A mitochondrial-targeting SOD mimetic
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MitoTEMPOL

Item No. 18796

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,2,6,6-tetramethyl-4-[[5-(triphenylphosphonio)pentyl]oxy]-1-piperidinyloxy, monobromide
CAS Number
1101113-39-6
Molecular Formula
C32H42NO2P • Br
Formula Weight
583.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
[O]N1C(C)(C)CC(OCCCCC[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)CC1(C)C.[Br-]
InChi Code
InChI=1S/C32H42NO2P.BrH/c1-31(2)25-27(26-32(3,4)33(31)34)35-23-15-8-16-24-36(28-17-9-5-10-18-28,29-19-11-6-12-20-29)30-21-13-7-14-22-30;/h5-7,9-14,17-22,27H,8,15-16,23-26H2,1-4H3;1H/q+1;/p-1
InChi Key
NCMZESLTQCMFES-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $256

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    Product Description

    MitoTEMPOL is a mitochondria-targeting superoxide dismutase mimetic that reduces mitochondrial O2- to H2O2.1,2 Like the related compound MitoTEMPO (Item No. 16621), MitoTEMPOL combines an antioxidant moiety (here, TEMPOL, also known as 4-hydroxy-TEMPO) with the lipophilic cation triphenylphosphonium, which allows it to pass through lipid bilayers and accumulate in mitochondria.1 MitoTEMPOL has been used to elucidate the role of mitochondria-derived superoxide in mitochondrial, cellular, and whole animal signaling.2,3,4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dikalov, S. Cross talk between mitochondria and NADPH oxidases. Free Radic. Biol. Med. 51(7), 1289-1301 (2011).

    2. Choi, H.C., Song, P., Xie, Z., et al. Reactive nitrogen species is required for the activation of the AMP-activated protein kinase by statin in vivo. The Journal of Biological Chemisty 283(29), 20186-20197 (2008).

    3. Cunniff, B., Benson, K., Stumpff, J., et al. Mitochondrial-targeted nitroxides disrupt mitochondrial architecture and inhibit expression of peroxiredoxin 3 and FOXM1 in malignant mesothelioma cells. J. Cell. Physiol. 228(4), 835-845 (2013).

    4. Dickey, J.S., Gonzalez, Y., Aryal, B., et al. Mito-tempol and dexrazoxane exhibit cardioprotective and chemotherapeutic effects through specific protein oxidation and autophagy in a syngeneic breast tumor preclinical model. PLoS One 8(8), (2013).

    5. Han, Y., Wang, Q., Song, P., et al. Redox regulation of the AMP-activated protein kinase. PLoS One 5(11), e15420 (2010).

    6. Khan, S.A., Nanduri, H., Yuan, G., et al. NADPH oxidase 2 mediates intermittent hypoxia-induced mitochondrial complex I inhibition: Relevance to blood pressure changes in rats. Antioxid. Redox Signal. 14(4), 533-542 (2011).