Charge Transfer Complex of Neostigmine with 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone: Synthesis, Spectroscopic Characterization, Antimicrobial Activity, and Theoretical Study

Abstract

Background

Electron donor–acceptor interactions are important molecular reactions for the activity of pharmacological compounds. The aim of the study is to develop a charge transfer (CT) complex: synthesis, characterization, antimicrobial activity, and theoretical study.

Method and Results

A solid CT complex of neostigmine (NSG) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was synthesized and characterized by infrared spectra, NMR, and UV–visible spectroscopy. The results confirm the formation of a CT complex. The stability of the CT complex between NSG and DDQ in acetonitrile was determined in solution via spectrophotometric measurement, ie, by calculating the formation constant, molar extinction coefficient, and different spectroscopic parameters. The stoichiometry of the formed NSG–DDQ complex was determined using Job’s method. The absorption band of the NSG–DDQ complex can be used for the quantification of NSG.

Conclusion

The DFT geometry optimization of NSG, DDQ, and the CT complex and the UV comparative study of both theoretical and experimental structures are presented. The experimental results confirm the charge transfer structure. The bacterial study shows that the NSG–DDQ complex has good antibacterial activity against both Gram-positive and Gram-negative bacteria as well as antifungal activity against Candida albicans.

Keywords:

• charge transfer complex
• neostigmine
• DDQ
• synthesis
• spectroscopic
• characterization
• antimicrobial activity
• theoretical study

Acknowledgments

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding the work through the research group project No. RGP-1436-024.

Disclosure

The authors report no conflicts of interest for this work.