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Ionic liquids have drawn a lot of attraction due to their unique properties. In this paper, a simple, inexpensive, easy to handle, and efficient method for the synthesis of 1-(4-((1-carboxyethyl)carbamoyl)benzyl)pyridin-1-ium chloride and 1-(4-(((1-carboxyethyl)carbamothioyl)carbamoyl)benzyl)pyridin-1-ium chloride as two novel chiral ionic liquids based on the L-(+)-alanine amino acid is introduced. Their structures were confirmed via 1 H-NMR, 13 C-NMR and FT-IR spectroscopies. Minimum inhibitory concentration method was used to study their antibacterial properties. Their antioxidant properties were investigated on 2,2-diphenyl-1-picrylhydrazyl as a free radical. Results confirmed these compounds as strong antibacterial and antioxidant ionic liquids, capable of replacing many antibiotic, and potentially, anticancer compounds.

Zinc ion (Zn2+) homeostasis is very important for sperm capacitation and hyperactivation. Zn2+ is a specific inhibitor of the voltage-dependent proton channel (Hv1). Intracellular alkalisation of human spermatozoa is mainly dependent on opening of Hv1. Anandamide may affect spermatozoa through activation of Hv1. An increase in intracellular pH and progesterone (P4) activate cation channels of spermatozoa (CatSper). This study was designed to elucidate the interaction between ZnCl2, P4 and anandamide on human sperm function and intracellular calcium concentrations ([Ca2+]i). Human normal semen samples (n = 30) were diluted (20 × 106 spermatozoa mL−1) and divided into control and ethanol (0.01%)-, anandamide (1 nM)-, ZnCl2 (1 mM)-, P4 (10µM)-, anandamide+ZnCl2- and P4+ZnCl2-treated groups. Sperm kinematics, viability, acrosome status and [Ca2+]i were assessed. The percentage of viable and motile spermatozoa and sperm velocity was reduced in the ZnCl2-treated groups. Anandamide and P4 attenuated the inhibitory effects of ZnCl2 on sperm kinematics. Loss of the acrosome membrane was observed in all experimental groups. P4 and anandamide are present naturally in secretions of the female reproductive tract and modulate the inhibitory effects of ZnCl2 on sperm kinematics. This attenuation is probably due to a change in [Ca2+]i and prevention of Hv1 inactivation by P4 and anandamide respectively.