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

收藏

页码：12017 / 12040

页数：24

相关论文

共 42 条

[1] CYCLITOLS .21. BENZYL ETHERS OF MYOINOSITOL . AROMATISATION OF TOSYL DERIVATIVE OF A MYOINOSITOL [J].

ANGYAL, SJ ;

TATE, ME .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (DEC) :6949-&

[2] A SIMPLE AND EFFECTIVE CHEMICAL PHOSPHORYLATION PROCEDURE FOR BIOMOLECULES [J].

BANNWARTH, W ;

TRZECIAK, A .

HELVETICA CHIMICA ACTA, 1987, 70 (01) :175-186

[3] A TRANSIENT CALCIUM-DEPENDENT CHLORIDE CURRENT IN THE IMMATURE XENOPUS OOCYTE [J].

BARISH, ME .

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 [J].

BAUDIN, G ;

GLANZER, BI ;

SWAMINATHAN, KS ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1988, 71 (05) :1367-1378

[5] INOSITOL PHOSPHATES AND CELL SIGNALING [J].

BERRIDGE, MJ ;

IRVINE, RF .

NATURE, 1989, 341 (6239) :197-205

[6] INOSITOL TRISPHOSPHATE AND CALCIUM SIGNALING [J].

BERRIDGE, MJ .

NATURE, 1993, 361 (6410) :315-325

[7] THE TOTAL SYNTHESIS OF MYOINOSITOL PHOSPHATES VIA MYOINOSITOL ORTHOFORMATE [J].

BILLINGTON, DC ;

BAKER, R ;

KULAGOWSKI, JJ ;

MAWER, IM ;

VACCA, JP ;

DESOLMS, SJ ;

HUFF, JR .

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 [J].

COOKE, AM ;

GIGG, R ;

POTTER, BVL .

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 [J].

FREED, JJ ;

FARQUHAR, D ;

HAMPTON, A .

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 [J].

GIGG, J ;

GIGG, R ;

PAYNE, S ;

CONANT, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (02) :423-429

← 1 2 3 4 5 →