Abstract
ABSTRACT. The electrochemical behavior of two chemically related acridine compounds: tacrine (TAC) and 9-aminoacridine (9-AA) was investigated on a hanging mercury drop electrode (HDME). The electrochemical study was carried out by using Osteryoung square wave voltammetry (OSWV) and cyclic voltammetry (CV) techniques in the Britton-Robinson (B-R) buffer solution at pH = 2.0–12.0, KCl (0.1/0.2/0.3 M) and methanol (0.0-50%) mixture as supporting electrolyte. TAC showed maximum current at pH 7.5 while 9-AA at pH 10, KCl (0.3M), and 10% methanol. The study of electrochemical reduction of 9-AA and TAC on the HDME by using CV resulted in a quasi-reversibility, mainly diffusion-controlled reaction. The reaction involved 1e–/1H+ reduction at nitrogen atom in the case of the 9-AA while the second process involved the 2e–/2H+ reduction of the intra-cyclic azomethine group. The reduction peak potential of structurally related acridine compounds is influenced by the pH values and percentage of the organic solvent of the supporting electrolytes. Also, the study may provide insight into the electron transfer pathways of biological reactions of the acridines and their electrochemical behavior on the electrode.
 
 KEY WORDS: Tacrine, 9-Aminoacridine, Cyclic voltammetry, Osteryoung square wave voltammetry, Hanging mercury dropping electrode
 
 Bull. Chem. Soc. Ethiop. 2021, 35(3), 639-646.
 DOI: https://dx.doi.org/10.4314/bcse.v35i3.14
Highlights
Acridine is a heterocyclic alkaloid nucleus of anthracene
The current study aims to exhibit the power of electrochemistry to differentiate between the electrochemical behavior of these two closely related acridine compounds on HMDE
Throughout the development of the Osteryoung square wave voltammetry (OSWV) to investigate the electrochemical behavior of TAC and 9-AA, the content of the supporting electrode was examined because it influences the medium and boundaries of the electrode surface and might modify the type and kinetics of the electrode reaction [23]
Summary
It has several chemical names such as; dibenzopyridine, 2,3,5,6-dibenzopyridine, and 10-azaanthracene (Figure 1a) It represents a medically active part of several pharmaceutical effective drugs for example; tacrine (TAC), aminoacridine (9-AA). These derivatives attracted much consideration because of their medicinal, physicochemical properties, and applications in many important chemical processes [1]. The 9-AA (Figure 1c) displays a mild antiseptic and antimalarial activity [11] It is considered the most effective base than other amino acridines. The inclusive study of the electrochemical behavior will be suitable in the explanation of the electron transfer pathways of biological reactions of the acridines which possess some pharmaceutical activities. The KCl solution (1.0-3.0 M) was prepared in water (Milli-Q), used as a supporting electrolyte. The solutions for further study were prepared from the stock solution by adequate dilution with supporting electrolytes
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