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S4

Names

[ CAS No. ]:
1330061-67-0

[ Name ]:
S4

[Synonym ]:
MFCD30182321
S4
Sulfamic acid, 4-[[[(3,5-dimethylphenyl)amino]carbonyl]amino]phenyl ester
4-(3'-(3",5"-Dimethylphenyl)ureido)phenyl sulfamate
4-{[(3,5-Dimethylphenyl)carbamoyl]amino}phenyl sulfamate
4-[(3,5-Dimethylphenyl)ureido]phenyl sulfamate
CAIX Inhibitor S4
4-[[[(3,5-Dimethylphenyl)amino]carbonyl]amino]phenyl sulfamic acid ester

Biological Activity

[Description]:

CAIX Inhibitor S4 is a potent and selective inhibitor of carbonic anhydrase IX/XII (CA IX/XII), with a Ki of 7 nM and 2 nM, respectively. CAIX Inhibitor S4 also inhibits CA II and CA I (Ki=546 and 5600 nM, respectively). CAIX Inhibitor S4 can inhibit the number of lung metastasis in orthotopic MDA-MB-231 mouse model without affecting primary tumor growth[1].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Metabolic Enzyme/Protease >> Carbonic Anhydrase

[Target]

Ki: 2 nM (CA XII), 7 nM (CA IX), 546 nM (CA II), 5600 nM (CA I)[1]


[In Vitro]

CAIX Inhibitor S4 (1-100 μM; 24 h) inhibits the proliferation of MDA-MB-231, HCT116 and HT29 cells in a dose-dependent manner[1]. CAIX Inhibitor S4 (3.3-33 μM; 24 h) inhibits the eGFP-MDA-MB-231 cell migration in anoxia in a concentration- dependent manner[1]. CAIX Inhibitor S4 (33 μM; 15-60 min) delays the cell spreading of MDA-MB-231 cells in anoxia but essentially not in normoxia[1]. Cell Proliferation Assay[1] Cell Line: MDA-MB-231, HCT116 and HT29 cells Concentration: 1, 10, 100 μM Incubation Time: 24 hours Result: Inhibited the cell proliferation of MDA-MB-231, HCT116 and HT29 cells, with IC50s of 481 μM, >1000 μM, and 20 μM, respectively.

[In Vivo]

CAIX Inhibitor S4 (10 mg/kg; i.p. for 14 days) inhibits metastatic tumor burden in MDA-MB-231 model while having no effect on primary tumor growth or mouse condition[1]. Animal Model: Female nu/nu CBA mice (10-12 weeks) were injected with eGFP-MDA-MB-231 cells[1] Dosage: 10 mg/kg Administration: I.p. daily on a “5 days on, 2 days off” dosing regimen for 14 days Result: Significantly reduced the metastatic tumor burden in lungs of mice bearing orthotopic eGFP-MDA-MB-231 tumors. The average body weights between vehicle and S4 treated mice were similar throughout the experiments.

[References]

[1]. Gieling RG, et, al. Antimetastatic effect of sulfamate carbonic anhydrase IX inhibitors in breast carcinoma xenografts. J Med Chem. 2012 Jun 14;55(11):5591-600.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Molecular Formula ]:
C15H17N3O4S

[ Molecular Weight ]:
335.378

[ Exact Mass ]:
335.093964

[ LogP ]:
2.51

[ Index of Refraction ]:
1.663

Related Compounds