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Literature summary for 2.5.1.60 extracted from

  • Tan, K.T.; Guiu-Rozas, E.; Bon, R.S.; Guo, Z.; Delon, C.; Wetzel, S.; Arndt, S.; Alexandrov, K.; Waldmann, H.; Goody, R.S.; Wu, Y.W.; Blankenfeldt, W.
    Design, synthesis, and characterization of peptide-based rab geranylgeranyl transferase inhibitors (2009), J. Med. Chem., 52, 8025-8037.
    View publication on PubMed
Search for more literature for 2.5.1.60

Crystallization (Commentary)

Crystallization (Comment) Organism
enzyme-inhibitor complex with an engeneered enzyme lacking the LRR- and Ig-domains, complexes are prepared by soaking of co-crystallization, diffraction data collection at -173°C Homo sapiens

Protein Variants

Protein Variants Comment Organism
additional information enzyme lacking the LRR- and Ig-domains for crystallization complexes Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
methyl N-undecanoyl-L-tyrosyl-L-histidyl-L-tyrosinate class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide) Homo sapiens
additional information peptidic library based on the farnesyl transferase inhibitor pepticinnamin E, a natural tripeptide from Streptomyces OH-4652 Homo sapiens
N-([[2-(benzyloxy)benzyl]oxy]carbonyl)-D-histidyl-L-tyrosyl-L-phenylalanine class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini) Homo sapiens
N-([[2-(benzyloxy)benzyl]oxy]carbonyl)-L-histidyl-L-tyrosyl-L-phenylalanine class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini) Homo sapiens
N-butanoyl-L-histidyl-L-phenylalanyl-N-methyl-N-[2-(pyridin-2-yl)ethyl]-L-tyrosinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide) Homo sapiens
N-octanoyl-L-histidyl-L-phenylalanyl-N-methyl-N-[2-(pyridin-2-yl)ethyl]-L-tyrosinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide) Homo sapiens
N-pentadecanoyl-L-histidyl-L-phenylalanyl-N-methyl-N-[2-(pyridin-2-yl)ethyl]-L-tyrosinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide) Homo sapiens
N-undecanoyl-L-histidyl-L-histidyl-N-(4-aminobutyl)-L-tyrosinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide) Homo sapiens
N-undecanoyl-L-histidyl-L-histidyl-N-methyl-N-[2-(pyridin-2-yl)ethyl]-L-tyrosinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide), not cytotoxic to COS-7 cells, fluorescence titration reveals competitive inhibition Homo sapiens
N-undecanoyl-L-histidyl-L-phenylalanyl-N-methyl-N-[2-(pyridin-2-yl)ethyl]-L-tyrosinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide), not cytotoxic to COS-7 cells, fluorescence titration reveals partial competitive inhibition which points to a different binding site Homo sapiens
N-undecanoyl-L-histidyl-L-phenylalanyl-N-[2-(pyridin-2-yl)ethyl]-L-tyrosinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide) Homo sapiens
N-undecanoyl-L-tyrosyl-L-histidyl-N-(4-aminobutyl)-L-tyrosinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide) Homo sapiens
N-undecanoyl-L-tyrosyl-L-histidyl-N-methyl-N-[2-(pyridin-2-yl)ethyl]-L-tyrosinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide), not cytotoxic to COS-7 cells, fluorescence titration reveals competitive inhibition Homo sapiens
N-[(2,5-dimethyl-1,3-oxazol-4-yl)carbonyl]glycyl-L-phenylalanyl-1-trityl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[(2,5-dimethyl-1,3-oxazol-4-yl)carbonyl]glycyl-L-phenylalanyl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[(2-phenyl-1,3-oxazol-4-yl)carbonyl]-1-trityl-L-histidylglycyl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[(2-phenyl-1,3-oxazol-4-yl)carbonyl]-1-trityl-L-histidylglycyl-L-phenylalanine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[(2-phenyl-1,3-oxazol-4-yl)carbonyl]-L-histidylglycyl-1-trityl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus), not cytotoxic to COS-7 cells, fluorescence titration reveals competitive inhibition Homo sapiens
N-[(2-phenyl-1,3-oxazol-4-yl)carbonyl]-L-histidylglycyl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[(2-phenyl-1,3-oxazol-4-yl)carbonyl]glycyl-L-phenylalanyl-1-(tert-butoxycarbonyl)-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[(2-phenyl-1,3-oxazol-4-yl)carbonyl]glycyl-L-phenylalanyl-1-benzyl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[(2-phenyl-1,3-oxazol-4-yl)carbonyl]glycyl-L-phenylalanyl-1-trityl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[(2-phenyl-1,3-oxazol-4-yl)carbonyl]glycyl-L-phenylalanyl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[(2-phenyl-1,3-oxazol-4-yl)carbonyl]histidylglycyl-L-phenylalanine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[(2E)-3-(biphenyl-4-yl)prop-2-enoyl]-D-histidyl-L-tyrosyl-L-tyrosine class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini) Homo sapiens
N-[(2E)-3-[2-[(1Z)-pent-1-en-1-yl]phenyl]prop-2-enoyl]-D-histidyl-L-tyrosyl-D-phenylalanine class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini) Homo sapiens
N-[(benzyloxy)carbonyl]-D-tyrosyl-L-phenylalanyl-L-tyrosine class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), fluorescence titration reveals competitive inhibition Homo sapiens
N-[(benzyloxy)carbonyl]-L-histidyl-N-methyl-L-phenylalanyl-L-tyrosine class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), fluorescence titration reveals competitive inhibition Homo sapiens
N-[(benzyloxy)carbonyl]-L-histidyl-N-methyl-L-phenylalanyl-N-hydroxy-D-tyrosinamide class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini) Homo sapiens
N-[(benzyloxy)carbonyl]-L-histidyl-N-methyl-L-phenylalanyl-N-hydroxy-L-tryptophanamide class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), not cytotoxic to COS-7 cells Homo sapiens
N-[(benzyloxy)carbonyl]-L-histidyl-N-methyl-L-phenylalanyl-N-hydroxy-L-tyrosinamide class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), not cytotoxic to COS-7 cells Homo sapiens
N-[3-(4-pentylphenyl)propanoyl]-D-histidyl-N-methyl-L-phenylalanyl-L-phenylalanine class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini) Homo sapiens
N-[3-(4-pentylphenyl)propanoyl]-D-tyrosyl-L-tyrosyl-L-phenylalanine class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini) Homo sapiens
N-[4-(undecyloxy)benzoyl]-L-histidyl-L-histidyl-N-(4-aminobutyl)-L-histidinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide) Homo sapiens
N-[4-(undecyloxy)benzoyl]-L-histidyl-L-histidyl-N-methyl-N-[2-(pyridin-2-yl)ethyl]-L-histidinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide) Homo sapiens
N-[4-(undecyloxy)benzoyl]-L-histidyl-L-tyrosyl-N-[3-(1H-imidazol-1-yl)propyl]-L-phenylalaninamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide) Homo sapiens
N-[4-(undecyloxy)benzoyl]-L-tyrosyl-L-tyrosyl-N-(4-aminobutyl)-L-tyrosinamide class III inhibitors (comprising a lipophilic N-terminus and an amine or N-heterocycle containing a C-terminal amide) Homo sapiens
N-[[2-(pyridin-3-yl)-1,3-thiazol-4-yl]carbonyl]glycyl-L-phenylalanyl-1-trityl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[[2-(pyridin-3-yl)-1,3-thiazol-4-yl]carbonyl]glycyl-L-phenylalanyl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[[2-(thiophen-2-yl)-1,3-thiazol-4-yl]carbonyl]glycyl-L-phenylalanyl-1-trityl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens
N-[[2-(thiophen-2-yl)-1,3-thiazol-4-yl]carbonyl]glycyl-L-phenylalanyl-L-histidine class II inhibitors (combining a heterocyclic ring system at the N-terminus with a free carboxylate at the C-terminus) Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate + Rab7 geranylgeranyl diphosphate analogue and Rab7 as substrates in the presence of Rab escort protein, in vitro inhibition assays Homo sapiens (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1)-Rab7 + diphosphate
-
 ?
biotinylated geranyl diphosphate + EYFP-Rab7 COS-7 cells are transfected with EYFP-Rab7 fusion protein and incubated with inhibitors, cells lysed after 24 h, clarified supernatant incubated in biotinylated geranyl diphosphate (geranylgeranyl diphosphate substrate analogue), recombinant RabGGTase and Rab escort protein, in vivo inhibitor studies Homo sapiens S-biotin-geranyl-Rab7 + diphosphate
-
 ?

Synonyms

Synonyms Comment Organism
GGTase-II
-
 Homo sapiens
Rab geranylgeranyl transferase
-
 Homo sapiens
RabGGTase
-
 Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0011
-
 N-undecanoyl-L-histidyl-L-histidyl-N-methyl-N-[2-(pyridin-2-yl)ethyl]-L-tyrosinamide displacement titration Homo sapiens
0.0028
-
 N-undecanoyl-L-tyrosyl-L-histidyl-N-methyl-N-[2-(pyridin-2-yl)ethyl]-L-tyrosinamide displacement titration Homo sapiens
0.0045
-
 N-[(benzyloxy)carbonyl]-L-histidyl-N-methyl-L-phenylalanyl-L-tyrosine 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens
0.0045
-
 N-[(benzyloxy)carbonyl]-L-histidyl-N-methyl-L-phenylalanyl-L-tyrosine displacement titration Homo sapiens
0.0053
-
 N-[(2-phenyl-1,3-oxazol-4-yl)carbonyl]-L-histidylglycyl-1-trityl-L-histidine displacement titration Homo sapiens
0.0054
-
 N-undecanoyl-L-histidyl-L-phenylalanyl-N-methyl-N-[2-(pyridin-2-yl)ethyl]-L-tyrosinamide displacement titration Homo sapiens
0.0145
-
 N-[(benzyloxy)carbonyl]-L-histidyl-N-methyl-L-phenylalanyl-N-hydroxy-L-tyrosinamide displacement titration Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
additional information
-
 chemicals that cause an activity decrease of more than 70% at 100 microM are selected for inhibition studies Homo sapiens additional information
0.0041
-
 most potent of the class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens N-[(benzyloxy)carbonyl]-D-tyrosyl-L-phenylalanyl-L-tyrosine
0.0052
-
 class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens N-[(benzyloxy)carbonyl]-L-histidyl-N-methyl-L-phenylalanyl-N-hydroxy-L-tryptophanamide
0.009
-
 class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens N-[(benzyloxy)carbonyl]-L-histidyl-N-methyl-L-phenylalanyl-N-hydroxy-L-tyrosinamide
0.011
-
 class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens N-[3-(4-pentylphenyl)propanoyl]-D-tyrosyl-L-tyrosyl-L-phenylalanine
0.0136
-
 class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens N-[(benzyloxy)carbonyl]-L-histidyl-N-methyl-L-phenylalanyl-N-hydroxy-D-tyrosinamide
0.0152
-
 class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens N-[(2E)-3-[2-[(1Z)-pent-1-en-1-yl]phenyl]prop-2-enoyl]-D-histidyl-L-tyrosyl-D-phenylalanine
0.0156
-
 class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens N-([[2-(benzyloxy)benzyl]oxy]carbonyl)-D-histidyl-L-tyrosyl-L-phenylalanine
0.019
-
 class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens N-[3-(4-pentylphenyl)propanoyl]-D-histidyl-N-methyl-L-phenylalanyl-L-phenylalanine
0.0193
-
 class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens N-([[2-(benzyloxy)benzyl]oxy]carbonyl)-L-histidyl-L-tyrosyl-L-phenylalanine
0.0227
-
 class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens N-[(benzyloxy)carbonyl]-L-histidyl-N-methyl-L-phenylalanyl-L-tyrosine
0.0227
-
 class I inhibitors (compounds possessing a free carboxylic or hydroxamic acid at the C-terminus and lipophilic N-termini), 9 microM (3,7,11-trimethyl-12-(7-nitrobenzo[1,2,5]oxadiazo-4-ylamino)-dodeca-2,6,19-trien-1) diphosphate, 3 microM Rab7, 3 microM Rab escort protein, 400 nM enzyme Homo sapiens N-[(2E)-3-(biphenyl-4-yl)prop-2-enoyl]-D-histidyl-L-tyrosyl-L-tyrosine

General Information

General Information Comment Organism
malfunction overexpression of Rabs Rab5a, Rab7, and Rab27 is observed in various cancers, elevated levels of Rab25 in breast and ovarian cancer cells are reported to increase the aggressiveness of these cancers Homo sapiens
physiological function attachment of geranylgeranyl isoprenoids to Rab guanine triphosphatases, which are key regulators in vesicular transport Homo sapiens