Dibutyryl-cAMP (Bucladesine sodium)

Alias: dbcAMP; DC-2797; Dibutyryl-cAMP sodium salt; DC2797; Sodium dibutyryl cAMP; DC 2797; Bucladesine sodium; DbcAMP sodium; Actosin; Sodium Dibutyryl cAMP; Cyclic dibutyryl-AMP sodium salt
Cat No.:V1846 Purity: =98.51%
Bucladesine sodium (also known as Dibutyryl-cAMP sodium), the sodium salt ofBucladesine, is a cell-permeable PKA activator and a cAMP analog that mimics the action of endogenous cAMP.
Dibutyryl-cAMP (Bucladesine sodium) Chemical Structure CAS No.: 16980-89-5
Product category: PKA
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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100mg
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Other Forms of Dibutyryl-cAMP (Bucladesine sodium):

  • Bucladesine calcium (DC2797)
Official Supplier of:
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Top Publications Citing lnvivochem Products
InvivoChem's Dibutyryl-cAMP (Bucladesine sodium) has been cited by 3 publications
Purity & Quality Control Documentation

Purity: =98.51%

Purity: ≥98%

Purity: ≥98%

Product Description

Bucladesine sodium (also known as Dibutyryl-cAMP sodium), the sodium salt of Bucladesine, is a cell-permeable PKA activator and a cAMP analog that mimics the action of endogenous cAMP. It is a cyclic nucleotide derivative (structurally similar to cAMP) and is also a phosphodiesterase inhibitor. Dibutyryl-cAMP preferentially activates cAMP-dependent protein kinase. The products releaes butyrate due to intracellular and extracellular esterase action. Butyrate was shown to have distinct biological effects. The compound is used in a wide variety of research applications because it mimics cAMP and can induce normal physiological responses when added to cells in experimental conditions.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
After PC12 cells were treated with bucladesine (dibutyryl cyclic AMP; dbcAMP), the amounts of mRNA for both choline acetyltransferase (ChAT) and vesicular acetylcholine transporter (VAChT) increased by almost four times. Bucladesine also increases PKA and ChAT activity[5].
ln Vivo
Bucladesine infused intrahippocampally into the CA1 region of male Albino-Wistar rats has been shown to enhance spatial memory in maze tasks. When 10 μM and 100 μM bucladesine are infused bilaterally, escape latency and journey distance significantly decrease (indicating improved spatial memory). Bucladesine enhanced the preservation of spatial memory by activating PKA and inducing the cAMP/PKA pathway[1].
Animal Protocol
For topical administration of bucladesine as 5% solution, 20 μl of drug or vehicle solution was administered onto the outer surface of both, left and right ears each, 60 min prior to arachidonic acid challenge. The inflammatory response was induced by administration of 20 μl arachidonic acid (Sigma-Aldrich, Munich, Germany; 5% in acetone) on the outer surface of left ears. The right ears were treated with acetone only to determine the individual differences in ear thicknesses.
Na ve male Albino Swiss mice
References
[1]. Sharifzadeh, M., et al., Post-training intrahippocampal infusion of nicotine-bucladesine combination causes a synergistic enhancement effect on spatial memory retention in rats. Eur J Pharmacol, 2007. 562(3): p. 212-20.
[2]. Mafune, E., M. Takahashi, and N. Takasugi, Effect of vehicles on percutaneous absorption of bucladesine (dibutyryl cyclic AMP) in normal and damaged rat skin. Biol Pharm Bull, 1995. 18(11): p. 1539-43.
[3]. Rundfeldt, C., et al., The stable cyclic adenosine monophosphate analogue, dibutyryl cyclo-adenosine monophosphate (bucladesine), is active in a model of acute skin inflammation. Arch Dermatol Res, 2012.
[4]. Salehi F, et al. Effect of bucladesine, pentoxifylline, and H-89 as cyclic adenosine monophosphate analog, phosphodiesterase, and protein kinase A inhibitor on acute pain. Fundam Clin Pharmacol. 2017 Aug;31(4):411-419.
[5]. Shimojo M, et al. The cholinergic gene locus is coordinately regulated by protein kinase A II in PC12 cells. J Neurochem. 1998 Sep;71(3):1118-26.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H23N5NAO8P
Molecular Weight
491.37
CAS #
16980-89-5
Related CAS #
Bucladesine calcium;938448-87-4
SMILES
O=P1(OC[C@H]2O[C@H]([C@@H]([C@@H]2O1)OC(CCC)=O)N3C4=NC=NC(NC(CCC)=O)=C4N=C3)[O-].[Na+]
Chemical Name
sodium (4aR,6R,7R,7aR)-6-(6-butyramido-9H-purin-9-yl)-7-(butyryloxy)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-olate 2-oxide
Synonyms
dbcAMP; DC-2797; Dibutyryl-cAMP sodium salt; DC2797; Sodium dibutyryl cAMP; DC 2797; Bucladesine sodium; DbcAMP sodium; Actosin; Sodium Dibutyryl cAMP; Cyclic dibutyryl-AMP sodium salt
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 98 mg/mL (199.4 mM)
Water:98 mg/mL (199.4 mM)
Ethanol: N/A
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 4.25 mg/mL (8.65 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 42.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 4.25 mg/mL (8.65 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 42.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 4.25 mg/mL (8.65 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 42.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 10%DMSO +ddH2O: 30 mg/mL

Solubility in Formulation 5: 100 mg/mL (203.51 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.0351 mL 10.1756 mL 20.3513 mL
5 mM 0.4070 mL 2.0351 mL 4.0703 mL
10 mM 0.2035 mL 1.0176 mL 2.0351 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
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