Synthesis, Characterization, and Determination of Biological Activity of Functional Molecules and Nanoconjugates Using Chiral N-Heterocyclic Carbene Ligands
Project no. 20195 · Status: Kapanmış · 2019
Summary
N-Heterocyclic carbenes (NHCs) are widely recognized as important structural models for the synthesis of pharmaceutical and biologically active substances. Carbohydrate-based NHC ligands initially caught the attention of organometallic chemists because carbohydrates are known to play key roles in a variety of biological recognition and signaling processes. Many carbohydrate-based ligands have been synthesized, designed and linked to different metal centers for the discovery of new metal-based drugs. In this study, aminochloralose derivatives of amino sugars (?-chloralose (a), galactochloralose (b) and mannochloralose (c), their imidazole derivatives (1a-c) and the final compounds 2,4,6-chiral furanoside-based NHC ligands) Trimethylbenzyl-linked imidazolium salts (2a-c) were resynthesized step by step according to our well-defined and proven synthesis methods. For biological activity measurements, a chiral furanoside-based NHC ligand (2b) conjugated with gold nanoparticles (AuNP-Cyt) and silver nanoparticles (AgNP-Cyt) with added a cysteamine (Cyt) binder was prepared. Obtained new gluconanoparticles (AuNP-Cyt-2b and AgNP-Cyt-2b), transmission electron microscopy (TEM), scanning electron microscope (SEM), dynamic light scattering (DLS), SEM energy dispersion X-ray spectroscopy (SEM/EDX) ), was characterized by X-ray photoelectron spectroscopy (XPS) and UV-visible spectrophotometric techniques. For other biological applications on HeLa, the A549 lung cancer cell line and human uterine cancer cell line used with the MTT cell proliferation method were exhibited in the biological evaluation of these NPs conjugated with sugar-based N-heterocyclic carbene ligand (2b). The satisfactory results obtained showed that these are radiotherapeutic agents. Antimicrobial activities of NHC ligands and their nanoconjugates were also evaluated against some test microorganisms by disk diffusion test method.