ChemicalBook CAS DataBase List 1680196-54-6

1680196-54-6

Name	FzM1
CAS	1680196-54-6
Molecular Formula	C21H16N2O2S
MDL Number	MFCD29079017
Molecular Weight	360.43
MOL File	1680196-54-6.mol

Chemical Properties

Boiling point	518.3±50.0 °C(Predicted)
density	1.401±0.06 g/cm3(Predicted)
storage temp.	Store at -20°C
solubility	DMF: 12 mg/ml; DMF:PBS (pH 7.2)(1:3): 0.2 mg/ml; DMSO: 10 mg/ml
form	A crystalline solid
pka	9.42±0.10(Predicted)
color	White to light brown
InChI	1S/C21H16N2O2S/c24-19-12-16(20-6-3-9-26-20)11-18(13-19)23-21(25)22-17-8-7-14-4-1-2-5-15(14)10-17/h1-13,24H,(H2,22,23,25)
InChIKey	OBTSACXGWYGCPK-UHFFFAOYSA-N
SMILES	O=C(NC1=CC(C=CC=C2)=C2C=C1)NC3=CC(C4=CC=CS4)=CC(O)=C3

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Hazard Information

Description

Wnt signaling proteins are small secreted proteins that are active in embryonic development, tissue homeostasis, and tumorigenesis. Wnt proteins initiate cell signaling by binding Frizzled (Fz) receptors, a family of G protein-coupled receptors. FzM1 is an allosteric ligand of Fz4. At 10 μM, it inhibits nuclear translocation of β-catenin in U87MG glioma cells treated with lithium chloride, a GSK3 inhibitor that enhances the Wnt canonical signaling pathway. FzM1 impairs the ability of U87MG cells to form neurospheres in culture and stimulates the differentiation of Caco-2 epithelial colorectal adenocarcinoma cells.

Uses

FzM1 is a negative allosteric modulator (NAM) of Frizzled receptor FZD4. FzM1 reduces WNT5A-dependent WNT responsive element (WRE) activity (log EC50inh=?6.2). FzM1 binds to an allosteric binding site located in intracellular loop 3 (ICL3) of FZD4 and alters the conformation of the receptor, ultimately inhibiting the WNT/β-catenin cascade[1][2].

in vivo

In the AGEs-RAGE activation model of Wistar rats, FPS-ZM1 (1 mg/kg/d; intraperitoneal injection; once a day; 4 weeks) reduced the production of Aβ1-40 and Aβ1-42 in the rat hippocampus, inhibited the increase of Aβ metabolism-related proteins (RAGE, BACE1 and APP), downregulated the expression of proinflammatory cytokines (p-NF-κB, TNF-α and IL-1β), upregulated the antioxidant defense system (reduced ROS and LPO levels, increased GSH content, SOD and GPx activity), and alleviated AGEs-induced memory impairment in rats^[1].

Animal Model:	AGEs-RAGE-activated (intrahippocampal injection) rat model in Wistar rats (male, 6 weeks old)^[1]
Dosage:	1 mg/kg/d
Administration:	Intraperitoneal injection, once daily, for 4 weeks
Result:	Reduced the levels of Aβ1-40 and Aβ1-42 in the hippocampus of rats. Inhibited the increased expressions of Aβ metabolism-related proteins (RAGE, BACE1, and APP), pro-inflammatory cytokines (p-NF-κB, TNF-α, and IL-1β) induced by AGEs. Upregulated the antioxidant defense system, with reduced levels of ROS and LPO, and increased content of GSH, and activities of SOD and GPx. Also, alleviated the memory impairment of rats induced by AGEs, as shown by a significant decrease in the escape latency in the Morris water maze test.

References

[1] Gennaro Riccio, et al. A Negative Allosteric Modulator of WNT Receptor Frizzled 4 Switches into an Allosteric Agonist. Biochemistry. 2018 Feb 6;57(5):839-851. DOI:10.1021/acs.biochem.7b01087
[2] Hong Y, et al. Effects of RAGE-Specific Inhibitor FPS-ZM1 on Amyloid-β Metabolism and AGEs-Induced Inflammation and Oxidative Stress in Rat Hippocampus. Neurochem Res. 2016 May;41(5):1192-9. DOI:10.1007/s11064-015-1814-8

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