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A2647

Sigma-Aldrich

Adenosine 5′-(β,γ-imido)triphosphate lithium salt hydrate

≥93% (HPLC), powder

Synonym(s):

β,γ-Imidoadenosine 5′-triphosphate lithium salt hydrate, AMP-PNP, ATP[β,γ-NH], Adenylyl imidodiphosphate lithium salt hydrate, App(NH)p

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About This Item

Empirical Formula (Hill Notation):
C10H17N6O12P3 · xLi+ · yH2O
CAS Number:
25612-73-1
Molecular Weight:
506.20 (free acid basis)
Beilstein/REAXYS Number:
6047109
UNSPSC Code:
41106305
PubChem Substance ID:
24890685
NACRES:
NA.51

biological source

natural (organic)

assay

≥93% (HPLC)

form

powder

color

white

solubility

H2O: 50 mg/mL

shipped in

dry ice

storage temp.

−20°C

SMILES string

[Li+].[Li+].[Li+].[Li+].[H]O[H].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP([O-])(=O)OP([O-])(=O)NP([O-])([O-])=O)[C@@H](O)[C@H]3O

InChI

1S/C10H17N6O12P3/c11-8-5-9(13-2-12-8)16(3-14-5)10-7(18)6(17)4(27-10)1-26-31(24,25)28-30(22,23)15-29(19,20)21/h2-4,6-7,10,17-18H,1H2,(H,24,25)(H2,11,12,13)(H4,15,19,20,21,22,23)/t4-,6-,7-,10-/m1/s1

InChI key

PVKSNHVPLWYQGJ-KQYNXXCUSA-N

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Application

Adenosine 5′-(β,γ-imido)triphosphate lithium salt hydrate has been used in a study to research the effects of monovalent cations Li+, Na+, K+, NH4+, Rb+ and Cs+ on the solid and solution structures of the nucleic acid components. Adenosine 5′-(β,γ-imido)triphosphate lithium salt hydrate has also been used in a study to determine that antidepressants inhibit interferon-γ-induced microglial production of IL-6 and nitric oxide.

Biochem/physiol Actions

A non-hydrolyzable ATP analog. AMP-PNP competitively inhibits ATP-dependent enzyme systems, such as glutamine synthetase. It inhibits a number of enzymes which require the hydrolysis of ATP such as DNA topoisomerase II, SV40 large T-antigen helicase and a number of kinases. Blocks ATP-sensitive calcium-dependent potassium channels.

Caution

AMP-PNP is very unstable in acidic conditions; rapidly hydrolyzes to the phosphoramidate and inorganic phosphate.

Reconstitution

A 10 mg/mL stock solution may be made, aliquoted and stored at -70 °C for up to 3 months.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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