28745-M

N⁶,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt

≥95% (HPLC), lyophilized solid, PKA activator, Calbiochem^®

• Synonym(s): Adenosine 3′,5′-cyclic Monophosphate, N⁶,O^2′-Dibutyryl-, Sodium Salt, Dibutyryl-cAMP, Na
• Empirical Formula (Hill Notation): C₁₈H₂₃N₅O₈P · Na
• CAS Number: 16980-89-5
• Molecular Weight: 491.37
• MDL number: MFCD00005843
• UNSPSC Code: 41106305
• NACRES: NA.77

Properties

• Product Name: Adenosine 3′,5′-cyclic Monophosphate, N⁶,O^2′-Dibutyryl-, Sodium Salt, This Dibutyryl-cAMP, CAS 16980-89-5, is a cell-permeable cAMP analog that preferentially activates PKA.
• description: RTECS - ES5055500
• Quality Level: 200
• Assay: ≥95% (HPLC)
• form: lyophilized solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; desiccated (hygroscopic)
• color: white
• solubility: water: 1 mg/mL
• storage temp.: −20°C
• SMILES string: [Na+].[P]1(=O)(O[C@@H]2[C@H](O[C@H]([C@@H]2OC(=O)CCC)[n]3c4ncnc(c4nc3)NC(=O)CCC)CO1)[O-]
• InChI: 1S/C18H24N5O8P.Na/c1-3-5-11(24)22-16-13-17(20-8-19-16)23(9-21-13)18-15(30-12(25)6-4-2)14-10(29-18)7-28-32(26,27)31-14;/h8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24);/q;+1/p-1/t10-,14-,15-,18-;/m1./s1
• InChI key: KRBZRVBLIUDQNG-JBVYASIDSA-M

Description

General description

Sodium N-6,2′-O-dibutyryl adenosine-3′,5′-cyclic phosphate (DBcAMP) can stimulate the production of several cytokines, such as interleukin-6 (IL-6), IL-8, and transforming growth factor-β, by keratinocytes and fibroblasts. It can accelerate neovascularization in wound healing, potentially by increasing the accumulation of endothelial progenitor cells (EPC) at wound sites. DBcAMP plays a key role in inducing various biological effects, including cell proliferation, differentiation, and migration.[1] Dibutyryl-cAMP (db-cAMP) can prevent acute pulmonary vascular injury induced by endotoxin and attenuate ischemia/reperfusion injury in rat lungs. It inhibits fibroblast proliferation and collagen production. DBcAMP also exhibits anti-fibrotic effects in vitro and in vivo.[2]

Biochem/physiol Actions

Primary Target
PKA

Preparation Note

Following reconstitution, aliquot and freeze (-20°C) for long-term storage or refrigerate (4°C) for short-term storage. Aqueous stock solutions are stable for up to 3 days at 4°C or for up to 3 months at -20°C. Avoid pH >8.5.

Other Notes

Noveen, A., et al. 1996. Biochem. Biophys. Res. Commun.219, 180.
Tsai, C.H., et al. 1995. J. Cell. Physiol.164, 108.
Leszczynski, D., et al. 1994. Am. J. Pathol.145, 1265.
Miller, C., et al. 1994. J. Neurosci. Res.38, 56.
Hinko, A., and Soloff, M.S. 1993. Endocrinology 132, 126.
Ikeda, K., et al. 1993. J. Biol. Chem. 268, 1174.
Park, E.A., et al. 1993. J. Biol. Chem.268, 613.
Hei, Y-J., et al. 1991. Mol. Pharmacol. 39, 233.
Posternak, T., and Weimann, G. 1974. Methods Enzymol. 38, 399.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable