Novel caged compounds of hydrolysis-resistant 8-Br-cAMP and 8-Br-cGMP: photolabile NPE esters.
The application of the 1-(2-nitrophenyl)ethyl (NPE) moiety as a photolabile ligand for the release of hydrolysis-resistant 8-Br-cAMP and 8-Br-cGMP was examined. NPE-caged 8-Br-cAMP and 8-Br-cGMP liberate 8-Br-cAMP and 8-Br-cGMP during irradiation with ultraviolet light. The synthesis procedure resulted in diastereoisomeric mixtures, which were chromatographically separated into the axial and equatorial isomers of NPE-caged 8-Br-cAMP and 8-Br-cGMP. The hydrolytic stability, solubility and photochemical properties of these derivatives were compared to the previously reported 4.5-dimethoxy-2-nitrobenzyl (DMNB) compounds. We found that the axial isomers of NPE-caged 8-Br-cAMP and 8-Br-cGMP had a considerably better solvolytic stability than the respective equatorial isomers as well as the DMNB-caged derivatives. Their usefulness for physiological studies was examined in a mammalian cell line expressing the cyclic nucleotide-gated (CNG) ion channel of bovine olfactory sensory neurons.
Hagen
V
V
Forschungsinstitut für Molekulare Pharmakologie, Berlin, Germany. hagen@fmp-berlin.de
Dzeja
C
C
Bendig
J
J
Baeger
I
I
Kaupp
U B
UB
D015124:8-Bromo Cyclic Adenosine Monophosphate / Q000031:analogs & derivatives / Q000737:chemistry*; D000818:Animals; D002417:Cattle; D002460:Cell Line; D000242:Cyclic AMP / Q000031:analogs & derivatives* / Q000737:chemistry; D006152:Cyclic GMP / Q000031:analogs & derivatives* / Q000737:chemistry; D054815:Cyclic Nucleotide-Gated Cation Channels; D004952:Esters; D006868:Hydrolysis; D007473:Ion Channels / Q000378:metabolism; D015394:Molecular Structure; D010777:Photochemistry; D010782:Photolysis
C089981:(2-nitrophenyl)ethyl-cyclic adenosine monophosphate; D054815:Cyclic Nucleotide-Gated Cation Channels; D004952:Esters; D007473:Ion Channels; D015124:8-Bromo Cyclic Adenosine Monophosphate; C016276:8-bromocyclic GMP; D000242:Cyclic AMP; D006152:Cyclic GMP