Synthesis of L-Dopa Modifier L-Dopa-L-His and its Interaction with DNA

Title:Synthesis of L-Dopa Modifier L-Dopa-L-His and its Interaction with DNA

Volume: 12 Issue: 7

Author(s): Dongxin Zhao, Li Ma and Kui Lu

Affiliation:

Keywords: DNA, fluorescence, intercalation, L-dopa-L-His, modification, purification, synthesis.

Abstract: Though L-dopa is an effective drug for Parkinson’s disease, the usage of L-dopa in clinical treatment is limited for its physico-chemical properties which affect the bioavailability of L-dopa and increase the side effects of L-dopa. For improving the availability of L-dopa, L-dopa-L-His was synthesized by Fmoc solid-phase peptide synthesis, purified by reversed-phase HPLC and characterized by using ¹H, ¹³C NMR and ESI-MS. The interaction of L-dopa-L-His and L-dopa with ctDNA has been investigated respectively by UV absorption and fluorescence spectroscopy. The results indicated that both L-dopa and L-dopa-L-His interacted with ctDNA through intercalative mode. The binding constant of L-dopa and Ldopa- L-His with ctDNA were 4.99x10¹⁰ L·mol^-1·s^-1 and 8.25x10¹¹ L·mol^-1·s^-1, which showed a higher affinity of L-dopa- L-His to DNA for the imidazole side-chain. Meanwhile, compared with the free L-dopa, gel electrophoresis assay also demonstrated that the L-dopa-L-His interacted with plasmid DNA by stronger intercalation.

Cite this article as:

Zhao Dongxin, Ma Li and Lu Kui, Synthesis of L-Dopa Modifier L-Dopa-L-His and its Interaction with DNA, Letters in Organic Chemistry 2015; 12 (7) . https://dx.doi.org/10.2174/1570178612666150506235651