Abstract
Owing to the pharmacological potential of ATRA (all trans-retinoic acid), a series of retinamides and a 1-(retinoyl)-1,3-dicyclohexylurea compound were prepared by reacting ATRA with long chain alkyl or alkenyl fatty amines by using a 4-demethylaminopyridine (DMAP)-catalyzed N,N'-dicyclohexylcarbodiimide (DCC) coupling. The successful synthesis of the target compounds was demonstrated using a range of spectroscopic techniques. The cytotoxicity of the compounds was measured along with their ability to induce cell cycle arrest and apoptosis in human cancer cell lines MCF-7 (breast cancer) and HepG2 (liver cancer) and normal human cell line HEK293 (embryonic kidney). The results of cytotoxicity and flow cytometry data showed that the compounds had a moderate to strong effect against MCF-7 and HepG2 cells and were less toxic to HEK293 cells. N-oleyl-retinamide was found to be the most potent anticancer agent and was more effective against MCF-7 cells than HepG2 cells.
Highlights
Non-contagious diseases, such as cancer, are responsible for 64% of deaths worldwide [1]
Vitamin A, its derivatives and its active metabolite all trans-retinoic acid (ATRA) play a pivotal role in cell growth, differentiation, apoptosis and other related processes [16,17]
The results indicated that ATRA was not effective at concentrations ranging from 10–50 μM (Table 1)
Summary
Non-contagious diseases, such as cancer, are responsible for 64% of deaths worldwide [1]. All trans-retinoic acid (ATRA) is known to induce differentiation in various cancer cells [3,4,5,6]. In view of the above-mentioned examples, it was speculated that the effectiveness of ATRA could be improved by conjugating its polar carboxylic acid group to various long chain fatty acid amines. These novel hybrids were prepared and tested against two human cancer cell lines—MCF-7 (breast cancer) and HepG2 (liver cancer)—to determine their cytotoxicity, their ability to inhibit cell cycle progression and their effect on apoptosis. The cytotoxic effect of the compounds against the normal cell line HEK293 (human embryonic kidney) was evaluated
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