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B3756

Sigma-Aldrich

8-Bromoadenosine 5′-triphosphate sodium salt

≥90% (HPLC)

Synonym(s):

8-Br-ATP

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About This Item

Linear Formula:
C10H15N5O13P3Br
CAS Number:
81035-56-5
Molecular Weight:
586.08
MDL number:
MFCD00070102
UNSPSC Code:
41106305
PubChem Substance ID:
24891733
NACRES:
NA.51

Quality Level

200

Assay

≥90% (HPLC)

form

powder

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.

Biochem/physiol Actions

P2X purinoceptor agonist similar in reactivity to ATP.

Linkage

8-Bromo form of adenosine 5′-triphosphate.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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M Picher et al.
Biochemical pharmacology, 51(11), 1453-1460 (1996-06-14)
Pharmacologists are becoming more and more aware of the possibility that certain ATP analogues currently used to classify the P2-purinoceptors are dephosphorylated by ectonucleotidases. In this study, we provide evidence that in the vascular system, these purine analogues are hydrolysed
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
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
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
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
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