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B5386

Sigma-Aldrich

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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About This Item

Formule empirique (notation de Hill):
C10H11BrN5O6P
Numéro CAS:
23583-48-4
Poids moléculaire :
408.10
Numéro Beilstein :
591930
Numéro CE :
245-760-6
Numéro MDL:
MFCD00075580
Code UNSPSC :
41106305
ID de substance PubChem :
24891835
Nomenclature NACRES :
NA.77

product name

8-Bromoadenosine 3′,5′-cyclic monophosphate, ≥97% (HPLC)

Pureté

≥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
  • 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)

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.

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)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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)
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)
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)
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)
Hisayuu Cho et al.
Fertility and sterility, 99(1), 248-255 (2012-10-06)
To investigate whether heart and neural crest derivatives expressed transcript 2 (HAND2) regulates fibulin-1 (FBLN1) expression during decidualization of human endometrial stromal cells (ESCs). In vitro experiment. Research laboratory. Twenty-four patients undergoing hysterectomy for benign reasons. ESCs were cultured with various
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Contenu apparenté

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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