Mitoquinone Bromide

Synonymes : Mitoquinone bromide, MitoQ, Mitoquinol mesylate, 10-(4,5-Dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)decyl triphenylphosphonium bromide, Ubiquinone-10 derivative

Mitoquinone bromide is a synthetic analog of coenzyme Q10 (ubiquinone) engineered to accumulate within mitochondria. Its structure features a triphenylphosphonium (TPP+) cation conjugated to a ubiquinone-like redox-active headgroup via a ten-carbon aliphatic linker. This design exploits the large mitochondrial membrane potential to drive selective uptake into the organelle, where the quinone moiety undergoes reversible reduction to a quinol, effectively scavenging reactive oxygen species (ROS) at the source.

Unlike natural ubiquinone, which distributes broadly across cellular membranes, mitoquinone bromide concentrates several-hundred-fold inside mitochondria. This targeted delivery makes it a valuable tool for studying mitochondrial oxidative stress in models of neurodegeneration, ischemia-reperfusion injury, and metabolic disorders. The bromide salt form enhances crystallinity and stability, facilitating accurate weighing and reproducible formulation in preclinical research.

As a research-grade compound, mitoquinone bromide is primarily supplied to pharmaceutical and biotechnology companies for drug discovery, mechanistic studies, and as a reference standard. Its well-characterized pharmacokinetics and safety profile in animal models have also spurred interest in developing mitochondria-targeted therapeutics, with several clinical trials exploring its potential in Parkinson’s disease and other age-related conditions.

Structure chimique et propriétés

Mitoquinone bromide consists of a redox-active 2,3-dimethoxy-5-methyl-1,4-benzoquinone core linked to a decyl chain terminating in a triphenylphosphonium group. The TPP+ cation confers lipophilicity and a delocalized positive charge, enabling rapid passage through lipid bilayers and electrophoretic accumulation in mitochondria. The compound is a orange to dark red crystalline solid, stable under recommended storage conditions, and exhibits strong UV absorbance around 270 nm. Its solubility profile supports dissolution in organic solvents for stock preparation, while aqueous formulations can be achieved with appropriate co-solvents.

Mécanisme d'action

• Mitochondrial targeting: The TPP+ moiety drives accumulation within the mitochondrial matrix, driven by the inner membrane potential (Δψm), achieving concentrations up to several hundred-fold higher than in the cytosol.
• ROS scavenging: The ubiquinone headgroup accepts electrons from complexes I and II of the electron transport chain, becoming reduced to ubiquinol, which neutralizes lipid peroxides and superoxide, thereby reducing oxidative damage.
• Redox cycling: Mitoquinone undergoes reversible oxidation-reduction, acting as a catalytic antioxidant that can be regenerated by the respiratory chain, providing sustained protection.
• Modulation of cell signaling: By lowering mitochondrial ROS, mitoquinone influences redox-sensitive pathways such as NF-κB and Nrf2, impacting inflammation and cellular stress responses.

Spécifications de qualité

Approvisionnement et documentation

• Capacité: Capacité de production mensuelle de 500 kg, extensible sur demande.
• Délai de livraison: 3 à 5 jours ouvrés (articles en stock)
• Documentation: COA, MSDS, TDS, and analytical reports (HPLC, NMR, MS) provided with each shipment.
• Emballage: Amber glass vials under argon, securely sealed and labeled; custom packaging options available for bulk orders.

Demande de devis

• LyvBio Co. — E-mail : info@lyvbio.com