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. 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.
Department of Biomolecular Science, Faculty of Science, Toho University, Chiba, Japan.
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Furuta
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Momotake
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Sugimoto
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Hatayama
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Torigai
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Iwamura
D015056:1-Methyl-3-isobutylxanthine / Q000494:pharmacology; D000818:Animals; D002463:Cell Membrane Permeability; D000242:Cyclic AMP / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D008297:Male; D008547:Melanophores / Q000187:drug effects* / Q000502:physiology; D009638:Norepinephrine / Q000494:pharmacology; D009990:Oryzias; D010782:Photolysis; D014466:Ultraviolet Rays
C102093:4-(7-propanoyloxycoumarinyl)methyl cAMP; D000242:Cyclic AMP; D015056:1-Methyl-3-isobutylxanthine; D009638:Norepinephrine