(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE

Bezeichnung:(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE

CAS-Nr658084-64-1

Englisch Name:(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE

CBNumberCB62454096

SummenformelC24H29N3O2

Molgewicht391.51

MOL-Datei658084-64-1.mol

(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE physikalisch-chemischer Eigenschaften

Siedepunkt	629.9±51.0 °C(Predicted)
Dichte	1.131
storage temp.	-20°C
Löslichkeit	DMSO: soluble10mg/mL, clear
pka	14.12±0.46(Predicted)
Aggregatzustand	Yellow liquid
Farbe	white to beige
InChIKey	KPBNHDGDUADAGP-VAWYXSNFSA-N

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22
WGK Germany	3
HS Code	2933399990

Gefahreninformationscode (GHS)

(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
FK-866 is a highly specific non-competitive inhibitor of Nampt (K_i = 0.4 nM), causing gradual NAD⁺ depletion. In HepG2 human liver carcinoma cells, NAD⁺ depletion by FK-866 directs delayed cell death by apoptosis (IC₅₀ = ~1 nM). In normal human smooth muscle cells, FK-866 causes premature senescence, an effect that may be linked to decreased activity of the NAD⁺-dependent enzyme SIRT1. Also, FK-866 induces autophagy in SH-SY5Y neuroblastoma cells, as indicated by the formation of LC3-positive vesicles.
Verwenden
FK866 hydrochloride hydrate has been used:
- to investigate its effects on intra-axonal NAD⁺ levels
- to induce NAD+ depletion
- to reduce the level of tumor necrosis factor-α (TNF-α), nicotinamide phosphoribosyltransferase (NAMPT) and interleukin-6 (IL-6) in the ischemic brain tissue
Definition
ChEBI: FK-866 is a member of benzamides and a N-acylpiperidine.
Allgemeine Beschreibung
A cell-permeable pyridinylacrylamide compound that acts as a selective, allosteric NAPRT/NAMPT (nicotinamide phosphoribosyltransferase) inhibitor (K_i = 0.4 nM for the enzyme/substrate complex; K_i^′ = 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.
Biochem/physiol Actions
FK866 is a potent inhibitor of NAD biosynthesis, and a specific inhibitor of NAMPT (Nicotinamide Phosphoribosyltransferase, visfatin, PBEF). NAMPT functions as an intra-cellular and extra-cellular NAD biosynthetic enzyme that is important for regulating metabolism and stress resistance through sirtuins and other NAD-consuming regulators. NAMPT also acts as a cytokine independent of its enzymatic activity, playing a major part in regulating immune responses.
target
NAMPT
Einzelnachweise
[1] nahimana a, attinger a, aubry d, greaney p, ireson c, thougaard av, tjørnelund j, dawson km, dupuis m, duchosal ma. the nad biosynthesis inhibitor apo866 has potent antitumor activity against hematologic malignancies. blood. 2009 apr 2; 113 (14): 3276-86.

(E)-N-[4-(1-BENZOYL-PIPERIDIN-4-YL)-BUTYL]-3-PYRIDIN-3-YL-ACRYLAMIDE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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