Merck
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B5386

Sigma-Aldrich

8-Bromoadenosine 3′,5′-cyclic monophosphate

≥97% (HPLC)

Synonym(s):
8-Br-A-3:5-MP, 8-Bromo-cAMP, 8-Br-cAMP
Empirical Formula (Hill Notation):
C10H11BrN5O6P
CAS Number:
Molecular Weight:
408.10
Beilstein:
591930
Número de EC:
Número MDL:
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

200

ensayo

≥97% (HPLC)

formulario

powder

mp

254 °C (dec.) (lit.)

solubilidad

aqueous base: soluble, clear

temp. de almacenamiento

−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

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Aplicación

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)

Envase

5 mg in glass bottle
25, 100 mg in poly bottle

Acciones bioquímicas o fisiológicas

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.

Características y beneficios

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.

Otras notas

8-Bromoadenosine 3′,5′-cyclic monophosphate is a membrane-permeable cAMP analog.
Sensitive to light and moisture

Precaución

Sensitive to light and moisture.

Código de clase de almacenamiento

13 - Non Combustible Solids

WGK

WGK 3

Punto de inflamabilidad F

Not applicable

Punto de inflamabilidad C

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

Certificate of Analysis

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Certificate of Origin

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Related Content

Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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