G5294

GGTI-2133

≥98% (HPLC), solid

• Synonym(s): N-[[4-(Imidazol-4-yl)methylamino]-2-(1-naphthyl)benzoyl]leucine trifluoroacetate salt
• Empirical Formula (Hill Notation): C₂₇H₂₈N₄O₃ · C₂HF₃O₂
• CAS Number: 1217480-14-2
• Molecular Weight: 570.56
• MDL number: MFCD07776925
• UNSPSC Code: 12352200
• PubChem Substance ID: 24724491
• NACRES: NA.77

Properties

• assay: ≥98% (HPLC)
• form: solid
• color: white to beige
• mp: 103-118.5 °C
• solubility: DMSO: 25 mg/mL; H₂O: insoluble
• storage temp.: −20°C
• SMILES string: OC(=O)C(F)(F)F.CC(C)C[C@H](NC(=O)c1ccc(NCc2c[nH]cn2)cc1-c3cccc4ccccc34)C(O)=O
• InChI: 1S/C27H28N4O3.C2HF3O2/c1-17(2)12-25(27(33)34)31-26(32)23-11-10-19(29-15-20-14-28-16-30-20)13-24(23)22-9-5-7-18-6-3-4-8-21(18)22;3-2(4,5)1(6)7/h3-11,13-14,16-17,25,29H,12,15H2,1-2H3,(H,28,30)(H,31,32)(H,33,34);(H,6,7)/t25-;/m0./s1
• InChI key: FXXUNOYBYJFSRB-UQIIZPHYSA-N
• Gene Information: human ... FNTA(2339) , PGGT1B(5229)

Description

Application

GGTI-2133 has been used

• To understand the role of geranylgeranyl transferase in the regulation of CXC chemokine production and neutrophil recruitment in the lung.
• To study the importance of geranylgeranylation in cell adhesion.
• To measure ligand-induced ADP-ribosylation factor 6 (Arf6) activation in breast cancer cells.

Biochem/physiol Actions

GGTI-2133 is a cell-permeable non-thiol peptidomimetic that acts as a potent and selective inhibitor of geranylgeranyltransferase I (GGTase I; IC50 = 38 nM) with a 140-fold selectivity over farnesyltransferase (FTase; IC₅₀ = 5.4 μM).

GGTase I mediates prenylation to induce the oncogenic functions of the Ras and Rho proteins. Thus, GGTase I inhibitors can be utilized as effective anticancer drugs. They are also useful in treating inflammation, atherosclerosis, multiple sclerosis and other diseases.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves