PeptideDB

Bucladesine (Dibutyryl-cAMP) 362-74-3

Bucladesine (Dibutyryl-cAMP) 362-74-3

CAS No.: 362-74-3

Bucladesine (DC2797; DC-2797; Dibutyryl-cAMP) is a potent and cell-permeable PKA activator and a cAMP analog that mimics
Data collection：peptidedb@qq.com
Contact PeptideDB

This product is for research use only, not for human use. We do not sell to patients.

Bucladesine (DC2797; DC-2797; Dibutyryl-cAMP) is a potent and 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.



Physicochemical Properties


Molecular Formula C18H24N5O8P
Molecular Weight 469.39
Exact Mass 469.136
Elemental Analysis C, 46.06; H, 5.15; N, 14.92; O, 27.27; P, 6.60
CAS # 362-74-3
Related CAS # 16980-89-5 (sodium);362-74-3;
PubChem CID 9687
Appearance Typically exists as solids at room temperature
Density 1.7±0.1 g/cm3
Melting Point 203 - 205 °C
Index of Refraction 1.717
LogP 1.763
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 11
Rotatable Bond Count 8
Heavy Atom Count 32
Complexity 759
Defined Atom Stereocenter Count 4
SMILES

CCCC(NC1N=CN=C2N(C3O[C@@H]4COP(O[C@H]4[C@H]3OC(CCC)=O)(O)=O)C=NC=12)=O

InChi Key CJGYSWNGNKCJSB-YVLZZHOMSA-N
InChi Code

InChI=1S/C18H24N5O8P/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)/t10-,14-,15-,18-/m1/s1
Chemical Name

[(4aR,6R,7R,7aR)-6-[6-(butanoylamino)purin-9-yl]-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate
Synonyms

dbcAMP;Dibutyryl-cAMP; DC2797; DC-2797; DC 2797; calcium dibutyryl cAMP; Bucladesine sodium; DbcAMP calcium; Actosin; calcium Dibutyryl cAMP; Cyclic dibutyryl-AMPcalcium salt;DT 5621; Actosin; Bucladesina; bucladesine; Dibutyryl cAMP; Dibutyryl cyclic AMP; dBcAMP; 362-74-3; Actosin; Dibutyryl-3',5'-AMP; Cyclic AMP dibutyrate; DBC-AMP
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
Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


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
Experimentally naïve male Albino Swiss mice (Laboratory Animals Breeding, Słaboszów, Poland) weighing 20–30 g were used in all experiments. The animals were housed in polycarbonate cages at a controlled temperature (23–25°C) and humidity (50–60%) with 12 h light/dark cycle (lights on at 6 h). Tap water and food pellets were available ad libitum. All experiments were performed after at least 7 days of acclimatization. The experimental protocols were approved by the Ethical Committee of the Medical University in Lublin (license number 40/2010). To allow for skin penetration of the cream formulations and based on preliminary experiments with ketoprofen cream in this model (data not presented), a pre-treatment time of 3 h was selected. To evaluate the effect of 0.5 or 1.5% bucladesine cream, an amount of 10 ± 1 mg cream each was spread onto the outer surface of both, left and right ears using small spatula. A third group of mice was administered with 2.5% ketoprofen gel. Corresponding vehicle treatment groups were administered either the respective cream base without bucladesine or, as reference for ketoprofen, a cosmetic night cream. To evaluate the effect of repeated administration, four separate groups of mice were dosed twice, i.e., 7 and 3 h before administration of arachidonic acid with the 0.5 and 1.5% cream or corresponding vehicle. Arachidonic acid or actetone were administered 3 h after the second cream administration onto left and right ears, respectively. The ear thickness was measured with a precise spring-loaded caliper (Mitutoyo, type 7309, Kawasaki, Japan) before and 60 min after application of arachidonic acid or vehicle.
Enzyme Assay PKA assay[2]
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 [2]
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 described for the PKA assay. As a control, the specific PKC peptide inhibitor 19-36, at 20 1.tM was used and shown to inhibit the activity in cell extracts by >90%.
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]. Exp Neurol.2001 Jan;167(1):59-64.
[2]. J Neurochem. 1998 Sep;71(3):1118-26.
Additional Infomation Bucladesine is a 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP. It has a role as an agonist, a vasodilator agent and a cardiotonic drug. It is a butyrate ester, a 3',5'-cyclic purine nucleotide and a member of butanamides. It is functionally related to a 3',5'-cyclic AMP.
A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed)

Solubility Data


Solubility (In Vitro)
DMSO:N/A
Water:N/A
Ethanol: N/A
Solubility (In Vivo)
10%DMSO+ddH2O: 30 mg/mL
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1304 mL 10.6521 mL 21.3042 mL
5 mM 0.4261 mL 2.1304 mL 4.2608 mL
10 mM 0.2130 mL 1.0652 mL 2.1304 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.

Diroximel fumarate 1577222-14-0

Dioctyl decanedioate 2432-87-3

Product Recommendation

Latest release

Hot list

Copyright © 2026 PeptideDB All Rights Reserved

Sitemaps | Contact

Is for research use only, not for human use. We do not sell to patients.