Abstract

A novel series of thiazolium ionic liquids (TILs) bound to chloride (2a–c), tetrafluoroborate (BF4) (3a–c), and bis-(trifluoromethanesulfonimide) (Tf2N) anions (4a–c) was synthesized and their physicochemical characteristics were investigated using various microanalytical techniques. The pharmacological potential of the new TILs was assessed as chemotherapeutic agents for bacterial infections and ovarian cancer (SKOV-3). Notably, ILs with the same cations become more bactericidal upon their binding with the strongest chaotropic anion (TN2f). The in vitro toxicity of the TILs toward ovarian carcinoma cell lines (SKOV-3) and normal human skin fibroblast cells (HSF) revealed that all tested TILs have the capacity to induce a dose- and time-dependent decline in SKOV-3 cell viability, with Tf2N-linked TILs (4a–c) having a preferable efficacy. In addition, the new compounds showed excellent selectivity for cancer cells (SKOV-3) over healthy cells (HSF). [iPBzTh][Tf2N] (4b) is the most cytotoxic and specific one and may act as a promising anti-ovarian cancer agent.

Highlights

  • Ovarian cancer (OC) is one of the main death causes among females and the 3rd most prevalent gynecological cancer in developing countries.[1]

  • Solvents and chemicals utilized in this study, as well as their suppliers, are listed in the Electronic supplementary information (ESI).† the chloromethylation protocol that was used in the preparation of benzyl derivatives was shown in detail in the ESI.† In addition, the structural characterization methods used for the obtained starting materials and ionic liquids have been described in the ESI.†

  • As part of our continued interest in exploring and synthesizing novel heterocyclic derivatives for many uses, in biological implementations,[31,32] we present here a set of novel thiazolium ionic liquid derivatives for biological applications

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Summary

Introduction

Ovarian cancer (OC) is one of the main death causes among females and the 3rd most prevalent gynecological cancer in developing countries.[1]. Its derivatives have been effectively applied in many pharmacological elds, such as antimicrobial, antitumor, antioxidant, antitubercular, anticonvulsant, anti-in ammatory, diuretic, and neuroprotective agents.[21] In addition, the thiazole ring acts as the main active ingredient in many promising biomolecules, pro-drugs, and clinical drugs.[14] This motivated us to fabricate novel room-temperature thiazolium ILs for chemotherapeutic applications. In continuation of our exploring trip for searching of novel multifunctional chemotherapeutic agents,[17,28] the aforesaid facts motivated us to synthesize a new series of thiazolium ionic liquids (TILs) bound to various N-aralkyl side chains and different anions. The pharmacological potentials of new thiazolium derivatives were in vitro investigated against two pathogenic bacterial strains as well as ovarian cancer cell lines

Materials and instrumentation
Biological studies
Results and discussion
Physical properties of new thiazolium ionic liquids
Structural characterization
Antimicrobial study
Cytotoxicity study
Conclusion
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