Electrochemical Characterization of Central Action Tricyclic Drugs by Voltammetric Techniques and Density Functional Theory Calculations

Edson Silvio Batista Rodrigues; Isaac Yves Lopes de Macêdo; Larissa Lesley da Silva Lima; Douglas Vieira Thomaz; Carlos Eduardo Peixoto da Cunha; Mayk Teles de Oliveira; Nara Ballaminut; Morgana Fernandes Alecrim; Murilo Ferreira de Carvalho; Bruna Guimarães Isecke; Karla Carneiro de Siqueira Leite; Fabio Bahls Machado; Freddy Fernandes Guimarães; Ricardo Menegatti; Vernon Somerset; Eric de Souza Gil

doi:10.3390/ph12030116

Electrochemical Characterization of Central Action Tricyclic Drugs by Voltammetric Techniques and Density Functional Theory Calculations

Pharmaceuticals (Basel). 2019 Aug 1;12(3):116. doi: 10.3390/ph12030116.

Authors

Edson Silvio Batista Rodrigues¹, Isaac Yves Lopes de Macêdo¹, Larissa Lesley da Silva Lima¹, Douglas Vieira Thomaz¹, Carlos Eduardo Peixoto da Cunha¹, Mayk Teles de Oliveira¹, Nara Ballaminut¹, Morgana Fernandes Alecrim¹, Murilo Ferreira de Carvalho¹, Bruna Guimarães Isecke¹, Karla Carneiro de Siqueira Leite¹, Fabio Bahls Machado¹, Freddy Fernandes Guimarães², Ricardo Menegatti¹, Vernon Somerset³, Eric de Souza Gil⁴

Affiliations

¹ Faculdade de Farmácia, Universidade Federal de Goiás, Goiânia GO 74690-970, Brazil.
² Bloco IQ-1, Campus Samambaia, Avenida Esperança s/n, Instituto de Química, Universidade Federal de Goiás, Goiânia CEP 74690-900, Brazil.
³ Department of Chemistry, Faculty of Applied Sciences, Cape Peninsula University of Technology, Bellville 7535, South Africa.
⁴ Faculdade de Farmácia, Universidade Federal de Goiás, Goiânia GO 74690-970, Brazil. ericsgil@gmail.com.

Abstract

This work details the study of the redox behavior of the drugs cyclobenzaprine (CBP), amitriptyline (AMP) and nortriptyline (NOR) through voltammetric methods and computational chemistry. Results obtained in this study show that the amine moiety of each compound is more likely to undergo oxidation at 1a at E_p1a ≈ 0.69, 0.79, 0.93 V (vs. Ag/AgCl/KClsat) for CBP, AMP and NOR, respectively. Moreover, CBP presented a second peak, 2a at E_p2a ≈ 0.98 V (vs. Ag/AgCl/KClsat) at pH 7.0. Furthermore, the electronic structure calculation results corroborate the electrochemical assays regarding the HOMO energies of the lowest energy conformers of each molecule. The mechanism for each anodic process is proposed according to electroanalytical and computational chemistry findings, which show evidence that the methods herein employed may be a valuable alternative to study the redox behavior of structurally similar drugs.

Keywords: computational chemistry; cyclobenzaprine; electrochemistry; electronic structure; oxidation mechanism.

Abstract

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