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J Biol Chem, Vol. 273, Issue 18, 11017-11024, May 1, 1998
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From the Phosphoinositide 3-OH kinases and their products,
D-3 phosphorylated phosphoinositides, are increasingly recognized as
crucial elements in many signaling cascades. A reliable means to
introduce these lipids into intact cells would be of great value for
showing the physiological roles of this pathway and for testing the
specificity of pharmacological inhibitors of the kinases. We have
stereospecifically synthesized
di-C8-PIP3/AM and
di-C12-PIP3/AM, the heptakis(acetoxymethyl) esters of dioctanoyl- and dilauroylphosphatidylinositol
3,4,5-trisphosphate, in 14 steps from myo-inositol. The
ability of these uncharged lipophilic derivatives to deliver
phosphatidylinositol 3,4,5-trisphosphate across cell membranes was
demonstrated on 3T3-L1 adipocytes and T84 colon carcinoma
monolayers. Insulin stimulation of hexose uptake into adipocytes was
inhibited by the kinase inhibitor wortmannin and was largely restored
by di-C8-PIP3/AM, which had no effect in the
absence of insulin. Thus phosphatidylinositol 3,4,5-trisphosphate or a
metabolite was necessary but not sufficient for stimulation of hexose
transport. In T84 epithelial monolayers,
di-C12-PIP3/AM mimicked epidermal growth factor
in inhibiting chloride secretion and potassium efflux, suggesting that
phosphatidylinositol 3,4,5-trisphosphate was sufficient to modulate
these fluxes and mediate epidermal growth factor's action.
Department of Pharmacology and Howard Hughes
Medical Institute, University of California San Diego, La Jolla,
California 92093-0647, the ¶ Division of Cell Biology, The
Hospital for Sick Children, Toronto, Ontario M5G 1X8, Canada, the
Institute of Organic Chemistry, University of Bremen UFT, 28359 Bremen, Germany, and the ** Department of Medicine, University of
California San Diego, La Jolla, California 92093
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