Coumarinylmethyl esters for ultrafast release of high concentrations of cyclic nucleotides upon one- and two-photon photolysis

被引：87

作者：

Hagen, V

Dekowski, B

Nache, V

Schmidt, R

Geissler, D

Lorenz, D

Eichhorst, J

Keller, S

Kaneko, H

Benndorf, K

Wiesner, B

机构：

[1] Forsch Inst Mol Pharmakol, D-13125 Berlin, Germany

[2] Univ Jena, Inst Physiol 2, D-6900 Jena, Germany

[3] Univ Frankfurt, Inst Phys & Theoret Chem, D-6000 Frankfurt, Germany

[4] Univ Heidelberg, Inst Zool, Heidelberg, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 48期

关键词：

ion channels; nucleotides; photoactivatable compounds; photolysis; signal transduction;

D O I：

10.1002/anie.200502411

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Shedding light: Efficient activation of cyclic nucleoside monophosphates (cNMPs) can be achieved upon one- and two-photon flash photolysis of novel photolabile coumarinylmethyl esters of cAMP and cGMP (A = adenosine, G = guanosine) as well as their 8-bromosubstituted derivatives. The phototriggers show high solubility in water and permit space- and time-resolved investigations of the molecular mechanisms of cyclic nucleotide dependent processes. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：7887 / 7891

页数：5

相关论文

共 19 条

[1] CYCLIC PHOSPHATES .7. SYNTHESIS AND REACTIVITY OF GUANOSINE 3',5'-PHOSPHORIC ACID ALKYL ESTERS [J].

ENGELS, J .

BIOORGANIC CHEMISTRY, 1979, 8 (01) :9-16

[2] SYNTHESIS, STRUCTURE, AND REACTIVITY OF ADENOSINE CYCLIC 3',5'-PHOSPHATE BENZYL TRIESTERS [J].

ENGELS, J ;

SCHLAEGER, EJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (07) :907-911

[3] Bhc-cNMPs as either water-soluble or membrane-permeant photoreleasable cyclic nucleotides for both one- and two-photon excitation [J].

Furuta, T ;

Takeuchi, H ;

Isozaki, M ;

Takahashi, Y ;

Kanehara, M ;

Sugimoto, M ;

Watanabe, T ;

Noguchi, K ;

Dore, TM ;

Kurahashi, T ;

Iwamura, M ;

Tsien, RY .

CHEMBIOCHEM, 2004, 5 (08) :1119-1128

[4]

Furuta T, 1998, Methods Enzymol, V291, P50

[5] Brominated 7-hydroxycoumarin-4-ylmethyls: Photolabile protecting groups with biologically useful cross-sections for two photon photolysis [J].

Furuta, T ;

Wang, SSH ;

Dantzker, JL ;

Dore, TM ;

Bybee, WJ ;

Callaway, EM ;

Denk, W ;

Tsien, RY .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (04) :1193-1200

[6]

Geiler D., 2005, ANGEW CHEM, V117, P1219

[7] (Coumarin-4-yl)methyl esters as highly efficient, ultrafast phototriggers for protons and their application to acidifying membrane surfaces [J].

Geissler, D ;

Antonenko, YN ;

Schmidt, R ;

Keller, S ;

Krylova, OO ;

Wiesner, B ;

Bendig, J ;

Pohl, P ;

Hagen, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (08) :1195-1198

[8] [7-(dialkylamino)coumarin-4-yl]methyl-caged compounds as ultrafast and effective long-wavelength phototriggers of 8-bromo-substituted cyclic nucleotides [J].

Hagen, V ;

Frings, S ;

Wiesner, B ;

Helm, S ;

Kaupp, UB ;

Bendig, J .

CHEMBIOCHEM, 2003, 4 (05) :434-442

[9]

Hagen V, 2001, ANGEW CHEM INT EDIT, V40, P1046

[10]

Hagen V, 2002, ANGEW CHEM INT EDIT, V41, P3625, DOI 10.1002/1521-3773(20021004)41:19<3625::AID-ANIE3625>3.0.CO