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D0627

Sigma-Aldrich

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

≥96% (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:
24893246
NACRES:
NA.51

biological source

synthetic (organic)

Assay

≥96% (HPLC)

form

powder

impurities

≤0.5% Cyclic AMP
≤3% monobutyryl derivatives

color

off-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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Application

Dibutyryl CAMP is a cell-permeable CAMP analogue that activates CAMP dependent protein kinase (PKA) or the CAMP/PKA signaling pathway. Dibutyryl CAMP is used as a morphological differentiation inducer and cell signaling modulator in cells such as Schwann cells. Dibutyrl cAMP is used in a variety of differentiation studies, such as neuron differentiation / neuronal differentiation.

Biochem/physiol Actions

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

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)

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Junji Yamauchi et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(35), 12579-12592 (2011-09-02)
In development of the peripheral nervous system, Schwann cells proliferate, migrate, and ultimately differentiate to form myelin sheath. In all of the myelination stages, Schwann cells continuously undergo morphological changes; however, little is known about their underlying molecular mechanisms. We
Steven L Coon et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(33), 13319-13324 (2012-08-07)
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De-Yi Liu et al.
Fertility and sterility, 99(1), 86-91 (2012-09-19)
To determine association between defective protein kinases C (PKC) and A (PKA) and disordered zona pellucida (ZP)-induced acrosome reaction (DZPIAR) in normozoospermic infertile men with normal sperm-ZP binding. Sperm from DZPIAR infertile men were treated without (control) or with (test)
Annelieke S Wentzel et al.
Scientific reports, 10(1), 13470-13470 (2020-08-12)
Mammalian macrophages can adopt polarization states that, depending on the exact stimuli present in their extracellular environment, can lead to very different functions. Although these different polarization states have been shown primarily for macrophages of humans and mice, it is
Ana Borrajo et al.
Neuropharmacology, 85, 1-8 (2014-06-01)
Several recent studies have shown that activation of the RhoA/Rho-associated kinase (ROCK) pathway is involved in the MPTP-induced dopaminergic cell degeneration and possibly in Parkinson's disease. ROCK inhibitors have been suggested as candidate neuroprotective drugs for Parkinson's disease. However, the
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