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Literature summary for 1.13.11.33 extracted from

  • Deschamps, J.D.; Ogunsola, A.F.; Jameson, J.B.; Yasgar, A.; Flitter, B.A.; Freedman, C.J.; Melvin, J.A.; Nguyen, J.V.; Maloney, D.J.; Jadhav, A.; Simeonov, A.; Bomberger, J.M.; Holman, T.R.
    Biochemical and cellular characterization and inhibitor discovery of Pseudomonas aeruginosa 15-lipoxygenase (2016), Biochemistry, 55, 3329-3340 .
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
gene loxA, recombinant expression of N-terminally His6-tagged enzyme LoxA in Escherichia coli strain BL21(DE3) Pseudomonas aeruginosa

Inhibitors

Inhibitors Comment Organism Structure
1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one
-
Pseudomonas aeruginosa
1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one
-
Pseudomonas aeruginosa
1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
-
Pseudomonas aeruginosa
1-[4-[4-([[5-(3-chlorophenyl)furan-2-yl]methyl]amino)phenyl]piperazin-1-yl]ethan-1-one
-
Pseudomonas aeruginosa
1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
-
Pseudomonas aeruginosa
2-(4-chlorophenyl)-5-cyclohexyl-1,3,4-oxadiazole
-
Pseudomonas aeruginosa
2-[4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy]-N,N-dimethylethan-1-amine
-
Pseudomonas aeruginosa
4,4'-(2,3-dimethylbutane-1,4-diyl)di(benzene-1,2-diol)
-
Pseudomonas aeruginosa
4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
-
Pseudomonas aeruginosa
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl benzoate
-
Pseudomonas aeruginosa
6-[4-([1,1'-biphenyl]-2-yl)piperazin-1-yl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)hexanamide
-
Pseudomonas aeruginosa
7-cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
-
Pseudomonas aeruginosa
8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
-
Pseudomonas aeruginosa
methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
-
Pseudomonas aeruginosa
additional information inhibitor library screening, none selectively targets LoxA over the human LOX isozymes, overview Pseudomonas aeruginosa
N-[(5-bromo-8-hydroxy-5,6,7,8-tetrahydroquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
Pseudomonas aeruginosa

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information Michaelis-Menten steady-state kinetics Pseudomonas aeruginosa
0.007
-
linoleic acid pH 6.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
0.012
-
arachidonate pH 6.5-7.0, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
0.013
-
arachidonate pH 7.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa

Localization

Localization Comment Organism GeneOntology No. Textmining
extracellular the enzyme is secreted Pseudomonas aeruginosa
-
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
arachidonate + O2 Pseudomonas aeruginosa
-
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
-
?

Organism

Organism UniProt Comment Textmining
Pseudomonas aeruginosa Q9I4G8
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant N-terminally His6-tagged enzyme LoxA from Escherichia coli strain BL21(DE3) by nickel affinity chromatography Pseudomonas aeruginosa

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
alpha-linoleic acid + O2 72% activity compared to arachidonate Pseudomonas aeruginosa ?
-
?
arachidonate + O2
-
Pseudomonas aeruginosa (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
-
?
arachidonate + O2 best substrate Pseudomonas aeruginosa (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
-
?
dihomo-gamma-linolenic acid + O2 44% activity compared to arachidonate Pseudomonas aeruginosa ?
-
?
docosahexaenoic acid + O2 72% activity compared to arachidonate Pseudomonas aeruginosa ?
-
?
eicosadienoic acid + O2 33% activity compared to arachidonate Pseudomonas aeruginosa ?
-
?
eicosapentanoic acid + O2 61% activity compared to arachidonate Pseudomonas aeruginosa ?
-
?
gamma-linolenic acid + O2 44% activity compared to arachidonate Pseudomonas aeruginosa ?
-
?
linoleic acid + O2 78% activity compared to arachidonate Pseudomonas aeruginosa (9Z,11E)-(13S)-13-hydroperoxy-octadeca-9,11-dienoate
-
?
additional information enzyme LoxA is capable of efficiently catalyzing the peroxidation of a broad range of free fatty acid substrates, e.g. arachidonate and linoleate with high positional specificity, indicating a 15-LOX, its mechanism includes hydrogen atom abstraction. LoxA also does not react with 5- or 15-15-hydroperoxyicosatetraenoates, or phosphoester fatty acids Pseudomonas aeruginosa ?
-
?

Synonyms

Synonyms Comment Organism
15-lipoxygenase
-
Pseudomonas aeruginosa
LoxA
-
Pseudomonas aeruginosa

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
22
-
assay at Pseudomonas aeruginosa

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2 8 linoleic acid pH 6.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
86
-
arachidonate pH 7.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
157
-
arachidonate pH 7.0, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
181
-
arachidonate pH 6.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.5
-
assay at Pseudomonas aeruginosa

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0041
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
0.0045
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
0.0058
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one
0.0067
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 2-[4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy]-N,N-dimethylethan-1-amine
0.008
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
0.0101
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one
0.011
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 4,4'-(2,3-dimethylbutane-1,4-diyl)di(benzene-1,2-diol)
0.0114
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 6-[4-([1,1'-biphenyl]-2-yl)piperazin-1-yl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)hexanamide
0.0131
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
0.0138
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
0.0162
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 7-cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
0.02
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl benzoate
0.046
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 1-[4-[4-([[5-(3-chlorophenyl)furan-2-yl]methyl]amino)phenyl]piperazin-1-yl]ethan-1-one
0.078
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 2-(4-chlorophenyl)-5-cyclohexyl-1,3,4-oxadiazole
0.1
-
pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa N-[(5-bromo-8-hydroxy-5,6,7,8-tetrahydroquinolin-7-yl)(thiophen-2-yl)methyl]acetamide

Expression

Organism Comment Expression
Pseudomonas aeruginosa the level of LoxA expression is increased when Pseudomonas aeruginosa undergoes the transition to a biofilm mode of growth up

General Information

General Information Comment Organism
physiological function enzyme LoxA is a poor catalyst against phosphoester fatty acids, suggesting that LoxA is not involved in membrane decomposition. LoxA also does not react with 5- or 15-HETEs, indicating poor involvement in lipoxin production. The level of LoxA expression is increased when Pseudomonas aeruginosa undergoes the transition to a biofilm mode of growth, but LoxA is not required for biofilm growth on abiotic surfaces. LoxA does appear to be required for biofilm growth in association with the host airway epithelium, suggesting a role for LoxA in mediating bacterium-host interactions during colonization Pseudomonas aeruginosa

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.0038
-
linoleic acid pH 6.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
0.0066
-
arachidonate pH 7.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
0.013
-
arachidonate pH 7.0, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
0.016
-
arachidonate pH 6.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa