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ZCL 278

Names

[ CAS No. ]:
587841-73-4

[ Name ]:
ZCL 278

[Synonym ]:
Acetamide, 2-(4-bromo-2-chlorophenoxy)-N-[[[4-[[(4,6-dimethyl-2-pyrimidinyl)amino]sulfonyl]phenyl]amino]thioxomethyl]-
2-(4-bromo-2-chlorophenoxy)-N-({4-[(4,6-dimethylpyrimidin-2-yl)sulfamoyl]phenyl}carbamothioyl)acetamide
2-(4-Bromo-2-chlorophenoxy)-N-({4-[(4,6-dimethyl-2-pyrimidinyl)sulfamoyl]phenyl}carbamothioyl)acetamide
ZCL 278
ZCL278

Biological Activity

[Description]:

ZCL278 is a selective Cdc42 modulator that directly binds to Cdc42 and inhibits its functions with Kd of 11.4 μM for Cdc42-ZCL278 affinity in surface plasmon resonance (SPR) experiment.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Ras
Research Areas >> Cancer

[Target]

Kd: 11.4 μM (Cdc42)[1]


[In Vitro]

ZCL278 as a potent, cell-permeable Cdc42-specific inhibitor that suppresses actin-based cellular functions, including Golgi organization and cell motility.In Swiss 3T3 fibroblast cultures, ZCL278 abolishes microspike formation and disrupted GM130-docked Golgi structures, two of the most prominent Cdc42-mediated subcellular events. ZCL278 reduces the perinuclear accumulation of active Cdc42 in contrast to NSC23766, a selective Rac inhibitor. ZCL278 suppresses Cdc42-mediated neuronal branching and growth cone dynamics as well as actin-based motility and migration in a metastatic prostate cancer cell line (i.e., PC-3) without disrupting cell viability[1]. ZCL278 inhibits Cdc42 function as an entry inhibitor for Junin virus (JUNV) and for vesicular stomatitis virus, lymphocytic choriomeningitis virus, and dengue virus but not for the nonenveloped poliovirus. In cells, ZCL278 is shown to efficiently inhibit chemically induced filopodium formation, a process dependent on Cdc42 activity. Dose-response experiments are first carried out in Vero cells, and while ZCL278 is not toxic at concentrations up to 200 μM, ZCL278 inhibits JUNV with IC50 of ~14 μM, as measured by flow cytometry[2].

[In Vivo]

ZCL278 reduces the JUNV RNA load in the spleen more than 33-fold, with JUNV RNA being undetectable in 5 out of 8 mice. These results are similar to those seen in Gabapentin-treated mice, demonstrating that ZCL278 can abrogate JUNV replication[2].

[Kinase Assay]

Lyophilized Cdc42 protein is reconstituted to 5 mg/mL in a buffer consisting of 50 mM Tris, 0.5 mM MgCl2, 50 mM NaCl, 3% (wt/vol) sucrose, and 0.6% dextran. The stock solution is then diluted to 1 μM in 5 mM phosphate buffer, pH 7.4. Into a quartz cuvettete containing Cdc42 solution, aliquots of ZCL278 are added and incubated for 5 min before each fluorescent measurement. The excitation wavelength is 275 nm, and the fluorescence of tryptophan at 350 nm is measured after each addition. The titration curve is fitted using the equimolar specific binding model in GraphPad, and the Kd is calculated[1].

[Cell Assay]

To determine cell viability, PC-3 cells are incubated for 24 h with or without the Cdc42 activator, ZCL278, or NSC23766. By using the trypan blue dye exclusion method, the numbers of live and dead cells are obtained with a Countess Automated Cell Counter. P values are assigned in each experiment, and any null hypothesis with probability level <95% is rejected[1].

[Animal admin]

Mice[2] Four-week-old C57BL/6 mice receive intravenous injections of Gabapentin or ZCL278 (100 μg/g, i.p.). At 1 h after treatment, the mice are inoculated intraperitoneally with JUNV Candid #1 (1×106 PFU) in no more than 1 mL with a 27 1/2-gauge needle. At the end of the experiment, the mice are sacrificed, their spleens are homogenized with a Dounce homogenizer and centrifuged to generate a cell pellet and supernatant, and RNA expression levels are determined.

[References]

[1]. Friesland A, et al. Small molecule targeting Cdc42-intersectin interaction disrupts Golgi organization and suppresses cell motility. Proc Natl Acad Sci U S A. 2013 Jan 22;110(4):1261-6.

[2]. Chou YY, et al. Identification and Characterization of a Novel Broad-Spectrum Virus Entry Inhibitor. J Virol. 2016 Apr 14;90(9):4494-510.


[Related Small Molecules]

ARS-853 | ARS-1620 | NSC 23766 | ML 141 | Salirasib | Pan-RAS-IN-1 | Rhosin hydrochloride | CASIN | EHT 1864 | EHop-016 | 1A-116 | CCG 1423 | K-Ras(G12C) inhibitor 12 | Y16 | BQU57

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Molecular Formula ]:
C21H19BrClN5O4S2

[ Molecular Weight ]:
584.894

[ Exact Mass ]:
582.975037

[ PSA ]:
166.27000

[ LogP ]:
4.45

[ Appearance of Characters ]:
white solid

[ Index of Refraction ]:
1.687

[ Storage condition ]:
-20℃


Related Compounds