Art. -Nr.: HY-135562

Ascofuranone

Ascofuranone is an orally active inhibitor of Trypanosoma brucei brucei (TAO) with a K_i value of 2.38 nM. Ascofuranone inhibits IGF-1-induced cancer cell migration, invasion, motility and actin cytoskeleton formation, and exerts anti-tumor effects. Ascofuranone can be used in research related to tumor metastasis, African trypanosomiasis, bacterial infections, lung cancer and hepatocellular carcinoma.

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CAS. Nr.: 38462-04-3
Formel: C₂₃H₂₉ClO₅
Molecular Weight:420.93

Speicherung:

Pure form -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month

Ascofuranone Chemical Structure

CAS. Nr.: 38462-04-3

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Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
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Biologische Aktivität

Beschreibung

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Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	0.9 μM Compound: 10	Cytotoxicity against human A549 cells assessed as reduction in cell viability incubated for 48 hrs by CCK8 assay Cytotoxicity against human A549 cells assessed as reduction in cell viability incubated for 48 hrs by CCK8 assay	[PMID: 34781681]
C3H 10T1/2	IC₅₀	3.2 μM Compound: 20	Concentration required for inhibition of C3H10T1/2 progenitor cell growth Concentration required for inhibition of C3H10T1/2 progenitor cell growth	[PMID: 12954063]
HepG2	IC₅₀	0.9 μM Compound: 10	Cytotoxicity against human HepG2 cells assessed as reduction in cell viability incubated for 48 hrs by CCK8 assay Cytotoxicity against human HepG2 cells assessed as reduction in cell viability incubated for 48 hrs by CCK8 assay	[PMID: 34781681]
MDA-MB-231	IC₅₀	5.2 μM Compound: 15	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability incubated for 24 hrs by CellTiter-Glo luminescent assay Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability incubated for 24 hrs by CellTiter-Glo luminescent assay	[PMID: 34516133]
MDA-MB-468	IC₅₀	7.1 μM Compound: 15	Cytotoxicity against human MDA-MB-468 cells assessed as reduction in cell viability incubated for 24 hrs by CellTiter-Glo luminescent assay Cytotoxicity against human MDA-MB-468 cells assessed as reduction in cell viability incubated for 24 hrs by CellTiter-Glo luminescent assay	[PMID: 34516133]

In Vitro

Ascofuranone (1-20 μM; 24 h) reduces cell viability in a dose-dependent manner in A549, PC3, and MCF-7 cancer cells, but shows limited cytotoxicity in LL24 normal lung cells at concentrations up to 20 μM^[1].
Ascofuranone (10 μM; 24 h) reduces baseline and IGF-1-induced cell invasion in A549, PC3, and MCF-7 cancer cells by approximately 0.5-fold, but does not alter invasion in LL24 normal lung cells, when used at 10 μM for 24 h^[1].
Ascofuranone (0.1-10 μM; 1 h pre-incubation followed by 10 min co-incubation with IGF-1) dose-dependently inhibits IGF-1-induced mTOR phosphorylation, and suppresses IGF-1-induced phosphorylation of the downstream mTOR effectors p70S6K and 4EBP1, in A549, PC3, and MCF-7 cancer cells^[1].
Ascofuranone (10 μM; 1 h pre-incubation followed by 4 h co-incubation with IGF-1) activates AMPK and ACC phosphorylation in an IGF-1-independent manner in A549 and PC3 cancer cells, when used at 10 μM with a 1 h pre-incubation followed by 4 h co-incubation with IGF-1^[1].
Ascofuranone (10 μM; 1 h pre-incubation followed by 10 min co-incubation with IGF-1) inhibits mTORC1 activity by inducing Raptor phosphorylation at Ser792 and modulating TSC2 phosphorylation, in an IGF-1-independent manner in A549 and PC3 cancer cells, when used at 10 μM with a 1 h pre-incubation followed by 10 min co-incubation with IGF-1^[1].
Ascofuranone (1-10 μM; 1 h pre-incubation followed by 10 min co-incubation with IGF-1) dose-dependently inhibits IGF-1-induced FAK phosphorylation in A549 and PC3 cancer cells^[1].
Ascofuranone (3 μM; 20 h) activates PXR transcriptional activity in U2OS cells with a minimum effective concentration of 3 μM^[2].
Ascofuranone (IC₅₀ 3.2 μM; 48 h) inhibits U2OS cell proliferation with an IC₅₀ of 3.2 μM^[2].
Ascofuranone significantly induces adipocyte differentiation of C3H10T1/2 cells, independent of PPARγ activation^[2].
Ascofuranone (50 nM) inhibits the ubiquinol oxidase activity of TAO-expressing E. coli BL21(DE3)pLysS cytoplasmic membranes, reducing activity to 31.6% of the uninhibited control^[3].
Ascofuranone (50 nM) inhibits 23% of the succinate-dependent oxygen consumption activity of TAO-expressing E. coli BL21(DE3)pLysS cytoplasmic membranes when used alone, and completely inhibits the cyanide-insensitive portion of this activity when combined with 5 mM K⁺CN^[3].
Ascofuranone (4-32 μg/mL) exhibits potent antimicrobial activity against select Gram-positive bacteria, including S. aureus, methicillin-resistant S. aureus, S. epidermidis, and B. subtilis, with MIC values ranging from 4 to 32 μg/mL, and against C. albicans with an MIC of 32 μg/mL, but is inactive against vancomycin-resistant E. faecalis (MIC >128 μg/mL)^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay^[1]

Cell Line:

LL24 normal lung cells, A549 lung cancer cells, PC3 prostate cancer cells, MCF-7 breast cancer cells
Concentration:

1-20 μM
Incubation Time:

24 h
Result:

Did not decrease cell viability at doses lower than 5 μM, and resulted in approximately 90% cell viability at 20 μM in LL24 normal lung cells. Significantly decreased cell viability at 5 μM.

Cell Invasion Assay^[1]

Cell Line:

LL24 normal lung cells, A549 lung cancer cells, PC3 prostate cancer cells, MCF-7 breast cancer cells
Concentration:

10 μM (co-incubated with IGF-1)
Incubation Time:

24 h (co-incubated with IGF-1)
Result:

Did not significantly affect cell invasion in LL24 cells. Inhibited cell invasion by approximately 0.5-fold alone, and also significantly inhibited IGF-1-induced cell invasion in A549, PC3, and MCF-7 cancer cells.

Immunofluorescence^[1]

Cell Line:

LL24 normal lung cells, A549 lung cancer cells, PC3 prostate cancer cells, MCF-7 breast cancer cells
Concentration:

10 μM (pre-incubated for 1 h, followed by 1 h co-incubation with IGF-1)
Incubation Time:

1 h pre-incubation, followed by 1 h co-incubation with IGF-1
Result:

Did not alter F-actin distribution in LL24 cells. Did not change F-actin distribution alone, but prevented IGF-1-stimulated F-actin cytoskeleton organization at the leading edges of cells (lamellipodia and filopodia) in A549, PC3, and MCF-7 cancer cells.

Western Blot Analysis^[1]

Cell Line:

A549 lung cancer cells, PC3 prostate cancer cells, MCF-7 breast cancer cells
Concentration:

0.1-10 μM (pre-incubated for 1 h, followed by 10 min co-incubation with IGF-1; mTOR analysis); 10 μM (pre-incubated for 1 h, followed by 10 min co-incubation with IGF-1; p70S6K and 4EBP1 analysis)
Incubation Time:

1 h pre-incubation, followed by 10 min co-incubation with IGF-1
Result:

Significantly decreased IGF-1-induced mTOR phosphorylation in a dose-dependent manner across all three cancer cell lines. Suppressed IGF-1-induced phosphorylation of p70S6K and 4EBP1, downstream effectors of mTOR, in all three cell lines.

Western Blot Analysis^[1]

Cell Line:

A549 lung cancer cells, PC3 prostate cancer cells
Concentration:

10 μM (pre-incubated for 1 h, followed by 4 h co-incubation with IGF-1)
Incubation Time:

1 h pre-incubation, followed by 4 h co-incubation with IGF-1
Result:

Increased phosphorylation of AMPK and its downstream target ACC, irrespective of the presence of IGF-1. Resulted in phosphorylation of AMPK and ACC similar to that observed with ascofuranone alone in the presence of IGF-1.

Western Blot Analysis^[1]

Cell Line:

A549 lung cancer cells, PC3 prostate cancer cells
Concentration:

10 μM (pre-incubated for 1 h, followed by 10 min co-incubation with IGF-1)
Incubation Time:

1 h pre-incubation, followed by 10 min co-incubation with IGF-1
Result:

Decreased IGF-1-induced Akt phosphorylation in A549 and PC3 cells.
Significantly increased phosphorylation of Raptor at Ser792, a residue that inhibits mTORC1, in an IGF-1-independent manner. Suppressed IGF-1-induced TSC2 phosphorylation at Thr1462, and stimulated TSC2 phosphorylation at Ser1387.

Western Blot Analysis^[1]

Cell Line:

A549 lung cancer cells, PC3 prostate cancer cells
Concentration:

10 μM (co-incubated with IGF-1)
Incubation Time:

12 h (co-incubated with IGF-1)
Result:

Decreased IGF-1-stimulated binding of mTOR to Raptor (mTORC1 complex assembly), but did not alter assembly of the mTOR-Rictor (mTORC2) complex.

In Vivo

Ascofuranone (50 mg/kg; i.p.; once every two days; 28 days) administered significantly reduces subcutaneous A549 xenograft tumor weight by approximately 71% relative to vehicle control (p ≤ 0.05)^[1].
Ascofuranone (50 mg/kg; i.p.; once every two days; 6 weeks) administered significantly reduces A549 lung metastasis by approximately 80% relative to vehicle control, associated with inhibition of FAK and mTORC1 pathway activity in lung tissues^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

BALB/c nude (male, 6 weeks old, subcutaneous xenograft model via A549 cell inoculation)^[1]
Dosage:

50 mg/kg
Administration:

i.p.; once every two days; 28 days
Result:

Reduced average tumor weight to 0.386 g, compared to 1.33 g in vehicle-treated controls, representing a 71% reduction.

Animal Model:

BALB/c nude (male, 6 weeks old, metastatic model via tail vein injection of A549 cells)^[1]
Dosage:

50 mg/kg
Administration:

i.p.; once every two days; 6 weeks
Result:

Reduced the number of metastatic lung nodules.
Decreased size and density of tumor cells in lung tissues via HE staining.
Suppressed Ki67 expression and significantly decreased phosphorylated mTOR levels in lung tissues via immunohistochemistry.
Confirmed suppressed phosphorylation of FAK and mTOR, and increased phosphorylation of Raptor in lung tissues via Western blot analysis, relative to vehicle control.

Chemical Information

CAS. Nr. 38462-04-3
Appearance Oil
Molecular Weight 420.93
Formel C₂₃H₂₉ClO₅
Color Colorless to light pink
SMILES

C/C([C@@H]1CC(C(C)(O1)C)=O)=C\CC/C(C)=C/CC2=C(C(C=O)=C(C(Cl)=C2O)C)O
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Pure form	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

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COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Jeong YJ, et al. Ascofuranone suppresses invasion and F-actin cytoskeleton organization in cancer cells by inhibiting the mTOR complex 1 signaling pathway. Cell Oncol (Dordr). 2020;43(5):793-805. [Content Brief]

[2]. Togashi M, et al. Ascochlorin derivatives as ligands for nuclear hormone receptors. J Med Chem. 2003;46(19):4113-4123. [Content Brief]

[3]. Fukai Y, et al. Functional expression of the ascofuranone-sensitive Trypanosoma brucei brucei alternative oxidase in the cytoplasmic membrane of Escherichia coli. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1999;124(2):141-148. [Content Brief]

[4]. Hao X, et al. Acremopeptaibols A-F, 16-Residue Peptaibols from the Sponge-Derived Acremonium sp. IMB18-086 Cultivated with Heat-Killed Pseudomonas aeruginosa. J Nat Prod. 2021 Nov 26;84(11):2990-3000. [Content Brief]

Calculators

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Help & FAQs

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Ascofuranone

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Biologische Aktivität

Chemical Information

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Calculators

Help & FAQs

Ascofuranone Related Classifications

HY-135562 Related Classifications