Safe and selective anticancer agents from tetrafluorinated azobenzene‐imidazolium ionic liquids: Synthesis, characterization, and cytotoxic effects

Abstract

A new series of tetrafluorinated azobenzene-imidazolium salts is reported. The azobenzene and imidazolium moieties were functionalized with long alkyl chains and connected via a methylene spacer of varying lengths (n = 3-12). They were characterized using FTIR and NMR spectroscopy, and elemental microanalysis.The cytotoxic potential of these ionic dimers against neuroblastoma (SHSY-5Y), estrogen-positive breast cancer cells (MCF-7), triple-negative breast cancer cells (MDA-MB-231), cervical cancer cells (HeLa), and human skin fibroblasts (Hs27) was evaluated using the MTT assay. The cytotoxicity of these ionic liquids (ILs) was dependent on the spacer length. A cut-off effect was observed, wherein the cytotoxicity of the ILs was enhanced by increasing the nonpolar, hydrophobic spacer length up to a threshold and the potency was leveled off upon chain elongation. All ILs exhibited selective and remarkable inhibition potentials against HeLa cells in a dose-dependent manner, which was 2-22 times stronger than that of etoposide, a clinical anticancer drug. These ILs were less toxic toward skin fibroblasts as implied by much higher IC 50 values. The long-spacer ILs (n = 7-10) were very selective toward HeLa cells. They had a broad safety window with selectivity indices ranging between 5.6 and 11.0. The selectivity of these compounds toward HeLa cells may serve as a new strategy for the design and development of safe and effective chemotherapeutics.

Boosting Ion Conductivities: Light-Modulated Azobenzene-Based Ionic Liquids in Vertical Nanochannels

“…Among all of the known chemical structures, azobenzene is a promising candidate that can undergo a trans–cis isomerization upon irradiation with different wavelengths. It is also worth mentioning that azobenzene-based materials can possess photomodulation of ion conductivities by synthesizing azobenzene-based ionic liquids. , For example, Zhang et al prepared a new class of azobenzene-based photoresponsive ionic liquids that exhibit reversible modulation of the ionic conductivity in specific solvents under alternating UV- and visible-light irradiation . They noted that this phenomenon may be related to the reversible changes in ion cluster aggregation induced by photoisomerization.…”

Novel pyridine bearing pentose moiety-based anticancer agents: design, synthesis, radioiodination and bioassessments

“…Furthermore, synthetic heterocyclic compounds containing nitrogen atoms have proven to have significant and diverse therapeutic potential. Thiazole, pyrazole, diazene and pyrimidine derivatives are reported to exhibit promising industry and biology applications [21][22][23][24][25] . Carbohydrates are natural products that are considered environmentally…”