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B7880

Sigma-Aldrich

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

≥97% (HPLC), powder

Synonym(s):

8-Br-cAMP

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About This Item

Empirical Formula (Hill Notation):
C10H10BrN5NaO6P
CAS Number:
76939-46-3
Molecular Weight:
430.08
Beilstein:
7739743
MDL number:
MFCD00005844
UNSPSC Code:
41106305
PubChem Substance ID:
24278020
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

color

off-white

solubility

H2O: 100 mg/mL

storage temp.

−20°C

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

InChI key

DMRMZQATXPQOTP-GWTDSMLYSA-M

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General description

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

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.

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

Membrane-permeable cAMP analog.

Caution

Sensitive to light and moisture.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
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)
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
Joseph R Blasic et al.
PloS one, 7(9), e45387-e45387 (2012-10-11)
The visual pigment melanopsin is expressed in intrinsically photosensitive retinal ganglion cells (ipRGCs) in the mammalian retina, where it is involved in non-image forming light responses including circadian photoentrainment, pupil constriction, suppression of pineal melatonin synthesis, and direct photic regulation
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