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2503-26-6

2503-26-6 structure
2503-26-6 structure
  • Name: Destruxin B
  • Chemical Name: .β.-Alanine, N-[N-[N-[N-[1-(D-2-hydroxy-4-methyl-1-oxopentyl)-L-prolyl]-L-isoleucyl]-N-methyl-L-valyl]-N-methyl-L-alanyl]-, .ρ.-lactone
  • CAS Number: 2503-26-6
  • Molecular Formula: C32H55N5O7
  • Molecular Weight: 593.75500
  • Catalog: Signaling Pathways Apoptosis Apoptosis
  • Create Date: 2016-09-06 19:24:15
  • Modify Date: 2024-01-09 17:00:43
  • Destruxin B, isolated from entomopathogenic fungus Metarhizium anisopliae, is one of the cyclodepsipeptides with insecticidal and anticancer activities. Destruxin B induces apoptosis via a Bcl-2 Family-dependent mitochondrial pathway in human nonsmall cell lung cancer cells[1]. Destruxin B significantly activates caspase-3 and reduces tumor cell proliferation through caspase-mediated apoptosis, not only in vitro but also in vivo[2].

Name .β.-Alanine, N-[N-[N-[N-[1-(D-2-hydroxy-4-methyl-1-oxopentyl)-L-prolyl]-L-isoleucyl]-N-methyl-L-valyl]-N-methyl-L-alanyl]-, .ρ.-lactone
Synonyms destruxin B
Description Destruxin B, isolated from entomopathogenic fungus Metarhizium anisopliae, is one of the cyclodepsipeptides with insecticidal and anticancer activities. Destruxin B induces apoptosis via a Bcl-2 Family-dependent mitochondrial pathway in human nonsmall cell lung cancer cells[1]. Destruxin B significantly activates caspase-3 and reduces tumor cell proliferation through caspase-mediated apoptosis, not only in vitro but also in vivo[2].
Related Catalog
Target

Bcl-2

Caspase-3

In Vitro Destruxin B (1-30 μM; 48 hours) inhibits cell proliferation of H1299 cells and A549 cells, with IC50s of 4.1 μM and 4.9 μM, respectively[1]. Activation of mitochondria-dependent caspase cascade plays an important role in Destruxin B (1-30 μM; 48 hours) induced apoptotic cell death in A549 cells[1]. Destruxin B (1.25-20.00 μM; 72 hours) treatment significantly inhibits HT-29 human colorectal cancer cells viability in time- and dose-dependent manners[2]. Destruxin B (10 or 20 μM; 12 and 24 hours) treatment markedly increases levels of the proapoptotic protein PUMA and reduces levels of antiapoptotic proteins Mcl-1 of A549 cells in a concentration- and time-dependent manner [1]. Cell Proliferation Assay[1] Cell Line: H1299 cells Concentration: 1, 5, 10, 20, 30 μM Incubation Time: 48  hours Result: Inhibited H1299 cells proliferation of H1299 cells with an IC50 of 4.1 μM. Apoptosis Analysis[1] Cell Line: Lung adenocarcinoma A549 cells Concentration: 1, 5, 10, 20, 30 μM Incubation Time: 48  hours Result: Induces caspase-dependent Lung adenocarcinoma A549 cells death. Cell Viability Assay[2] Cell Line: HT-29 human colorectal cancer cells Concentration: 1.25, 2.50, 5.00, 10.00 and 20.00 μM Incubation Time: 72 hours Result: The IC50s at 24 h, 48 h and 72h were determined as 14.97, 2.00 and 0.67 μM, respectively. Western Blot Analysis[1] Cell Line: A549 cells Concentration: 10 or 20 μM Incubation Time: 12 and 24  hours Result: Regulates Mcl-1 and PUMA.
In Vivo Destruxin B (DB) ( injection; 0.6-15 mg/kg/day for 6 weeks) attenuates the tumor growth in time- and dose-dependent manners[2]. Animal Model: Athymic female nude mice (BALB/cAnN.Cg-Foxn1nu/CrlNarl), approximately 4-5 weeks old on arrival[2] Dosage: Low dose (0.6 mg/kg), medium dose (3 mg/kg), high dose (15 mg/kg) Administration: Injection; daily; for 6 weeks Result: Low dose, medium dose and high dose indicated a reduction of 23.9%, 33.4% and 55.8% in mean tumor size, respectively.
References

[1]. Wu CC, et al. Destruxin B Isolated from Entomopathogenic Fungus Metarhizium anisopliae Induces Apoptosis via a Bcl-2 Family-Dependent Mitochondrial Pathway in Human NonsmallCell Lung Cancer Cells. Evid Based Complement Alternat Med. 2013;2013:548929.

[2]. Lee YP, et al. In vitro and in vivo anticancer effects of destruxin B on human colorectal cancer. Anticancer Res. 2012 Jul;32(7):2735-45.

Density 1.17g/cm3
Boiling Point 875ºC at 760mmHg
Molecular Formula C32H55N5O7
Molecular Weight 593.75500
Flash Point 483ºC
Exact Mass 593.37900
PSA 145.43000
LogP 1.78730
Vapour Pressure 4.15E-31mmHg at 25°C
Index of Refraction 1.535

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HH1500100
CHEMICAL NAME :
Destruxin B
CAS REGISTRY NUMBER :
2503-26-6
LAST UPDATED :
199612
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C30-H51-N5-O7
MOLECULAR WEIGHT :
593.86

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
16900 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - coma
REFERENCE :
ABCHA6 Agricultural and Biological Chemistry. (Maruzen Co. Ltd., POB 5050, Tokyo International, Tokyo 100-31, Japan) V.25- 1961- Volume(issue)/page/year: 26,36,1962