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Merck

B5386

8-Bromoadenosine 3′,5′-cyclic monophosphate

≥97% (HPLC), powder, protein kinase A activator

Sinónimos:

8-Br-A-3:5-MP, 8-Br-cAMP, 8-Bromo-cAMP

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Fórmula empírica (notación de Hill):
C10H11BrN5O6P
Número CAS:
23583-48-4
Peso molecular:
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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Nombre del producto

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

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

SMILES string

Nc1ncnc2n([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)c(Br)nc12

InChI key

DVKQVRZMKBDMDH-UUOKFMHZSA-N

assay

≥97% (HPLC)

form

powder

mp

254 °C (dec.) (lit.)

solubility

aqueous base: soluble, clear

storage temp.

−20°C

Quality Level

200

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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.
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.

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
0000276013
0000276015
0000276013
0000276015
SLCC7982

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  1. How does the storage temperature relate to shipping conditions?

    The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.

  2. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  3. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  5. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  6. How can I solubilize 8-Bromoadenosine 3',5'-cyclic monophosphate (Product No. B5386)?

    This product is soluble in alkaline conditions. Sigma routinely tests solubility at 50 mg/ml in 1 N ammonium hydroxide.

  7. How can I store solutions of 8-Bromoadenosine 3',5'-cyclic monophosphate (Product No. B5386)?

    The solution should be stored at -20°C, protected from light and will be stable for up to 6 months.

  8. What is the difference between Product No. B5386 and Product No. B7880?

    Product No. B5386 is the free acid form of the material, while Product No. B7880 is the sodium salt. The sodium salt aids in the water solubility of the compund.  The biological function of the compounds, once dissolved, is identical.

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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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