Cation-π interactions in ligand recognition and catalysis

被引:400
作者
Zacharias, N [1 ]
Dougherty, DA [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
关键词
D O I
10.1016/S0165-6147(02)02027-8
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
The cation-pi interaction is a potent, general noncovalent binding force that is observed in a wide range of biological contexts. Here, we present an overview of well documented cases in which a cation-pi interaction makes an important contribution to small-molecule recognition at a protein binding site. From these and other studies it is clear that, in addition to the hydrophobic effect, hydrogen bonding and ion pairing, the cation-it interaction must be considered when evaluating drug-receptor interactions.
引用
收藏
页码:281 / 287
页数:7
相关论文
共 77 条
  • [61] Chemically reactive immunogens lead to functional convergence of the immune response
    Shulman, H
    Makarov, C
    Ogawa, AK
    Romesberg, F
    Keinan, E
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) : 10743 - 10753
  • [62] A glia-derived acetylcholine-binding protein that modulates synaptic transmission
    Smit, AB
    Syed, NI
    Schaap, D
    van Minnen, J
    Klumperman, J
    Kits, KS
    Lodder, H
    van der Schors, RC
    van Elk, R
    Sorgedrager, B
    Brejc, K
    Sixma, TK
    Geraerts, WPM
    [J]. NATURE, 2001, 411 (6835) : 261 - 268
  • [63] Escherichia coli dimethylallyl diphosphate:tRNA dimethylallyltransferase:: Site-directed mutagenesis of highly conserved residues
    Soderberg, T
    Poulter, CD
    [J]. BIOCHEMISTRY, 2001, 40 (06) : 1734 - 1740
  • [64] The role of tryptophan residues in the 5-hydroxytryptamines receptor ligand binding domain
    Spier, AD
    Lummis, SCR
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (08) : 5620 - 5625
  • [65] St Charles R, 2000, PROTEIN SCI, V9, P265
  • [66] Crystal structure of the B7-1/CTLA-4 complex that inhibits human immune responses
    Stamper, CC
    Zhang, Y
    Tobin, JF
    Erbe, DV
    Ikemizu, S
    Davis, SJ
    Stahl, ML
    Seehra, J
    Somers, WS
    Mosyak, L
    [J]. NATURE, 2001, 410 (6828) : 608 - 611
  • [67] Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase
    Starks, CM
    Back, KW
    Chappell, J
    Noel, JP
    [J]. SCIENCE, 1997, 277 (5333) : 1815 - 1820
  • [68] Tansey TR, 2001, PROG NUCLEIC ACID RE, V65, P157
  • [69] van Veen HW, 2001, J MOL MICROB BIOTECH, V3, P185
  • [70] Alanine-scanning mutagenesis of transmembrane domain 6 of the M1 muscarinic acetylcholine receptor suggests that Tyr381 plays key roles in receptor function
    Ward, SDC
    Curtis, CAM
    Hulme, EC
    [J]. MOLECULAR PHARMACOLOGY, 1999, 56 (05) : 1031 - 1041