Rates of reaction of indoleacetic acids with horseradish peroxidase compound I and their dependence on the redox potentials

被引:59
作者
Candeias, LP [1 ]
Folkes, LK [1 ]
Porssa, M [1 ]
Parrick, J [1 ]
Wardman, P [1 ]
机构
[1] BRUNEL UNIV,DEPT CHEM,UXBRIDGE UB8 3PH,MIDDX,ENGLAND
关键词
D O I
10.1021/bi9514424
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The rates of reaction of seven indole-3-acetic acid derivatives with horseradish peroxidase compound I at pH 5 were measured by stopped flow, and the reduction potentials and pK(a) of their radical cations were determined by pulse radiolysis, Reasonable correlation of these properties with Hammett substituent parameters was found, but not with Brown-Okamoto (sigma(+)) parameters. The rates of reaction with compound I correlate well with the reduction potentials under the same conditions, with rates of reaction that increase by ca. 2.5 orders of magnitude with a 100 mV decrease in the reduction potential. This relationship is in agreement with that previously estimated for the reaction of compound I with phenols and anilines, suggesting that the rate of reaction depends solely on the reduction potential of the substrate radical, even for compounds of dissimilar structure.
引用
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页码:102 / 108
页数:7
相关论文
共 30 条
  • [1] [Anonymous], 1990, PULSE RADIOLYSIS
  • [2] FREE-RADICAL INDUCED ONE-ELECTRON OXIDATION OF THE PHENOTHIAZINES CHLORPROMAZINE AND PROMETHAZINE
    BAHNEMANN, D
    ASMUS, KD
    WILLSON, RL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (11): : 1661 - 1668
  • [3] A PULSE-RADIOLYSIS STUDY OF THE REACTION OF OZONE WITH CL2-RADICAL-ANION IN AQUEOUS-SOLUTIONS
    BIELSKI, BHJ
    [J]. RADIATION PHYSICS AND CHEMISTRY, 1993, 41 (03): : 527 - 530
  • [4] Brownlee R. T. C., 1973, PROGR PHYS ORG CHEM, V10, P1, DOI DOI 10.1002/9780470171899.CH1
  • [5] FREE-RADICAL INTERMEDIATES AND STABLE PRODUCTS IN THE OXIDATION OF INDOLE-3-ACETIC-ACID
    CANDEIAS, LP
    FOLKES, LK
    DENNIS, MF
    PATEL, KB
    EVERETT, SA
    STRATFORD, MRL
    WARDMAN, P
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (40) : 10131 - 10137
  • [6] ENHANCEMENT OF LIPID-PEROXIDATION BY INDOLE-3-ACETIC-ACID AND DERIVATIVES - SUBSTITUENT EFFECTS
    CANDEIAS, LP
    FOLKES, LK
    PORSSA, M
    PARRICK, J
    WARDMAN, P
    [J]. FREE RADICAL RESEARCH, 1995, 23 (05) : 403 - 418
  • [7] FREE-RADICAL INTERMEDIATES IN THE OXIDATION OF FLAVONE-8-ACETIC ACID - POSSIBLE INVOLVEMENT IN ITS ANTITUMOR-ACTIVITY
    CANDEIAS, LP
    EVERETT, SA
    WARDMAN, P
    [J]. FREE RADICAL BIOLOGY AND MEDICINE, 1993, 15 (04) : 385 - 394
  • [8] A MECHANISTIC STUDY OF THE OXIDATION OF PHENOLS IN AQUEOUS-SOLUTION BY OXOIRON(IV) TETRA(N-METHYLPYRIDYL)PORPHYRINS - A MODEL FOR HORSERADISH-PEROXIDASE COMPOUND-II
    COLCLOUGH, N
    SMITH, JRL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (06): : 1139 - 1149
  • [9] PULSE RADIOLYTIC MEASUREMENT OF REDOX POTENTIALS - THE TYROSINE AND TRYPTOPHAN RADICALS
    DEFELIPPIS, MR
    MURTHY, CP
    FARAGGI, M
    KLAPPER, MH
    [J]. BIOCHEMISTRY, 1989, 28 (11) : 4847 - 4853
  • [10] KINETIC STUDY OF REACTION OF HORSERADISH-PEROXIDASE WITH HYDROGEN-PEROXIDE
    DOLMAN, D
    NEWELL, GA
    THURLOW, MD
    DUNFORD, HB
    [J]. CANADIAN JOURNAL OF BIOCHEMISTRY, 1975, 53 (05): : 495 - 501