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28745-M

Sigma-Aldrich

Adenosine 3′,5′-cyclic Monophosphate, N6,O2′-Dibutyryl-, sodium salt

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

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Synonym(s):
Adenosine 3′,5′-cyclic Monophosphate, N⁶,O2′-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

product name

Adenosine 3′,5′-cyclic Monophosphate, N⁶,O2′-Dibutyryl-, Sodium Salt, This Dibutyryl-cAMP, CAS 16980-89-5, is a cell-permeable cAMP analog that preferentially activates PKA.

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

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

Related Categories

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. 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.

Biochem/physiol Actions

Primary Target
PKA

Warning

Toxicity: Standard Handling (A)

Reconstitution

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dibutyryl-cAMP attenuates pulmonary fibrosis by blocking myofibroblast differentiation via PKA/CREB/CBP signaling in rats with silicosis
Liu Y, et al.
Respiratory Research, 18, 1-11 (2017)
Dibutyryl cAMP influences endothelial progenitor cell recruitment during wound neovascularization
Asai J, et al.
The Journal of Investigative Dermatology, 126, 1159-1167 (2006)

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