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D0260

Sigma-Aldrich

N6,2′-O-Dibutyryladénosine 3′,5′-monophosphate cyclique sodium salt

≥97% (HPLC), powder

Synonyme(s) :

Bucladésine sodium salt, Dibutyryl AMP cyclique sodium salt, Dibutyryl AMPc sodium salt

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About This Item

Formule linéaire :
C18H23N5O8PNa
Numéro CAS:
16980-89-5
Poids moléculaire :
491.37
Numéro CE :
241-059-4
Numéro MDL:
MFCD00005843
Code UNSPSC :
41106305
ID de substance PubChem :
24893221
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Pureté

≥97% (HPLC)

Forme

powder

Impuretés

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

Couleur

white

Solubilité

H2O: 100 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

[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

Clé InChI

KRBZRVBLIUDQNG-JBVYASIDSA-M

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Description générale

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

Actions biochimiques/physiologiques

Analogue de l'AMPc perméable aux cellules qui active la protéine kinase AMPc-dépendante (PKA).

Caractéristiques et avantages

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.

Attention

Loses 2′-O-butyryl group at pH 8.5

Autres remarques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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