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G5294

GGTI-2133

Name: GGTI-2133
Brand: SIGMA

≥98% (HPLC), solid

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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

PubChem Substance ID:

24724491

NACRES:

NA.77

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

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

GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Precautionary Statements

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)

Presence and distribution of progerin in HGPS cells is ameliorated by drugs that impact on the mevalonate and mTOR pathways.

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 pyrophosphate synthase facilitates the organization of cardiomyocytes during mid-gestation through modulating protein geranylgeranylation in mouse heart

Chen Z, et al.

Cardiovascular Research, 114(7), 965-978 (2018)

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