A PKA activator
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Alternative(s)
181418-bromo Cyclic AMP
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8-bromo Cyclic AMP (sodium salt)

Item No. 14431

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-bromo-cyclic 3',5'-(hydrogen phosphate)-adenosine, monosodium salt
CAS Number
76939-46-3
Synonyms
  • 8-Bromoadenosine 3',5'-cyclic monophosphate
  • 8-bromo cAMP
Molecular Formula
C10H10BrN5O6P • Na
Formula Weight
430.1
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: 25 mg/ml
λmax
265 nm
SMILES
O[C@H]1[C@H](N2C(Br)=NC3=C2N=CN=C3N)O[C@H]4[C@H]1OP(OC4)([O-])=O.[Na+]
InChi Code
InChI=1S/C10H11BrN5O6P.Na/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6;/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14);/q;+1/p-1/t3-,5-,6-,9-;/m1./s1
InChi Key
DMRMZQATXPQOTP-GWTDSMLYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    25 mg

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    Product Description

    8-bromo Cyclic AMP is an activator of protein kinase A (PKA) with a half-maximal activation (Ka) value of 0.05 µM.1 It is selective for PKA over cGMP-dependent protein kinase (PKG; Ka = 5.8 µM) and is more resistant to hydrolysis by phosphodiesterases (PDEs) compared with cAMP (Item No. 18820).1,2 8-bromo Cyclic AMP inhibits the proliferation of HL-60 leukemia cells (IC50 = 18 µM after six days).2 It induces relaxation of isolated rabbit carotid or renal arterial rings precontracted with phenylephrine when used at concentrations ranging from 10 to 300 µM.3 Intradermal administration of 8-bromo cyclic AMP (10 nmol/site) prevents scratching and increases in cutaneous leukotriene B4 (LTB4) production induced by the proteinase-activated receptor 2 (PAR2) agonist SLIGRL-NH2 (Item No. 16723) in mice.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sandberg, M., Butt, E., Nolte, C., et al. Characterization of Sp-5,6-dichloro-1-β-D-ribofuranosylbenzimidazole-3',5'-monophosphorothioate (Sp-5,6-DCl-cBiMPS) as a potent and specific activator of cyclic-AMP-dependent protein kinase in cell extracts and intact cells. Biochem. J. 279(Pt 2), 521-527 (1991).

    2. Yokozaki, H., Tortora, G., Pepe, S., et al. Unhydrolyzable analogues of adenosine 3':5'-monophosphate demonstrating growth inhibition and differentiation in human cancer cells. Cancer Res. 52(9), 2504-2508 (1992).

    3. Minonishi, T., Ogawa, K., Tokinaga, Y., et al. Differential vasodilation response to olprinone in rabbit renal and common carotid arteries. J. Anesth. 24(1), 61-66 (2010).

    4. Andoh, T., and Kuraishi, Y. Antipruritic mechanisms of topical E6005, a phosphodiesterase 4 inhibitor: Inhibition of responses to proteinase-activated receptor 2 stimulation mediated by increase in intracellular cyclic AMP. J. Dermatol. Sci. 76(3), 206-213 (2014).

    Product Citations

    Sahoo, N., Gu, M., Zhang, X., et al. Gastric acid secretion from parietal cells is mediated by a Ca2+ efflux channel in the tubulovesicle. Dev. Cell 41(3), 262-273 (2017).