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

[7-(Dimethylamino)coumarin-4-yl]methyl (DMACM) and [7-(diethylamino)coumarin-4-yl]methyl (DEACM) esters of 8bromoadenosine 3′,5′-cyclic monophosphate (8-Br-cAMP) and 8bromoguanosine 3′,5′-cyclic monophosphate (8-Br-cGMP) are described as novel caged compounds for 8bromo-substituted cyclic nucleotide...

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Bibliographische Detailangaben
Hauptverfasser: Hagen, Volker (VerfasserIn) , Frings, Stephan (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 5 May 2003
In: ChemBioChem
Year: 2003, Jahrgang: 4, Heft: 5, Pages: 434-442
ISSN:1439-7633
DOI:10.1002/cbic.200300561
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1002/cbic.200300561
Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/cbic.200300561/abstract
Volltext
Verfasserangaben:Volker Hagen, Stephan Frings, Burkhard Wiesner, Siegrun Helm, U. Benjamin Kaupp, and Jürgen Bendig
Beschreibung
Zusammenfassung:[7-(Dimethylamino)coumarin-4-yl]methyl (DMACM) and [7-(diethylamino)coumarin-4-yl]methyl (DEACM) esters of 8bromoadenosine 3′,5′-cyclic monophosphate (8-Br-cAMP) and 8bromoguanosine 3′,5′-cyclic monophosphate (8-Br-cGMP) are described as novel caged compounds for 8bromo-substituted cyclic nucleotides. Synthesis is accomplished by treatment of the free acids of the cyclic nucleotides with the corresponding 7(dialkylamino)-substituted 4(diazomethyl)coumarins. Irradiation of the DMACM- and DEACM-caged cyclic nucleotides with UV light stimulates the release of the cyclic nucleotides within roughly a nanosecond. The new caged compounds are resistant to hydrolysis in aqueous buffers and exhibit long-wavelength absorption properties with maxima at 400 nm, high extinction coefficients, and high quantum yields (0.15-0.31). Their favorable properties render these compounds the most efficient and rapid phototriggers of 8bromo-substituted cyclic nucleotides known. The usefulness of the compounds for physiological studies under nondamaging light conditions was examined in HEK293 cells expressing the α subunit of the cyclic-nucleotide-gated (CNG) channel of cone photoreceptors (CNGA3) and of olfactory neurons (CNGA2) by using confocal laser scanning microscopy and the patch clamp technique.
Beschreibung:Gesehen am 04.05.2017
Beschreibung:Online Resource
ISSN:1439-7633
DOI:10.1002/cbic.200300561

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