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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 12 , Issue 7 , 2015

Page: [459 - 464] Pages: 6

DOI: 10.2174/1570178612666150506235651

Price: $65


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.

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

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