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D0627

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

≥96% (HPLC), synthetic (organic), powder

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

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:
Molecular Weight:
491.37
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
241-059-4
MDL number:
Assay:
≥96% (HPLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
H2O: 100 mg/mL
Storage temp.:
−20°C
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Product Name

N6,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt, ≥96% (HPLC), powder

biological source

synthetic (organic)

Quality Level

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

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).

Disclaimer

Loses 2′-O-butyryl group at pH 8.5

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This Item
D0260C9630A9376
biological source

synthetic (organic)

biological source

-

biological source

synthetic

biological source

synthetic (organic)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

assay

≥96% (HPLC)

assay

≥97% (HPLC)

assay

≥95% (HPLC)

assay

≥93%

form

powder

form

powder

form

powder

form

powder

color

off-white

color

white

color

-

color

-

solubility

H2O: 100 mg/mL

solubility

H2O: 100 mg/mL

solubility

water: 50 mg/mL, clear, colorless

solubility

water: 50 mg/mL, clear, colorless


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Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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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
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
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)



Global Trade Item Number

SKUGTIN
D0627-100MG04061833557877
D0627-1G04061833557884
D0627-5X1G04061833557914
D0627-250MG04061833557891
D0627-25MG04061833557907

Questions

1–2 of 2 Questions  
  1. is this product sterile?

    1 answer
    1. This product is not sterile. Prepared solutions may be filter sterilized.

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  2. How long is it stable in -20ºC after reconstitution in DMSO or H2O at 200mM? Do you have any recommendations for stability once the product is in solution?

    1 answer
    1. This product is soluble in water at 100 mg/mL. The solubility in DMSO has not been determined. Following reconstitution, aliquot and freeze at -20°C for up to 3 months or refrigerate at 2 - 8°C for up to 3 days. Avoid pH of 8.5 or greater as hydrolysis will occur. Please see the link below to review the product datasheet:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/368/353/d0627pis-ms.pdf

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