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D0260

Sigma-Aldrich

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

≥97% (HPLC), 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

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.

Caution

Loses 2′-O-butyryl group at pH 8.5

Other Notes

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
Han Zhao et al.
The Science of the total environment, 908, 168307-168307 (2023-11-11)
Atrazine (ATZ) is one of the most used herbicides in the US and a known endocrine disruptor. ATZ is frequently detected in drinking water, especially in Midwestern regions of the United States, exceeding the EPA regulation of maximum contamination level
F Schwede et al.
Pharmacology & therapeutics, 87(2-3), 199-226 (2000-09-29)
Cyclic AMP (cAMP) and cyclic GMP (cGMP) are key second messengers involved in a multitude of cellular events. From the wealth of synthetic analogs of cAMP and cGMP, only a few have been explored with regard to their therapeutic potential.
Wen-Kai Chen et al.
Journal of neuroinflammation, 17(1), 202-202 (2020-07-08)
Spinal cord injury (SCI) triggers the primary mechanical injury and secondary inflammation-mediated injury. Neuroinflammation-mediated insult causes secondary and extensive neurological damage after SCI. Microglia play a pivotal role in the initiation and progression of post-SCI neuroinflammation. To elucidate the significance
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