| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Endogenous Metabolite; Microbial Metabolite
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|---|---|
| ln Vitro |
Cyclic adenosine monophosphate, or cyclic AMP, sodium controls the production of mediators. Cyclic AMP sodium increases the synthesis of the anti-inflammatory cytokine IL-10 while suppressing the expression of pro-inflammatory cytokines such as TNF-α and IL-12.
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| Cell Assay |
cAMP was the first second messenger to be identified. Its three main effectors are PKA (which phosphorylates numerous metabolic enzymes), EPAC (a guanine-nucleotide-exchange factor), and cyclic-nucleotide-gated ion channels.[2]
Cyclic adenosine monophosphate (cAMP) is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Once believed to signal exclusively through its ability to bind protein kinase A (PKA), recent research has revealed alternative cAMP-binding targets involved in PKA-independent processes. In this study we addressed the hypothesis that the guanine nucleotide exchange protein directly activated by cAMP (Epac-1) and PKA differentially regulate inflammatory mediator production in distinct phagocytic cell types. To accomplish this, we compared the release of cAMP-regulated polypeptide inflammatory mediators in both macrophages (obtained from the lung and peritoneum) and bone marrow-derived dendritic cells (DCs) stimulated with bacterial endotoxin. Using the highly selective Epac-1 and PKA activating cAMP analogs 8-pCPT-2 -O-Me-cAMP and 6-Bnz-cAMP, respectively, we found that macrophages differ from DCs in the involvement of these distinct cAMP pathways in modulating inflammatory mediator release in response to endotoxin. Whereas the regulation of cytokine and chemokine production in macrophages by cAMP was solely dependent on PKA, we found that both Epac-1 and PKA activation could regulate mediator production in DCs. This finding may be important in the pharmacologic regulation of immune responses through manipulation of cAMP signaling cascades and contributes to our understanding of the differences between these cell types. [3] |
| Toxicity/Toxicokinetics |
23669773 Mice oral LD50 14300 mg/kg Behavior: altered sleep duration (including altered righting reflex); Behavior: lethargy (reduced overall activity); Gastrointestinal: other changes. Journal of Toxicological Science, 1(2)(15), 1976
23669773 Mice intraperitoneal LD50 395 mg/kg Behavior: altered sleep duration (including altered righting reflex); Behavior: tremor; Behavior: ataxia. Journal of Toxicological Science, 1(2)(15), 1976 23669773 Mice intravenous LD50 645 mg/kg Behavior: altered sleep duration (including altered righting reflex); Behavior: tremor; Behavior: ataxia. Journal of Toxicological Science, 1(2)(15), 1976 |
| References |
[1]. Cyclic AMP signaling. J Cell Sci. 2001 Jun;114(Pt 11):1971-2.
[2]. The cyclic AMP pathway. Cold Spring Harb Perspect Biol. 2012 Dec 1;4(12):a011148. [3]. Short communication: differences between macrophages and dendritic cells in the cyclic AMP-dependent regulation of lipopolysaccharide-induced cytokine and chemokine synthesis. J Interferon Cytokine Res. 2006 Nov;26(11):827-33. |
| Additional Infomation |
3',5'-Cyclic adenosine monophosphate (cAMP) is a 3',5'-cyclic purine nucleotide with adenine as its nucleobase. It is a metabolite found in humans, E. coli, and mice. It is an adenosine monophosphate ribonucleotide and also a 3',5'-cyclic purine nucleotide. It is the conjugate acid of 3',5'-cyclic adenosine monophosphate (1-). Cyclic adenosine monophosphate (cAMP, cyclic AMP, or 3'-5'-cyclic adenosine monophosphate) is a molecule that plays an important role in many biological processes; it is derived from adenosine triphosphate (ATP). Cyclic adenosine monophosphate (cAMP) is present in or produced by E. coli (K12 strain, MG1655 strain). cAMP has also been reported in jujube (Ziziphus jujuba), rye (Secale cereale), and other organisms with relevant data. cAMP is a second messenger molecule composed of an adenine nucleotide whose glycosyl moiety has oxygen atoms at the 3' and 5' positions bound to a phosphate group. Cyclic adenosine monophosphate (cAMP) is synthesized from ATP by the intracellular enzyme adenylate cyclase and regulates various hormone-dependent signal transduction pathways. 3',5'-Cyclic adenosine monophosphate (cAMP) is a metabolite found or produced in Saccharomyces cerevisiae. It is an adenine nucleotide with its glycosyl moiety esterified to a phosphate group at both the 3' and 5' positions. cAMP is a second messenger and a key intracellular regulator that mediates the activity of various hormones, including adrenaline, glucagon, and adrenocorticotropic hormone. See also: Jujube (partial).
|
| Molecular Formula |
C10H11N5NAO6P
|
|---|---|
| Molecular Weight |
351.19
|
| Exact Mass |
351.034
|
| CAS # |
37839-81-9
|
| Related CAS # |
Cyclic AMP;60-92-4
|
| PubChem CID |
23669773
|
| Appearance |
White to off-white solid powder
|
| Boiling Point |
701.5ºC at 760 mmHg
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| Melting Point |
219 - 220ºC
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| Flash Point |
378ºC
|
| LogP |
0.202
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
10
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
23
|
| Complexity |
504
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)[O-].[Na+]
|
| InChi Key |
BXJBFCKTIWRKMQ-MCDZGGTQSA-M
|
| InChi Code |
InChI=1S/C10H12N5O6P.Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7;/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13);/q;+1/p-1/t4-,6-,7-,10-;/m1./s1
|
| Chemical Name |
sodium;(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
|
| Synonyms |
Cyclic AMP sodium; 37839-81-9; cAMP-Na; 3',5'-Amp sodium salt; Cyclic 3',5'-amp sodium salt; Cyclic AMP (sodium); MFCD00069736; Cyclic 3',5'-(hydrogen phosphate)adenosine monosodium salt;
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| 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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: 50 mg/mL (142.37 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.12 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 (7.12 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8475 mL | 14.2373 mL | 28.4746 mL | |
| 5 mM | 0.5695 mL | 2.8475 mL | 5.6949 mL | |
| 10 mM | 0.2847 mL | 1.4237 mL | 2.8475 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.
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.
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