Synonym
ITX3; ITX-3; ITX 3;
IUPAC/Chemical Name
2-[(2,5-Dimethyl-1-phenyl-1H-pyrrol-3-yl)methylene]-thiazolo[3,2-a]benzimidazol-3(2H)-one
InChi Key
SJMYMKPBODEZSH-MOSHPQCFSA-N
InChi Code
InChI=1S/C22H17N3OS/c1-14-12-16(15(2)24(14)17-8-4-3-5-9-17)13-20-21(26)25-19-11-7-6-10-18(19)23-22(25)27-20/h3-13H,1-2H3/b20-13-
SMILES Code
O=C(N1C2=CC=CC=C2N=C1S/3)C3=C\C4=C(C)N(C5=CC=CC=C5)C(C)=C4
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
ITX3 is a specific and nontoxic inhibitor of TrioN (N-terminal GEF domain of the multidomain Trio protein) with an IC50 value of 76 μM.
In vitro activity:
A total of 68 of the 79 patient samples had >10% viable cells and could be assessed with the Annexin V/PI apoptosis assay. ITX3 induced more substantial apoptosis and necrosis than the other compounds; this was also true for the IC40.
Reference: Biomedicines. 2022 Aug 4;10(8):1881. https://pubmed.ncbi.nlm.nih.gov/36009428/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
2.0 |
5.38 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
371.46
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Hemsing AL, Rye KP, Hatfield KJ, Reikvam H. NPM1-Mutated Patient-Derived AML Cells Are More Vulnerable to Rac1 Inhibition. Biomedicines. 2022 Aug 4;10(8):1881. doi: 10.3390/biomedicines10081881. PMID: 36009428; PMCID: PMC9405324.
2. Son K, Smith TC, Luna EJ. Supervillin binds the Rac/Rho-GEF Trio and increases Trio-mediated Rac1 activation. Cytoskeleton (Hoboken). 2015 Jan;72(1):47-64. doi: 10.1002/cm.21210. Epub 2015 Feb 28. PMID: 25655724; PMCID: PMC4361246.
In vitro protocol:
1. Hemsing AL, Rye KP, Hatfield KJ, Reikvam H. NPM1-Mutated Patient-Derived AML Cells Are More Vulnerable to Rac1 Inhibition. Biomedicines. 2022 Aug 4;10(8):1881. doi: 10.3390/biomedicines10081881. PMID: 36009428; PMCID: PMC9405324.
2. Son K, Smith TC, Luna EJ. Supervillin binds the Rac/Rho-GEF Trio and increases Trio-mediated Rac1 activation. Cytoskeleton (Hoboken). 2015 Jan;72(1):47-64. doi: 10.1002/cm.21210. Epub 2015 Feb 28. PMID: 25655724; PMCID: PMC4361246.
1: Son K, Smith TC, Luna EJ. Supervillin binds the Rac/Rho-GEF Trio and increases Trio-mediated Rac1 activation. Cytoskeleton (Hoboken). 2015 Jan;72(1):47-64. doi: 10.1002/cm.21210. Epub 2015 Feb 28. PubMed PMID: 25655724; PubMed Central PMCID: PMC4361246.
2: Yan Y, Eipper BA, Mains RE. Kalirin-9 and Kalirin-12 Play Essential Roles in Dendritic Outgrowth and Branching. Cereb Cortex. 2015 Oct;25(10):3487-501. doi: 10.1093/cercor/bhu182. Epub 2014 Aug 21. PubMed PMID: 25146373; PubMed Central PMCID: PMC4585498.
3: Yano T, Yamazaki Y, Adachi M, Okawa K, Fort P, Uji M, Tsukita S, Tsukita S. Tara up-regulates E-cadherin transcription by binding to the Trio RhoGEF and inhibiting Rac signaling. J Cell Biol. 2011 Apr 18;193(2):319-32. doi: 10.1083/jcb.201009100. Epub 2011 Apr 11. PubMed PMID: 21482718; PubMed Central PMCID: PMC3080255.
4: Bouquier N, Vignal E, Charrasse S, Weill M, Schmidt S, Léonetti JP, Blangy A, Fort P. A cell active chemical GEF inhibitor selectively targets the Trio/RhoG/Rac1 signaling pathway. Chem Biol. 2009 Jun 26;16(6):657-66. doi: 10.1016/j.chembiol.2009.04.012. PubMed PMID: 19549603.
