New insight into the role of glutathione reductase in glutathione peroxidase-like activity determination by coupled reductase assay: Molecular Docking Study

被引:7
|
作者
Yu, Sun-Chol [1 ]
Kim, In-Chol [1 ]
Ri, Kum-Ju [1 ]
Ri, Jin [1 ]
Kuehn, Hartmut [2 ]
机构
[1] Pyongyang Univ Med Sci, Fac Pharm, Ryonhwa Dong 2, Central Dist, Pyongyang, North Korea
[2] Univ Med Berlin Charite, Inst Biochem, Charitepl 1, D-10117 Berlin, Germany
关键词
Substituted salicyloyl 5-seleninic acids; Glutathione peroxidase mimics; Ebselen; Glutathione reductase; Molecular docking; Selenenylsulfide; ANTIOXIDANT ACTIVITY; ORGANOSELENIUM COMPOUNDS; HYDROGEN-PEROXIDE; MECHANISM; EBSELEN; ANALOGS; BINDING; MIMICS; ACID; TRYPANOTHIONE;
D O I
10.1016/j.jinorgbio.2020.111276
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
Previously we have shown that among 15 substituted salicyloyl (2-hydroxybenzoyl) 5-seleninic acids (SSAs) 4 compounds with longer side chains or a cyclohexyl group exhibit no glutathione peroxidase (GPx)-like activity in the coupled reductase assay. Experimental inhibition of glutathione reductase (GR) by the selenenylsulfide (a main intermediate in the catalytic cycle for GPx-like activity determination) of one of the inactive compounds led us to assess the interactions between 15 selenenylsulfide compounds and the active site of GR by molecular docking. Docking results showed that S and Se atoms in selenenylsulfides of the compounds with no GPx-like activity were beyond 5 angstrom from S atom of Cys-58 or N atom of imidazole ring of His-467 (Root Mean Square Distances for general assessment of 3 major distances were over 4.8 angstrom) in the active site, so that they could not be catalyzed to be reduced by GR. Furthermore, their docking scores over 89 Kcal/mol meant that the selenenylsulfides were bound too strongly to the active site to leave it, leading eventually to inhibition of GR. We also applied the molecular docking to other GPx mimics such as ebselen, cyclic seleninate esters and di(propylaminomethylphenyl) diselenides to explain the differences in their GPx-like activity depending to the assays used. Our results suggest that the reduction of a selenenylsulfide by GR plays a positive role in GPx-like activity of GPx mimics in the coupled assay and recommended the prediction of possibility and strength of GPx-like activity by molecular docking before entering experimental research.
引用
收藏
页数:10
相关论文
共 50 条
  • [41] MICROMETHODS IN SINGLE MUSCLE-FIBERS .2. DETERMINATION OF GLUTATHIONE REDUCTASE AND GLUTATHIONE-PEROXIDASE
    AUSTIN, L
    ARTHUR, H
    DENIESE, M
    GURUSINGHE, A
    BAKER, MS
    ANALYTICAL BIOCHEMISTRY, 1988, 174 (02) : 575 - 579
  • [42] AGE-RELATED-CHANGES OF GLUTATHIONE CONTENT, GLUTATHIONE-REDUCTASE AND GLUTATHIONE-PEROXIDASE ACTIVITY OF HUMAN ERYTHROCYTES
    MATSUBARA, LS
    MACHADO, PEA
    BRAZILIAN JOURNAL OF MEDICAL AND BIOLOGICAL RESEARCH, 1991, 24 (05) : 449 - 454
  • [43] DEVELOPMENTAL-STUDY OF RAT-BRAIN GLUTATHIONE-PEROXIDASE AND GLUTATHIONE-REDUCTASE
    BRANNAN, TS
    MAKER, HS
    WEISS, C
    NEUROCHEMICAL RESEARCH, 1981, 6 (01) : 41 - 45
  • [44] Assaying phenothiazine derivatives as trypanothione reductase and glutathione reductase inhibitors by theoretical docking and Molecular Dynamics studies
    Iribarne, F.
    Paulino, M.
    Aguilera, S.
    Tapia, O.
    JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2009, 28 (04): : 371 - 381
  • [45] AUTOMATED ASSAYS FOR SUPEROXIDE-DISMUTASE, CATALASE, GLUTATHIONE-PEROXIDASE, AND GLUTATHIONE-REDUCTASE ACTIVITY
    WHEELER, CR
    SALZMAN, JA
    ELSAYED, NM
    OMAYE, ST
    KORTE, DW
    ANALYTICAL BIOCHEMISTRY, 1990, 184 (02) : 193 - 199
  • [46] GLUTATHIONE PEROXIDASE AND GLUTATHIONE REDUCTASE-ACTIVITY OF RAT-LIVER AFTER ADMINISTRATION OF SODIUM SELENITE
    KRUGLIKOVA, GO
    SHTUTMAN, TM
    UKRAINSKII BIOKHIMICHESKII ZHURNAL, 1976, 48 (02): : 223 - 228
  • [47] Relationship between molecular structure and glutathione peroxidase-like activity of selected selenoorganic compounds.
    Piatek, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 101 - MEDI
  • [48] A MOLECULAR-DYNAMICS STUDY OF GLUTATHIONE-REDUCTASE
    HIKICHI, N
    PAULINO, M
    HANSZ, M
    TAPIA, O
    JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 1995, 335 : 243 - 254
  • [49] Colorimetric glutathione assay based on the peroxidase-like activity of a nanocomposite consisting of platinum nanoparticles and graphene oxide
    Hui-Huang Xu
    Hao-Hua Deng
    Xiao-Qing Lin
    Yan-Yu Wu
    Xiu-Ling Lin
    Hua-Ping Peng
    Ai-Lin Liu
    Xing-Hua Xia
    Wei Chen
    Microchimica Acta, 2017, 184 : 3945 - 3951
  • [50] Colorimetric glutathione assay based on the peroxidase-like activity of a nanocomposite consisting of platinum nanoparticles and graphene oxide
    Xu, Hui-Huang
    Deng, Hao-Hua
    Lin, Xiao-Qing
    Wu, Yan-Yu
    Lin, Xiu-Ling
    Peng, Hua-Ping
    Liu, Ai-Lin
    Xia, Xing-Hua
    Chen, Wei
    MICROCHIMICA ACTA, 2017, 184 (10) : 3945 - 3951