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BCMCM-caged cGMP

[6, 7- Bis(carboxymethoxy)coumarin- 4- yl]methylguanosine- 3', 5'- cyclic monophosphate ( BCMCM-caged cGMP )
Caged cyclic GMP, releasing a fluorescent coumarin upon uncaging
Cat. No.: B 017
    
CAS No.: [339291-52-0]
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Product Name Price (net) Qty
Cat. No.: B 017-001
Unit: 0.1 µmol / ~69 µg
$160.00
Equatorial isomer. BCMCM-caged cGMP is an only weakly fluorescent, caged precursor of the second messenger cyclic cGMP, which upon irradiation, releases both cGMP and a fluorescent coumarin analogue. Excellent solubility in water or buffers. Reference: Hagen et al., Angew. Chem. Int. Ed., 40, 1046 - 1048 (2001).
Cat. No. B 017
Patent Information Protection by patent DE 100 21 256.5 and foreign equivalents
CAS number [339291-52-0]
Purity > 98% HPLC
Storage temperature -20°C / -4°F
Light-sensitive True
Molecular formula C₂₄H₂₂N₅O₁₅P x 3 H₂O
Molecular weight [g/mol] 705,5
Target PKG (cGK) Activator
Absorption max [nm] 347
Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] 11200
  • 1. Gonzalez-Iglesias A. E., Jiang Y., Tomic M., Kretschmannova K., Andric S. A., Zemkova H.Stojilkovic S. S., Mol. Endocrinol., 20, 2231 - 2246 (2006), "Dependence of Electrical Activity and Calcium Influx-controlled Prolactin Release on Adenylyl Cyclase Signaling Pathway in Pituitary Lactotrophs"
  • 2. 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"
  • 3. 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"
  • 4. Kaupp U. B.Seifert R., Physiol. Rev., 82, 769 - 824 (2002), "Cyclic Nucleotide-Gated Ion Channels"
  • 5. 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"
  • 6. 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"