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02070

Sigma-Aldrich

Adenosine 5′-triphosphate P3-[1-(2-nitrophenyl)ethyl ester] disodium salt

≥95% (HPLC)

Synonym(s):

NPE caged ATP, ‘Caged ATP’

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About This Item

Empirical Formula (Hill Notation):
C18H21N6Na2O15P3
CAS Number:
171800-68-3
Molecular Weight:
700.29
MDL number:
MFCD00077294
UNSPSC Code:
41106305
PubChem Substance ID:
329747384

Assay

≥95% (HPLC)

storage temp.

−20°C

SMILES string

[Na+].[Na+].CC(OP([O-])(=O)OP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23)c4ccccc4[N+]([O-])=O

InChI

1S/C18H23N6O15P3.2Na/c1-9(10-4-2-3-5-11(10)24(27)28)37-41(31,32)39-42(33,34)38-40(29,30)35-6-12-14(25)15(26)18(36-12)23-8-22-13-16(19)20-7-21-17(13)23;;/h2-5,7-9,12,14-15,18,25-26H,6H2,1H3,(H,29,30)(H,31,32)(H,33,34)(H2,19,20,21);;/q;2*+1/p-2/t9?,12-,14-,15-,18-;;/m1../s1

InChI key

DWGOHIKVVKFGGU-DZHDPEGHSA-L

Application

Adenosine 5′-triphosphate γ-(1-[2-nitrophenyl]ethyl) ester (“Caged” ATP) is used as a photolyzing substrate of luciferase-mediated firefly bioluminescence and other ATP-dependent photolytic processes. Caged ATP has also been used to study the dynamics of ATP-driven linear molecular motors such as myosin Va. Caged ATP is used to study intracellular mechanisms; Irradiation with a short light pulse of 360 nm wavelength releases the parent compound from its cage resulting in a time- and quantity-specific concentration increase of ATP within the cell; Relaxation of muscle fibres by photolysis of caged ATP.

Other Notes

Used to study intracellular mechanisms.; Irradiation with a short light pulse of 360 nm wavelength releases the parent compound from its cage, resulting in a time- and quantity-specific concentration increase of ATP within the cell.; Relaxation of muscle fibres by photolysis of caged ATP; Caged ATP as a tool in active transport research

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

12 - Non Combustible Liquids

WGK

WGK 2

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Direct observation of the myosin Va recovery stroke that contributes to unidirectional stepping along actin.
Shiroguchi K, Chin HF, et al.
PLoS Biology, e1001031-e1001031 (2011)
Caged ATP as a tool in active transport research.
J H Kaplan
Society of General Physiologists series, 40, 385-396 (1986-01-01)
Christian Völlmecke et al.
The FEBS journal, 276(21), 6172-6186 (2009-09-29)
The mechanism of ATP hydrolysis of a shortened variant of the heavy metal-translocating P-type ATPase CopB of Sulfolobus solfataricus was studied. The catalytic fragment, named CopB-B, comprises the nucleotide binding and phosphorylation domains. We demonstrated stoichiometric high-affinity binding of one
Takeshi Kageyama et al.
Photochemistry and photobiology, 87(3), 653-658 (2011-01-07)
The reaction process of firefly bioluminescence was studied by photolyzing caged-ATP to adenosine triphosphate (ATP) within 100 ms. The intensity of luminescence increases markedly to reach a maximum within 1 s, maintains almost the same intensity up to 5 s
Y E Goldman et al.
Nature, 300(5894), 701-705 (1982-12-23)
A novel method has been developed for studying the reaction kinetics of the force-generating mechanism in muscle. Inert photolabile precursors of ATP or ADP are incorporated into muscle fibres having their surface membrane barrier removed. The nucleotide is then rapidly
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