A competitive inhibitor of cGK
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Rp-8-bromo-Cyclic GMPS (sodium salt)

Item No. 18441

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-bromo-guanosine cyclic 3',5'-[(R)-(hydrogen phosphorothioate)], monosodium salt
CAS Number
208445-06-1
Synonyms
  • Rp-8-bromo-cGMPS
Molecular Formula
C10H10BrN5O6PS • Na
Formula Weight
462.2
Purity
≥99%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: soluble
SMILES
O[C@H]1[C@H](N2C(Br)=NC3=C2N=C(N)NC3=O)O[C@H]4[C@H]1O[P@@](OC4)([S-])=O.[Na+]
InChi Code
InChI=1S/C10H11BrN5O6PS.Na/c11-9-13-3-6(14-10(12)15-7(3)18)16(9)8-4(17)5-2(21-8)1-20-23(19,24)22-5;/h2,4-5,8,17H,1H2,(H,19,24)(H3,12,14,15,18);/q;+1/p-1/t2-,4-,5-,8-,23-;/m1./s1
InChi Key
CHTSSROWUAICIL-GMKUFTCMSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Rp-8-bromo-Cyclic GMPS (Rp-8-bromo-cGMPS) is a cell-permeable cGMP analog that adds an equatorial exocyclic (Rp) sulfur substitution in the axial position of the cyclophosphate ring of 8-bromo-cGMP. Like 8-bromo-cGMP, Rp-8-bromo-cGMPS is resistant to hydrolysis by phosphodiesterases. This Rp isomer binds cGK without activating it, resulting in competitive inhibition.1,2 At 10 µM, it blocks the relaxation of rat tail arteries induced by the nitric oxide donor SIN-1 (Item No. 82220).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Butt, E., van Bemmelen, M., Fischer, L., et al. Inhibition of cGMP-dependent protein kinase by (Rp)-guanosine 3',5'-monophosphorothioates. FEBS Lett. 263(1), 47-50 (1990).

    2. Butt, E., Pöhler, D., Genieser, H.G., et al. Inhibition of cyclic GMP-dependent protein kinase-mediated effects by (Rp)-8-bromo-PET-cyclic GMPS. Br. J. Pharmacol. 116(8), 3110-3116 (1995).

    3. Ouedraogo, S., Tschöp, M., Stoclet, J.C., et al. Effects of cyclic GMP and analogues on neurogenic transmission in the rat tail artery. Br. J. Pharmacol. 112, 867-872 (1994).