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DFT and electrochemical studies on nortriptyline oxidation sites

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Abstract

A study on the possible sites of oxidation and epoxidation of nortriptyline was performed using electrochemical and quantum chemical methods; these sites are involved in the biological responses (for example, hepatotoxicity) of nortriptyline and other similar antidepressants. Quantum chemical studies and electrochemical experiments demonstrated that the oxidation and epoxidation sites are located on the apolar region of nortriptyline, which will useful for understanding the molecule’s activity. Also, for the determination of the compound in biological fluids or in pharmaceutical formulations, we propose a useful analytical methodology using a graphite-polyurethane composite electrode, which exhibited the best performance when compared with boron-doped diamond or glassy carbon surfaces.

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Acknowledgments

The authors wish to thank the Brazilian Funding Institutions CNPq (The National Council for Scientific and Technological Development) and FAPESP (The State of São Paulo Research Foundation), processes numbers 01/14629-0, 01/06029-3, 05/59992-6, 07/05370-0 and 07/05155-1, for the financial support of this research.

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Authors and Affiliations

  1. Embrapa Instrumentação Agropecuária (CNPDIA), Rua XV de Novembro 1452, 13560-970, São Carlos, SP, Brazil

    Renata A. de Toledo

  2. Centro de Ciências Naturais e Humanas, Universidade Federal do ABC (UFABC), Rua Santa Adélia, 166, Bairro Bangu, 09210-170, Santo André, SP, Brazil

    Mauro C. Santos, Hugo B. Suffredini, Paula Homem-de-Mello & Kathia M. Honorio

  3. Escola de Artes, Ciências e Humanidades, Universidade de São Paulo (USP), Av. Arlindo Bettio, 1000, 03828-000, São Paulo, SP, Brazil

    Kathia M. Honorio

  4. Instituto de Química de São Carlos, Universidade de São Paulo (USP), Av. Trabalhador São-Carlense, 400, Caixa Postal 780, 13560-970, São Carlos, SP, Brazil

    Luiz H. Mazo

Authors
  1. Renata A. de Toledo
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  2. Mauro C. Santos
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  3. Hugo B. Suffredini
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  4. Paula Homem-de-Mello
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  5. Kathia M. Honorio
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  6. Luiz H. Mazo
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Corresponding author

Correspondence to Hugo B. Suffredini.

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de Toledo, R.A., Santos, M.C., Suffredini, H.B. et al. DFT and electrochemical studies on nortriptyline oxidation sites. J Mol Model 15, 945–952 (2009). https://doi.org/10.1007/s00894-009-0451-z

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  • DOI: https://doi.org/10.1007/s00894-009-0451-z

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