1-Methoxy-5-Methylphenazinium Methyl Sulfate

Hisada, Ryuki; Yagi, Takeshi

doi:10.1093/oxfordjournals.jbchem.a131836

Cited by 69 publications

(18 citation statements)

References 3 publications

(3 reference statements)

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“…The spcctra of phenazine derivatives prepared in this case and those reported previously [3,13] are related to the following structural characteristics: alkylation (i.e. the cationic charge) at position 5, substitution at position 1 and ionization of the hydroxyl group at position 1.…”

Section: Discussionmentioning

confidence: 60%

“…These spectral properties are almost the same as those of 1-methoxy-5-methylphenazine (1 F) [3] and pyocyanine (lE, at which is very similar to that of 2B; at pH 12, the spectrum of 3C is the same as that at pH 7, but that of 3E is different ( A, , , = 373 nm, Fig. 2).…”

Section: Spectral Propertiesmentioning

confidence: 52%

“…the cationic charge) at position 5, substitution at position 1 and ionization of the hydroxyl group at position 1. Therefore, we can group these spectra into five patterns which correspond to the following compounds: (a) 1A and 2A; (b) 3C (at pH 7) and 3E (at pH 7);(c)3E(atpH 12);(d)lB,lE(atpH 2) [13], 1F [3], 2B, 2C, 2D, 3C (at pH 1) and 3E (at pH 1); (e) 1E (at pH 7) [I 31. On the basis of the above results, we identified the photoand alkali-decomposed compounds of the phenazine derivdtives and can indicate the structural factors affecting on the stability of the derivatives.…”

Section: Discussionmentioning

confidence: 99%

“…the values for lA, lB, 2A, 2B, 2C and 2D are 1.83 m M -' s-', 3.33 mM-' s-', 0.75 mM-' s-', 1.42 mM-' s-', 1.68 mM-' s -' and 2.03 mM-' s -I , respectively. The rate constants, k, and k3, for the reactions of the reduced form of 2B with oxygen and with 3-(4,5'-dimethyl~hiazole-2-yl)-2,5-diphenyltetrazolium ion, respectively, were k2 = 1.21 mM-' sC1 and k3 = 91 mM-' s-'.…”

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confidence: 87%

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Synthesis and characterization of 1‐substituted 5‐alkylphenazine derivatives carrying functional groups

Yomo

Sawai

Urabe

et al. 1989

European Journal of Biochemistry

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The following 1-substituted derivatives of Smethylphenazine and 5-ethylphenazine were synthesized: 1-(3-carboxypropyloxy)-5-methylphenazine (lB), l-(3-carboxypropyloxy)-5-ethylphenazine (2B), 1-(3-ethoxycarbonylpropyloxy)-5-ethylphenazine (2C) and l-[N-(2-aminoethyl)carbamoylpropyloxy]-5-~thylphenazine (2D); their spectra, stability and reactivity as electron mediators were investigated, together with those of 5-methylphenazine (1A) and 5-ethylphenazine (2A). The 1-substituted derivatives are all insensitive to light and the derivatives of 5-ethylphenazine are more stable than those of 5-methylphenazine under neutral and alkaline conditions; 2 8 is the most stable of all the derivatives. The spectral properties of the decomposed compounds showed that photodecomposition of 1A and 2A is associated with hydroxylation at position 1, alkali decomposition of 1A and 1 B with elimination of the 5-methyl group and alkali decomposition of 2A, 2B, and 2D with a ring-opening reaction. The second-order rate constant kl for the reaction of the phenazine derivatives with NADH was measured under steady-state conditions. The k l values vary depending on the substituents at positions 1 and 5 :the values for lA, lB, 2A, 2B, 2C and 2D are 1.83 m M -' s-', 3.33 mM-' s-', 0.75 mM-' s-', 1.42 mM-' s-', 1.68 mM-' s -' and 2.03 mM-' s -I , respectively. The rate constants, k, and k3, for the reactions of the reduced form of 2B with oxygen and with 3-(4,5'-dimethyl~hiazole-2-yl)-2,5-diphenyltetrazolium ion, respectively, were k2 = 1.21 mM-' sC1 and k3 = 91 mM-' s-'. These phenazine derivatives have potential applications in the biochemical field. (Fig. 1, 1A) is a unique electron mediator as it can accept electrons from NAD(P)H and is widely used in various redox reactions. However, its application is still limited, mainly because of its instability to light and to alkaline solution. 5-Ethylphenazine (Fig. 1, 2A) has been recommended as a more stable electron mediator in alkaline solutions [l, 21 and light-insensitive derivatives have also been prepared and used in the assay of dehydrogenases [3 -61, but the mechanisms of these instabilities are still unclear. 5-MethylphenazineWe have studied co-enzyme-recycling systems [7 -91 and now we intend to use phenazine derivatives as NAD(P)+ regenerators. For this purpose, it is necessary to prepare stable phenazine derivatives with a functional group suitable for binding them to other molecules, such as water-soluble polymers, solid supports and enzymes. These derivatives are also useful for investigating the mechanisms of the electron-transfer reactions from NAD(P)H. Here, we describe the preparation of new phenazine derivatives carrying a carboxyl group (Fig. I , 1 B and 2B) and an amino group (Fig. 1, 2D) and also their stability and electron-transfer activity. The kinetic constants obtained in this work are necessary for understanding the coupled-reaction system of NAD(P)+ regeneration.

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Section: Discussionmentioning

confidence: 60%

Section: Spectral Propertiesmentioning

confidence: 52%

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 87%

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Synthesis and characterization of 1‐substituted 5‐alkylphenazine derivatives carrying functional groups

Yomo

Sawai

Urabe

et al. 1989

European Journal of Biochemistry

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“…(16) With mPMS as a mediator, which is used as one mediator in a commercial sensor based on LOx, (17) higher currents were achieved than with ferricyanide (Fig. 3).…”

Section: Electrochemical Measurements With Different Mediatorsmentioning

confidence: 99%

Characterization of Electron Mediator Preference of Aerococcus viridans-Derived Lactate Oxidase for Use in Disposable Enzyme Sensor Strips

2017

Sensors and Materials

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Keywords: lactate oxidase, screen-printed carbon electrode, electron mediator, 1-methoxy-5-methyl phenazinium methyl sulfate, potassium ferricyanide, hexaammineruthenium(III) chloride, biomedical engineering Monitoring blood lactate concentration is important in clinical diagnosis and evaluation of fitness care. Electrochemical enzyme sensors are commonly used for the measurement of lactate owing to their simplicity and sensitivity. Lactate oxidases (LOxs) are widely used for the construction of lactate enzyme sensors, especially the LOx derived from Aerococcus viridans (AvLOx). To minimize interference from redox substances, most lactate sensors utilize artificial mediators. However, reports on the comparison of different mediators in lactate measurements are limited. In this study, the preferences of AvLOx for electron mediators were investigated electrochemically. We concluded that the charge of the mediator plays a significant role in determining its suitability as a mediator for AvLOx. The relatively uncharged 1-methoxy-5-methyl phenazinium methylsulfate (mPMS) was the preferred mediator for AvLOx, the strongly negative ferricyanide was a less preferential mediator, and the strongly positive hexaammineruthenium(III) was not utilized as a mediator by AvLOx. This suggests that the protein scaffold of AvLOx can almost completely block the access to the co-factor for very small electron acceptors, depending on their charge.

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Chemiluminescent assay of co‐factors

Tsuji

Maeda

Arakawa

1989

J. Biolumin. Chemilumin.

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Bioluminescent methods are widely used for the assay of the co-factors, NADH and ATP. Although the bioluminescent method is highly sensitive, the enzymes used are unstable and expensive. Therefore a chemiluminescent method would be valuable in clinical routine assay. We have developed a chemiluminescent method for the assay of NADH using the 1-methoxy-5-methylphenazinium methyl sulphate (1-MPMS)/isoluminol(IL)/microperoxidase(m-POD) system. In order to increase the sensitivity of this method, enzymatic cycling system was coupled to the chemiluminescent assay of NADH. Alcohol dehydrogenase and malate dehydrogenase were used as the cycling enzyme. The standard curve was obtained in the range from 3 X 10(-14) to 5 X 10(-12) mol/assay. The detection limit of NADH was 30 fmol/assay which was comparable to that of the bioluminescent method using bacterial luciferase. Two chemiluminescent methods for the assay of ATP have been developed. Method 1 is the system using hexokinase/G6PDH and 1-PMS/IL/m-POD, and method 2 is the system based on the enzymatic cycling reaction of ATP using hexokinase/pyruvate kinase. Method 2 is 1000/fold more sensitive than the method 1. The detection limit of ATP was 10 fmol/assay.

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1-Methoxy-5-Methylphenazinium Methyl Sulfate

Cited by 69 publications

References 3 publications

Synthesis and characterization of 1‐substituted 5‐alkylphenazine derivatives carrying functional groups

Synthesis and characterization of 1‐substituted 5‐alkylphenazine derivatives carrying functional groups

Characterization of Electron Mediator Preference of Aerococcus viridans-Derived Lactate Oxidase for Use in Disposable Enzyme Sensor Strips

Chemiluminescent assay of co‐factors

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