B5386

8-Bromoadenosine 3′,5′-cyclic monophosphate

≥97% (HPLC), powder, protein kinase A activator

• Synonym(s): 8-Br-A-3:5-MP, 8-Br-cAMP, 8-Bromo-cAMP
• Empirical Formula (Hill Notation): C₁₀H₁₁BrN₅O₆P
• CAS Number: 23583-48-4
• Molecular Weight: 408.10
• Beilstein: 591930
• EC Number: 245-760-6
• MDL number: MFCD00075580
• UNSPSC Code: 41106305
• PubChem Substance ID: 24891835
• NACRES: NA.77

Properties

• Product Name: 8-Bromoadenosine 3′,5′-cyclic monophosphate, ≥97% (HPLC)
• Assay: ≥97% (HPLC)
• form: powder
• mp: 254 °C (dec.) (lit.)
• solubility: aqueous base: soluble, clear
• storage temp.: −20°C
• SMILES string: 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
• InChI key: DVKQVRZMKBDMDH-UUOKFMHZSA-N

Description

Application

8-Bromoadenosine 3′,5′-cyclic monophosphate has been used:

• to treat H295R cells as positive controls for CYP19 induction
• as a membrane permeable cAMP analog to study its effect on short-circuit current (I_sc)
• to investigate its potential as an inducer of differentiation in Wharton′s jelly-derived mesenchymal stem cells (WJ-MSCs)

Biochem/physiol Actions

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.

Cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP.

Features and Benefits

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.

Other Notes

8-Bromoadenosine 3′,5′-cyclic monophosphate is a membrane-permeable cAMP analog.

Sensitive to light and moisture

Caution

Sensitive to light and moisture.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves