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
Sign In to View Organizational & Contract Pricing.
Select a Size
Change View
About This Item
Empirical Formula (Hill Notation):
C10H11BrN5O6P
CAS Number:
Molecular Weight:
408.10
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
245-760-6
MDL number:
Beilstein/REAXYS Number:
591930
Product Name
8-Bromoadenosine 3′,5′-cyclic monophosphate, ≥97% (HPLC)
Quality Level
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
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 (Isc)
- to investigate its potential as an inducer of differentiation in Wharton′s jelly-derived mesenchymal stem cells (WJ-MSCs)
Biochem/physiol Actions
8-bromo-adenosine 3′,5′-cyclic monophosphate (8-bromo-cAMP), added to hepatocytes during plating helps to increase the acquisition of beta-adrenoceptors.
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.
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
Disclaimer
Sensitive to light and moisture.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Articles
Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.
Related Content
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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| B5386-5MG | 04061832895789 |
| B5386-25MG | 04061833433799 |
| B5386-100MG | 04061833433782 |