8-Bromoadenosine 3′,5′-cyclic monophosphate

SIGMA/B5386 - ≥97% (HPLC)

Synonym: 8-Br-A-3:5-MP; 8-Br-cAMP; 8-Bromo-cAMP

CAS Number: 23583-48-4
Empirical Formula (Hill Notation): C₁₀H₁₁BrN₅O₆P
Molecular Weight: 408.10
EC Number: 245-760-6
MDL Number: MFCD00075580
Linear Formula: C₁₀H₁₁BrN₅O₆P
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-B5386-5MG	5 mg	$46.40 1/EA	Add To Favorites
45-B5386-25MG	25 mg	$156.00 1/EA	Add To Favorites
45-B5386-100MG	100 mg	$468.00 1/EA	Add To Favorites

ATR-IR Spectra for 8-Bromoadenosine 3′,5′-cyclic monophosphate.

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: B5386-100MG

Properties
Descriptions
Safety Info.
Basic Data

assay	≥97% (HPLC)
form	powder
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
mp	254 °C (dec.) (lit.)
Quality Level	200
SMILES string	Nc1ncnc2n([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)c(Br)nc12
solubility	aqueous base: soluble, clear
storage temp.	−20°C

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-bromo-adenosine 3′,5′-cyclic monophosphate (8-bromo-cAMP), added to hepatocytes during plating helps to increase the acquisition of beta-adrenoceptors.
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.
Biochem/physiol Actions:	Cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP.
Disclaimer:	Sensitive to light and moisture.
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.
Other Notes:	Sensitive to light and moisture
Packaging:	25, 100 mg in poly bottle
Packaging:	5 mg in glass bottle

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥97% (HPLC)
mp	254 °C (dec.) (lit.)
Storage Temp.	−20°C
UNSPSC	41106305

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