| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| Other Sizes |
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| Targets |
cAMP analog
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|---|---|
| ln Vitro |
8-Bromo-cAMP sodium salt is a brominated derivative of cyclic AMP that enhances cell reprogramming. 8-Bromo-cAMP sodium salt increases the reprogramming effectiveness of human newborn foreskin fibroblasts (HFF1). 8-Bromo-cAMP sodium salt reduces the proliferation, differentiation, and death of malignant glioma cell lines (A-172) and esophageal cancer cell lines (Eca-109) [3].
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| ln Vivo |
Researhers examined effects of adenine nucleotide on ischemic myocardial stunning in dogs. Pentobarbitalanesthetized open-chest dogs were subjected to 20-min ligation of the left anterior descending coronary artery (LAD), followed by reperfusion for 30 min. Either saline, 5 mM 8-bromo-5'-AMP (tributyryl-AMP), or 30 mM N6, 2', 3'-tributyryl-5'-AMP (tributyryl-AMP), 5 mM 5-amino-4-imidazole carboxamide riboside (AICAr) as a positive reference, was infused at 0.1 ml/kg/min in the left femoral vein throughout the experiment. The myocardial contractile function was measured by ultrasonometry. The tissue levels of high-energy phosphates in the reperfused heart were determined. Myocardial contractile function assessed by % segment shortening (%SS) in the saline-infused group decreased during ischemia and returned toward the preischemic level during reperfusion but incompletely. A significant improvement in the %SS during reperfusion was observed in the 8-bromo-AMP- and AICAr-infused groups but not in the tributyryl-AMP-infused group. The magnitude of the protective effect of the drugs on myocardial contractility during reperfusion was 8-bromo-AMP > AICAr > tributyryl-AMP = saline. Only in the 8-bromo-AMP-infused group were the levels of ATP, ADP, and total adenine nucleotides in the reperfused heart significantly higher than those in the saline-infused group. The present result indicates that 8-bromo-AMP improves the ability of the heart to recover from ischemia and reperfusion associated with a significant restoration of ATP[2].
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| Enzyme Assay |
Human endometrium decidualization, a differentiation process involving biochemical and morphological changes, is a prerequisite for embryo implantation and successful pregnancy. Here, we show that the mammalian target of rapamycin (mTOR) is a crucial regulator of 8-bromoadenosine 3',5'-cyclic monophosphate (8-Br-cAMP )-induced decidualization in human endometrial stromal cells. The level of mSin1 in mTOR complex 2 (mTORC2) and DEPTOR in mTOR complex 1 (mTORC1) decreases during 8-Br-cAMP -induced decidualization, resulting in decreased mTORC2 activity and increased mTORC1 activity. Notably, DEPTOR displacement increases the association between raptor and insulin receptor substrate-1 (IRS-1), facilitating IRS-1 phosphorylation at serine 636/639. Finally, both S473 and T308 phosphorylation of Akt are reduced during decidualization, followed by a decrease in forkhead box O1 (FOXO1) phosphorylation and an increase in the mRNA levels of the decidualization markers prolactin (PRL) and insulin-like growth factor-binding protein-1 (IGFBP-1). Taken together, our findings reveal a critical role for mTOR in decidualization, involving the differential regulation of mTORC1 and mTORC2[5].
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| Cell Assay |
The apoptotic rate of E2 group was significantly higher compared to E1 group, while there was no difference in the ratio of differentiated cells/proliferating cells between E1 and E2 groups. The signals of wt p53 and iNOS were markedly stronger, while the signals of c-myc and EGFR were obviously weaker in E1 group than those in C1 group (P<0.05). Moreover, the signals of wt p53, iNOS, p38 kinase, caspase-3 and NOS activity were significantly stronger, whereas, the signals of bcl-2, c-myc and Fas/FasL were markedly weaker in E2 group than those in C2 group (P<0.05).[4]
Conclusion: The differentiation and apoptosis of human esophageal cancer cell Eca-109 can be induced after 24- and 48-h treatment with 8-Br-cAMP , respectively. Upregulation of wt p53, iNOS and downregulation of c-myc may be associated with differentiation and apoptosis of Eca-109 cells. Furthermore, upregulation of FasL, p38 kinase and caspase-3 as well as downregulation of bcl-2, and Fas may be involved in the apoptosis of Eca-109 cells.[4] |
| Animal Protocol |
Thirty-six mice received the implantation of CT26 carcinoma tissue in their cecum. After general anesthesia and sterilization, a 2 cm vertical incision was made at the right lower quadrant of the abdomen. The cecum was then pulled out of the abdomen. The serosa of the cecum that was exposed out was scratched, and a 2 mm diameter tumor tissue was attached with fibrin glue. Finally, the cecum was put back into place and the skin was sealed. After tumor implantation, mice were randomly divided into a control group and an experimental group. In the experimental group, the intraperitoneal injection of 8-Br-cAMP (60 mg/kg/day) was performed for 7 days, while control mice received injection of normal saline. Mice were sacrificed on the 7th, 14th, and 28th days, and tumor tissue was harvested for the evaluation of gene expression. However, due to a high mortality rate, the number of mice for sacrifice at each time point was adjusted in order to guarantee that mice were available for culling on the 28th day. [6]
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| References |
[1]. Jiang J, et, al. Evidences for involvement of endogenous cAMP in Arabidopsis defense responses to Verticillium toxins. Cell Res. 2005 Aug;15(8):585-92.
[2]. Nakai T, et, al. Effects of adenine nucleotide analogues on myocardial dysfunction during reperfusion after ischemia in dogs. J Cardiovasc Pharmacol. 1996 Aug;28(2):264-70. [3]. A cyclic AMP analog, 8-Br-cAMP, enhances the induction of pluripotency in human fibroblast cells. Stem Cell Rev. 2011 Jun;7(2):331-41. [4]. Dual effects of 8-Br-cAMP on differentiation and apoptosis of human esophageal cancer cell line Eca-109. World J Gastroenterol. 2005 Nov 7;11(41):6538-42. [5]. Differential regulation of mTORC1 and mTORC2 is critical for 8-Br-cAMP-induced decidualization. Exp Mol Med. 2018 Oct 30;50(10):1-11. [6]. Angiogenesis and vasculogenic mimicry are inhibited by 8-Br-cAMP through activation of the cAMP/PKA pathway in colorectal cancer. Onco Targets Ther. 2018 Jul 2;11:3765-3774. |
| Additional Infomation |
Although there were reports suggesting the involvement of endogenous cAMP in plant defense signaling cascades, there is no direct evidence supporting this notion yet and the detailed mechanism is unclear. In the present study, we have used pathogenic fungi Verticillium dahliae and Arabidopsis plants as a model system of plant-microb interaction to demonstrate the function of endogenous cAMP in Arabidopsis defense responses. Both V. dahliae inoculation and Verticillium toxins injection induced typical "wilt" symptoms in Arabidopsis seedlings. When either 8-Br-AMP (a membrane permeable cAMP analogue) or salicylic acid (SA) was applied to Arabidopsis, the plants became resistant to V. dahliae toxins. However, addition of 8-Br-AMP did not increase the resistance of Arabidopsis transgenic plants deficient in SA to the toxins, suggesting that cAMP might act upstream of SA in plant defense signaling pathway. Indeed, 8-Br-cAMP and forskolin, an activator of adenylyl cyclase, significantly stimulated the endogenous SA level in plants, whereas DDA, an inhibitor of adenylyl cyclase dramatically reduced toxin-induced SA increase. Both the endogenous cAMP and SA increased significantly in Arabidopsis seedlings treated with toxins. Furthermore, transcription level of pathogenesis-related protein 1 gene (PR1) was strongly induced by both 8-Br-cAMP and the toxin treatment. Taken together, our data demonstrate that endogenous cAMP is involved in plant defense responses against Verticillium-secreted toxins by regulating the production of the known signal SA in plant defense pathway.[1]
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| Molecular Formula |
C10H13BRN5O7P
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|---|---|
| Molecular Weight |
426.12
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| Exact Mass |
422.958
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| CAS # |
23567-96-6
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| Related CAS # |
8-Bromo-cAMP sodium salt;76939-46-3
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| PubChem CID |
168120
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| Appearance |
White to off-white solid powder
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| LogP |
0.357
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
24
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| Complexity |
514
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C1=NC(=C2C(=N1)N(C(=N2)Br)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N
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| InChi Key |
DNPIJKNXFSPNNY-UUOKFMHZSA-N
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| InChi Code |
InChI=1S/C10H13BrN5O7P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,13,14)(H2,19,20,21)/t3-,5-,6-,9-/m1/s1
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| Chemical Name |
[(2R,3S,4R,5R)-5-(6-amino-8-bromopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
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| Synonyms |
23567-96-6; 8-Bromo-AMP; 8-BROMO-ADENOSINE-5'-MONOPHOSPHATE; 8-Bromoadenosine 5'-monophosphate; 8-Bromoadenosine 5'-(dihydrogen phosphate); 5'-Adenylic acid, 8-bromo-; CHEMBL1230617; 8-Bromo-Adenosine Mono Phosphate;
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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) |
H2O: 125 mg/mL (293.34 mM)
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|---|---|
| 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 | 2.3468 mL | 11.7338 mL | 23.4676 mL | |
| 5 mM | 0.4694 mL | 2.3468 mL | 4.6935 mL | |
| 10 mM | 0.2347 mL | 1.1734 mL | 2.3468 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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