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203800

8-Bromoadenosine 3′,5′-cyclic monophosphate sodium salt

Name: 8-Bromoadenosine 3′,5′-cyclic monophosphate sodium salt
Brand: MM

≥98% (HPLC), protein kinase (PKA) activator, solid

Synonym(s):

Adenosine 3′,5′-cyclic Monophosphate, 8-Bromo-, Sodium Salt, 8-Bromo-cAMP, Na

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₀BrN₅O₆P · Na

CAS Number:

76939-46-3

Molecular Weight:

430.08

UNSPSC Code:

41106305

NACRES:

NA.77

MDL number:

MFCD00005844

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

Storage condition:

OK to freeze, desiccated (hygroscopic)

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Properties

Product Name

Adenosine 3′,5′-cyclic Monophosphate, 8-Bromo-, Sodium Salt, Cell-permeable cAMP analog that has greater resistance to phosphodiesterases than cAMP.

Quality Level

100

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, desiccated (hygroscopic)

color

white

solubility

water: soluble

shipped in

ambient

storage temp.

−20°C

SMILES string

[Na+].[P]1(=O)(O[C@@H]2[C@H](O[C@H]([C@@H]2O)[n]3c4ncnc(c4nc3Br)N)CO1)[O-]

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

Description

General description

Cell-permeable cAMP analog that has greater resistance to phosphodiesterases than cAMP. Preferentially activates protein kinase A (PKA). Directly activates Epac, a Rap1 guanine-nucleotide exchange factor.

Cell-permeable cAMP analog that is more resistant to phosphodiesterases than cAMP. Preferentially activates cAMP-dependent protein kinase (PKA). Induces the guanine-nucleotide-exchange factor activity of GEFI, also known as Epac (exchange protein directly activated by cAMP), and GEFII toward Rap1 both in vivo and in vitro.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
PKA

Product does not compete with ATP.

Reversible: no

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C. Avoid pH >8.5.

Other Notes

Kawasaki, H., et al. 1998. Science 282, 2275.
de Rooij, J., et al. 1998. Nature 396, 474.
Boyer, B., and Thiery, J.P. 1993. J. Cell Biol.120, 767.
Hei, Y.-J., et al. 1991. Mol. Pharmacol. 39, 233.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c