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Literature summary for 3.4.11.18 extracted from

  • Wang, W.L.; Chai, S.C.; Huang, M.; He, H.Z.; Hurley, T.D.; Ye, Q.Z.
    Discovery of inhibitors of Escherichia coli methionine aminopeptidase with the Fe(II)-form selectivity and antibacterial activity (2008), J. Med. Chem., 51, 6110-6120.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.4.11.18

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli BL21(DE3) cells Escherichia coli

Crystallization (Commentary)

Crystallization (Comment) Organism
in complex with inhibitor 4-(3-ethylthiophen-2-yl)benzene-1,2-diol, hanging drop vapour diffusion method, using 100 mM MES, pH 6.5, 2 mM MnCl2, and 17% PEG 20000 Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
4-(1,3-thiazol-2-yl)benzene-1,2-diol does only inhibit Fe2+-activated MetAP enzyme, but not Mn2+- or Co2+-activated MetAP enzymes Escherichia coli
4-(2,5-dichlorothiophen-3-yl)benzene-1,2-diol
-
 Escherichia coli
4-(2,5-dimethylthiophen-3-yl)benzene-1,2-diol specific inhibition of Fe2+-loaded MetAP Escherichia coli
4-(2-aminothiazol-4-yl)benzene-1,2-diol specific inhibition of Fe2+-loaded MetAP Escherichia coli
4-(2-methyl-1,3-thiazol-4-yl)benzene-1,2-diol does only inhibit Fe2+-activated MetAP enzyme, but not Mn2+- or Co2+-activated MetAP enzymes Escherichia coli
4-(3-(2-bromoethyl)thiophen-2-yl)benzene-1,2-diol
-
 Escherichia coli
4-(3-butylthiophen-2-yl)benzene-1,2-diol
-
 Escherichia coli
4-(3-ethylthiophen-2-yl)benzene-1,2-diol
-
 Escherichia coli
4-(3-methylthiophen-2-yl)benzene-1,2-diol
-
 Escherichia coli
4-(3-propylthiophen-2-yl)benzene-1,2-diol
-
 Escherichia coli
4-(4-bromo-2,5-dimethylthiophen-3-yl)benzene-1,2-diol
-
 Escherichia coli
4-(5-chlorothiophen-2-yl)benzene-1,2-diol
-
 Escherichia coli
4-(5-methylthiophen-2-yl)benzene-1,2-diol
-
 Escherichia coli
4-(thiophen-2-yl)benzene-1,2-diol
-
 Escherichia coli
4-(thiophen-3-yl)benzene-1,2-diol
-
 Escherichia coli
5-(3,4-dihydroxyphenyl)-N-isopropyl-2-methylthiazole-4-carboxamide specific inhibition of Fe2+-loaded MetAP Escherichia coli
5-(3,4-dihydroxyphenyl)thiophene-2-carbonitrile
-
 Escherichia coli
cyclopropyl 5-(3,4-dihydroxyphenyl)-2-methyl-1,3-thiazole-4-carboxylate
-
 Escherichia coli
N-cyclopropyl-2-(3,4-dihydroxyphenyl)thiophene-3-carboxamide specific inhibition of Fe2+-loaded MetAP Escherichia coli
N-cyclopropyl-5-(3,4-dihydroxyphenyl)thiophene-2-carboxamide
-
 Escherichia coli

Metals/Ions

Metals/Ions Comment Organism Structure
Co2+
-
 Escherichia coli
Fe2+ Fe2+ is the likely metal cofactor used by MetAP in the cellular environment Escherichia coli
Mn2+
-
 Escherichia coli

Organism

Organism UniProt Comment Textmining
Escherichia coli P0AE18
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Escherichia coli

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
L-Met-7-amido-4-methylcoumarin + H2O
-
 Escherichia coli L-Met + 7-amino-4-methylcoumarin
-
 ?

Synonyms

Synonyms Comment Organism
MetAP
-
 Escherichia coli
methionine aminopeptidase
-
 Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0021
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(4-bromo-2,5-dimethylthiophen-3-yl)benzene-1,2-diol
0.0024
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(4-bromo-2,5-dimethylthiophen-3-yl)benzene-1,2-diol
0.0031
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(4-bromo-2,5-dimethylthiophen-3-yl)benzene-1,2-diol
0.0038
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 Escherichia coli 4-(thiophen-3-yl)benzene-1,2-diol
0.0051
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(thiophen-2-yl)benzene-1,2-diol
0.0066
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(2-aminothiazol-4-yl)benzene-1,2-diol
0.0066
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(2-aminothiazol-4-yl)benzene-1,2-diol
0.0073
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(3-(2-bromoethyl)thiophen-2-yl)benzene-1,2-diol
0.0074
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(2,5-dimethylthiophen-3-yl)benzene-1,2-diol
0.0078
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli N-cyclopropyl-2-(3,4-dihydroxyphenyl)thiophene-3-carboxamide
0.008
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(3-methylthiophen-2-yl)benzene-1,2-diol
0.0092
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(3-butylthiophen-2-yl)benzene-1,2-diol
0.0111
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli cyclopropyl 5-(3,4-dihydroxyphenyl)-2-methyl-1,3-thiazole-4-carboxylate
0.0128
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(5-chlorothiophen-2-yl)benzene-1,2-diol
0.0129
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(3-ethylthiophen-2-yl)benzene-1,2-diol
0.013
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(2-methyl-1,3-thiazol-4-yl)benzene-1,2-diol
0.014
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(3-(2-bromoethyl)thiophen-2-yl)benzene-1,2-diol
0.014
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(3-propylthiophen-2-yl)benzene-1,2-diol
0.0148
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 5-(3,4-dihydroxyphenyl)thiophene-2-carbonitrile
0.0154
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 5-(3,4-dihydroxyphenyl)-N-isopropyl-2-methylthiazole-4-carboxamide
0.0154
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 5-(3,4-dihydroxyphenyl)-N-isopropyl-2-methylthiazole-4-carboxamide
0.0157
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(thiophen-2-yl)benzene-1,2-diol
0.0166
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(1,3-thiazol-2-yl)benzene-1,2-diol
0.0202
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(2,5-dichlorothiophen-3-yl)benzene-1,2-diol
0.0224
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(3-(2-bromoethyl)thiophen-2-yl)benzene-1,2-diol
0.023
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(3-methylthiophen-2-yl)benzene-1,2-diol
0.0237
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(thiophen-2-yl)benzene-1,2-diol
0.0238
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli N-cyclopropyl-5-(3,4-dihydroxyphenyl)thiophene-2-carboxamide
0.0275
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(thiophen-3-yl)benzene-1,2-diol
0.028
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(5-methylthiophen-2-yl)benzene-1,2-diol
0.0285
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli N-cyclopropyl-5-(3,4-dihydroxyphenyl)thiophene-2-carboxamide
0.0304
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 5-(3,4-dihydroxyphenyl)thiophene-2-carbonitrile
0.0327
-
 Fe2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.05 mM FeCl2 with 0.1 mM ascorbic acid Escherichia coli 4-(5-methylthiophen-2-yl)benzene-1,2-diol
0.034
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli N-cyclopropyl-5-(3,4-dihydroxyphenyl)thiophene-2-carboxamide
0.0343
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(3-propylthiophen-2-yl)benzene-1,2-diol
0.0363
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 5-(3,4-dihydroxyphenyl)thiophene-2-carbonitrile
0.0404
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(thiophen-3-yl)benzene-1,2-diol
0.0427
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(3-methylthiophen-2-yl)benzene-1,2-diol
0.0448
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(5-chlorothiophen-2-yl)benzene-1,2-diol
0.0482
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(3-butylthiophen-2-yl)benzene-1,2-diol
0.0486
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(2,5-dichlorothiophen-3-yl)benzene-1,2-diol
0.0515
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(5-methylthiophen-2-yl)benzene-1,2-diol
0.0557
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(3-ethylthiophen-2-yl)benzene-1,2-diol
0.0624
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(2,5-dichlorothiophen-3-yl)benzene-1,2-diol
0.0626
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(3-ethylthiophen-2-yl)benzene-1,2-diol
0.0923
-
 Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli cyclopropyl 5-(3,4-dihydroxyphenyl)-2-methyl-1,3-thiazole-4-carboxylate
0.1
-
 IC50 above 0.1 mM, Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli N-cyclopropyl-2-(3,4-dihydroxyphenyl)thiophene-3-carboxamide
0.1
-
 IC50 above 0.1 mM, Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(5-chlorothiophen-2-yl)benzene-1,2-diol
0.1
-
 IC50 above 0.1 mM, Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(3-propylthiophen-2-yl)benzene-1,2-diol
0.1
-
 IC50 above 0.1 mM, Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(3-butylthiophen-2-yl)benzene-1,2-diol
0.1
-
 IC50 above 0.1 mM, Co2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.01 mM CoCl2 Escherichia coli 4-(2,5-dimethylthiophen-3-yl)benzene-1,2-diol
0.1
-
 IC50 above 0.1 mM, Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli N-cyclopropyl-2-(3,4-dihydroxyphenyl)thiophene-3-carboxamide
0.1
-
 IC50 above 0.1 mM, Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(2,5-dimethylthiophen-3-yl)benzene-1,2-diol
0.1
-
 IC50 above 0.1 mM, Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 4-(2-aminothiazol-4-yl)benzene-1,2-diol
0.1
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli cyclopropyl 5-(3,4-dihydroxyphenyl)-2-methyl-1,3-thiazole-4-carboxylate
0.1
-
 Mn2+-loaded wild type enzyme, in 50 mM MOPS (pH 7.0), 0.02 mM MnCl2 Escherichia coli 5-(3,4-dihydroxyphenyl)-N-isopropyl-2-methylthiazole-4-carboxamide