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481908

Sigma-Aldrich

Nicotinamide Phosphoribosyltransferase Inhibitor, FK866

The Nicotinamide Phosphoribosyltransferase Inhibitor, FK866, also referenced under CAS 658084-64-1, controls the biological activity of Nicotinamide Phosphoribosyltransferase. This small molecule/inhibitor is primarily used for Neuroscience applications.

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Synonym(s):
Nicotinamide Phosphoribosyltransferase Inhibitor, FK866, (E)-N-(4-(1-Benzoylpiperidin-4-yl)butyl)-3-(pyridin-3-yl)acrylamide, NAMPT Inhibitor, APO866, NAMPTase Inhibitor I, PBEF Inhibitor I, Visfatin Inhibitor I, NAPRT Inhibitor, APO866, NAMPTase Inhibitor I, PBEF Inhibitor I, Visfatin Inhibitor I, NAPRT Inhibitor, (E)-N-(4-(1-Benzoylpiperidin-4-yl)butyl)-3-(pyridin-3-yl)acrylamide, NAMPT Inhibitor
Empirical Formula (Hill Notation):
C24H29N3O2
CAS Number:
658084-64-1
Molecular Weight:
391.51

Quality Level

100

Assay

≥97% (HPLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

yellow

solubility

DMSO: 100 mg/mL

shipped in

ambient

storage temp.

2-8°C

InChI

1S/C24H29N3O2/c28-23(12-11-21-8-6-15-25-19-21)26-16-5-4-7-20-13-17-27(18-14-20)24(29)22-9-2-1-3-10-22/h1-3,6,8-12,15,19-20H,4-5,7,13-14,16-18H2,(H,26,28)/b12-11+

InChI key

KPBNHDGDUADAGP-VAWYXSNFSA-N

General description

A cell-permeable pyridinylacrylamide compound that acts as a selective, allosteric NAPRT/NAMPT (nicotinamide phosphoribosyltransferase) inhibitor (Ki = 0.4 nM for the enzyme/substrate complex; Ki′ = 0.3 nM for the free enzyme), while exhibiting no effect toward NPRT (nicotinic acid phosphoribosyltransferase) activity (82% inhibition of NAPRT activity at 10 nM vs no inhibition of NPRT activity at 1 µM in K-562 extract). FK866 treatment is shown to induce cell death by depleting NAD+ (Cat. Nos. 481911 & 481915) in HepG2 and NIH-3T3 cultures (by >95% after 24 h treatment of 10 nM FK866), likewise the addition of exogenous NAD+ is demonstrated to rescue NIH-3T3 and SH-SY5Y from FK866-induced NAD+-depletion and cell death.
A cell-permeable pyridinylacrylamide compound that acts as a selective, allosteric NAPRT/NAMPT (nicotinamide phosphoribosyltransferase) inhibitor (Ki = 0.4 nM for the enzyme/substrate complex; Ki′ = 0.3 nM for the free enzyme), while exhibiting no effect toward NPRT (nicotinic acid phosphoribosyltransferase) activity (82% inhibition of NAPRT activity at 10 nM vs no inhibition of NPRT activity at 1 µM in K-562 extract). FK866 treatment is shown to induce cell death by depleting NAD+ (Cat. Nos. 481911 & 481915) in HepG2 and NIH-3T3 cultures (by >95% after 24 h treatment of 10 nM FK866), likewise the addition of exogenous NAD+ is demonstrated to rescue NIH-3T3 and SH-SY5Y from FK866-induced NAD+-depletion and cell death.

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Physical form

Supplied as a 50 mM (2 mg/102.17 µl) solution in DMSO.

Other Notes

Formentini, L., et al. 2009. Biochem. Pharmacol.77, 1612.
Nakahata, Y., et al. 2009. Science324, 654.
Ramsey. K.M., et al. 2009. Science324, 651.
Billington, R.A., et al. 2008. J. Biol. Chem.283, 6367.
Hasmann, M. and Schemainda, I., 2003. Cancer Res.63, 7436.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Xiangguo Shi et al.
Science advances, 7(30) (2021-07-23)
Metabolic dysregulation underlies malignant phenotypes attributed to cancer stem cells, such as unlimited proliferation and differentiation blockade. Here, we demonstrate that NAD+ metabolism enables acute myeloid leukemia (AML) to evade apoptosis, another hallmark of cancer stem cells. We integrated whole-genome

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