Sambutoxin
Sambutoxin is a fungal secondary metabolite with mitochondrial respiratory chain inhibitory activity and antitumor activity. Sambutoxin targets mitochondrial respiratory chain complex III, inhibits electron transfer between cytochrome b and c1, elevates intracellular ROS levels, and induces oxidative stress and DNA damage. Sambutoxin exhibits proliferation-inhibitory activity against MDA‑MB‑231, MCF‑7, A549, HeLa, and HT‑29, activates the ROS/JNK signaling axis, and induces cell cycle arrest and apoptosis. Sambutoxin inhibits the growth of MDA‑MB‑231 xenograft tumors in vivo. Sambutoxin can be used for research on breast cancer and oxidative stress.
For research use only. We do not sell to patients.
- CAS No.: 160047-56-3
- Formula: C28H39NO4
- Molecular Weight:453.61
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Protocols
- Purity & Documentation
- References
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Help & FAQs
All Endogenous Metabolite Isoforms
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Biological Activity
Description
Sambutoxin is a fungal secondary metabolite with mitochondrial respiratory chain inhibitory activity and antitumor activity. Sambutoxin targets mitochondrial respiratory chain complex III, inhibits electron transfer between cytochrome b and c1, elevates intracellular ROS levels, and induces oxidative stress and DNA damage. Sambutoxin exhibits proliferation-inhibitory activity against MDA‑MB‑231, MCF‑7, A549, HeLa, and HT‑29, activates the ROS/JNK signaling axis, and induces cell cycle arrest and apoptosis. Sambutoxin inhibits the growth of MDA‑MB‑231 xenograft tumors in vivo. Sambutoxin can be used for research on breast cancer and oxidative stress[1].
IC50 & Target
[1]|
JNK |
Bax |
Bcl-2 |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| MDA-MB-231 | IC50 |
7.96 μM
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Antiproliferative activity against human MDA-MB-231 breast cancer cells assessed as viability reduction incubated 48 hrs by MTT assay.
Antiproliferative activity against human MDA-MB-231 breast cancer cells assessed as viability reduction incubated 48 hrs by MTT assay.
|
30223653 |
| MCF7 | IC50 |
9.36 μM
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Antiproliferative activity against human MCF-7 breast cancer cells assessed as viability reduction incubated 48 hrs by MTT assay.
Antiproliferative activity against human MCF-7 breast cancer cells assessed as viability reduction incubated 48 hrs by MTT assay.
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30223653 |
| A549 | IC50 |
16.90 μM
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Antiproliferative activity against human A549 lung cancer cells assessed as viability reduction incubated 48 hrs by MTT assay.
Antiproliferative activity against human A549 lung cancer cells assessed as viability reduction incubated 48 hrs by MTT assay.
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30223653 |
| HeLa | IC50 |
13.80 μM
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Antiproliferative activity against human HeLa cervical cancer cells assessed as viability reduction incubated 48 hrs by MTT assay.
Antiproliferative activity against human HeLa cervical cancer cells assessed as viability reduction incubated 48 hrs by MTT assay.
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30223653 |
| HT-29 | IC50 |
15.13 μM
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Antiproliferative activity against human HT-29 colorectal cancer cells assessed as viability reduction incubated 48 hrs by MTT assay.
Antiproliferative activity against human HT-29 colorectal cancer cells assessed as viability reduction incubated 48 hrs by MTT assay.
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30223653 |
In Vitro
Anti-cancerApoptosisOxidative StressCell Cycle RegulationMitochondrial FunctionMitochondrial Oxidative Phosphorylation
Anti-cancer
Anti-cancer
Apoptosis
Sambutoxin (5-20 μM; 24-36 h) increases apoptosis in MDA-MB-231 and MCF-7 cells in a dose-dependent manner, induces apoptotic nuclear morphology in MDA-MB-231 cells, and does not activate the extrinsic apoptosis pathway[1].
Sambutoxin (5-20 μM) promotes the cleavage of caspase-3 and PARP in MDA-MB-231 and MCF-7 cells and selectively activates JNK phosphorylation[1].
Sambutoxin (20 μM; 36 h) induces caspase-9-dependent intrinsic apoptosis in MDA-MB-231 and MCF-7 cells[1].
Sambutoxin (5-20 μM) promotes the cleavage of caspase-3 and PARP in MDA-MB-231 and MCF-7 cells and selectively activates JNK phosphorylation[1].
Sambutoxin (20 μM; 36 h) induces caspase-9-dependent intrinsic apoptosis in MDA-MB-231 and MCF-7 cells[1].
Anti-cancer
Apoptosis
Oxidative Stress
Anti-cancer
Cell Cycle Regulation
Anti-cancer
Mitochondrial Function
Sambutoxin (5-20 μM; 36 h) induces loss of mitochondrial membrane potential in MDA-MB-231 and MCF-7 cells[1].
Anti-cancer
Oxidative Stress
Sambutoxin (5-20 μM; 24 h) induces ROS accumulation and ROS-dependent DNA damage in MDA-MB-231 and MCF-7 cells in a dose-dependent manner; it activates the ATM/Chk2 DNA damage signaling pathway and increases γ-H2AX[1].
Mitochondrial Function
Mitochondrial Oxidative Phosphorylation
Sambutoxin reduces the respiratory control ratio of isolated mitochondria with an ID50 < 50 pmol/mg protein by inhibiting state 3 respiration; it inhibits NADH oxidase (ID50 = 0.2 nmol/mg protein), succinate oxidase (ID50 = 1.5 nmol/mg protein), and DHQ oxidase (ID50 = 0.45 nmol/mg protein), acts selectively on respiratory chain complex III, and blocks electron transfer between cytochrome b and c1[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Cell Viability Assay[1]
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Cell Line:MDA-MB-231 and MCF-7 cells
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Concentration:2.5, 5, 10, 20, 40 μM
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Incubation Time:24, 48, and 72 h
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Result:Inhibited MDA-MB-231 and MCF-7 viability in a dose- and time-dependent manner.
Cell Cycle Analysis[1]
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Cell Line:MDA-MB-231 and MCF-7 cells
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Concentration:5, 10, 20 μM
5 mM (NAC pre-exposure) -
Incubation Time:24 h
1 h (NAC pre-exposure) -
Result:Induced G2/M phase arrest with a corresponding decrease in the G0/G1 population in both MDA-MB-231 and MCF-7 cells.
Prior 5 mM NAC exposure reversed the G2/M arrest.
Western Blot Analysis[1]
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Cell Line:MDA-MB-231 and MCF-7 cells
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Concentration:5, 10, 20 μM
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Incubation Time:24 h
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Result:Decreased cdc25C, cdc2, and cyclin B1 expression and increased phospho-cdc25C (Ser216) and phospho-cdc2 (Tyr15) in both cell lines.
Apoptosis Analysis[1]
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Cell Line:MDA-MB-231 and MCF-7 cells
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Concentration:5, 10, 20 μM
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Incubation Time:36 h
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Result:Increased apoptosis in MDA-MB-231 and MCF-7 cells in a dose-dependent manner.
Immunofluorescence[1]
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Cell Line:MDA-MB-231 and MCF-7 cells
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Concentration:5, 20 μM
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Incubation Time:24 h; with or without NAC pre-exposure
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Result:Significantly and dose-dependently increased γ-H2AX foci formation and the percentage of γ-H2AX foci-positive cells; prior NAC exposure inhibited γ-H2AX foci formation.
Western Blot Analysis[1]
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Cell Line:MDA-MB-231 and MCF-7 cells
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Concentration:5, 10, 20 μM
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Incubation Time:24 h; with or without NAC pre-exposure
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Result:Increased phospho-ATM and phospho-Chk2 at 10 and 20 μM and upregulated γ-H2AX expression; NAC inhibited γ-H2AX and phospho-Chk2 changes.
Apoptosis Analysis[1]
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Cell Line:MDA-MB-231 and MCF-7 cells
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Concentration:20 μM
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Incubation Time:36 h; with Ac-LEHD-FMK pre-exposure
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Result:Apoptosis decreased from 16.3% to 6.8% in MDA-MB-231 cells and from 20.8% to 9.3% in MCF-7 cells with Ac-LEHD-FMK; cleaved PARP increase was also inhibited.
In Vivo
Anti-cancerOthers
Anti-cancer
Others
Sambutoxin is toxic to rats, and dietary supplementation at 0.05% and 0.1% causes body weight loss, gastrointestinal bleeding, and even death in rats; it is also toxic to chicken embryos, with an LC50 of 29.6 μg/egg in chicken embryos[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Related Protocols :
- Annexin V plus membrane-impermeant dye apoptosis staining
- ROS/oxidative-stress fluorescent staining
- BrdU Incorporation Assay
- Protocol for Cell Cycle
- Breast Cancer Modeling
- Cell Viability Determination by MTT Colorimetric Assay
- Detection of Apoptosis
- TUNEL staining for apoptotic DNA fragmentation
- Flow cytometric DNA-content cell-cycle staining
- Patient-Derived Xenograft (PDX)
- Apoptosis Solutions
- Splenic/Portal-Vein Liver Metastasis Xenograft
- Subcutaneous Cell-Line-Derived Xenograft
- Genotoxicity/Mutagenicity Study
- Orthotopic Cell-Line Xenograft
- Intraperitoneal/Peritoneal Dissemination Xenograft
Chemical Information
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CAS No. 160047-56-3
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Molecular Weight 453.61
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Formula C28H39NO4
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SMILES
O=C1C([C@@H]2CC[C@@H](C)[C@H](/C(C)=C/[C@H](C)C[C@@H](C)CC)O2)=C(O)C(C3=CC=C(O)C=C3)=CN1C
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Structure Classification
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Initial Source
Fusarium sambucinum
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
Select Batch:
Purity:
99.98%
Assay:
99.98%
ee.:
99.98%
References
Calculators
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Dilution Calculator
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Sambutoxin Related Classifications
HY-N1320 Related Classifications
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Keywords
- Sambutoxin
- 160047-56-3
- Endogenous Metabolite
- JNK
- Bcl-2 Family
- Mitochondrial Metabolism
- Reactive Oxygen Species (ROS)
- Apoptosis
- ATM/Chk2 checkpoint signaling
- ATP synthesis
- DNA double-strand breaks
- G2/M arrest
- JNK activation
- cytochrome bc1 complex
- intrinsic mitochondrial apoptosis
- mitochondrial respiration
- oxidative stress
- reactive oxygen species
- Inhibitor
- inhibitor
- inhibit