Menadione - CAS 58-27-5
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Not Intended for Therapeutic Use. For research use only.
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Menadione shows vitamin K activity, used as a nutritional supplement.
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Vitamin K3
1.The aza-analogues of 1,4-naphthoquinones are potent substrates and inhibitors of plasmodial thioredoxin and glutathione reductases and of human erythrocyte glutathione reductase
Christophe Morin, Tatiana Besset, Jean-Claude Moutet. Org. Biomol. Chem., 2008, 6, 2731–2742
It is well known that reduction of quinones in aqueous electrolytes consumes two electrons and two protons to form the corresponding hydroquinones and that the reduction potential is pH-dependent.60 It has been established that the quinolinediones present a similar reduction behavior.61 For the quinoxalinediones, the reduction occurs in a two-step process since the reduction of the quinone moiety is followed at a more negative potential than the value observed for the reduction of the quinoxaline moiety. The reduction of 1,4-naphthoquinone, menadione, and different aza-analogues of naphthoquinone has been studied under physiological conditions in phosphate buffer at pH 7. The cyclic voltammetry data are summarized in Table 1. The reduction peak potential values follow the same trends as the half-wave potentials measured in organic electrolytes. As a matter of fact, the absence of an electron-donating methyl group in the 1,4-naphthoquinone makes it easier to reduce than the menadione. Moreover, the mono-substituted quinoline-5,8-diones 2 and 3, at the 6 or 7 positions by methyl groups, are easier to reduce than menadione itself; the absence of an electron-donating methyl group in the quinolinedione 1 makes it much easier to reduce but the presence of two methyl groups in the di-substituted quinoline-5,8-dione 4 affects the redox potential to more negative values. As expected, the quinoxalinedione 5 presents the more oxidant character, while its 2,3-dimethyl derivative 6 appears slightly more difficult to reduce. A similar trend was observed for the reduction of aza-anthraquinones in DMF, where the 1,4,5,6-tetraazaanthra-9,10-quinone appeared easier to reduce than its 2,3,6,7-tetramethyl derivative.59 Noteworthy is that recent studies on humanNAD(P)H:quinone oxidoreductase, identified as a twoelectron reductase upregulated in tumour cells, was shown to be inhibited by heterocyclic quinones with increased oxidant character and acting as excellent substrates of this flavoenzyme.
2.High performance enzyme fuel cells using a genetically expressed FAD-dependent glucose dehydrogenase α-subunit of Burkholderia cepacia immobilized in a carbon nanotube electrode for low glucose conditions
Deby Fapyane, Soo-Jin Lee, Seo-Hee Kang. Phys. Chem. Chem. Phys., 2013, 15, 9508--9512
In the anode, electrons from glucose oxidation are accepted by menadione, thus reducing menadione to menadiol form by two electrons during each reaction step. The reduced menadione oxidizes FADH2 back to FAD, thereby maintaining redox cycling during BFC operation. The menadione oxidation peak occurred at a potential around 0.2 to 0.25 V versus Ag/AgCl. Therefore, the oxidation peak of glucose by FAD was expected to occur in the range of the menadione redox potential; the oxidation of FADH2 back to FAD occurred in the range of the FAD redox potential ( 0.4 V vs. Ag/AgCl). However, based on the cyclic voltammogram (CV), the glucose oxidation peak was at 0.2 V (vs. Ag/AgCl), whereas the reverse oxidation (FADH2 to FAD) occurred at 0.26 V vs. Ag/AgCl (Fig. 2A). In the absence of menadione as a mediator, the enzyme was not able to transfer electrons to the electrode; thus, no peak was observed (Fig. 2Ab).
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CAS 58-27-5 Menadione

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