TPP-IOA
TPP-IOA is a cytochrome c peroxidase inhibitor. TPP-IOA inhibits apoptosis by preventing cardiolipin oxidation and cytochrome c release to the cytosol. TPP-IOA disrupts oxidative phosphorylation in isolated mitochondria. TPP-IOA inhibits cell death in SH-SY5Y cells grown in glucose, but not galactose. TPP-IOA causes mitochondrial depolarization and network fragmentation. TPP-lOA mitigates radiation induced death in mice.
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- CAS No.: 1423018-61-4
- Formula: C42H56BrN2O2P
- Molecular Weight:731.78
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
Biological Activity
Description
In Vitro
TPP-IOA (0-10 μM) physically interacts with cytochrome c, dose-dependently inhibiting both ascorbate-mediated cytochrome c reduction and the rate of resorufin formation in cytochrome c/cardiolipin solution[1].
TPP-IOA (0.5-10 μM) suppresses resorufin formation in isolated mitochondria, with significant inhibition at 5 μM, which is due to its imidazole-containing oleic acid moiety[1].
TPP-IOA (0-10 μM) exhibits IC50 values of 0.65 nmol per nmol cytochrome c for peroxidase activity and 5.28 nmol per nmol cytochrome c for reduction activity[1].
TPP-IOA (0.5-10 μM) dose-dependently reduces the respiratory control ratio and oxidative phosphorylation coupling efficiency in rat liver mitochondria[1].
TPP-IOA (1 μM, 3 h) reduces mitochondrial membrane potential, disrupts mitochondrial reticulum morphology, decreases mitochondrial content, and inhibits FCCP-uncoupled respiration while maintaining basal oxygen consumption in SH-SY5Y cells[1].
TPP-IOA (0.25-5 μM) inhibits H2O2-induced total death & caspase-3 activity in SH-SY5Y cells in glucose but not galactose medium[1][2].
TPP-IOA (2.5-5 μM, 48 h) shows radiation mitigating effects on mouse embryonic cells in a model of intrinsic apoptosis induced in mouse embryonic cells by γirradiation as evidenced by PS externalization, caspase 3/7 activation and cyt c release[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
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Cell Line:SH-SY5Y cells
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Concentration:1 μM
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Incubation Time:3 h
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Result:Showed a less interconnected, more fragmented mitochondrial reticulum.
Increased the absolute number of individual mitochondrial network-like structures in cells.
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6NTac female mice were exposed to total body irradiation to a dose of 9.25 Gy using a cesium source[2].
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Dosage:5 mg/kg
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Administration:i.p. daily for 52 days (10 min, 1 h before irradiation or 10 min, 1 h, 5 h 24 h after irradiation)
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Result:Showed a strong radiomitigative effect.
Chemical Information
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CAS No. 1423018-61-4
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Molecular Weight 731.78
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Formula C42H56BrN2O2P
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SMILES
CCCCCC[C@H](N1C=CN=C1)C/C=C\CCCCCCCC(OCCC[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)=O.[Br-]
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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.
Protocols
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Kinase activity and phosphorylation assays
Kinase activity assays measure the ability of kinases to transfer phosphate groups from ATP to specific substrates, while phosphorylation assays detect the presence and levels of phosphorylated proteins. Common methods include radiolabeled ATP incorporation (e. g. ,), ADP release detection via bioluminescence (e. g. ,[3]), enzyme-linked immunosorbent assays (ELISA) for phospho-specific epitopes (e. g. ,[6]), and microtiter-based formats for high-throughput screening (e. g. ,[8]). The ADP-Glo assay quantifies kinase activity by measuring ADP produced during phosphorylation using a luciferase-based system. Radiometric assays involve autoradiography or scintillation counting after incorporation of 32P-labeled ATP into substrate proteins. ELISA-based approaches rely on phospho-specific antibodies to detect activated kinases in cell lysates or purified samples.
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Western Blot
Western blotting (WB) is a commonly used experimental method in molecular biology, biochemistry, and immunogenetics for identifying and quantifying target proteins. It combines gel electrophoresis with immunoassay, enabling researchers to analyze protein expression, post-translational modifications, and molecular weight.
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Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
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TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
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Mitochondrial membrane-potential fluorescent assay
Mitochondrial membrane potential fluorescent assays estimate ΔΨm in living cells using lipophilic cationic dyes such as TMRM, TMRE, rhodamine 123, and JC-1, which accumulate in mitochondria according to membrane polarization; loss of signal after FCCP or CCCP treatment is interpreted as mitochondrial depolarization. TMRM/TMRE and rhodamine 123 are commonly used for semi-quantitative live-cell microscopy or flow cytometry, while JC-1 can report a shift from red aggregate fluorescence to green monomer fluorescence during depolarization; interpretation requires controls because dye concentration, quenching mode, cell type, dye efflux, and mitochondrial mass can affect fluorescence independently of ΔΨm.
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Cell Cytotoxicity Assay
Cytotoxicity assays are usually based on the assessment of cell membrane damage, which can also be indirectly detected by measuring cell viability. Detection methods include MTT assay, CKK-8 assay, LDH assay and ATP assay, etc.
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Mammalian live/dead viability and cytotoxicity staining
Live/dead viability and cytotoxicity staining assays are based on the simultaneous detection of intracellular esterase activity in metabolically active (viable) cells and membrane integrity loss in non-viable cells. In commonly used dual-staining approaches, membrane-permeant fluorogenic substrates are converted by intracellular esterases into fluorescent products in live cells, while impermeant DNA-binding dyes selectively enter cells with compromised plasma membranes and label nucleic acids in dead or dying cells, enabling discrimination between viable and non-viable populations by fluorescence microscopy or flow cytometry.
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Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
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Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
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Protocol for Kinase activity and phosphorylation assays
Kinase activity assays measure transfer of phosphate from ATP to a protein or peptide substrate, generating phosphorylated substrate, ADP, or incorporated radiolabeled phosphate as the readout; phosphorylation assays measure site-specific phosphorylation in cells or tissues as a proxy for kinase-pathway activation, inhibition, or substrate regulation. Phosphorylation can be detected by phospho-specific Western blot, immunoprecipitation kinase assay, phospho-immunofluorescence, phospho-flow cytometry, luminescent ADP detection, radiolabeled ATP incorporation, or reporter-based pathway assays, and these readouts can be applied to cancer cells, primary neurons, mouse tumors, organoids, inflammatory macrophages, ferroptosis studies, and mitophagy studies when the kinase target is biologically relevant.
Purity & Documentation
References
[1]. Maddalena LA, et al. The mitochondria-targeted imidazole substituted oleic acid 'TPP-IOA' affects mitochondrial bioenergetics and its protective efficacy in cells is influenced by cellular dependence on aerobic metabolism. Biochim Biophys Acta Bioenerg. 2017 Jan;1858(1):73-85. [Content Brief]
[2]. Atkinson J, et al. A mitochondria-targeted inhibitor of cytochrome c peroxidase mitigates radiation-induced death. Nat Commun. 2011 Oct 11;2:497. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)