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Sigma-Aldrich

8-Bromoadenosine

≥99.0% (HPLC)

Synonym(s):

6-Amino-8-bromopurine riboside, 8-Bromoadenine-9-β-D-ribofuranoside

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About This Item

Empirical Formula (Hill Notation):
C10H12BrN5O4
CAS Number:
2946-39-6
Molecular Weight:
346.14
Beilstein:
627737
EC Number:
220-959-0
MDL number:
MFCD00005733
UNSPSC Code:
41106305

Assay

≥99.0% (HPLC)

optical activity

[α]20/D −33±2°, c = 1% in 1 M HCl

mp

210-212 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

Nc1ncnc2n([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c(Br)nc12

InChI

1S/C10H12BrN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)/t3-,5-,6-,9-/m1/s1

InChI key

VJUPMOPLUQHMLE-UUOKFMHZSA-N

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Other Notes

Inhibits the binding of cyclic AMP and adenosine to the activated cyclic AMP/adenosine binding protein

replaced by

Product No.
Description
Pricing

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

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An adenosine 3':5'-monophosphate/adenosine binding protein from mouse liver. A study of its interaction with synthetic and naturally occurring adenosine derivatives.
P M Ueland
European journal of biochemistry, 86(1), 27-34 (1978-05-01)
Y T van den Hoogen et al.
European journal of biochemistry, 182(3), 629-637 (1989-07-01)
NMR and model-building studies were carried out on pA2'-5'A2'-5'A and analogs in which one or more of the A residues were replaced by 8-bromoadenosine. Chemical shifts, coupling constants and NOE data were used to obtain structural information. The N/S equilibrium
R J Hegeman et al.
Thrombosis and haemostasis, 79(4), 853-858 (1998-05-06)
The effect of compounds increasing intracellular adenosine 3':5'-cyclic monophosphate [cAMP]i levels (prostacyclin, isoproterenol, forskolin, cholera toxin), and of the cAMP analogs 8-bromo-cAMP and dibutyryl-cAMP, on the regulated secretion (acute release) of tissue-type plasminogen activator (tPA) and von Willebrand factor (vWF)
F P Gasparro et al.
Nucleic acids research, 14(10), 4239-4251 (1986-05-27)
Characteristic fluorescence excitation and emission is induced by either acetone-sensitized 313 nm irradiation of mixtures of 8-bromoadenosine and adenosine or 254 nm irradiation of oligo- and polynucleotides containing adenine neighbors. The acetone-sensitized reaction involves cleavage of bromine from 8-bromoadenosine with
D Pinsky et al.
The Journal of clinical investigation, 92(6), 2994-3002 (1993-12-01)
Current organ preservation strategies subject graft vasculature to severe hypoxia (PO2 approximately 20 Torr), potentially compromising vascular function and limiting successful transplantation. Previous work has shown that cAMP modulates endothelial cell (EC) antithrombogenicity, barrier function, and leukocyte/EC interactions, and that
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