhibits HIV-1 integrase.5
Chemical PropertiesWhite powder
UsesBeauvericin is a cyclic depsipeptide isolated from several fungal genera, notably Beauveria and Fusarium, first reported in 1969. Beauvericin exhibits broad antifungal, antibacterial, antiprotozoan and insecticidal activities. At the molecular level, beauvericin exhibits ionophoric properties, and inhibits acyl-CoA:cholesterol acyltransferase activity. Beauvericin induces apoptosis by elevating intracellular calcium levels.
UsesToxic depsipeptide with antibiotic and insecticidal effects.Beauvericin is a toxic depsipeptide with antibiotic and insecticidal effects.
DefinitionChEBI: A trimeric cyclodepsipeptide composed from alternating methylphenylalanyl and hydroxyvaleryl residues.
References1) Lu et al. (2016), Beauvericin-induced cell apoptosis through the mitogen-activated protein kinase pathway in human nonsmall cell lung cancer A549 cells.; J. Toxicol. Sci., 41 429 2) Tonshin et al. (2010), The Fusarium mycotoxins enniatins and beauvericin cause mitochondrial dysfunction by affecting the mitochondrial volume regulation, oxidative phosphorylation and ion homeostasis.; Toxicology, 276 49 3) Shekhar-Guturja et al. (2016), Dual action antifungal small molecule modulates multidrug efflux and TOR signaling; Nat. Chem. Biol., 12 867 4) Taevernier et al. (2016), Blood-brain barrier transport kinetics of the cyclic depsipeptide mycotoxins beauvericin and enniatins; Toxicol. Lett., 258 175 5) Shin et al. (2009), Beauvericin and enniatins H,I and MK1688 are new potent inhibitors of human immunodeficiency virus type-1 integrase; J. Antibiot. (Tokyo), 62 687
BEAUVERICIN Preparation Products And Raw materials
Raw materialsPotassium Phosphate Monobasic
Emamectin GLYCINE N-PROPYL ESTER HYDROCHLORIDE 1,5-DIAMINO-3-OXAPENTANE Propanamide, 2-hydroxy-N,N-dimethyl- (9CI) Bis(2-dimethylaminoethyl) ether BEAUVERICIN N,N-DIMETHYL-2-METHOXYACETAMIDE 1,5-BIS(METHYLAMINO)-3-OXAPENTANE, 98 AC-PHE-OET N-(2-HYDROXYETHYL)LACTAMIDE AC-PHE-OME N,N-Dimethylglycine ethyl ester beauvericin synthetase N,N-DIMETHYL-L-PHENYLALANINE 2-((2-(2-(DIMETHYLAMINO)ETHOXY)ETHYL) METHYLAMINO)ETHANOL, 97 N,N-DI(2-METHOXY)ETHYLAMMONIUM ACETATE ethyl 2-(butylamino)acetate ethyl 2-(propylamino)acetate

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