Design and synthesis of novel bis-pyridinium based-ionic liquids as potent antiparasitic agents

Esraa Abdelhamid Moneer; Basant A Bakr; Sara H Akl; Yahya H Shahin; Bassma H Elwakil; Mohamed Hagar; Keshav Raj Paudel; Ateyatallah Aljuhani; Mohamed Reda Aouad; Nadjet Rezki

doi:10.1016/j.heliyon.2023.e15431

Design and synthesis of novel bis-pyridinium based-ionic liquids as potent antiparasitic agents

Heliyon. 2023 Apr 14;9(4):e15431. doi: 10.1016/j.heliyon.2023.e15431. eCollection 2023 Apr.

Affiliations

¹ Department of Medical Laboratory Technology, Faculty of Applied Health Sciences Technology, Pharos University in Alexandria, Alexandria, Egypt.
² Department of Zoology, Faculty of Science, Alexandria University, Alexandria, 21321, Egypt.
³ Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, 21321, Egypt.
⁴ Department of Oriental Medicine Resources, Mokpo National University, Muan-gun, Jeonnam, 58554, Republic of Korea.
⁵ Department of Chemistry, College of Science, Taibah University, Al-Madinah Al-Munawarah, 30002, Saudi Arabia.

Abstract

Focused bis-pyridinium based-ionic liquids were successfully synthesized through the quaternization of the selected 1,2-di(pyridin-4-yl)ethane followed by metathetical anion exchange. The synthesized pyridinium derivatives were fully characterized using various NMR-spectroscopic techniques including ¹H, ¹³C, ¹¹B, ³¹P and ¹⁹F NMR. The synthesized compounds were tested for their potential effect against Toxoplasma gondii. It was revealed that compound 5 had higher antiparasitic activity compared to other compounds. Parasitic reduction percentage reached 38, 50, 77 and 79 for groups III, IV, V and VI respectively in the liver with noticed distortion and deformation in tachyzoites' shape. Surprisingly there was no statistically significant difference between the synthesized compound 5 and the known anti-toxoplasmosis drug pyrimethamine. Histopathological study proved the effectiveness of the synthesized compound 5 on liver, spleen and brain tissues with observed better histological features compared to pyrimethamine treated group. The present investigation may pave the way to the possible use of compound 5 to replace the known drug pyrimethamine with better antiparasitic profile and fewer side effects.

Keywords: Antiparasitic agents; Dicationic ionic liquids; Ionic liquids; Toxoplasmosis infections.