Potent 2,2-Diphenyl-1-picrylhydrazyl Radical-Scavenging Activity of Novel Antioxidants, Double-Stranded Tyrosine Residues Conjugating Pyrocatechol

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  • Kobayashi Shigeki
    Division of Analytical Chemistry of Medicines, Showa Pharmaceutical University
  • Waki Tsukasa
    Division of Analytical Chemistry of Medicines, Showa Pharmaceutical University
  • Nakanishi Ikuo
    Radiation Modifier Research Team, Heavy-Ion Radiobiology Research Group, Research Center for Charged Particle Therapy, National Institute of Radiological Sciences
  • Matsumoto Ken-ichiro
    Radiation Modifier Research Team, Heavy-Ion Radiobiology Research Group, Research Center for Charged Particle Therapy, National Institute of Radiological Sciences
  • Anzai Kazunori
    Radiation Modifier Research Team, Heavy-Ion Radiobiology Research Group, Research Center for Charged Particle Therapy, National Institute of Radiological Sciences

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New potent antioxidants conjugating the catechol (=pyrocatechol; pyrCat) group to two N-termini of modified double-stranded tyrosine residues were synthesized and showed radical scavenging activity with 2,2-diphenyl-1-picrylhydrazyl radical (DPPH radical, DPPH˙) as a free radical model, second-order rate constants for the DPPH˙ scavenging reaction, and the results from electron spin resonance (ESR) studies. It was found that the tyrosine (Tyr) residue and pyrCat containing new antioxidants developed in the study have about 3—20 times more potent antioxidative activity than Trolox, pyrCat, and L-ascorbic acid (VC). In order to elucidate the relationship between antioxidant activity and the molecular orbital states, and to design potent antioxidants we present an interesting approach using an absolute hardness (η)–absolute electronegativity (χ) diagram based on chemical hardness. It was shown that quantum chemicals were required to develop potent antioxidants.

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