4′‐Phenyl‐2, 2′:6′, 2′′‐terpyridine Derivatives Containing 1‐Substituted‐2, 3‐Triazole Ring: Synthesis, Characterization and Anticancer Activity. Issue 24 (27th June 2018)

• Record Type: Journal Article
• Authors: Zych, Dawid; Slodek, Aneta; Krompiec, Stanisław; Malarz, Katarzyna; Mrozek‐Wilczkiewicz, Anna; Musiol, Robert
• Is Part Of: ChemistrySelect. Volume 3:Issue 24(2018)
• Page Start: 7009
• Page End: 7017
• Publication Date: 2018-06-27
• Subjects: anticancer activity -- DFT study -- organic synthesis -- terpyridine derivatives -- photophysical study; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201801204
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Terpyridine moiety is known for chelating and interesting physicochemical properties enabling some applications. Its biological activity, particularly anticancer potency is not well studied. Herein we present six 4′‐(1‐substituted‐2, 3‐triazol‐4‐yl)phenyl‐2, 2′:6′, 2′′‐terpyridine derivatives with glycidyl, cyclohexylmethyl, benzyl, 4‐ tert ‐butylbenzyl, pentafluorobenzyl, and 2, 6‐dichlorobenzyl groups which were obtained via Cu(I)‐catalysed 1, 3‐dipolar cycloaddition reaction. The photophysical such as optical (absorption and photoluminescence spectra, quantum yields and lifetimes) and thermal (by using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA)) properties were examined. In addition, theoretical studies (DFT and TD‐DFT) were performed to provide a deeper understanding of the experimental results. In vitro studies on the obtained novel structures were conducted with selected series of cell lines to check their bioactivity and toxicity. The most active compound reached a nanomolar level with good selectivity index better than doxorubicin. Mechanism of action for these terpyridines was also investigated which suggest intercalation of DNA as a trigger of cell death. Abstract : Novel derivatives of 4′‐(1‐substituted‐2, 3‐triazol‐4‐yl)phenyl‐2, 2′:6′, 2′′‐terpyridine derivatives with various substituents were obtained. The photophysical such as optical and thermal properties were examined. The structural properties were analyzed by using theoretical calculations. Antiproliferative activity of target compounds in a panel of cancer cells was studied.