Novel Dipyridinium Lipophile-Based Ionic Liquids Tethering Hydrazone Linkage: Design, Synthesis and Antitumorigenic Study

Abstract

Novel dicationic pyridinium ionic liquids tethering amphiphilic long alkyl side chains and fluorinated counter anions have been successfully synthesized by means of the quaternization of the dipyridinium hydrazone through its alkylation with different alkyl halides. The resulting halogenated di-ionic liquids underwent a metathesis reaction in order to incorporate some fluorinated counter anions in their structures. The structures of all the resulting di-ionic liquids were characterized by several spectroscopic experiments. The antitumorigenic activities of the investigated compounds were further studied against three different human lung cancer cell lines. Compared to the standard chemotherapeutic agent, cisplatin, the synthesized di-ionic liquids exerted equal, even more active, moderate, or weak anticancer activities against the various lung cancer cell lines under investigation. The observed anticancer activity appears to be enhanced by increasing the length of the aliphatic side chains. Moreover, dicationic pyridinium bearing a nine carbon chain as counter cation and hexafluoro phosphate and/or tetrafluoro bororate as counter anion were selected for further evaluation and demonstrated effective and significant antimetastatic effects and suppressed the colonization ability of the lung cancer cells, suggesting a therapeutic potential for the synthesized compounds in lung cancer treatment.

Dicationic Bis-Pyridinium Hydrazone-Based Amphiphiles Encompassing Fluorinated Counteranions: Synthesis, Characterization, TGA-DSC, and DFT Investigations

“…The third range corresponds to the evaporation of any residual decomposition products. It is obvious from Table 1 that there is a large difference between the melting points of the investigated compounds and their previously reported analogues [47]. The present series contains linear compounds which permit a high degree of intermolecular forces; however, the previously reported ones are angular geometrical structures that are not suitable for close-packed positioning of the molecules.…”

Unlocking the Anticancer Potential of Ionic Liquids

“…Betulinic acid [38] [Bet][Tau] and [Car][Tau] L-(-)-carnitine and betaine Taurine [39] Dicationic pyridinium lipophile-based ILs incorporating hydrazone anion Lipophilic pyridinium Hydrazone [40] derived from biocompatible choline, amino acids, and ammonia showed improved aqueous solubility that was at least 78-fold higher than that of the free FAV [56]. In addition to improving the solubility of FAV, the FAV-ILs had improved pharmacokinetic and pharmacodynamic properties, compared with free FAV.…”

Ionic Liquids: Momentous Tools in Transdermal Delivery of Biomacromolecules

“…[36] Initially, ILs were used as a substitute for organic solvents. [37] Subsequently, ILs based on choline, [28,38] pyridine, [39] and imidazole [40] were developed. For example, choline-based [Chl][FAs] increased the permeability of peptides 28-fold when compared with aqueous delivery vehicles.…”