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I1411

Sigma-Aldrich

ITX3

≥98% (HPLC)

Synonym(s):

2-[(2,5-Dimethyl-1-phenyl-1H-pyrrol-3-yl)methylene]-thiazolo[3,2-a]benzimidazol-3(2H)-one

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About This Item

Empirical Formula (Hill Notation):
C22H17N3OS
CAS Number:
347323-96-0
Molecular Weight:
371.45
MDL number:
MFCD02629172
UNSPSC Code:
12352202
PubChem Substance ID:
329815351
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

solubility

DMSO: ≥4 mg/mL

storage temp.

room temp

SMILES string

Cc1cc(\C=C2\Sc3nc4ccccc4n3C2=O)c(C)n1-c5ccccc5

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+

InChI key

SJMYMKPBODEZSH-DEDYPNTBSA-N

Biochem/physiol Actions

ITX3 is a specific inhibitor of endogenous TrioN activity acting on the GEF domain and selective cell active inhibitor of the Trio/RhoG/Rac1 pathway. The compound is active in whole cell assay where it inhibits the formation of TrioN-dependent cell structures. ITX3 appears to be specific for TrioN inhibition rather than other RhoGEFs.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GTP Binding Proteins (Low Molecular Weight) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jos Van Rijssel et al.
Biology open, 2(6), 569-579 (2013-06-22)
Inflammation is characterized by endothelium that highly expresses numerous adhesion molecules to trigger leukocyte extravasation. Central to this event is increased gene transcription. Small Rho-GTPases not only control the actin cytoskeleton, but are also implicated in gene regulation. However, in
Kiran A Vaidya et al.
Cardiovascular pathology : the official journal of the Society for Cardiovascular Pathology, 58, 107414-107414 (2022-01-26)
Calcific aortic valve disease (CAVD), a major cause for surgical aortic valve replacement, currently lacks available pharmacological treatments. Cadherin-11 (Cad11), a promising therapeutic target, promotes aortic valve calcification in vivo, but direct Cad11 inhibition in clinical trials has been unsuccessful.
J-W Jang et al.
Oncogene, 36(7), 999-1011 (2016-07-19)
The tumor-suppressor RUNX3 has a critical role in a lineage determination, cell cycle arrest and apoptosis. Lozenge (Lz), a Drosophila homolog of mammalian RUNX family members, has integral roles in these processes and specifically in eye cell fate determination. To
Tao Tao et al.
Journal of genetics and genomics = Yi chuan xue bao, 46(2), 87-96 (2019-03-10)
As a critical guanine nucleotide exchange factor (GEF) regulating neurite outgrowth, Trio coordinates multiple processes of cytoskeletal dynamics through activating Rac1, Cdc42 and RhoA small GTPases by two GEF domains, but the in vivo roles of these GEF domains and corresponding
JinSeok Park et al.
Nature communications, 10(1), 2797-2797 (2019-06-28)
Collective cell migration occurs in many patho-physiological states, including wound healing and invasive cancer growth. The integrity of the expanding epithelial sheets depends on extracellular cues, including cell-cell and cell-matrix interactions. We show that the nano-scale topography of the extracellular
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