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Bucladesine calcium (DC2797)

Alias: dbcAMP;Dibutyryl-cAMP calcium salt; DC2797; DC-2797; DC 2797; calcium dibutyryl cAMP; Bucladesine sodium; DbcAMP calcium; Actosin; 938448-87-4; Calcium Dibutyryladenosine Cyclophosphate; Dibutyryl-cAMP Calcium Salt; Bucladesine calcium- Bio-X; Dibutyryl cAMP calcium salt; BD164626; F85088; calcium Dibutyryl cAMP; Cyclic dibutyryl-AMPcalcium salt
Cat No.:V4272 Purity: ≥98%
Bucladesine calcium (Dibutyryl-cAMP calcium; DC2797 calcium salt) is a cell-permeable PKA activator/agonist and a cAMP analog that mimics the action of endogenous cAMP.
Bucladesine calcium (DC2797)
Bucladesine calcium (DC2797) Chemical Structure CAS No.: 938448-87-4
Product category: PKA
This product is for research use only, not for human use. We do not sell to patients.
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50mg
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Other Forms of Bucladesine calcium (DC2797):

  • Dibutyryl-cAMP (Bucladesine sodium)
  • Bucladesine (Dibutyryl-cAMP)
Official Supplier of:
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Top Publications Citing lnvivochem Products
InvivoChem's Bucladesine calcium (DC2797) has been cited by 1 publication
Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Bucladesine calcium (Dibutyryl-cAMP calcium; DC2797 calcium salt) is a cell-permeable PKA activator/agonist 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-cAMPpreferentially 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)
Targets
PKA; PDE
ln Vitro

In vitro activity: Bucladesine sodium (also known as Dibutyryl-cAMP) 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.


Kinase Assay: Bucladesine sodium (also known as Dibutyryl-cAMP) 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.

ln Vivo
Male rats were given either a bilateral infusion of 10 mM or 100 mM of bucladesine, and the results showed a significant reduction in escape latency and distance traveled (indicating improvement in spatial memory) when compared to controls. Male rats' ability to retain spatial memory is enhanced when they receive an infusion of 1 or 5 mM buclodesin minutes after receiving 0.5 mg of nicotine [1]. ChAT and VAChT immunoreactivity in the CA1 region rose significantly when Bucladesine (10 mM/side) and nicotine (0.5 mM/side) were combined. Additionally, there was a considerable increase in the optical density and quantity of ChAT and VAChT immunostaining with nicotine and low-dose Bucladesine therapy. decrease in the rats' escape delay and distance traveled [2]. Following the application of the aqueous solution to the skin-excision site, bucladesine is almost entirely absorbed very quickly. Bucladesine is absorbed more slowly but more quickly in the absence of skin peeling than in the full-thickness abrasion rat model [3]. In a mouse ear edema model caused by arachidonic acid, bucladesine (containing 1.5% emulsion for single or several injections) can considerably reduce inflammatory edema [4].
Enzyme Assay
PKA assay[5]
Cells were washed twice with 10 mM sodium phosphate buffer, pH 7.4, 0.15 M NaC1, and then scraped from the culture plate in 1 ml of the same buffer. The cells were collected by centrifugation, and then homogenized by brief sonication in cell homogenization buffer [50 mMTris-HC1, pH 7.4, 1 mM EDTA, 1 mM dithiothreitol (DTT), 50 mM leupeptin, and 0.1 mM phenylmethylsulfonyl fluorideI. The particulate fraction was removed by centrifugation in a microcentrifuge at 14,000 rpm at 4°Cfor 20 mm. PKA activity was measured in the supernatant by the method ofRoskoski (1983), using the synthetic peptide substrate Leu-Arg-ArgAla-Ser-Leu-Gly (Kemptide). The reaction mixture of 50 ~.tlcontained cell lysate and a final concentration of 25 mM Tris-HC1 buffer (pH7.4), 5 mM magnesium acetate, 5 mM DTT, 5 mM cAMP, 20 ,~iMKemptide, 0.25 mM isobutylmethylxanthine, and 0.1 mM [y- 32P I ATP (200 cpm/pmol), and, when added, 20 ,uM PKA peptide inhibitor 5-24. Reactions were incubatedfor 10 mm at 30°Candterminated by addition of 50 j.tl of 7.5 mM phosphoric acid. Fifty microliters of the reaction mixture was spotted onto a P81 filter and washed five times with 75 mM phosphoric acid and counted as previously described. The difference in activity in the presence versus absence of PKA peptide inhibitor 5-24 was used to calculate PKA activity.
PKC assay [5]
Cell lysates were prepared as described for thePKA assay. The reaction mixture of 50 j.el contained cell lysate and a final concentration of 25 mM Tris-HC1 buffer (pH 7.4), 5 mM magnesium acetate, 5 mM DTT, 20 ~.tM synthetic substrate (Pro-Leu-Ser-Arg-Thr-Leu-Ser-Val-Ala-Ala-LysLys), 0.25 mM isobutylmethyixanthine, and 0.1 mM [y32p] ATP (200 cpm/pmol). Reactions were incubated for 10 mm at 30°C,terminated with phosphoric acid, and analyzed as de
Cell Assay
The vesicular acetylcholine transporter (VAChT) gene and the choline acetyltransferase (ChAT) gene comprise the cholinergic gene locus. We have studied the coordinate regulation of these genes by cyclic AMP-dependent protein kinase (PKA) in the rat pheochromocytoma cell line PC12 and PC12 PKA-deficient mutants. Both ChAT and VAChT mRNA increased approximately fourfold after treatment of PC12 cells with dibutyryl cyclic AMP (dbcAMP). ChAT and PKA activity were also increased by dbcAMP. The basal levels of ChAT and VAChT mRNAs in the PKA-deficient cell lines were both about six times lower than in wild-type PC12 cells, and were induced less than twofold by addition of dbcAMP. H-89 and H-9, specific inhibitors for PKA, reduced ChAT and VAChT mRNA levels to approximately one-third that of untreated cells and ChAT activity to approximately one-fourth that of untreated PC12 cells. Activation of PKA type II, but not PKA type I, increased ChAT activity approximately threefold. Analysis of reporter gene constructs indicates that PKA affects gene transcription at an upstream site in the cholinergic gene locus. These results demonstrate that the expression of the ChAT and VAChT genes is regulated coordinately at the transcriptional level, and a signaling pathway specifically involving PKA II plays an important role in this process[5].
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]. 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]. 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]. 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]. 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
C18H24CAN5O8P
Molecular Weight
509.463624000549
Exact Mass
976.219
CAS #
938448-87-4
Related CAS #
Bucladesine sodium;16980-89-5; 362-74-3
PubChem CID
44514776
Appearance
White to off-white solid
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
22
Rotatable Bond Count
16
Heavy Atom Count
65
Complexity
751
Defined Atom Stereocenter Count
8
SMILES
CCCC(=O)NC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)[O-])OC(=O)CCC.CCCC(=O)NC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)[O-])OC(=O)CCC.[Ca+2]
InChi Key
DRYMTGFYEAYJQR-NGVPHMJWSA-N
InChi Code
InChI=1S/2C18H24N5O8P.Ca/c2*1-3-5-11(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;/h2*8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24);/t2*10-,14-,15-,18-;/m11./s1
Chemical Name
calcium;[(4aR,6R,7R,7aR)-6-[6-(butanoylamino)purin-9-yl]-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate
Synonyms
dbcAMP;Dibutyryl-cAMP calcium salt; DC2797; DC-2797; DC 2797; calcium dibutyryl cAMP; Bucladesine sodium; DbcAMP calcium; Actosin; 938448-87-4; Calcium Dibutyryladenosine Cyclophosphate; Dibutyryl-cAMP Calcium Salt; Bucladesine calcium- Bio-X; Dibutyryl cAMP calcium salt; BD164626; F85088; calcium Dibutyryl cAMP; Cyclic dibutyryl-AMPcalcium salt
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
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: >100 mg/mL
Water:>100 mg/mL
Ethanol: N/A
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.12 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 25.0 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: ≥ 2.5 mg/mL (5.12 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 25.0 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: ≥ 2.5 mg/mL (5.12 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 25.0 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: 110 mg/mL (225.22 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 1.9629 mL 9.8143 mL 19.6286 mL
5 mM 0.3926 mL 1.9629 mL 3.9257 mL
10 mM 0.1963 mL 0.9814 mL 1.9629 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.

Calculator

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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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)
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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
  • Bucladesine calcium salt

    Anti-inflammatory effect of 0.5 and 1.5% bucladesine cream given(a)3h before administration of arachidonic acid or given(b)twice, i.e., 7 and 3h before administration of arachidonic acid.2012 May;304(4):313-7.

  • Bucladesine calcium salt

    Anti-inflammatory effect of 5% bucladesine given 1h before administration of arachidonic acid.2012 May;304(4):313-7.

  • Bucladesine calcium salt

    Anti-inflammatory effect of 2.5% ketoprofen gel given 3h before administration of arachidonic acid.2012 May;304(4):313-7.

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