Abstract
The aim of this study was to synthesize and examine possible in vitro antioxidant effects of indole-based melatonin analogue compounds. As a part of our ongoing study nineteen indole hydrazide/hydrazone derivatives were synthesized, characterized and their in vitro antioxidant activity was investigated by three different assays: by evaluating their reducing effect against oxidation of a redox sensitive fluorescent probe, by examining their protective effect against H2O2-induced membrane lipid peroxidation and by determining their inhibitory effect on AAPH–induced hemolysis of human erythrocytes. The results indicated significant strong antioxidant activity for most of the compounds, when compared to melatonin.
Highlights
Antioxidants are molecules which can interact with free radicals and stop their chain reactions before important and essential molecules are damaged
Three parts of the MLT molecule were modified to develop new indole-based MLT analogue compounds. These modifications were done mainly on the acylamino group (Figure 1). These chemically significant modulations of the lead structure were made at three different points: the methoxy group replaced with hydrogen at the 5-position of the indole ring and acetylaminoethyl side chain modified by formation of imine and hydrogen replaced with methyl on nitrogen
[26] MLT scavenges the radicals most likely via electron donation, thereby neutralizing the radicals and generating nitrogen centered radical, the indolyl cation radical. These results suggest a new approach for the in vitro antioxidant activity properties and structure activity relationship of 1 and 3 substituted indole ring regarding to antioxidant activity
Summary
Antioxidants are molecules which can interact with free radicals and stop their chain reactions before important and essential molecules are damaged. Free radicals are produced basically during cellular metabolism and some functional activities and have essential roles. Excessive free radical attack can damage DNA, proteins and lipids, resulting very important diseases. Antioxidants can decrease the oxidative damage by reacting with free radicals or by inhibiting their activity. It is well known that indole derivatives, extensively present in natural compounds, are very important substances for their medicinal and biological aspects. Antioxidant effects of the indole ringcontaining substance melatonin (MLT) have been well described and evaluated by Tan et al [1]. It is a highly conserved molecule that it acts as a free radical scavenger and a broad-spectrum antioxidant [2]
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