[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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| Main Authors: | , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
5 May 2003
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| In: |
ChemBioChem
Year: 2003, Volume: 4, Issue: 5, Pages: 434-442 |
| ISSN: | 1439-7633 |
| DOI: | 10.1002/cbic.200300561 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/cbic.200300561 Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/cbic.200300561/abstract 
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| Author Notes: | Volker Hagen, Stephan Frings, Burkhard Wiesner, Siegrun Helm, U. Benjamin Kaupp, and Jürgen Bendig |
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| 245 | 1 | 0 | |a [7-(Dialkylamino)coumarin-4-yl]methyl-caged compounds as ultrafast and effective long-wavelength phototriggers of 8Bromo-substituted cyclic nucleotides |c Volker Hagen, Stephan Frings, Burkhard Wiesner, Siegrun Helm, U. Benjamin Kaupp, and Jürgen Bendig |
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| 520 | |a [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. | ||
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