4-IPP

Names

[ Name ]:
4-IPP

[Synonym ]:
4-Jod-2-methyl-6-nitro-anilin
iodomethylnitroaniline
4-iodo-2-methyl-6-nitro-aniline
4-iodo-6-phenyl-pyrimidine
4-iodo-2-methyl-6-nitrobenzenamine
4-iodo-6-methyl-2-nitroaniline
5-Jod-3-nitro-2-amino-toluol

Biological Activity

[Description]:

4-IPP (4-Iodo-6-phenylpyrimidine) is a specific suicide substrate and irreversible inhibitor of macrophage migration inhibitory factor (MIF)[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[Target]

MIF[1]

[In Vitro]

4-IPP is a specific suicide substrate for MIF that binds covalently and irreversibly to MIF to inhibit its biologic activity[1]. 4-IPP inhibits RANKL-induced p65 phosphorylation and nuclear translocation by preventing the interaction of MIF with thioredoxin-interacting protein-p65 complexes[1]. 4-IPP can inhibit receptor activator of NF-κB ligand (RANKL)-induced osteoclastogenesis and potentiate osteoblast-mediated mineralization and bone nodule formation[1]. 4-IPP (0.5-200μM;24-72 hours) inhibits osteoclastogenesis in a dose-dependent manner[1]. 4-IPP(5-20μM; 5 days) inhibits RANKL-induced osteoclast differentiation and bone resorption [1]. Cell Cytotoxicity Assay[1] Cell Line: BMMs Concentration: 0.5 μM, 1 μM, 2.5 μM, 5 μM, 10 μM, 25 μM, 50 μM, 100 μM, 200 μM Incubation Time: 24 hours, 72 hours Result: Inhibited osteoclastogenesis in a dose-dependent manner. Western Blot Analysis[1] Cell Line: BMMs Concentration: 5 μM,10 μM, 20 μM Incubation Time: 1 day, 3 days, 5 days Result: Inhibited RANKL-induced osteoclast differentiation and bone resorption.

[In Vivo]

4-IPP (1 mg/kg, 5 mg/kg; every 2 days; for 8 weeks) ameliorates the bone loss associated with estrogen deficiency by reducing osteoclastic activities and enhancing osteoblastic bone formation[1]. Animal Model: 8-weeks-old C57BL/6J male mice[1] Dosage: 1 mg/kg, 5 mg/kg Administration: Intraperitoneal injection; every 2 days; for 8 weeks Result: Alleviated OVX-induced osteoporosis.

[References]

[1]. Zheng L, et al. Macrophage migration inhibitory factor (MIF) inhibitor 4-IPP suppresses osteoclast formation and promotes osteoblast differentiation through the inhibition of the NF-κB signaling pathway. FASEB J. 2019 Jun;33(6):7667-7683.

Chemical & Physical Properties

[ Density]:
1.728±0.06 g/cm3

[ Boiling Point ]:
380.2±30.0 °C

[ Molecular Formula ]:
C₁₀H₇IN₂

[ Molecular Weight ]:
282.08000

[ Exact Mass ]:
281.96500

[ PSA ]:
25.78000

[ LogP ]:
2.74820

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS05, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H315-H318-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Hazard Codes ]:
C

[ RIDADR ]:
NONH for all modes of transport

Articles

Podocyte injury-driven lipid peroxidation accelerates the infiltration of glomerular foam cells in focal segmental glomerulosclerosis.

Am. J. Pathol. 185 , 2118-31, (2015)

Intracapillary foam cell infiltration with podocyte alterations is a characteristic pathology of focal segmental glomerulosclerosis (FSGS). We investigated the possible role of podocyte injury in glom...

Macrophage migration inhibitory factor - a therapeutic target in gallbladder cancer.

BMC Cancer 15 , 843, (2015)

Poor prognosis in gallbladder cancer is due to late presentation of the disease, lack of reliable biomarkers for early diagnosis and limited targeted therapies. Early diagnostic markers and novel ther...

Macrophage migration inhibitory factor and stearoyl-CoA desaturase 1: potential prognostic markers for soft tissue sarcomas based on bioinformatics analyses.

PLoS ONE 8 , e78250, (2013)

The diagnosis and treatment of soft tissue sarcomas (STSs) has been particularly difficult, because STSs are a group of highly heterogeneous tumors in terms of histopathology, histological grade, and ...

Related Compounds

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