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Key Documents

G5294

Sigma-Aldrich

GGTI-2133

≥98% (HPLC), 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:
Molecular Weight:
570.56
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

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

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.

pictograms

Exclamation mark

signalword

Warning

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


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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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
P53-and mevalonate pathway-driven malignancies require Arf6 for metastasis and drug resistance
Hashimoto A, et al.
The Journal of Cell Biology, 213(1), 81-95 (2016)
Geranylgeranyl transferase regulates CXC chemokine formation in alveolar macrophages and neutrophil recruitment in septic lung injury
Hasan Z, et al.
American Journal of Physiology. Lung Cellular and Molecular Physiology, 304(4), L221-L229 (2012)
Geranylgeranyltransferase I inhibitors target RalB to inhibit anchorage-dependent growth and induce apoptosis and RalA to inhibit anchorage-independent growth
Falsetti SC, et al.
Molecular and cellular biology, 27(22), 8003-8014 (2007)
Staci L Haney et al.
Oncogene, 38(26), 5308-5320 (2019-03-29)
Rab proteins play an essential role in regulating intracellular membrane trafficking processes. Rab activity is dependent upon geranylgeranylation, a post-translational modification that involves the addition of 20-carbon isoprenoid chains via the enzyme geranylgeranyl transferase (GGTase) II. We have focused on

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