8-Bromoguanosine 3prime, 5prime -cyclic monophosphoric acidCAS: 31356-94-2, MF: C10H11BrN5O7P, MW: 424.1

8-Bromoguanosine 3′, 5′ -cyclic monophosphoric acid (CAS 31356-94-2)

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Synonym: 8-Br-CGMP
CAS Number: 31356-94-2
Molecular Weight: 424.1
Molecular Formula: C10H11BrN5O7P
* Refer to Certificate of Analysis for lot specific data (including water content).
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This product is known to activate cGMP-dependent protein kinase. In human platelets, it has been shown to inhibit arachidonic acid release that is induced by thrombin. It has been reported to slow down or inhibit oscillations of intracellular calcium in response to acetylcholine in tracheal smooth muscle cells. It has been observed to mimic the effect of drugs that generate nitric oxide. It is membrane-permeable, and offers greater hydrolysis resistance by phosphodiesterases than cGMP.


References

1. Blatter, L.A. and Weir, W.G., "Nitric oxide decreases [Ca2+]i in vascular smooth muscle by inhibition of the calcium current." Cell Calcium, v. 15, 122 (1994). 2. Choi, J. and Farley, J.M., "Effects of 8-bromo-cyclic GMP on membrane potential of single swine tracheal smooth muscle cells." J. Pharmacol. Exp. Ther., v. 285, 588-594 (1998). 3. Francis, S., et al., "Relaxation of vascular and tracheal smooth muscle by cyclic nucleotide analogs that preferentially activate purified cGMP-dependent protein kinase." Mol. Pharmacol., v. 34, 506 (1988) 4. Garg, U.C. and Hassid, A., "Inhibition of rat mesangial cell mitogenesis by nitric oxide-generating vasodilators." Am. J. Physiol., v. 257, F60-F66 (1989). 5. Garg, U.C. and Hassid, A., "Nitric oxide-generating vasodilators and 8-bromo-cyclic guanosine monophosphate inhibit mitogenesis and proliferation of cultured rat vascular smooth muscle cells." J. Clin. Invest., v. 83, 1774 (1989). 6. Kosolapov, A.V., Khalifa-Zade, M.Ch., Kolesnikov, S.S., "Photosensitivity of 8BrcGMP-induced conductance in ROS-Excised patches." FEBS Lett., v. 305, 174 (1992). 7. Lermioglu, F., Goyal, J. and Hassid, A., "Cell density modulates the decrease of cytosolic free Ca2+ induced by atrial natriuretic hormone, S-Nitroso-N-acetylpenicillamine and 8-Bromo cyclic GMP in cultured rat mesangial cells." Biochem. J., v. 274, 323 (1991). 8. Matsuoka, I., Nakahata, N. and Nakanishi, H., "Inhibitory effect of 8-bromo cyclic GMP on an extracellular Ca2+-dependent arachidonic acid liberation in collagen-stimulated rabbit platelets." Biochem. Pharmacol., v. 38, 1841 (1989). 9. Meyer, R.B. and Miller, J.P., Life Sci., v. 14, 1019 (1974). 10. Moyer, M.L., et al., "Modulation of cell signaling pathway can enhance or impair glucocorticoid-induced gene expression without altering the state of receptor phosphorylation." J. Biol. Chem., v. 268, 22933 (1993). 11. Prakash, Y.S., et al., "Nitric oxide inhibits ACh-induced intracellular calcium oscillations in porcine tracheal smooth muscle." Am. J. Physiol., v. 272, L588 (1997). 12. Ruth, P., et al., "The activation of expressed cGMP-dependent protein kinase isozymes I alpha and I beta is determined by the different amino-termini." Eur. J. Biochem., v. 202, 1339 (1991). 13. Schultz, K.D., et al., Naunyn-Schmiedeberg's Arch. Pharmacol., v. 306, 1 (1979) 14. Sane, D.C., et al., Biochem. Biophys. Res. Commun., v. 165, 708 (1989). 15. Zatz, M. and Mullen, D.A., "Photoendocrine transduction in cultured chick pineal cells. II. Effects of forskolin, 8-bromocyclic AMP, an d8-bromocyclic GMP on the melatonin rhythm." Brain Res., v. 453, 51 (1988).

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in 0.1 N HCl, and water (moderately soluble).
Storage :
Store at 4° C
Density :
~2.96 g/cm3 (Predicted)
Refractive Index :
n20D ~2.09 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
104767
MDL Number :
MFCD00038423
EC Number :
256-993-8
SMILES :
C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C4=C(C(=O)N=C(N4)N)N=C3Br)O)OP(=O)(O1)O

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Certificate of Analysis

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