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B5386

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C10H11BrN5O6P
CAS Number:
23583-48-4
Molecular Weight:
408.10
Beilstein/REAXYS Number:
591930
EC Number:
245-760-6
MDL number:
MFCD00075580
UNSPSC Code:
41106305
PubChem Substance ID:
24891835
NACRES:
NA.77

product name

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

Quality Level

200

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

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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)

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.

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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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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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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