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G5294

GGTI-2133

≥98% (HPLC), geranylgeranyltransferase I inhibitor, solid

Synonym(s):

N-[[4-(Imidazol-4-yl)methylamino]-2-(1-naphthyl)benzoyl]leucine trifluoroacetate salt

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About This Item

Empirical Formula (Hill Notation):
C27H28N4O3 · C2HF3O2
CAS Number:
1217480-14-2
Molecular Weight:
570.56
UNSPSC Code:
12352200
PubChem Substance ID:
24724491
NACRES:
NA.77
MDL number:
MFCD07776925
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
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Product Name

GGTI-2133, ≥98% (HPLC), solid

Quality Level

100

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)

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

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.
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).

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000159561
0000159561
0000445095
0000445095
0000159560

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Craig S Clements et al.
Biogerontology, 20(3), 337-358 (2019-05-02)
Hutchinson-Gilford progeria syndrome (HGPS) is a rare, premature ageing syndrome in children. HGPS is normally caused by a mutation in the LMNA gene, encoding nuclear lamin A. The classical mutation in HGPS leads to the production of a toxic truncated
Discovery of Geranylgeranyltransferase-I Inhibitors with Novel Scaffolds by the Means of Quantitative Structure-Activity Relationship Modeling, Virtual Screening, and Experimental Validation
Peterson YK, et al.
Journal of medicinal chemistry, 52(14), 4210-4220 (2009)
Hong-Li Jiao et al.
Cell death & disease, 11(7), 571-571 (2020-07-28)
Oxysterol-binding protein like protein 3 (OSBPL3) has been shown involving in the development of several human cancers. However, the relationship between OSBPL3 and colorectal cancer (CRC), particularly the role of OSBPL3 in the proliferation, invasion and metastasis of CRC remains
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Global Trade Item Number

SKUGTIN
G5294-5MG04061832981673
G5294-1MG04061833633984