Nitroradical Anion Formation From Nitrofurantoin in Carbon Electrodes

Tijoux, María Emilia; Carbajo, J.; Nuñez-Vergara, L.J.; Squella, J. A.

doi:10.4067/s0366-16442000000100013

Cited by 2 publications

(5 citation statements)

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“…Similarly to other nitroheterocyclic drugs, 13,19,22,23 the current ratio (Ia pN0 /Ic pN0 ) increases towards unity as a function of the scan rate, a typical behavior of an irreversible chemical reaction following a charge transfer step. 9,39 We have assumed that NF undergoes the same mechanism as that proposed by other authors, 13,19,22,23 as is depicted in the reaction mechanism below:…”

Section: Voltammetric Generation Of Nitro-radical Anion From Nitrofurmentioning

confidence: 91%

“…The use of mixed medium can improve this separation. 22,23 On the other hand, the nitro-radical generation in aqueous media can be more useful for further studies with biological targets, in which the experimental conditions should be as close as possible to the biological system.…”

Section: Voltammetric Generation Of Nitro-radical Anion From Nitrofurmentioning

confidence: 99%

“…9,39 We have assumed that NF undergoes the same mechanism as that proposed by other authors, 13,19,22,23 as is depicted in the reaction mechanism below:…”

Section: Voltammetric Generation Of Nitro-radical Anion From Nitrofurmentioning

confidence: 99%

“…12 Many reports on the electrochemistry behavior of nitrofurans can be found in the literature. 14,[19][20][21][22] The voltammetric behavior of nitrofurazone and its electrochemical determination in pharmaceutical samples have also been registered. [23][24][25][26][27] In this study, the voltammetric behavior of nitrofurazone, and its hydroxymethyl derivative, on a glassy carbon electrode in aqueous media is reported.…”

Section: Introductionmentioning

confidence: 99%

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Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity

La-Scalea¹,

Menezes²,

Julião³

et al. 2005

J. Braz. Chem. Soc.

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A doença de Chagas é um grave problema de saúde pública para a América Latina, situação agravada pela inexistência de quimioterapia eficiente. Os dois fármacos comercialmente encontrados, benznidazol e nifurtimox, são eficazes apenas na fase aguda da doença. A nitrofurazona é ativa contra Trypanosoma cruzi, entretanto, a alta toxicidade impede seu uso na parasitose. A hidroximetilnitrofurazona é um pró-fármaco da nitrofurazona, que apresenta maior atividade contra Trypanosoma cruzi, além de ser menos tóxico. Estudou-se o comportamento voltamétrico da nitrofurazona por voltametria cíclica, varredura linear e pulso diferencial, comparando-o ao do metronidazol e do cloranfenicol. Os coeficientes de difusão dos três fármacos foram estimados aplicando-se a equação de Wilke-Chang. Este artigo também apresenta o estudo do derivado hidroximetilnitrofurazona por voltametria cíclica. A redução de nitrofurazona é pH-dependente e em meio ácido o derivado hidroxilamínico, envolvendo quatro elétrons, é o principal produto formado. Em meio alcalino e com prévio tratamento do eletrodo de carbono vítreo, a redução de nitrofurazona ocorre em duas etapas: a primeira envolve um elétron para formar o nitro-radical aniônico e a segunda etapa corresponde à formação da hidroxilamina. Hidroximetilnitrofurazona possui comportamento voltamétrico semelhante e, de forma análoga, apresentou a mesma eletroatividade e capacidade de estabilização do nitro-radical, indicando que a modificação molecular de nitrofurazona não introduziu alterações no seu comportamento voltamétrico. Uma breve discussão das diferenças de atividade biológica entre os compostos também é apresentada.Chagas' disease is a serious health problem for Latin America. The situation is worsened by the lack of efficient chemotherapy. The two available commercial drugs, benznidazole and nifurtimox, are more effective in the acute phase of the disease. Nitrofurazone is active against Trypanosoma cruzi, however its high toxicity precludes its current use in parasitosis. Hydroxymethylnitrofurazone is a prodrug of nitrofurazone. It is more active against Trypanosoma cruzi than nitrofurazone, besides being less toxic. This work shows the voltammetric behavior of nitrofurazone and a comparison with those of metronidazole and chloramphenicol using cyclic, linear sweep and differential pulse voltammetries. For these drugs also the prediction of the diffusion coefficients using Wilke-Chang equation was performed. The reduction of nitrofurazone is pH-dependent and in acidic medium the hydroxylamine derivative, involving four electrons, is the principal product formed. In aqueousalkaline medium and with a glassy carbon electrode pre-treatment the reduction of nitrofurazone occurs in two steps, the first involving one electron to form the nitro-radical anion and the second corresponding to the hydroxylamine derivative formation. Hydroxymethylnitrofurazone presented the same voltammetric behavior and electroactivity, indicating that the molecular modification performed in nitrofurazone did no...

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Section: Voltammetric Generation Of Nitro-radical Anion From Nitrofurmentioning

confidence: 91%

Section: Voltammetric Generation Of Nitro-radical Anion From Nitrofurmentioning

confidence: 99%

“…9,39 We have assumed that NF undergoes the same mechanism as that proposed by other authors, 13,19,22,23 as is depicted in the reaction mechanism below:…”

Section: Voltammetric Generation Of Nitro-radical Anion From Nitrofurmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Voltammetric behavior of nitrofurazone and its hydroxymethyl prodrug with potential anti-Chagas activity

La-Scalea¹,

Menezes²,

Julião³

et al. 2005

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…Sem embargo, a maioria destes métodos podem apresentar dificuldades, como a não regeneração do elétrodo, causada pela adsorção de produtos de oxidação, uso de metais nobres, cujos compostos são muito caros, e a resposta instável, que revela a presença de instabilidades eletroquímicas [29][30][31][32]. Resolver-se-ia o problema se fossem usados os nanotubos de carbono, cujas propriedades excepcionais [33-47] lhes dão excelentes propriedades eletroanalíticas [48][49][50][51][52][53][54][55].…”

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