26048-05-5 Usage
Description
Beauvericin is a trimeric cyclodepsipeptide composed of alternating methylphenylalanyl and hydroxyvaleryl residues, isolated from various fungal genera, including Beauveria and Fusarium. It was first reported in 1969 and is known for its chemical properties as a white powder. Beauvericin exhibits a range of biological activities, such as antifungal, antibacterial, antiprotozoan, and insecticidal effects. At the molecular level, it acts as an ionophore and inhibits acyl-CoA:cholesterol acyltransferase activity. Additionally, beauvericin induces apoptosis by elevating intracellular calcium levels.
Uses
Used in Pharmaceutical Industry:
Beauvericin is used as an antibiotic and insecticidal agent due to its toxic depsipeptide nature, which exhibits broad-spectrum antimicrobial and insecticidal activities.
Used in Anticancer Applications:
Beauvericin is used as an anticancer agent, inducing apoptosis in A549 cancer cells by disrupting mitochondrial volume regulation. It has potential applications in the development of novel cancer treatments.
Used in Antifungal Applications:
Beauvericin is used as an antifungal agent, acting via the inhibition of both multidrug efflux and TORC1 kinase, which contributes to its effectiveness against fungal infections.
Used in Neurological Applications:
Beauvericin is used in the development of treatments for neurological disorders, as it has been shown to cross the blood-brain barrier in mice, indicating its potential for central nervous system targeting.
Used in HIV Treatment:
Beauvericin is used as an inhibitor of HIV-1 integrase, a crucial enzyme in the viral replication process, making it a potential candidate for the development of anti-HIV drugs.
References
1) 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
Check Digit Verification of cas no
The CAS Registry Mumber 26048-05-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,0,4 and 8 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 26048-05:
(7*2)+(6*6)+(5*0)+(4*4)+(3*8)+(2*0)+(1*5)=95
95 % 10 = 5
So 26048-05-5 is a valid CAS Registry Number.
InChI:InChI=1/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
26048-05-5Relevant articles and documents
Synthesis of Natural and Unnatural Cyclooligomeric Depsipeptides Enabled by Flow Chemistry
Lücke, Daniel,Dalton, Toryn,Ley, Steven V.,Wilson, Zoe E.
, p. 4206 - 4217 (2016/03/16)
Flow chemistry has been successfully integrated into the synthesis of a series of cyclooligomeric depsipeptides of three different ring sizes including the natural products beauvericin (1 a), bassianolide (2 b) and enniatin C (1 b). A reliable flow chemistry protocol was established for the coupling and macrocyclisation to form challenging N-methylated amides. This flexible approach has allowed the rapid synthesis of both natural and unnatural depsipeptides in high yields, enabling further exploration of their promising biological activity. Harnessing technology: Flow chemistry has been successfully integrated into the synthesis of a series of cyclooligomeric depsipeptides of three different ring sizes including the natural products beauvericin (1 a), bassianolide (2 b) and enniatin C (1 b), resulting in increased overall yields, while decreasing the effort required for the researcher.
