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B5386

8-Bromoadenosine 3′,5′-cyclic monophosphate

Name: 8-Bromoadenosine 3&#8242;,5&#8242;-cyclic monophosphate
Brand: SIGMA

≥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

NACRES:

NA.77

PubChem Substance ID:

24891835

UNSPSC Code:

41106305

EC Number:

245-760-6

MDL number:

MFCD00075580

Beilstein/REAXYS Number:

591930

Assay:

≥97% (HPLC)

Form:

powder

Quality level:

200

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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

Related Categories

Bioactive Small Molecules

Phosphates

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.

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)

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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)

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)

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)

GDNF and endothelin 3 regulate migration of enteric neural crest-derived cells via protein kinase A and Rac1.

Akihiro Goto et al.

The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(11), 4901-4912 (2013-03-15)

Enteric neural crest-derived cells (ENCCs) migrate from the anterior foregut in a rostrocaudal direction to colonize the entire gastrointestinal tract and to form the enteric nervous system. Genetic approaches have identified many signaling molecules regulating the migration of ENCCs; however

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Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

Global Trade Item Number

SKU	GTIN
B5386-5MG	04061832895789
B5386-25MG	04061833433799
B5386-100MG	04061833433782

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