Electrochemical study of the oxidation of .alpha.-methyldopamine, .alpha.-methylnoradrenaline, and dopamine

Young, Thomas E.; Babbitt, Brion W.

doi:10.1021/jo00152a029

Cited by 73 publications

(60 citation statements)

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“…Figure 4 displays typical chromatograms of solutions containing DA−Fe(III)−ATP, Fe(III)−DA, or DA that had been incubated at room temperature for 6 h. In all three cases, DACHR (retention time = 3.1 min) was detected, suggesting that DA is oxidized to DAQ, which readily cyclizes to DACHR. 37 Also, in all cases, a peak at a retention time of 6.3 min emerged. This peak was verified to be 6-hydroxydopamine (6-OHDA), since it is the same as the peak corresponding to the elution of a 6-OHDA standard out of the chromatographic column.…”

Section: ■ Resultsmentioning

confidence: 83%

Inhibition of the Fe(III)-Catalyzed Dopamine Oxidation by ATP and Its Relevance to Oxidative Stress in Parkinson’s Disease

Jiang

Shi

Zhang

et al. 2013

ACS Chem. Neurosci.

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Parkinson's disease (PD) is characterized by the progressive degeneration of dopaminergic cells, which implicates a role of dopamine (DA) in the etiology of PD. A possible DA degradation pathway is the Fe(III)-catalyzed oxidation of DA by oxygen, which produces neuronal toxins as side products. We investigated how ATP, an abundant and ubiquitous molecule in cellular milieu, affects the catalytic oxidation reaction of dopamine. For the first time, a unique, highly stable DA−Fe(III)−ATP ternary complex was formed and characterized in vitro. ATP as a ligand shifts the catecholate−Fe(III) ligand metal charge transfer (LMCT) band to a longer wavelength and the redox potentials of both DA and the Fe(III) center in the ternary complex. Remarkably, the additional ligation by ATP was found to significantly reverse the catalytic effect of the Fe(III) center on the DA oxidation. The reversal is attributed to the full occupation of the Fe(III) coordination sites by ATP and DA, which blocks O 2 from accessing the Fe(III) center and its further reaction with DA. The biological relevance of this complex is strongly implicated by the identification of the ternary complex in the substantia nigra of rat brain and its attenuation of cytotoxicity of the Fe(III)−DA complex. Since ATP deficiency accompanies PD and neurotoxin 1-methyl-4-phenylpyridinium (MPP + ) induced PD, deficiency of ATP and the resultant impairment toward the inhibition of the Fe(III)-catalyzed DA oxidation may contribute to the pathogenesis of PD. Our finding provides new insight into the pathways of DA oxidation and its relationship with synaptic activity.

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Section: ■ Resultsmentioning

confidence: 83%

Inhibition of the Fe(III)-Catalyzed Dopamine Oxidation by ATP and Its Relevance to Oxidative Stress in Parkinson’s Disease

Jiang

Shi

Zhang

et al. 2013

ACS Chem. Neurosci.

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“…Then, leucodopaminechrome is further oxidized to dopaminechrome, producing 5,6-dihydroxiindole, which is oxidized to indole quinine that stars the polymerization process. Concerning the cathodic process, the waves illustrated in Fig.3 are attributed to the reduction of the DA to 5,6-dihydroxyindole and aminochrome involving twoelectrons for each reduction process [41][42][43][44][45][46] . CuPc.…”

Section: Preparation Of the Modified Electrodesmentioning

confidence: 99%

Simultaneous Electrochemical Detection of Dopamine, Ascorbic Acid and Uric Acid Using Copper-Phthalocyanine Functionalized MWCNTS

Sancy

Silva

Pavez

et al. 2013

J. Chil. Chem. Soc.

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Multiwalled carbon nanotububes functionalized with amino groups (MWCNT-NH 2) and further modified with copper-phthalocyaninetetrasulphonate (4β(SO 3 ) CuPc) were used for preparing a hybrid electrode [MWCNT-NH 2 /4β(SO 3 )CuPc/GC] using glassy carbon (GC) as a support. This hybrid electrode was tested for the detection of dopamine (DA) in the presence of ascorbic acid (AA) and uric acid (UA) in a PBS buffer solution at pH 6.8. The presence of the macrocyclic increased the resolution of the oxidation signals of AA, DA and UA into three very well distinct oxidation peaks. This effect was enhanced when the complex is adsorbed on multiwalled carbon nanotubes. In addition, the hybrid films provide a simple method for selective detection of DA, AA and UA in biological samples. The calibration curves for DA were obtained over the range of 1x10 -6 -1x10 -3M, obtaining a good selectivity and sensitivity

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“…The principal goals of this investigation were (a) to determine whether CySH diverts the normal oxidation pathway of EPI, and (b) if so, to characterize the major initial products formed. Previous investigators have established that chemical, enzyme-mediated, and electrochemically driven oxidations of DA, NE, and EPI all generate o-quinones as the proximate product (1,2,(8)(9)(10)(11)(12)(35)(36)(37)(38)(39). Electrochemical techniques in particular have permitted further insights into the subsequent reactions of these o-quinones, summarized in Scheme 1 (37).…”

Section: Introductionmentioning

confidence: 99%

Influence ofL-Cysteine on the Oxidation Chemistry of (-)-Epinephrine: Formation of Cysteinyl Conjugates and Novel Dihydrobenzothiazines

Shen

Dryhurst

1996

Bioorganic Chemistry

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Electrochemical study of the oxidation of .alpha.-methyldopamine, .alpha.-methylnoradrenaline, and dopamine

Abstract: The instrument used to record the 2H NMR spectra was funded in part by the NSF.

Cited by 73 publications

References 0 publications

Inhibition of the Fe(III)-Catalyzed Dopamine Oxidation by ATP and Its Relevance to Oxidative Stress in Parkinson’s Disease

Inhibition of the Fe(III)-Catalyzed Dopamine Oxidation by ATP and Its Relevance to Oxidative Stress in Parkinson’s Disease

Simultaneous Electrochemical Detection of Dopamine, Ascorbic Acid and Uric Acid Using Copper-Phthalocyanine Functionalized MWCNTS

Influence ofL-Cysteine on the Oxidation Chemistry of (-)-Epinephrine: Formation of Cysteinyl Conjugates and Novel Dihydrobenzothiazines

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