SML0737

MitoTEMPO

Name: MitoTEMPO
Brand: SIGMA

≥98% (HPLC), powder, antioxidant

Synonym(s):

(2-(2,2,6,6-Tetramethylpiperidin-1-oxyl-4-ylamino)-2-oxoethyl)triphenylphosphonium chloride, Mito-TEMPO

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₃₅N₂O₂P · Cl

CAS Number:

1334850-99-5

Molecular Weight:

510.03

UNSPSC Code:

12352200

NACRES:

NA.77

Product Name

MitoTEMPO, ≥98% (HPLC)

SMILES string

[P+](CC(=O)NC4CC(N(C(C4)(C)C)[O])(C)C)(c3ccccc3)(c2ccccc2)c1ccccc1.[Cl-]

InChI

1S/C29H34N2O2P.ClH/c1-28(2)20-23(21-29(3,4)31(28)33)30-27(32)22-34(24-14-8-5-9-15-24,25-16-10-6-11-17-25)26-18-12-7-13-19-26;/h5-19,23H,20-22H2,1-4H3;1H

InChI key

WKKFJIJNGHNQQW-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

color

white to light brown

solubility

H₂O: 10 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Bioactive Small Molecules

Application

MitoTEMPO has been used as a mitochondria-targeted antioxidant.

Biochem/physiol Actions

MitoTEMPO is a mitochondrially targeted antioxidant, a specific scavenger of mitochondrial superoxide.

MitoTEMPO is a mitochondrially targeted antioxidant, a specific scavenger of mitochondrial superoxide. MitoTEMPO is a combination of the antioxidant piperidine nitroxide TEMPO with the lipophilic cation triphenylphosphonium, giving MitoTEMPO the ability to pass through lipid bilayers with ease and accumulate several hundred-fold in mitochondria. Mitochondrial dysfunction and oxidative stress contribute to a variety of disorders involving cardiovascular, kidney, liver disorders, Parkinson′s and Alzheimer′s disease.

Other Notes

Light sensitive

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Regulation of morphine-induced synaptic alterations: Role of oxidative stress, ER stress, and autophagy

Yu C, et al.

The Journal of Biological Chemistry (2016)

Mitochondrial Reactive Oxygen Species Contribute to Pathological Inflammation During Influenza A Virus Infection in Mice.

Eunice E To et al.

Antioxidants & redox signaling, 32(13), 929-942 (2019-06-14)

Aims: Reactive oxygen species (ROS) are highly reactive molecules generated in different subcellular sites or compartments, including endosomes via

Caveolin 1-related autophagy initiated by aldosterone-induced oxidation promotes liver sinusoidal endothelial cells defenestration

Xiaoying L, et al.

Redox Biology, 508-521 (2017)

Modulation of mitochondrial antiviral signaling by human herpesvirus 8 interferon regulatory factor 1

Young KH, et al.

Journal of Virology (2016)

The Potent Antioxidant MitoQ Protects Against Preeclampsia During Late Gestation but Increases the Risk of Preeclampsia When Administered in Early Pregnancy.

Yike Yang et al.

Antioxidants & redox signaling, 34(2), 118-136 (2020-04-02)

Aims: Although preeclampsia (PE) has been attributed to excessive oxidative stress (OS) in the placenta, mild antioxidants failed to prevent PE in clinical trials. As mitochondria are a major source of OS, this study assessed the potential of a potent

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