Synthesis and Preliminary Study on the DNA-binding Property of Tranexamic Acid Derivatives

Abstract

Tranexamic acid derivatives modified by amino acids, i.e. tranexamic acid-His, tranexamic acid-Leu-His, tranexamic acid-Glu-Phe, tranexamic acid-Glu-Lys, tranexamic acid-Ser-Tyrand, tranexamic acid-Ser-Phe, were synthesized by Fmoc solid-phase peptide synthesis, purified by reversed-phase high performance liquid chromatography and characterized by 1 H and electrospray ionisation mass spectrometry. The interactions of tranexamic acid and derivatives with calf thymus DNA were preliminarily investigated by ultravioletvisible absorption spectroscopy. The adsorption spectra of calf thymus DNA show a hypochromic effect, indicating that tranexamic acid and derivative scan interact with calf thymus DNA through a mixture mode of groove-binding and electrostatic interaction. The higher affinity of tranexamic acid derivatives for calf thymus DNA compared with free tranexamic acid indicates that the side chains of amino acid residues helped form a special surrounding and spatial structure to interact with calf thymus DNA. The stronger interaction of tranexamic acid derivatives with calf thymus DNA suggested that the modified tranexamic acid probably had significant practical value and should be further studied.