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Literature summary extracted from

  • Auld, D.S.; Southall, N.T.; Jadhav, A.; Johnson, R.L.; Diller, D.J.; Simeonov, A.; Austin, C.P.; Inglese, J.
    Characterization of chemical libraries for luciferase inhibitory activity (2008), J. Med. Chem., 51, 2372-2386.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.13.12.5 analysis analysis of luciferase inhibitors by quantitative high-throughput screening and comparison of and structure-activity relationship using various luciferase-based detection reagents Renilla reniformis

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.12.5 (2Z)-3-[(2-bromophenyl)amino]-1-pyridin-2-ylprop-2-en-1-one
-
 Renilla reniformis
1.13.12.5 (2Z)-3-[[4-(dimethylamino)cyclohexa-1,5-dien-1-yl]amino]-1-phenylprop-2-en-1-one
-
 Renilla reniformis
1.13.12.5 (3Z)-3-[[4-(dimethylamino)phenyl]methylidene]-1,3-dihydro-2H-indol-2-one common name SU4312 Renilla reniformis
1.13.12.5 2-(4-ethoxyphenyl)-4-[(4-methylpiperazin-1-yl)carbonyl]quinoline
-
 Renilla reniformis
1.13.12.5 2-(4-ethoxyphenyl)-4-[(4-pyridin-2-ylpiperazin-1-yl)carbonyl]quinoline
-
 Renilla reniformis
1.13.12.5 2-(4-methylphenyl)-4-[(4-pyrimidin-2-ylpiperazin-1-yl)carbonyl]quinoline
-
 Renilla reniformis
1.13.12.5 2-(5-naphthalen-2-yl-1,2,4-oxadiazol-3-yl)pyridine
-
 Renilla reniformis
1.13.12.5 2-hydroxy-N'-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide common name SCS Renilla reniformis
1.13.12.5 2-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]pyridine
-
 Renilla reniformis
1.13.12.5 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)-2-(4-ethoxyphenyl)quinoline
-
 Renilla reniformis
1.13.12.5 4-amino-6-[(E)-[4'-[(Z)-(8-amino-1-hydroxy-5,7-disulfonato-6,7-dihydronaphthalen-2-yl)diazenyl]-3-methylbiphenyl-4-yl]diazenyl]-5-hydroxy-2,3-dihydronaphthalene-1,3-disulfonate common name Evans Blue Renilla reniformis
1.13.12.5 4-[1-(1,3-benzothiazol-2-yl)-2-(4-methylpiperazin-1-yl)-2-oxoethyl]phenol
-
 Renilla reniformis
1.13.12.5 6-methyl-2-[(Z)-phenyldiazenyl]pyridin-3-ol common name SIB1757 Renilla reniformis
1.13.12.5 ethyl 4-[[2-(4-ethoxyphenyl)quinolin-4-yl]carbonyl]piperazine-1-carboxylate
-
 Renilla reniformis
1.13.12.5 additional information structure-activity relationship of luciferase inhibitors determined by quantitative high-throughput screening. Comparison of effect on various luciferase-based detection reagents Renilla reniformis
1.13.12.5 N'-(3-chlorophenyl)-N-[(1Z)-(3-chlorophenyl)methylidene]imidoformamide common name DCB Renilla reniformis
1.13.12.7 (2R)-2-[4-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]propanoic acid common name indoprofen Photinus pyralis
1.13.12.7 (2Z)-1-(4-chlorophenyl)-3-(pyridin-2-ylamino)prop-2-en-1-one
-
 Photinus pyralis
1.13.12.7 (2Z)-3-[(2-bromophenyl)amino]-1-pyridin-2-ylprop-2-en-1-one
-
 Photinus pyralis
1.13.12.7 (2Z)-3-[(4-fluorophenyl)amino]-1-furan-2-ylprop-2-en-1-one
-
 Photinus pyralis
1.13.12.7 (2Z)-3-[[4-(dimethylamino)cyclohexa-1,5-dien-1-yl]amino]-1-phenylprop-2-en-1-one
-
 Photinus pyralis
1.13.12.7 (3Z)-3-[[4-(dimethylamino)phenyl]methylidene]-1,3-dihydro-2H-indol-2-one common name SU4312 Photinus pyralis
1.13.12.7 1-[3-(6-ethoxy-1,3-benzothiazol-2-yl)thiophen-2-yl]urea
-
 Photinus pyralis
1.13.12.7 2,4-dimethoxy-N-(5-methylpyridin-2-yl)benzamide
-
 Photinus pyralis
1.13.12.7 2-(2-amino-3-methoxyphenyl)-4H-chromen-4-one common name PD98059 Photinus pyralis
1.13.12.7 2-(2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3(2H)-yl)-1-(4-methylphenyl)ethanone common name pifithrin-alpha Photinus pyralis
1.13.12.7 2-(4-ethoxyphenyl)-4-[(4-methylpiperazin-1-yl)carbonyl]quinoline
-
 Photinus pyralis
1.13.12.7 2-(4-ethoxyphenyl)-4-[(4-pyridin-2-ylpiperazin-1-yl)carbonyl]quinoline
-
 Photinus pyralis
1.13.12.7 2-(4-methylphenyl)-4-[(4-pyrimidin-2-ylpiperazin-1-yl)carbonyl]quinoline
-
 Photinus pyralis
1.13.12.7 2-(5-biphenyl-4-yl-1,2,4-oxadiazol-3-yl)pyridine
-
 Photinus pyralis
1.13.12.7 2-(5-naphthalen-2-yl-1,2,4-oxadiazol-3-yl)pyridine
-
 Photinus pyralis
1.13.12.7 2-hydroxy-N'-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide common name SCS Photinus pyralis
1.13.12.7 2-methyl-6-(phenylethynyl)pyridine common name MPEB Photinus pyralis
1.13.12.7 2-methyl-6-[(Z)-2-phenylethenyl]pyridine common name SIB1893 Photinus pyralis
1.13.12.7 2-[5-(3,4-dichlorophenyl)-1,2,4-oxadiazol-3-yl]pyridine
-
 Photinus pyralis
1.13.12.7 2-[5-(3-chloro-4-methylphenyl)-1,2,4-oxadiazol-3-yl]pyridine
-
 Photinus pyralis
1.13.12.7 2-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]pyridine
-
 Photinus pyralis
1.13.12.7 2-[5-(5-bromofuran-2-yl)-1,2,4-oxadiazol-3-yl]pyridine
-
 Photinus pyralis
1.13.12.7 3-(2-hydroxyphenyl)-1H-benzo[f]chromen-1-one common name flavonoid Photinus pyralis
1.13.12.7 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)-2-(4-ethoxyphenyl)quinoline
-
 Photinus pyralis
1.13.12.7 4-amino-6-[(E)-[4'-[(Z)-(8-amino-1-hydroxy-5,7-disulfonato-6,7-dihydronaphthalen-2-yl)diazenyl]-3-methylbiphenyl-4-yl]diazenyl]-5-hydroxy-2,3-dihydronaphthalene-1,3-disulfonate common name Evans Blue Photinus pyralis
1.13.12.7 4-methoxy-N-[(4-methylpyridin-2-yl)carbamoyl]benzamide
-
 Photinus pyralis
1.13.12.7 4-[1-(1,3-benzothiazol-2-yl)-2-(4-methylpiperazin-1-yl)-2-oxoethyl]phenol
-
 Photinus pyralis
1.13.12.7 5-(2,4-dimethoxyphenyl)-3-phenyl-1,2,4-oxadiazole
-
 Photinus pyralis
1.13.12.7 5-(2-bromophenyl)-3-(4-methylphenyl)-1,2,4-oxadiazole
-
 Photinus pyralis
1.13.12.7 5-(2-chloro-4-methylphenyl)-3-phenyl-1,2,4-oxadiazole
-
 Photinus pyralis
1.13.12.7 5-methyl-N-[6-(methylsulfonyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide
-
 Photinus pyralis
1.13.12.7 5-naphthalen-2-yl-3-phenyl-1,2,4-oxadiazole
-
 Photinus pyralis
1.13.12.7 6-methyl-2-[(Z)-phenyldiazenyl]pyridin-3-ol common name SIB1757 Photinus pyralis
1.13.12.7 ethyl 4-[[2-(4-ethoxyphenyl)quinolin-4-yl]carbonyl]piperazine-1-carboxylate
-
 Photinus pyralis
1.13.12.7 N'-(3-chlorophenyl)-N-[(1Z)-(3-chlorophenyl)methylidene]imidoformamide common name DCB Photinus pyralis
1.13.12.7 N-(4-ethoxyphenyl)-2-methoxybenzamide
-
 Photinus pyralis
1.13.12.7 N-(6-ethoxy-1,3-benzothiazol-2-yl)-2-methylfuran-3-carboxamide
-
 Photinus pyralis
1.13.12.7 N-(6-methoxy-1,3-benzothiazol-2-yl)-2-methylfuran-3-carboxamide
-
 Photinus pyralis
1.13.12.7 N-(6-methyl-1,3-benzothiazol-2-yl)thiophene-2-carboxamide
-
 Photinus pyralis
1.13.12.7 N-[5-[(2,2-dimethylpropanoyl)amino]pyridin-2-yl]-3-hydroxybenzamide
-
 Photinus pyralis
1.13.12.7 N-[6-(methylsulfonyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide
-
 Photinus pyralis

Organism

EC Number Organism UniProt Comment Textmining
1.13.12.5 Renilla reniformis
-
-
-
1.13.12.7 Photinus pyralis Q27758
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.13.12.5 D-luciferin + O2 + ATP
-
 Renilla reniformis oxidized D-luciferin + CO2 + H2O + AMP + diphosphate + hv
-
 ?
1.13.12.7 D-luciferin + O2 + ATP
-
 Photinus pyralis oxidized D-luciferin + CO2 + H2O + AMP + diphosphate + hv
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.13.12.5 firefly luciferase
-
 Renilla reniformis
1.13.12.5 Luc
-
 Renilla reniformis
1.13.12.7 firefly luciferase
-
 Photinus pyralis
1.13.12.7 Luc
-
 Photinus pyralis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.13.12.5 0.01
-
-
 Renilla reniformis 4-amino-6-[(E)-[4'-[(Z)-(8-amino-1-hydroxy-5,7-disulfonato-6,7-dihydronaphthalen-2-yl)diazenyl]-3-methylbiphenyl-4-yl]diazenyl]-5-hydroxy-2,3-dihydronaphthalene-1,3-disulfonate
1.13.12.5 0.011
-
-
 Renilla reniformis (2Z)-3-[[4-(dimethylamino)cyclohexa-1,5-dien-1-yl]amino]-1-phenylprop-2-en-1-one
1.13.12.5 0.011
-
-
 Renilla reniformis 2-(4-ethoxyphenyl)-4-[(4-pyridin-2-ylpiperazin-1-yl)carbonyl]quinoline
1.13.12.5 0.011
-
-
 Renilla reniformis 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)-2-(4-ethoxyphenyl)quinoline
1.13.12.5 0.011
-
 pH 7.2, 22°C Renilla reniformis (2Z)-3-[[4-(dimethylamino)cyclohexa-1,5-dien-1-yl]amino]-1-phenylprop-2-en-1-one
1.13.12.5 0.011
-
 pH 7.2, 22°C Renilla reniformis 2-(4-ethoxyphenyl)-4-[(4-pyridin-2-ylpiperazin-1-yl)carbonyl]quinoline
1.13.12.5 0.011
-
 pH 7.2, 22°C Renilla reniformis 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)-2-(4-ethoxyphenyl)quinoline
1.13.12.5 0.019
-
-
 Renilla reniformis (3Z)-3-[[4-(dimethylamino)phenyl]methylidene]-1,3-dihydro-2H-indol-2-one
1.13.12.5 0.019
-
 pH 7.2, 22°C Renilla reniformis (3Z)-3-[[4-(dimethylamino)phenyl]methylidene]-1,3-dihydro-2H-indol-2-one
1.13.12.5 0.02
-
-
 Renilla reniformis 2-hydroxy-N'-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide
1.13.12.5 0.02
-
-
 Renilla reniformis ethyl 4-[[2-(4-ethoxyphenyl)quinolin-4-yl]carbonyl]piperazine-1-carboxylate
1.13.12.5 0.02
-
 pH 7.2, 22°C Renilla reniformis 2-hydroxy-N'-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide
1.13.12.5 0.02
-
 pH 7.2, 22°C Renilla reniformis ethyl 4-[[2-(4-ethoxyphenyl)quinolin-4-yl]carbonyl]piperazine-1-carboxylate
1.13.12.5 0.0225
-
-
 Renilla reniformis 4-[1-(1,3-benzothiazol-2-yl)-2-(4-methylpiperazin-1-yl)-2-oxoethyl]phenol
1.13.12.5 0.0225
-
 pH 7.2, 22°C Renilla reniformis 4-[1-(1,3-benzothiazol-2-yl)-2-(4-methylpiperazin-1-yl)-2-oxoethyl]phenol
1.13.12.5 0.025
-
-
 Renilla reniformis 2-(5-naphthalen-2-yl-1,2,4-oxadiazol-3-yl)pyridine
1.13.12.5 0.025
-
 IC50 above 0.025 mM Renilla reniformis 2-(4-ethoxyphenyl)-4-[(4-methylpiperazin-1-yl)carbonyl]quinoline
1.13.12.5 0.025
-
 IC50 above 0.025 mM Renilla reniformis 2-(4-methylphenyl)-4-[(4-pyrimidin-2-ylpiperazin-1-yl)carbonyl]quinoline
1.13.12.5 0.025
-
 pH 7.2, 22°C Renilla reniformis 2-(5-naphthalen-2-yl-1,2,4-oxadiazol-3-yl)pyridine
1.13.12.5 0.036
-
-
 Renilla reniformis 6-methyl-2-[(Z)-phenyldiazenyl]pyridin-3-ol
1.13.12.5 0.05
-
 IC50 above 0.05 mM Renilla reniformis (2Z)-3-[(2-bromophenyl)amino]-1-pyridin-2-ylprop-2-en-1-one
1.13.12.5 0.05
-
 IC50 above 0.05 mM Renilla reniformis 2-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]pyridine
1.13.12.5 0.05
-
 IC50 above 0.05 mM Renilla reniformis N'-(3-chlorophenyl)-N-[(1Z)-(3-chlorophenyl)methylidene]imidoformamide
1.13.12.7 0.00005
-
-
 Photinus pyralis 3-(2-hydroxyphenyl)-1H-benzo[f]chromen-1-one
1.13.12.7 0.00008
-
-
 Photinus pyralis (2Z)-3-[(2-bromophenyl)amino]-1-pyridin-2-ylprop-2-en-1-one
1.13.12.7 0.00008
-
-
 Photinus pyralis 2,4-dimethoxy-N-(5-methylpyridin-2-yl)benzamide
1.13.12.7 0.0001
-
-
 Photinus pyralis 2-(5-biphenyl-4-yl-1,2,4-oxadiazol-3-yl)pyridine
1.13.12.7 0.0001
-
-
 Photinus pyralis 2-(5-naphthalen-2-yl-1,2,4-oxadiazol-3-yl)pyridine
1.13.12.7 0.00015
-
-
 Photinus pyralis 5-(2,4-dimethoxyphenyl)-3-phenyl-1,2,4-oxadiazole
1.13.12.7 0.00015
-
-
 Photinus pyralis 5-(2-chloro-4-methylphenyl)-3-phenyl-1,2,4-oxadiazole
1.13.12.7 0.0002
-
-
 Photinus pyralis (2R)-2-[4-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]propanoic acid
1.13.12.7 0.00021
-
-
 Photinus pyralis (2Z)-3-[[4-(dimethylamino)cyclohexa-1,5-dien-1-yl]amino]-1-phenylprop-2-en-1-one
1.13.12.7 0.00022
-
-
 Photinus pyralis 2-[5-(3-chloro-4-methylphenyl)-1,2,4-oxadiazol-3-yl]pyridine
1.13.12.7 0.0003
-
-
 Photinus pyralis 4-[1-(1,3-benzothiazol-2-yl)-2-(4-methylpiperazin-1-yl)-2-oxoethyl]phenol
1.13.12.7 0.00032
-
-
 Photinus pyralis 2-(2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3(2H)-yl)-1-(4-methylphenyl)ethanone
1.13.12.7 0.00041
-
-
 Photinus pyralis 2-(4-ethoxyphenyl)-4-[(4-pyridin-2-ylpiperazin-1-yl)carbonyl]quinoline
1.13.12.7 0.00041
-
-
 Photinus pyralis 4-methoxy-N-[(4-methylpyridin-2-yl)carbamoyl]benzamide
1.13.12.7 0.00041
-
-
 Photinus pyralis 5-naphthalen-2-yl-3-phenyl-1,2,4-oxadiazole
1.13.12.7 0.0005
-
-
 Photinus pyralis 2-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]pyridine
1.13.12.7 0.0005
-
-
 Photinus pyralis N-(6-methyl-1,3-benzothiazol-2-yl)thiophene-2-carboxamide
1.13.12.7 0.0006
-
-
 Photinus pyralis 1-[3-(6-ethoxy-1,3-benzothiazol-2-yl)thiophen-2-yl]urea
1.13.12.7 0.0006
-
-
 Photinus pyralis N-(4-ethoxyphenyl)-2-methoxybenzamide
1.13.12.7 0.00065
-
-
 Photinus pyralis N-(6-ethoxy-1,3-benzothiazol-2-yl)-2-methylfuran-3-carboxamide
1.13.12.7 0.0007
-
-
 Photinus pyralis 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)-2-(4-ethoxyphenyl)quinoline
1.13.12.7 0.0007
-
-
 Photinus pyralis N-[5-[(2,2-dimethylpropanoyl)amino]pyridin-2-yl]-3-hydroxybenzamide
1.13.12.7 0.0008
-
-
 Photinus pyralis (3Z)-3-[[4-(dimethylamino)phenyl]methylidene]-1,3-dihydro-2H-indol-2-one
1.13.12.7 0.0008
-
-
 Photinus pyralis 2-hydroxy-N'-[(1E)-(2-hydroxyphenyl)methylidene]benzohydrazide
1.13.12.7 0.00084
-
-
 Photinus pyralis 2-[5-(3,4-dichlorophenyl)-1,2,4-oxadiazol-3-yl]pyridine
1.13.12.7 0.0009
-
-
 Photinus pyralis ethyl 4-[[2-(4-ethoxyphenyl)quinolin-4-yl]carbonyl]piperazine-1-carboxylate
1.13.12.7 0.001
-
-
 Photinus pyralis (2Z)-3-[(4-fluorophenyl)amino]-1-furan-2-ylprop-2-en-1-one
1.13.12.7 0.001
-
-
 Photinus pyralis 5-(2-bromophenyl)-3-(4-methylphenyl)-1,2,4-oxadiazole
1.13.12.7 0.0011
-
-
 Photinus pyralis 5-methyl-N-[6-(methylsulfonyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide
1.13.12.7 0.0011
-
-
 Photinus pyralis N-[6-(methylsulfonyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide
1.13.12.7 0.0012
-
-
 Photinus pyralis N-(6-methoxy-1,3-benzothiazol-2-yl)-2-methylfuran-3-carboxamide
1.13.12.7 0.0013
-
-
 Photinus pyralis 2-(4-ethoxyphenyl)-4-[(4-methylpiperazin-1-yl)carbonyl]quinoline
1.13.12.7 0.0017
-
-
 Photinus pyralis 4-amino-6-[(E)-[4'-[(Z)-(8-amino-1-hydroxy-5,7-disulfonato-6,7-dihydronaphthalen-2-yl)diazenyl]-3-methylbiphenyl-4-yl]diazenyl]-5-hydroxy-2,3-dihydronaphthalene-1,3-disulfonate
1.13.12.7 0.002
-
-
 Photinus pyralis (2Z)-1-(4-chlorophenyl)-3-(pyridin-2-ylamino)prop-2-en-1-one
1.13.12.7 0.0032
-
-
 Photinus pyralis 2-[5-(5-bromofuran-2-yl)-1,2,4-oxadiazol-3-yl]pyridine
1.13.12.7 0.004
-
-
 Photinus pyralis 2-(4-methylphenyl)-4-[(4-pyrimidin-2-ylpiperazin-1-yl)carbonyl]quinoline
1.13.12.7 0.0043
-
-
 Photinus pyralis 2-methyl-6-[(Z)-2-phenylethenyl]pyridine
1.13.12.7 0.0045
-
-
 Photinus pyralis 6-methyl-2-[(Z)-phenyldiazenyl]pyridin-3-ol
1.13.12.7 0.0045
-
-
 Photinus pyralis N'-(3-chlorophenyl)-N-[(1Z)-(3-chlorophenyl)methylidene]imidoformamide
1.13.12.7 0.0047
-
-
 Photinus pyralis 2-methyl-6-(phenylethynyl)pyridine
1.13.12.7 0.0062
-
-
 Photinus pyralis 2-(2-amino-3-methoxyphenyl)-4H-chromen-4-one