733767-34-5

Basic information

• Product Name: NSC 23766 TETRAHYDROCHLORIDE
• Synonyms: NSC 23766 TETRAHYDROCHLORIDE;NSC 23766;N6-[2-[[4-(DIETHYLAMINO)-1-METHYLBUTYL]AMINO]-6-METHYL-4-PYRIMIDINYL]-2-METHYL-4,6-QUINOLINEDIAMINE TRIHYDROCHLORIDE;N6-[2-(4-Diethylamino-1-methylbutylamino)-6-methylpyrimidin-4-yl]-2-methylquinoline-4,6-diamine tetrahydrochloride;N6-(2-(5-(Diethylamino)pentan-2-ylamino)-6-methylpyrimidin-4-yl)-2-methylquinoline-4,6-diamine
• CAS NO: 733767-34-5
• Molecular Formula: C24H38Cl3N7
• Molecular Weight: 530.96442
• Product Categories: G-Protein;Other enzyme inhibitors and activators;Rac1 Inhibitor.
• Mol File: 733767-34-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 632.4°C at 760 mmHg
• Flash Point: 336.2°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 6.73E-16mmHg at 25°C
• Refractive Index: 1.646
• Storage Temp.: Desiccate at RT
• Solubility: Soluble in DMSO (50 mg/ml); Water (50 mg/ml)
• Water Solubility: Soluble in water.
• Sensitive: Light Sensitive & Hygroscopic
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: NSC 23766 TETRAHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: NSC 23766 TETRAHYDROCHLORIDE(733767-34-5)
• EPA Substance Registry System: NSC 23766 TETRAHYDROCHLORIDE(733767-34-5)

Safety Data

• Hazardous Substances Data: 733767-34-5(Hazardous Substances Data)

Usage

Description

NSC 23766 TETRAHYDROCHLORIDE, also known as NSC-23766, is a selective inhibitor of Rac1-GEF interaction. It prevents Rac1 activation by Rac-specific guanine nucleotide exchange factors (GEFs) Trio and Tiam1 with an IC50 of approximately 50 μM. NSC 23766 TETRAHYDROCHLORIDE does not affect the closely related Cdc42 or RhoA. In cells, it blocks serum or PDGF-induced Rac-1 activation and lamellipodia formation. NSC 23766 is a useful tool to probe the involvement of Rac1 in cell signaling and has off-target effects as an antagonist at muscarinic acetylcholine receptors. It is cell permeable.

Uses

Used in Pharmaceutical Research:
NSC 23766 TETRAHYDROCHLORIDE is used as a research tool for investigating the role of Rac1 in cell signaling. Its ability to selectively inhibit Rac1-GEF interaction makes it valuable for studying the effects of Rac1 activation on various cellular processes.
Used in Platelet Aggregation Studies:
NSC 23766 TETRAHYDROCHLORIDE is used as an inhibitor of ADP-mediated platelet aggregation. This application helps researchers understand the role of Rac1 in platelet function and blood clotting.
Used in Cancer Research:
NSC 23766 TETRAHYDROCHLORIDE is used as a potential therapeutic agent to restore sensitivity to trastuzumab, a monoclonal antibody used in the treatment of breast cancer. By inhibiting Rac1, it can help restore the down-regulation of ErbB2, a protein that is often overexpressed in cancer cells and contributes to resistance to trastuzumab.
Used in Cell Biology Research:
NSC 23766 TETRAHYDROCHLORIDE is used to study the effects of Rac1 inhibition on membrane type 1-matrix metalloproteinases (MT-1MMP) expression in CB CD34+ cells. Its presence has been reported to decrease MT-1MMP expression, providing insights into the role of Rac1 in cell migration and invasion.
Used in Endomembrane Cycling Studies:
NSC 23766 TETRAHYDROCHLORIDE is used to investigate the effects of Rac1 inhibition on endomembrane cycling, polar adhesive secretion, and tip growth. Its ability to depolarize endomembrane cycling can help researchers understand the role of Rac1 in cellular transport and communication.

Biological Activity

Selective inhibitor of Rac1-GEF interaction. Prevents Rac1 activation by Rac-specific guanine nucleotide exchange factors (GEFs) TrioN and Tiam1 (IC 50 ~ 50 μ M) without affecting Cdc42 or RhoA activation. Inhibits Rac1-mediated cell functions and reported to reverse tumor cell phenotyes in prostate cancer cells.

References

Gao et al. (2004), Rational design and characterization of a Rac GTPase-specific small molecule inhibitor; Proc. Natl. Acad. Sci. USA, 101 7618 Shankar et al. (2013), Raft endocytosis of AMF regulates mitochondrial dynamics through Rac1 signaling and the Gp78 ubiquitin ligase; J. Cell Sci., 126 3295 Levay et al. (2013), NSC23766, a widely used inhibitor of Rac1 activation, additionally acts as a competitive antagonist at muscarinic acetylcholine receptors; J. Pharmacol. Exp. Ther., 347 69

InChI:InChI=1/C24H35N7/c1-6-31(7-2)12-8-9-16(3)27-24-28-18(5)14-23(30-24)29-19-10-11-22-20(15-19)21(25)13-17(4)26-22/h10-11,13-16H,6-9,12H2,1-5H3,(H2,25,26)(H2,27,28,29,30)

Upstream product

• 852808-01-6 N⁶-(2-chloro-6-methylpyrimidin-4-yl)-2-methylquinoline-4,6-diamine 
• 140-80-7 5-diethylamino-2-pentylamine 

Relevant articles and documents

GTPase inhibitors and methods of use and crystal structure of RAC-1 GTPase

The preferred embodiments generally relate to methods and compositions that affect the GTP-binding activity of members of the Rho family GTPases, preferably Rac (Rac1, Rac2 and/or Rac3), such compositions include compounds that modulate the GTP/GDP exchan

GTPASE INHIBITORS AND METHODS OF USE

The preferred embodiments generally relate to methods and compositions that affect the GTP-binding activity of members of the Rho family GTPases, preferably Rac (Rac1, Rac2 and/or Rac3), such compositions include compounds that modulate the GTP/GDP exchan