Acyloxycoumarinylmethyl-Caged cAMP, the Photolabile and Membrane-Permeable Derivative of cAMP That Effectively Stimulates Pigment-Dispersion Response of Melanophores

Two acyloxycoumarinylmethyl-caged cAMPs (ACM- and PCM-cAMP) have been synthesized using a silver (I) oxide promoted method. Introduction of the acyloxy group to the 7-position on the coumarin ring not only enhanced the membrane permeability but diminished the photolability of the coumarin-cage. Beca...

Full description

Saved in:
Bibliographic Details
Published in:Biochemical and biophysical research communications 1996-11, Vol.228 (1), p.193-198
Main Authors: Furuta, Toshiaki, Momotake, Atsuya, Sugimoto, Masazumi, Hatayama, Minoru, Torigai, Hiromi, Iwamura, Michiko
Format: Article
Language:English
Subjects:
1-Methyl-3-isobutylxanthine - pharmacology
Animals
Cell Membrane Permeability
Cyclic AMP - analogs & derivatives
Cyclic AMP - chemical synthesis
Cyclic AMP - chemistry
Cyclic AMP - pharmacology
Female
Male
Melanophores - drug effects
Melanophores - physiology
Norepinephrine - pharmacology
Oryzias
Photolysis
Ultraviolet Rays
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Two acyloxycoumarinylmethyl-caged cAMPs (ACM- and PCM-cAMP) have been synthesized using a silver (I) oxide promoted method. Introduction of the acyloxy group to the 7-position on the coumarin ring not only enhanced the membrane permeability but diminished the photolability of the coumarin-cage. Because intracellular enzymatic hydrolysis of the 7-acyloxy group would produce the 7-hydroxy moiety which is more hydrophilic and photolabile, application of acyloxycoumarinylmethyl-caged cAMPs in biological studies would be expected to be efficient. Thus, the effect of extracellularly applied ACM- and PCM-cAMP had been investigated using the motile response of fish melanophores. After irradiation, a significant enhancement in the motility responses was observed. The observed magnitudes of the dispersions are comparable to that of Bt2cAMP/AM which is known as a membrane permeable cAMP derivative.
ISSN:0006-291X
1090-2104
DOI:10.1006/bbrc.1996.1638