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D0260

Sigma-Aldrich

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

≥97% (HPLC), PKA activator, powder

Synonym(s):

Bucladesine sodium salt, Dibutyryl cAMP sodium salt, Dibutyryl cyclic-AMP sodium salt

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About This Item

Linear Formula:
C18H23N5O8PNa
CAS Number:
16980-89-5
Molecular Weight:
491.37
EC Number:
241-059-4
MDL number:
MFCD00005843
UNSPSC Code:
41106305
PubChem Substance ID:
24893221
NACRES:
NA.77

Key Documents

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Product Name

N6,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt, ≥97% (HPLC), powder

Quality Level

200

assay

≥97% (HPLC)

form

powder

impurities

≤0.5% cyclic AMP and 2′-O-monobutyryl-cyclic AMP
≤3% N6-monobutyryl-cyclic AMP

color

white

solubility

H2O: 100 mg/mL

storage temp.

−20°C

SMILES string

[Na+].CCCC(=O)Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3OC(=O)CCC

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

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General description

Dibutyrylcyclic adenosine monophosphate (cAMP) mimics the activity of endogenous cAMP.It is lipophilic, allows it to be more cell-permeable, and has higherresistance towards hydrolysis by cAMP phosphodiesterase. Dibutyryl cAMPinhibits phosphodiesterases and plays a vital role as a probe in signaltransduction pathways.

Application

It has been used as a component of the differentiation medium to induce differentiationof dopaminergic neurons from floor plate progenitors. It has also been usedasa supplement in DMEM: F12 to culture neuronal cells from human pluripotent stemcells.
N6,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt has been used:
  • as a medium supplement for neural crest stem cells (NCSCs) differentiation
  • as a component of thawing medium for cryopreserved human iPSC (induced pluripotent stem cell)-derived neurons
  • in serum-free Dulbecco′s modified eagle′s medium (DMEM) to induce astrocyte differentiation

Biochem/physiol Actions

Cell-permeable cAMP analog that activates cAMP dependent protein kinase (PKA).

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Disclaimer

Loses 2′-O-butyryl group at pH 8.5

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCH2409
SLCB8357
SLBT7387
SLBR2629V
SLBL6352V

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Differentiation of human induced pluripotent stem cell (hiPSC)-derived neurons in mouse hippocampal slice cultures
Hiragi T, et al.
Frontiers in Cellular Neuroscience, 11, 143-143 (2017)
Annagrazia Adornetto et al.
FEBS open bio, 3, 459-466 (2013-11-20)
In the central nervous system, alteration of glial cell differentiation can affect brain functions. Polychlorinated biphenyls (PCBs) are persistent environmental chemical contaminants that exert neurotoxic effects in glial and neuronal cells. We examined the effects of a commercial mixture of
Daniel Sobrido-Cameán et al.
Disease models & mechanisms, 12(2) (2019-02-03)
Classical neurotransmitters are mainly known for their roles as neuromodulators, but they also play important roles in the control of developmental and regenerative processes. Here, we used the lamprey model of spinal cord injury to study the effect of serotonin
Witold Korytowski et al.
FEBS letters, 588(1), 65-70 (2013-11-26)
StAR family proteins in vascular macrophages participate in reverse cholesterol transport (RCT). We hypothesize that under pathophysiological oxidative stress, StARs will transport not only cholesterol to macrophage mitochondria, but also pro-oxidant cholesterol hydroperoxides (7-OOHs), thereby impairing early-stage RCT. Upon stimulation
Uniaxial mechanical strain modulates the differentiation of neural crest stem cells into smooth muscle lineage on micropatterned surfaces
Li X, et al.
PLoS ONE, 6(10), e26029-e26029 (2011)
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