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116812

Adenosine 3′,5′-cyclic Monophosphate, 8-(4-Chlorophenylthio)-, Sodium Salt

Name: Adenosine 3′,5′-cyclic Monophosphate, 8-(4-Chlorophenylthio)-, Sodium Salt
Brand: MM

Cell-permeable cAMP analog that activates both protein kinase A and protein kinase G.

Synonym(s):

Adenosine 3′,5′-cyclic Monophosphate, 8-(4-Chlorophenylthio)-, Sodium Salt, Adenosine 3ʹ,5ʹ-cyclic Monophosphate, 8-(4-Chlorophenylthio)-, Sodium Salt

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₁₄ClN₅O₆PS · Na

CAS Number:

93882-12-3

Molecular Weight:

493.79

UNSPSC Code:

41106305

NACRES:

NA.77

MDL number:

MFCD00057683

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

Storage condition:

OK to freeze, desiccated (hygroscopic)

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Properties

Quality Level

100

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, desiccated (hygroscopic)

color

white

solubility

water: 10 mg/mL

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(c4nc3Sc5ccc(cc5)Cl)N)CO1)[O-]

InChI

1S/C16H15ClN5O6PS.Na/c17-7-1-3-8(4-2-7)30-16-21-10-13(18)19-6-20-14(10)22(16)15-11(23)12-9(27-15)5-26-29(24,25)28-12;/h1-4,6,9,11-12,15,23H,5H2,(H,24,25)(H2,18,19,20);/q;+1/p-1/t9-,11-,12-,15-;/m1./s1

InChI key

YIJFVHMIFGLKQL-DNBRLMRSSA-M

Description

General description

Cell-permeable cAMP analog that activates both protein kinase A and protein kinase G. Induces the guanine-nucleotide-exchange factor activity of EGFI, also known as Epac (exchange protein directly activated by cAMP), and EGFII towards Rap1 both in vivo and in vitro. Also acts as a potent inhibitor of cGMP specific phosphodiesterase (IC₅₀ = 900 nM). Also inhibits cAMP-specific phosphodiesterases at much higher concentrations (IC₅₀ = 25 µM).

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Protein kinase A and protein kinase G

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 900 nM against cGMP-specific phosphodiesterase

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C

Other Notes

de Rooij, J., et al. 1998. Nature.396, 474.
Kawasaki, H., et al. 1998. Science.282, 2275.
Moed, P.J., et al. 1993. Comp. Biochem. Physiol.105A, 711.
Connolly, B.J., et al. 1992. Biochem. Pharmacol.44, 2303.
Phillips, M.E., and Taylor, A. 1992. J. Physiol.456, 591.
Shipston, M.J., and Antoni, F.A. 1992. Endocrinology130, 2213.
Datta, R., et al. 1991. Blood78, 83.
Peters, D.J.M., et al. 1991. Proc. Natl. Acad. Sci. USA88, 9219.
Sandberg, M., et al. 1991. Biochem. J.279, 521.
Unterman, T.G., et al. 1991. Endocrinology128, 2693.
Xu, H., et al. 1989. Brain Res.504, 36.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c