Coenzyme Q. I. Structure Studies on the Coenzyme Q Group

Wolf, Donald E.; Hoffman, Carl H.; Trenner, Nelson R.; Arison, Byron H.; Shunk, Clifford H.; Linn, Bruce O.; McPherson, James F.; Folkers, Karl

doi:10.1021/ja01550a096

Cited by 122 publications

(24 citation statements)

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“…9 CoQ10 is a benzoquinone derivative with 10 monounsaturated transisoprenoid units in the side chain ( Figure 1). 10 It functions primarily as a cofactor for the mitochondrial enzymes (complexes I−III) for the oxidative phosphorylation production of adenosine triphosphate (ATP) and is involved in several aspects of cellular metabolism. 11 In its reduced form (CoQ10H 2 , ubiquinol), it acts as a potent antioxidant and free radical scavenger, protecting membranes and lipoproteins from protein oxidation and lipid peroxidation.…”

Section: ■ Introductionmentioning

confidence: 99%

Design and Evaluation of Multifunctional Nanocarriers for Selective Delivery of Coenzyme Q10 to Mitochondria

et al. 2011

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Impairments of mitochondrial functions have been associated with failure of cellular functions in different tissues, leading to various pathologies. We report here a mitochondria-targeted nanodelivery system for coenzyme Q10 (CoQ10) that can reach mitochondria and deliver CoQ10 in adequate quantities. Multifunctional nanocarriers based on ABC miktoarm polymers (A = poly(ethylene glycol (PEG), B = polycaprolactone (PCL), and C = triphenylphosphonium bromide (TPPBr)) were synthesized using a combination of click chemistry with ring-opening polymerization, self-assembled into nanosized micelles, and were employed for CoQ10 loading. Drug loading capacity (60 wt %), micelle size (25−60 nm), and stability were determined using a variety of techniques. The micelles had a small critical association concentration and were colloidally stable in solution for more than 3 months. The extraordinarily high CoQ10 loading capacity in the micelles is attributed to good compatibility between CoQ10 and PCL, as indicated by the low Flory−Huggins interaction parameter. Confocal microscopy studies of the fluorescently labeled polymer analog together with the mitochondria-specific vital dye label indicated that the carrier did indeed reach mitochondria. The high CoQ10 loading efficiency allowed testing of micelles within a broad concentration range and provided evidence for CoQ10 effectiveness in two different experimental paradigms: oxidative stress and inflammation. Combined results from chemical, analytical, and biological experiments suggest that the new miktoarm-based carrier provides a suitable means of CoQ10 delivery to mitochondria without loss of drug effectiveness. The versatility of the click chemistry used to prepare this new mitochondria-targeting nanocarrier offers a widely applicable, simple, and easily reproducible procedure to deliver drugs to mitochondria or other intracellular organelles.

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Section: ■ Introductionmentioning

confidence: 99%

Design and Evaluation of Multifunctional Nanocarriers for Selective Delivery of Coenzyme Q10 to Mitochondria

et al. 2011

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“…They also indicated that these compounds have the same chromophoric group as does coenzyme Qlo and that they differ from the next lower homolog by a five-carbon isoprenoid unit. Finally, Wolf et al (7) established the total molecular structure of the coenzyme Q group of compounds (cf. generic formula I).…”

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confidence: 99%

Coenzyme Q (Ubiquinone)

Hatefi¹

1963

Advances in Enzymology - And Related Areas of Molecular Biology

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“…The structure of CoQ was determined by Wolf et al in 1958. The compound is a 2,3-dimethoxy-5-methylbenzoquinone with the redox active benzoquinone ring connected to a long isoprenoid side chain.…”

Section: Fundamental Concepts About Coqmentioning

confidence: 99%