Membrane-permeant esters of inositol polyphosphates, chemical syntheses and biological applications

被引:65
|
作者
Li, WH
Schultz, C
Llopis, J
Tsien, RY
机构
[1] UNIV CALIF SAN DIEGO, DEPT CHEM & BIOCHEM, LA JOLLA, CA 92093 USA
[2] UNIV CALIF SAN DIEGO, DEPT PHARMACOL, LA JOLLA, CA 92093 USA
[3] UNIV CALIF SAN DIEGO, HOWARD HUGHES MED INST, LA JOLLA, CA 92093 USA
关键词
D O I
10.1016/S0040-4020(97)00714-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Membrane-permeant derivatives of inositol polyphosphates are useful tools for biological studies. Racemic 2,3,6-tri-O-butyryl-myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester(Bt(3)IP(3)/AM), myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester (IP3/AM), hexakis(propionyloxymethyl) ester (IP3/PM) and hexakis(butyryloxymethyl) ester (IP3/BM) were therefore synthesized, Whereas extracellular application of up to 200 mu M of Bt(3)IP(3)/AM or IP3/AM to 1321N1 astrocytoma cells failed to mobilize internal calcium, IP3/PM and IP3/BM released internal calcium at concentrations as low as 20 mu M and 2 mu M, respectively. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:12017 / 12040
页数:24
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共 20 条
  • [1] Membrane-permeant bioactivatable inositol polyphosphates
    Schultz, C
    Rudolf, MT
    Gillandt, H
    TraynorKaplan, AE
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 65 - CARB
  • [2] Membrane-permeant, bioactivatable derivatives of inositol polyphosphates and phosphoinositides
    Institut für Organische Chemie, Abt. Bioorganische Chemie, Universität Bremen, UFT, 28359 Bremen, Germany
    不详
    不详
    [J]. ACS Symp Ser, (232-243):
  • [3] A practical guide to the synthesis and use of membrane-permeant acetoxymethyl esters of caged inositol polyphosphates
    Srinivas Kantevari
    Grant R J Gordon
    Brian A MacVicar
    Graham C R Ellis-Davies
    [J]. Nature Protocols, 2011, 6 : 327 - 337
  • [4] A practical guide to the synthesis and use of membrane-permeant acetoxymethyl esters of caged inositol polyphosphates
    Kantevari, Srinivas
    Gordon, Grant R. J.
    MacVicar, Brian A.
    Ellis-Davies, Graham C. R.
    [J]. NATURE PROTOCOLS, 2011, 6 (03) : 327 - 337
  • [5] MEMBRANE-PERMEANT DERIVATIVES OF INOSITOL POLYPHOSPHATES APPLIED TO REF-52 FIBROBLASTS
    SCHULTZ, C
    TSIEN, RY
    [J]. FASEB JOURNAL, 1992, 6 (05): : A1924 - A1924
  • [6] Membrane-permeant esters of phosphatidylinositol 3,4,5-trisphosphate
    Jiang, T
    Sweeney, G
    Rudolf, MT
    Klip, A
    Traynor-Kaplan, A
    Tsien, RY
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1998, 273 (18) : 11017 - 11024
  • [7] Transient theory for scanning electrochemical microscopy of biological membrane transport: uncovering membrane-permeant interactions
    Huang, Siao-Han
    Amemiya, Shigeru
    [J]. ANALYST, 2024, 149 (11) : 3115 - 3122
  • [8] Membrane-permeant analogues of the putative second messenger myo-inositol 3,4,5,6-tetrakisphosphate
    Roemer, S
    Stadler, C
    Rudolf, MT
    Jastorff, B
    Schultz, C
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (14): : 1683 - 1694
  • [9] Bioactivatable, membrane-permeant analogs of cyclic nucleotides as biological tools for growth control of C6 glioma cells
    Bartsch, M
    Zorn-Kruppa, M
    Kühl, N
    Genieser, HG
    Schwede, F
    Jastorff, B
    [J]. BIOLOGICAL CHEMISTRY, 2003, 384 (09) : 1321 - 1326
  • [10] Modification of intracellular Ca2+ dynamics by laser inactivation of inositol 1,4,5-trisphosphate receptor using membrane-permeant probes
    Yogo, T
    Kikuchi, K
    Inoue, T
    Hirose, K
    Iino, M
    Nagano, T
    [J]. CHEMISTRY & BIOLOGY, 2004, 11 (08): : 1053 - 1058