A geranylgeranyl transferase I inhibitor
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GGTI 2133 (trifluoroacetate salt)

Item No. 23418

Technical Information
Formal Name
N-[4-[(1H-imidazol-5-ylmethyl)amino]-2-(1-naphthalenyl)benzoyl]-L-leucine, 2,2,2-trifluoroacetate salt
CAS Number
1217480-14-2
Molecular Formula
C27H28N4O3 • XCF3COOH
Formula Weight
Purity
≥95%
Formulation
A crystalline solid
DMSO: 25 mg/ml
λmax
222, 285 nm
SMILES
O=C(N[C@H](C(O)=O)CC(C)C)C1=CC=C(NCC2=CNC=N2)C=C1C3=C4C(C=CC=C4)=CC=C3.FC(F)(C(O)=O)F
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    GGTI 2133 is a peptidomimetic inhibitor of geranylgeranyl transferase type I (GGTase I; IC50 = 38 nM).1 It is 140-fold selective for GGTase I over farnesyltransferase (IC50 = 5,400 nM). In vitro, it inhibits geranylgeranylation of RAP1A (IC50 = 10 µM) without inhibiting farnesylation of H-Ras (IC50 = >30 µM). It also inhibits cell growth and decreases migration and invasion of oral squamous cell carcinoma (OSSC) cells to 75, 45, and 27% of control values, respectively.2 GGTI 2133 (5 mg/kg per day, i.p.) prevents ovalbumin-induced eosinophil infiltration into airways in a mouse model of allergic bronchial asthma but does not prevent an increase in chemokines.3 It also blocks naloxone-induced contraction of ileum isolated from rats with morphine withdrawal syndrome and dose-dependently decreases withdrawal severity in vivo (ED50 = 0.076 mg/kg).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vasudevan, A., Qian, Y., Vogt, A., et alPotent, highly selective, and non-thiol inhibitors of protein geranylgeranyltransferase-I. J. Med. Chem. 42(8), 1333-1340 (1999).

    2. Hamada, M., Miki, T., Iwai, S., et alInvolvement of RhoA and RalB in geranylgeranyltransferase I inhibitor-mediated inhibition of proliferation and migration of human oral squamous cell carcinoma cells. Cancer Chemother. Pharmacol. 68(3), 559-569 (2011).

    3. Chiba, Y., Sato, S., and Misawa, M. GGTI-2133, an inhibitor of geranylgeranyltransferase, inhibits infiltration of inflammatory cells into airways in mouse experimental asthma. Int. J. Immunopathol. Pharmacol. 22(4), 929-935 (2009).

    4. Rehni, A.K., and Signh, T.G. Pharmacological modulation of geranylgeranyltransferase and farnesyltransferase attenuates opioid withdrawal in vivo and in vitro. Neuropharmacology 71, 19-26 (2013).