Charge-transfer chemistry of azithromycin, the antibiotic used worldwide to treat the coronavirus disease (COVID-19). Part I: Complexation with iodine in different solvents

• Published in: Journal of molecular liquids 2021-03, Vol.325, p.115187-115187, Article 115187
• Main Authors: Adam, Abdel Majid A., Saad, Hosam A., Alsuhaibani, Amnah M., Refat, Moamen S., Hegab, Mohamed S.
• Format: Article
• Language: English
• Subjects: Azithromycin; Charge–transfer; Iodine; Solvent effect; Tri–iodide ion
• ISSN: 0167-7322; 1873-3166
• DOI: 10.1016/j.molliq.2020.115187

Around the world, the antibiotic azithromycin (AZM) is currently being used to treat the coronavirus disease (COVID-19) in conjunction with hydroxychloroquine or chloroquine. Investigating the chemical and physical properties of compounds used alone or in combination to combat the COVID-19 pandemic is of vital and pressing importance. The purpose of this study was to characterize the charge transfer (CT) complexation of AZM with iodine in four different solvents: CH2Cl2, CHCl3, CCl4, and C6H5Cl. AZM reacted with iodine at a 1:1 M ratio (AZM to I2) in the CHCl3 solvent and a 1:2 M ratio in the other three solvents, as evidenced by data obtained from an elemental analysis of the solid CT products and spectrophotometric titration and Job's continuous variation method for the soluble CT products. Data obtained from UV–visible and Raman spectroscopies indicated that AZM strongly interacted with iodine in the CH2Cl2, CCl4, and C6H5Cl solvents by a physically potent n→σ* interaction to produce a tri-iodide complex formulated as [AZM·I+]I3−. XRD and TEM analyses revealed that, in all solvents, the AZM-I2 complex possessed an amorphous structure composed of spherical particles ranging from 80 to 110 nm that tended to aggregate into clusters. The findings described in the present study will hopefully contribute to optimizing the treatment protocols for COVID-19. [Display omitted] •CT interaction between azithromycin and iodine was investigated.•Complex structures were characterized using several physicochemical techniques.•Striking color changes were observed in both soluble and solid forms.•This CT interaction occurred through the formation of a tri-iodide complex.