Potent 2,2-diphenyl-1-picrylhydrazyl radical-scavenging activity of novel antioxidants, double-stranded tyrosine residues conjugating pyrocatechol.
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.
Showa Pharmaceutical University, Tokyo, Japan. kobayasi@ac.shoyaku.ac.jp
Shigeki
S
Kobayashi
Tsukasa
T
Waki
Ikuo
I
Nakanishi
Ken-ichiro
K
Matsumoto
Kazunori
K
Anzai
D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000378:metabolism*; D002396:Catechols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004578:Electron Spin Resonance Spectroscopy; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005609:Free Radicals / Q000378:metabolism; D015394:Molecular Structure; D010851:Picrates / Q000378:metabolism*; D014443:Tyrosine / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000975:Antioxidants; D001713:Biphenyl Compounds; D002396:Catechols; D016166:Free Radical Scavengers; D005609:Free Radicals; D010851:Picrates; D014443:Tyrosine; C004931:1,1-diphenyl-2-picrylhydrazyl; C034221:catechol