Bucladesine sodium Chemical Properties

Melting point:

>173°C (dec.)

storage temp. 

-20°C

solubility 

H₂O: 50 mg/mL

form 

powder

color 

white

biological source

synthetic (organic)

Water Solubility 

water: 1mg/mL

Merck 

14,1463

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.

InChIKey

DBXVIQJWMFGXGO-AOTDUVMNNA-N

SMILES

O([C@@H]1[C@]2([H])OP(O)(=O)OC[C@@]2([H])O[C@H]1N1C=NC2C(=NC=NC1=2)NC(=O)CCC)C(=O)CCC.[NaH] |&1:1,2,10,13,r|

Safety Information

Safety Statements 

24/25

WGK Germany 

2

RTECS 

ES5055500

F 

10-21

HS Code 

29349990

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

Bucladesine sodium Usage And Synthesis

Description

Bucladesine sodium is a derivative of cyclic-AMP with cardiac stimulant and peripheral vasodilatory properties. It is reported to be useful in cardiac insufficiency, especially after heart surgery.

Originator

Daiichi Seiyaku; Seishin Seiyaku (Japan)

Uses

Bucladesine sodium is an analog of cyclic AMP that stimulates cAMP-dependent protein kinase. It has vasodilator properties and is used as a cardiac stimulant.

Definition

ChEBI: Bucladesine sodium is a 3',5'-cyclic purine nucleotide.

Application

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

brand name

ACTOCIN

General Description

A cell-permeable cAMP analog that preferentially activates cAMP-dependent protein kinase (PKA). Causes an increase in the steady state level of parathyroid hormone-related peptide mRNA. Also acts as a Hh pathway antagonist. Shown to induce apoptosis in vascular smooth muscle cells.

Biochem/physiol Actions

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

Synthesis

Preparation of bucladesine sodium: in the flask containing cyclic adenosine monophosphate slowly added sodium hydroxide aqueous solution (3 mol/L), the process of temperature control, the drop is completed warmed to room temperature, with HCl solution (20%) to adjust the pH to 7-8, add anhydrous ethanol precipitation of white solids, filtration, drying of the sodium salt of a white solid; the sodium salt and n-butyl anhydride under the protection of N2 warmed to 140 ?? reaction, TLC monitoring the reaction is complete, and then reduced to room temperature. TLC monitoring, the reaction is complete after the drop to room temperature, slowly add methyl tert-butyl ether, the process of vigorous stirring, get nearly white solid crude product. A mixed solution of methyl tert-butyl ether and acetone was resuspended to obtain a white powdery target product.

storage

Store at -20°C

Background

Dibutyryl-cAMP, also known as bucladesine, is an analog of the second messenger cyclic adenosine 3'5'-monophosphate. Dibutyryl-cAMP is a phosphodiesterase inhibitor and a cAMP-dependent protein kinase activator that mimics the action of cAMP in cells. The anti-inflammatory activity of Dibutyryl-cAMP makes it an option for the treatment of skin inflammation. Exposure of rat glial cells to Dibutyryl-cAMP inhibited cell growth and increased glial fibrillary acidic protein levels, resulting in a change toward an astrocytic phenotype. Treatment of rat hepatocytes with Dibutyryl-cAMP suppressed both iNOS mRNA and protein expression, decreased iNOS promoter activity, and reduced DNA binding of the transcription factor NF-κB. Dibutyryl-cAMP treatment increased phosphorylated cAMP-response element-binding protein via protein kinase A signaling in rat pulmonary fibroblasts. Cells treated with Dibutyryl-cAMP exhibited a reduced number and size of silicosis nodules, and inhibited myofibroblast differentiation and extracellular matrix deposition.

References

1) Bartsch?et al.?(2003),?Bioactivatable, membrane-permeant analogs of cyclic nucleotides as biological tools for growth control of C6 glioma cells; Biol. Chem.,?384?1321
2) Carranza?et al.?(1998),?Protein kinase A induces recruitment of active Na+,K+-ATPase units to the plasma membrane of rat proximal convoluted tubule cells; J. Physiol.,?15?511
3) Hei?et al.?(1991),?Lack of correlation between activation of cyclic AMP-dependent protein kinase and inhibition of contraction of rat vas deferens by cyclic AMP analogs; Mol. Pharmacol.,?39?233
4) Imamura?et al.?(1998),?Differential expression of dystrophin isoforms and utrophin during dibutyryl-cAMP-induced morphological differentiation of rat brain astrocytes; Proc. Natl. Acad. Sci. USA,?95?6139
5) Xia?et al.?(2016),?Transcriptional comparison of human induced and primary midbrain dopaminergic neurons; Sci. Rep.,?6?20270

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