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BCMCM-caged cAMP

[6, 7- Bis(carboxymethoxy)coumarin- 4- yl]methyladenosine- 3', 5'- cyclic monophosphate ( BCMCM-caged cAMP )
Caged cyclic AMP, releasing a fluorescent coumarin upon uncaging
Cat. No.: B 016
    
CAS No.: [339291-51-9]
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Equatorial isomer, for the corresponding isomeric mixture please inquire. BCMCM-caged cAMP is an only weakly fluorescent, caged precursor of the second messenger cyclic AMP, which upon irradiation, releases both cAMP and a fluorescent coumarin analogue. Excellent solubility in water or buffers. Detailed technical information available. Reference: Hagen et al., Angew. Chem. Int. Ed., 40, 1045 - 1048 (2001).

 

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Cat. No. B 016
Patent Information Protected by patent DE 100 21 256.5 and foreign equivalents
CAS number [339291-51-9]
Purity > 98% HPLC
Storage temperature -20°C / -4°F
Light-sensitive True
Molecular formula C₂₄H₂₂N₅O₁₄P
Molecular weight [g/mol] 680,5
Target PKA (cAK) Activator
Absorption max [nm] 347
Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] 12400
  • 1. Hagen V., Benndorf K.Kaupp U. B., aus: Dynamic Studies in Biology - Phototriggers R. Givens) Wiley-VCH Verlag Weinheim, 0, 0 - 0 (2005), "Photochemical Release of Second Messengers - Caged Cyclic Nucleotides"
  • 2. Hagen V., Frings S., Bendig J., Lorenz D., Wiesner B.Kaupp U. B., Angew. Chem.-Int. Edit., 4, 3625 - 3628 (2002), "Fluorescence Spectroscopic Quantification of the Release of Cyclic Nucleotides from Photocleavable [bis(carboxymethoxy)coumarin-4-yl]methyl Esters inside Cells"
  • 3. Kaupp U. B.Seifert R., Physiol. Rev., 82, 769 - 824 (2002), "Cyclic Nucleotide-Gated Ion Channels"
  • 4. Hagen V., Bendig J., Frings S., Eckardt T., Helm S., Reuter D.Kaupp U. B., Angew. Chem. Int. Ed., 40, 1046 - 47 (2001), "Highly Efficient and Ultrafast Phototriggers for cAMP and cGMP by Using Long-Wavelength UV/Vis-Activation"
  • 5. Hagen V., Kaupp U. B., Bendig J.Wiesner B., Deutsche Offenlegungsschrift of 20.04.2000, 0, 0 - 0 (2000), "Neue, photolabile Cumarinylmethylester von cyclischen Nucleotiden, Verfahren zu deren Herstellung und ihre Verwendung"