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<p>A series of 2-phenylindoles were synthesized and studied the radical quenching properties towards compounds with nitrogen radical. The present indoles exhibit radical quenching properties in a substituent dependent manner through proton and electron transfer mechanisms. <i>ortho-</i>Hydroxy-2-phenylindole and <i>para-</i>hydroxy-2-phenylindole show strong radical quenching properties towards DPPH radical as comparable to vitamin C, whereas <i>meta</i>-hydroxy-2-phenylindole and 2-phenylindole exhibit radical quenching properties with lower efficacy. All these indoles, however, exhibit efficient radical quenching properties towards ABTS radical as comparable to DPPH radical (IC<sub>50</sub> towards DPPH/ABTS: 1: 335/22 µM, <b>2</b>: 15/7 µM, <b>3</b>: 102/8 µM, <b>4</b>: 9/10 µM, vitamin C: 10/3 µM). These compounds also bind to lipoxygenase (LOX) and inhibit LOX activity with IC<sub>50</sub> : 18–44 µM. It is shown that O-H bond dissociation energy and ionization energy play important role in deciding the radical quenching properties of present indole compound. The compound-LOX binding affinity and binding interface is computed through autodock vina. The indole-LOX binding interface comprises of hydrophobic amino acid residues. In the presence of. indole molecule, the radical quenching occurs through hydrogen atom and/or through electron and subsequently proton transfer mechanism.</p> Graphical Abstract <p>2-phenylindole derivatives exhibit antioxidant properties in a substituent dependent manner towards DPPH, ABTS and LOX mediated formation of lipid perhydroxyl radical. The mechanism involves hydrogen atom and/or electron and subsequent proton transfer pathway. The IC<sub>50</sub> of inhibition of lipoxygenase (LOX) activity is in the range of 18-44 microM.</p> <p></p>

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Radical Quenching and LOX Inhibiting Properties of Indole Derivatives: A Plausible Mechanism of Action Through HAT, SET-PT and SPLET Pathway

  • 期刊论文

  • 发表日期：

    2026年5月6日

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  • Km Srishti,
  • Oseen Negi,
  • Anamika Gusain,
  • Naresh Kumar,
  • Rahul Kumar Vishwakarma,
  • Prasanta Kumar Hota

摘要

A series of 2-phenylindoles were synthesized and studied the radical quenching properties towards compounds with nitrogen radical. The present indoles exhibit radical quenching properties in a substituent dependent manner through proton and electron transfer mechanisms. ortho-Hydroxy-2-phenylindole and para-hydroxy-2-phenylindole show strong radical quenching properties towards DPPH radical as comparable to vitamin C, whereas meta-hydroxy-2-phenylindole and 2-phenylindole exhibit radical quenching properties with lower efficacy. All these indoles, however, exhibit efficient radical quenching properties towards ABTS radical as comparable to DPPH radical (IC50 towards DPPH/ABTS: 1: 335/22 µM, 2: 15/7 µM, 3: 102/8 µM, 4: 9/10 µM, vitamin C: 10/3 µM). These compounds also bind to lipoxygenase (LOX) and inhibit LOX activity with IC50 : 18–44 µM. It is shown that O-H bond dissociation energy and ionization energy play important role in deciding the radical quenching properties of present indole compound. The compound-LOX binding affinity and binding interface is computed through autodock vina. The indole-LOX binding interface comprises of hydrophobic amino acid residues. In the presence of. indole molecule, the radical quenching occurs through hydrogen atom and/or through electron and subsequently proton transfer mechanism.

Graphical Abstract

2-phenylindole derivatives exhibit antioxidant properties in a substituent dependent manner towards DPPH, ABTS and LOX mediated formation of lipid perhydroxyl radical. The mechanism involves hydrogen atom and/or electron and subsequent proton transfer pathway. The IC50 of inhibition of lipoxygenase (LOX) activity is in the range of 18-44 microM.