B7880

8-Bromoadenosine 3′,5′-cyclic monophosphate sodium salt

Name: 8-Bromoadenosine 3′,5′-cyclic monophosphate sodium salt
Brand: SIGMA

≥97% (HPLC), PKA activator, powder

Synonym(s):

8-Br-cAMP

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All Photos(3)

About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₀BrN₅NaO₆P

CAS Number:

76939-46-3

Molecular Weight:

430.08

NACRES:

NA.77

PubChem Substance ID:

24278020

UNSPSC Code:

41106305

MDL number:

MFCD00005844

Beilstein/REAXYS Number:

7739743

Product Name

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

InChI key

DMRMZQATXPQOTP-GWTDSMLYSA-M

SMILES string

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

InChI

1S/C10H11BrN5O6P.Na/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);/q;+1/p-1/t3-,5-,6-,9-;/m1./s1

assay

≥97% (HPLC)

form

powder

color

off-white

solubility

H₂O: 100 mg/mL

storage temp.

−20°C

Quality Level

200

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Related Categories

Bioactive Small Molecules

Phosphates

Application

8-Bromoadenosine 3′,5′-cyclic monophosphate sodium salt has been used:

to study its effect on fas and caspase-3 mRNA expression and on P4 production in bovine mid luteal cell culture
used to treat choriocarcinoma BeWo cell line and study its effect on cell viability, apoptosis and morphological changes in the nuclei
in superfusion medium for head kidneys stimulation

Biochem/physiol Actions

Cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP. Activates protein kinase A, inhibits growth, decreases proliferation, increases differentiation, and induces apoptosis of cultured cells.

Cell-permeable cAMP analog with greater resistance to hydrolysis by phosphodiesterases than cAMP.

Disclaimer

Sensitive to light and moisture.

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.

General description

8-Bromoadenosine 3′:5′-cyclic monophosphate is a brominated cyclic mononucleotide.

Other Notes

Membrane-permeable cAMP analog.

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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Effects of corticotrophin releasing hormone (CRH) on cell viability and differentiation in the human BeWo choriocarcinoma cell line: a potential syncytialisation inducer distinct from cyclic adenosine monophosphate (cAMP)

Chen Y, et al.

Reproductive Biology and Endocrinology, 11(1), 30-30 (2013)

Corticotropin-releasing factor (CRF) and CRF-binding protein expression in and release from the head kidney of common carp: evolutionary conservation of the adrenal CRF system

Huising MO, et al.

The Journal of Endocrinology, 193(3), 349-357 (2007)

Control of human endometrial stromal cell motility by PDGF-BB, HB-EGF and trophoblast-secreted factors.

Maren Schwenke et al.

PloS one, 8(1), e54336-e54336 (2013-01-26)

Human implantation involves extensive tissue remodeling at the fetal-maternal interface. It is becoming increasingly evident that not only trophoblast, but also decidualizing endometrial stromal cells are inherently motile and invasive, and likely contribute to the highly dynamic processes at the

Possible roles of intracellular cyclic AMP, protein kinase C and calcium ion in the apoptotic signaling pathway in bovine luteal cells}

Tatsukawa Y, et al.

Journal of Reproduction and Development, 52(4), 517-522 (2006)

Anti-Inflammatory Effects of β2-Receptor Agonists Salbutamol and Terbutaline Are Mediated by MKP-1.

Tiina Keränen et al.

PloS one, 11(2), e0148144-e0148144 (2016-02-06)

Mitogen-activated protein kinase phosphatase 1 (MKP-1) expression is induced by inflammatory factors, and it is an endogenous suppressor of inflammatory response. MKP-1 expression is increased by PDE4 inhibitor rolipram suggesting that it is regulated by cAMP-enhancing compounds. Therefore, we investigated

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