Preparation and Anticancer Activities of Some Amino Acid Methyl Ester Schiff Bases

Abstract

In this study, we prepared nine Schiff bases by condensation of amino acid methyl esters (isoleucine, phenylalanine and methionine) with salicylaldehyde derivatives (2,4-dihydroxybenzaldehyde, 2-hydroxy-3-methoxybenzaldehyde and 5-bromo-2-hydroxybenzaldehyde) and characterized by various spectroscopic methods (FT-IR, UV-Vis and NMR techniques). FT-IR and UV-Vis spectra exhibited characteristic peaks for all imine compounds. NMR spectra pointed out the imine bond which is the indicator of the formation of Schiff bases. Besides, antiproliferative and cytotoxic features of the Schiff bases were examined by using MTT cell proliferation and LDH cytotoxicity assays, respectively. Amongst the synthesized Schiff bases, compound 3d exhibited a very strong antiproliferative effect against all cells except A549. The experimental studies revealed that the Schiff bases synthesized in this study, especially 3d, have an important potential to enter drug development studies.

Keywords

• amino acid schiff base
• salicylaldehyde
• antiproliferative activity
• cytotoxicity
• anticancer activity