116812

3′,5′-cykliczny monofosforan adenozyny, 8-(4-chlorofenylo-tio)-, sól sodowa

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

• Synonim(y): 3ʹ,5ʹ-cykliczny monofosforan adenozyny, 8-(4-chlorofenyloetio)-, sól sodowa
• Wzór empiryczny (zapis Hilla): C₁₆H₁₄ClN₅O₆PS · Na
• Numer CAS: 93882-12-3
• Masa cząsteczkowa: 493.79
• UNSPSC Code: 41106305
• NACRES: NA.77
• MDL number: MFCD00057683
• Assay: ≥98% (HPLC)
• Form: solid
• Storage condition: OK to freeze, desiccated (hygroscopic)

Właściwości

• Quality Segment: 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

Opis

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)

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Informacja o środkach bezpieczeństwa

• Klasa składowania: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable