All Photos(2)

B3756

Sigma-Aldrich

8-Bromoadenosine 5′-triphosphate sodium salt

≥90% (HPLC)

Synonym(s):
8-Br-ATP
Linear Formula:
C10H15N5O13P3Br
CAS Number:
Molecular Weight:
586.08
MDL number:
PubChem Substance ID:

Quality Level

assay

≥90% (HPLC)

storage temp.

−20°C

SMILES string

[Na].Nc1ncnc2n(C3OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C3O)c(Br)nc12

InChI

1S/C10H15BrN5O13P3.Na.H/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21;;/h2-3,5-6,9,17-18H,1H2,(H,22,23)(H,24,25)(H2,12,13,14)(H2,19,20,21);;

InChI key

BWSZHFBRMPXNSH-UHFFFAOYSA-N

Application

8-Bromoadenosine 5′-triphosphate (8-Br-ATP) is as an ATP analogue used in conjunction with other ATP analogues to study and resolve ATP-site binding effects on receptor and enzyme function and specificity.

Packaging

5 mg in glass bottle
25 mg in poly bottle

Biochem/physiol Actions

P2X purinoceptor agonist similar in reactivity to ATP.

Linkage

8-Bromo form of adenosine 5′-triphosphate.

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

S Maruta et al.
European journal of biochemistry, 256(1), 229-237 (1998-09-24)
Numerous analytical experiments have shown that, in solution, ATP analogues with bulky substitutions at the eighth position of the adenine ring predominantly assume the syn conformation with respect to the adenine-ribose bond. Two such analogues, 3'-O-(N-methylanthraniloyl)-8-azido-ATP (Mant-8-N3-ATP) and 8-Br-ATP, were
S A Thomas et al.
British journal of pharmacology, 103(4), 1963-1969 (1991-08-01)
1. Extracellular adenosine 5'-triphosphate (ATP) activated an early excitatory conductance followed by a late potassium conductance in developing chick skeletal muscle. A series of ATP analogues were tested for their ability to activate these two conductances. All compounds tested were
J Stutchfield et al.
FEBS letters, 262(2), 256-258 (1990-03-26)
We have recently characterised the presence of a Ca2(+)-mobilising receptor for ATP which stimulates exocytosis in differentiated HL60 cells. Here we demonstrate that the undifferentiated HL60 cells also respond to extracellular ATP by stimulating an increase in inositol phosphates and
Hiroyuki Iwamoto
Journal of muscle research and cell motility, 29(1), 45-55 (2008-07-11)
Previous studies using solubilized fragments of myosins have shown that an ATP analogue, 8-bromoadenosine triphosphate (8-Br-ATP) is a poor substrate for fast skeletal myosin isoform. We further characterized the analogue by using vertebrate skeletal muscle fibers. In the absence of
Lisa S Chen et al.
The Journal of biological chemistry, 279(39), 40405-40411 (2004-07-22)
The nucleotide substrate specificity of yeast poly(A) polymerase (yPAP) toward various C-2- and C-8-modified ATP analogs was examined. 32P-Radiolabeled RNA oligonucleotide primers were incubated with yPAP in the absence of ATP to assay polyadenylation using unnatural ATP substrates. The C-2-modified

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