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

来源：

TETRAHEDRON | 1997年 / 53卷 / 35期

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

页码：12017 / 12040

页数：24

共 42 条

[1] CYCLITOLS .21. BENZYL ETHERS OF MYOINOSITOL . AROMATISATION OF TOSYL DERIVATIVE OF A MYOINOSITOL
ANGYAL, SJ
TATE, ME
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1965, (DEC): : 6949 - &
[2] A SIMPLE AND EFFECTIVE CHEMICAL PHOSPHORYLATION PROCEDURE FOR BIOMOLECULES
BANNWARTH, W
TRZECIAK, A
[J]. HELVETICA CHIMICA ACTA, 1987, 70 (01) : 175 - 186
[3] A TRANSIENT CALCIUM-DEPENDENT CHLORIDE CURRENT IN THE IMMATURE XENOPUS OOCYTE
BARISH, ME
[J]. JOURNAL OF PHYSIOLOGY-LONDON, 1983, 342 (SEP): : 309 - 325
[4] A SYNTHESIS OF 1D-MYO-INSITOL AND 1L-MYO-INOSITOL 1,3,4,5-TETRAPHOSPHATE
BAUDIN, G
GLANZER, BI
SWAMINATHAN, KS
VASELLA, A
[J]. HELVETICA CHIMICA ACTA, 1988, 71 (05) : 1367 - 1378
[5] INOSITOL PHOSPHATES AND CELL SIGNALING
BERRIDGE, MJ
IRVINE, RF
[J]. NATURE, 1989, 341 (6239) : 197 - 205
[6] INOSITOL TRISPHOSPHATE AND CALCIUM SIGNALING
BERRIDGE, MJ
[J]. NATURE, 1993, 361 (6410) : 315 - 325
[7] THE TOTAL SYNTHESIS OF MYOINOSITOL PHOSPHATES VIA MYOINOSITOL ORTHOFORMATE
BILLINGTON, DC
BAKER, R
KULAGOWSKI, JJ
MAWER, IM
VACCA, JP
DESOLMS, SJ
HUFF, JR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08): : 1423 - 1429
[8] MYOINOSITOL 1,4,5-TRISPHOSPHOROTHIOATE - A NOVEL ANALOG OF A BIOLOGICAL 2ND MESSENGER
COOKE, AM
GIGG, R
POTTER, BVL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (20) : 1525 - 1526
[9] EVIDENCE FOR ACYLOXYMETHYL ESTERS OF PYRIMIDINE 5'-DEOXYRIBONUCLEOTIDES AS EXTRACELLULAR SOURCES OF ACTIVE 5'-DEOXYRIBONUCLEOTIDES IN CULTURED-CELLS
FREED, JJ
FARQUHAR, D
HAMPTON, A
[J]. BIOCHEMICAL PHARMACOLOGY, 1989, 38 (19) : 3193 - 3198
[10] THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE-CHEMISTRY .18. ALLYL AND BENZYL ETHERS OF MYOINOSITOL - INTERMEDIATES FOR THE SYNTHESIS OF MYOINOSITOL TRISPHOSPHATES
GIGG, J
GIGG, R
PAYNE, S
CONANT, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (02): : 423 - 429

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