| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
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| 1g |
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| 10g |
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| 1kg |
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| Other Sizes |
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Purity: ≥98%
| Targets |
Endogenous Metabolite; Microbial Metabolite
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|---|---|
| ln Vitro |
Cyclic adenosine monophosphate, or cyclic AMP, controls the synthesis of mediators. Cyclic AMP 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] |
| 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 AMP is a 3',5'-cyclic purine nucleotide having having adenine as the nucleobase. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an adenyl ribonucleotide and a 3',5'-cyclic purine nucleotide. It is a conjugate acid of a 3',5'-cyclic AMP(1-).
Cyclic adenosine monophosphate (cAMP, cyclic AMP or 3'-5'-cyclic adenosine monophosphate) is a molecule that is important in many biological processes; it is derived from adenosine triphosphate (ATP). Cyclic AMP is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Cyclic AMP has been reported in Ziziphus jujuba, Secale cereale, and other organisms with data available. Cyclic AMP is a second messenger molecule comprised of an adenine ribonucleotide bearing a phosphate group bound to the oxygen molecules at the 3' and 5' positions of the sugar moiety. Cyclic AMP, which is synthesized from ATP by the intracellular enzyme adenylate cyclase, modulates the activity of several hormone-dependent signal transduction pathways. 3',5'-cyclic AMP is a metabolite found in or produced by Saccharomyces cerevisiae. An adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. It is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon, and ACTH. See also: Jujube fruit (part of). |
| Molecular Formula |
C10H14N5O7P
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|---|---|
| Molecular Weight |
347.22
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| Exact Mass |
329.052
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| Elemental Analysis |
C, 34.59; H, 4.06; N, 20.17; O, 32.25; P, 8.92
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| CAS # |
60-92-4
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| Related CAS # |
37839-81-9 (mono-hydrochloride salt)
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| PubChem CID |
6076
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| Appearance |
White to off-white solid powder
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| Density |
2.5±0.1 g/cm3
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| Boiling Point |
701.5±70.0 °C at 760 mmHg
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| Melting Point |
260 °C (dec.)(lit.)
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| Flash Point |
378.0±35.7 °C
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| Vapour Pressure |
0.0±2.3 mmHg at 25°C
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| Index of Refraction |
2.012
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| LogP |
-2.6
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
22
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| Complexity |
498
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| Defined Atom Stereocenter Count |
4
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| SMILES |
P1(=O)(O[H])OC([H])([H])[C@]2([H])[C@]([H])([C@]([H])([C@]([H])(N3C([H])=NC4=C(N([H])[H])N=C([H])N=C34)O2)O[H])O1
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| InChi Key |
IVOMOUWHDPKRLL-KQYNXXCUSA-N
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| InChi Code |
InChI=1S/C10H12N5O6P/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)/t4-,6-,7-,10-/m1/s1
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| Chemical Name |
Adenosine cyclic 3',5'-monophosphate
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| Synonyms |
Cyclic AMP; NSC-94017; NSC94017; Cyclic AMP; cAMP; 60-92-4; Adenosine 3',5'-cyclic monophosphate; 3',5'-cyclic AMP; Adenosine 3',5'-cyclophosphate; Adenosine 3',5'-phosphate; cyclic 3',5'-AMP; NSC 94017
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
0.1 M NaOH : ~30 mg/mL (~91.13 mM)
H2O : ~2.4 mg/mL (~7.29 mM) DMSO : ~1 mg/mL (~3.04 mM) |
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8800 mL | 14.4001 mL | 28.8002 mL | |
| 5 mM | 0.5760 mL | 2.8800 mL | 5.7600 mL | |
| 10 mM | 0.2880 mL | 1.4400 mL | 2.8800 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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