This product is soluble in alkaline conditions. Sigma routinely tests solubility at 50 mg/ml in 1 N ammonium hydroxide.
B5386
8-Bromoadenosine 3′,5′-cyclic monophosphate
≥97% (HPLC), powder, protein kinase A activator
Synonyme(s) :
8-Br-A-3:5-MP, 8-Br-cAMP, 8-Bromo-cAMP
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5 MG
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25 MG
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About This Item
Formule empirique (notation de Hill):
C10H11BrN5O6P
Numéro CAS:
Poids moléculaire :
408.10
Beilstein:
591930
Numéro CE :
Numéro MDL:
Code UNSPSC :
41106305
ID de substance PubChem :
Nomenclature NACRES :
NA.77
54,80 $
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Nom du produit
8-Bromoadenosine 3′,5′-cyclic monophosphate, ≥97% (HPLC)
Niveau de qualité
Essai
≥97% (HPLC)
Forme
powder
Pf
254 °C (dec.) (lit.)
Solubilité
aqueous base: soluble, clear
Température de stockage
−20°C
Chaîne SMILES
Nc1ncnc2n([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)c(Br)nc12
InChI
1S/C10H11BrN5O6P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
Clé InChI
DVKQVRZMKBDMDH-UUOKFMHZSA-N
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Application
8-Bromoadenosine 3′,5′-cyclic monophosphate has been used:
- to treat H295R cells as positive controls for CYP19 induction[1]
- as a membrane permeable cAMP analog to study its effect on short-circuit current (Isc)[2]
- to investigate its potential as an inducer of differentiation in Wharton′s jelly-derived mesenchymal stem cells (WJ-MSCs)[3]
Actions biochimiques/physiologiques
8-Bromoadenosine 3′,5′-cyclic monophosphate is a cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP. 8-Bromoadenosine 3′,5′-cyclic monophosphate activates protein kinase A, inhibits growth, decreases proliferation, increases differentiation, and induces apoptosis of cultured cells.
8-bromo-adenosine 3′,5′-cyclic monophosphate (8-bromo-cAMP), added to hepatocytes during plating helps to increase the acquisition of beta-adrenoceptors.[4]
Caractéristiques et avantages
This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
Autres remarques
8-Bromoadenosine 3′,5′-cyclic monophosphate is a membrane-permeable cAMP analog.
Sensitive to light and moisture
Attention
Sensitive to light and moisture.
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 3
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
Équipement de protection individuelle
Eyeshields, Gloves, type N95 (US)
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Les clients ont également consulté
8-Bromo-cAMP and 8-CPT-cAMP Increase the Density of beta-Adrenoceptors in Hepatocytes by a Mechanism Not Mimicking the Effect of cAMP
Sandnes D, et al.
Pharmacology & Toxicology, 79(1), 15-22 (1996)
Differentiation of human umbilical cord Wharton?s jelly-derived mesenchymal stem cells into endometrial cells
Shi Q, et al.
Stem Cell Research & Therapy, 8(1), 246-246 (2017)
Dopamine increases Na+ absorption in the Reissner's membrane of the gerbil cochlea
Kim C H, et al.
Auris, Nasus, Larynx, 40(3), 266-272 (2013)
2, 3, 7, 8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells
Sanderson J T, et al.
Toxicological Sciences, 61(1), 40-48 (2001)
Akihiro Goto et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(11), 4901-4912 (2013-03-15)
Enteric neural crest-derived cells (ENCCs) migrate from the anterior foregut in a rostrocaudal direction to colonize the entire gastrointestinal tract and to form the enteric nervous system. Genetic approaches have identified many signaling molecules regulating the migration of ENCCs; however
Articles
Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.
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How can I solubilize 8-Bromoadenosine 3',5'-cyclic monophosphate (Product No. B5386)?
1 answer-
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How does the storage temperature relate to shipping conditions?
1 answer-
The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment.
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How can I store solutions of 8-Bromoadenosine 3',5'-cyclic monophosphate (Product No. B5386)?
1 answer-
The solution should be stored at -20°C, protected from light and will be stable for up to 6 months.
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What is the difference between Product No. B5386 and Product No. B7880?
1 answer-
Product No. B5386 is the free acid form of the material, while Product No. B7880 is the sodium salt. The sodium salt aids in the water solubility of the compund. The biological function of the compounds, once dissolved, is identical.
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What is the Department of Transportation shipping information for this product?
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Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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