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(13Z)-docos-13-enoic acid
(25S)-(+)-12alpha-hydroxy-3alpha-methylcarboxyacetate-24-methyllanosta-8,24(31)-diene-26-oic acid
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from Piptoporus betulinus inhibiting bacterial hyaluronate lyase, structure determination by NMR, IC50 is 0.0035 mM
(2E)-1-furan-2-yl-3-(4-nitrophenyl)prop-2-en-1-one
IC50 at enzyme optimum pH 5.0 is 0.31 mM, and 0.16 mM at physiological pH 7.4
(3-chlorophenyl)(2-thioxo-1H-benzo[d]imidazol-1-yl)methanone
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(E)-3-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)prop-2-en-1-one
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36% inhibition
1,10-phenanthroline
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5 mM, 75% residual activity
1,3-benzoxazole-2(3H)-thione
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1,3-diacetyl-1H-benzo[d]imidazol-2(3H)-one
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10% inhibition
1,3-diacetyl-benzimidazole-2-thione
IC50 at enzyme optimum pH 5.0 is 0.16 mM, and 0.005 mM at physiological pH 7.4
1,3-diacetylbenzimidazole-2-thione
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1,3-dihydro-2H-benzimidazole-2-thione
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1-(2-thioxo-1H-benzo[d]imidazol-1-yl)-3-phenylpropan-1-one
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1-(2-thioxo-1H-benzo[d]imidazol-1-yl)butan-1-one
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1-(2-thioxo-1H-benzo[d]imidazol-1-yl)ethanone
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1-(2-thioxo-1H-benzo[d]imidazol-1-yl)hexan-1-one
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1-(2-thioxo-1H-benzo[d]imidazol-1-yl)propan-1one
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1-(2-thioxobenzo[d]oxazol-3(2H)-yl)decan-1-one
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1-(2-thioxobenzo[d]oxazol-3(2H)-yl)ethanone
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1-(2-thioxobenzo[d]oxazol-3(2H)-yl)hexadecan-1-one
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1-(2-thioxobenzo[d]oxazol-3(2H)-yl)hexan-1-one
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1-(2-thioxobenzo[d]oxazol-3(2H)-yl)propan-1-one
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1-(3-acetyl-1,2-dihydro-2-thioxobenzo[d]imidazol-1-yl)hexan-1-one
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1-(3-ethyl-1,2-dihydro-2-thioxobenzo[d]imidazole-1-yl)ethanone
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1-decyl-2-(4-sulfamoyloxyphenyl)-1-indol-6-yl sulfamate
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1-decyl-2-(4-sulfamoyloxyphenyl)-1H-indol-6-yl sulfamate
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inhibitor fits in the enzymatic active site via interactions resembling the binding mode of the natural hyaluronan substrate
1-ethyl-1H-benzo[d]imidazole-2(3H)-thione
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28% inhibition
2,2'-benzene-1,4-diyldiacetic acid
IC50 at enzyme optimum pH 5.0 is 0.37 mM, and 0.90 mM at physiological pH 7.4
2,3-Butanedione
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inactivation, arginine-specific reagent
2-Hydroxy-5-nitrobenzylbromide
2.5 mM, 87.4% inhibition
2-phenoxy-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)ethanone
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2-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)ethanone
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3-acetylbenzo[d]oxazol-2(3H)-one
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3-cyclohexyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)propan-1-one
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3-ethylbenzo[d]oxazole-2(3H)-thione
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17% inhibition
3-hexanoylbenzo[d]oxazol-2(3H)-one
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3-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)propan-1-one
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3alpha-acetylpolyporenic acid A
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from Piptoporus betulinus inhibiting bacterial hyaluronate lyase, structure determination by NMR, IC50 is 0.040 mM
4-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)butan-1-one
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benzyl 2-thioxobenzo[d]oxazol-3(2H)-carboxylate
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beta1,4-galacto-oligosaccharides
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partially sulfated and non-sulfated forms, IC50 values
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Co2+
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complete inhibition
D-isoascorbic acid
Streptomyces hyalurolyticus
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strong inhibition
D-saccharic-1,4-lactone
Streptomyces hyalurolyticus
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strong inhibition
dehydroascorbic acid
Streptomyces hyalurolyticus
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dithiothreitol
5 mM, 30% inhibition
guanidine hydrochloride
strong inhibition, unfolding within 1 h
guanidine isothiocyanate
strong inhibition
hyaluronate
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substrate inhibition above 7.5 mg/ml
L-arginine
strong inhibition
L-arginine methyl ester
strong inhibition
L-ascorbate
noncompetitive inhibition, inhibition kinetics, overview. Residues involved in the binding of L-ascorbate are confined to HylP135-308
L-ascorbic acid-6-hexadecanoate
lanostanoid
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from Piptoporus betulinus inhibiting bacterial hyaluronate lyase, structure determination by NMR, IC50 is 0.051 mM
Li+
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50 mM, 68% residual activity
methyl (9Z)-octadecenoate
methyl 2-sulfanylbenzo[d]oxazole-5-carboxylate
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27% inhibition
methyl-3-(3-phenylpropanoyl)-2,3-dihydro-2-thioxobenzo[d]oxazole-5-carboxylate
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N-(3-phenylpropionyl)-benzoxazole-2-thione
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N-(3-phenylpropionyl)benzoxazole-2-thione
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N-bromosuccinimide
5 mM, slight inhibition
N-ethylmaleimide
5 mM, slight inhibition
NaCl
slight inhibition, wild-type and mutant enzymes
Ni2+
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complete inhibition
p-chloromercuribenzoate
5 mM, 30% inhibition
partially sulfated neomycin
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the non-sulfated neomycin is not inhibitory
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partially sulfated planteose
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the non-sulfated planteose is not inhibitory, IC50 is 0.015 mM
partially sulfated verbascose
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2 forms, the non-sulfated verbascose is not inhibitory, IC50 are 0.030 mM and 0.001 mM
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polyporenic acid
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from Piptoporus betulinus inhibiting bacterial hyaluronate lyase, structure determination by NMR, IC50 is 0.0125 mM
saccharic acid
Streptomyces hyalurolyticus
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sulfated 2-hydroxyphenyl monolactobioside
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IC50 is 0.35 mM
sulfated hydroquinone galactoside
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IC50 is 0.080 mM
Tetranitromethane
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inactivation, tyrosine-specific reagent
Triton X-100
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weak inhibition
(13Z)-docos-13-enoic acid
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strong inhibition
(13Z)-docos-13-enoic acid
Streptomyces hyalurolytics
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weak inhibition
arachidic acid
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weak inhibition
arachidic acid
Streptomyces hyalurolytics
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weak inhibition
behenic acid
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weak inhibition
behenic acid
Streptomyces hyalurolytics
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weak inhibition
Ca2+
slight inhibition by 30% unfolding of the enzyme by ion binding
Ca2+
interacts with the collagenous Gly-X-Y motif of the enzyme, activates up to 20 mM, but inhibits at higher concentrations, inactivation above 50 mM
capric acid
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weak inhibition
capric acid
Streptomyces hyalurolytics
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weak inhibition
Cu2+
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50 mM, no residual activity
Cu2+
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complete inhibition
EDTA
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5 mM, 84% residual activity
eicosadienoic acid
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strong inhibition
eicosadienoic acid
Streptomyces hyalurolytics
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weak inhibition
eicosanoic acid
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strong inhibition
eicosanoic acid
Streptomyces hyalurolytics
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weak inhibition
eicosapentaenoic acid
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strong inhibition
eicosapentaenoic acid
Streptomyces hyalurolytics
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weak inhibition
eicosatetraenoic acid
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strong inhibition
eicosatetraenoic acid
Streptomyces hyalurolytics
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weak inhibition
eicosatrienoic acid
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strong inhibition
eicosatrienoic acid
Streptomyces hyalurolytics
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weak inhibition
elaidic acid
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elaidic acid
Streptomyces hyalurolytics
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weak inhibition
iodoacetate
5 mM, slight inhibition
iodoacetate
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10 mM, complete inhibition
L-ascorbic acid
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L-ascorbic acid
i.e. vitamin C, reversible, competitive, one molecule binds to the active site of all 3 catalytic positions, interacts with enzyme residues R243, N290, W292, Y408, R462, R466, and N580, inhibits the invasion and spreading of the bacterium in tissues in vivo
L-ascorbic acid
Streptomyces hyalurolyticus
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strong inhibition
L-ascorbic acid-6-hexadecanoate
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L-ascorbic acid-6-hexadecanoate
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lauric acid
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weak inhibition
lauric acid
Streptomyces hyalurolytics
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weak inhibition
linoleic acid
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linoleic acid
Streptomyces hyalurolytics
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weak inhibition
linolenic acid
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linolenic acid
Streptomyces hyalurolytics
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weak inhibition
methyl (9Z)-octadecenoate
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methyl (9Z)-octadecenoate
Streptomyces hyalurolytics
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weak inhibition
Mg2+
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50 mM, 68% residual activity
Mg2+
slight inhibition by 30% unfolding of the enzyme by ion binding
myristic acid
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weak inhibition
myristic acid
Streptomyces hyalurolytics
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weak inhibition
myristoleic acid
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myristoleic acid
Streptomyces hyalurolytics
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weak inhibition
nervonic acid
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strong inhibition
nervonic acid
Streptomyces hyalurolytics
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weak inhibition
oleic acid
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oleic acid
Streptomyces hyalurolytics
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weak inhibition
palmitic acid
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weak inhibition
palmitic acid
Streptomyces hyalurolytics
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weak inhibition
palmitoleic acid
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palmitoleic acid
Streptomyces hyalurolytics
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weak inhibition
petroselinic acid
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strong inhibition
petroselinic acid
Streptomyces hyalurolytics
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weak inhibition
ricinoleic acid
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ricinoleic acid
Streptomyces hyalurolytics
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weak inhibition
SDS
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5 mM, 4.6% residual activity
SDS
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complete inhibition
stearic acid
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weak inhibition
stearic acid
Streptomyces hyalurolytics
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weak inhibition
Tween 80
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5 mM, 84% residual activity
Tween 80
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weak inhibition
vaccenic acid
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strong inhibition
vaccenic acid
Streptomyces hyalurolytics
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weak inhibition
Zn2+
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additional information
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inhibition curves, overview
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additional information
structure-based design of bacterial hyaluronan lyase inhibitors, combinatorial chemistry database and crystal structure, method, overview
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additional information
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development of structure-based 1-acylated benzimidazole-2-thiones and benzoxazole-2-thiones inhibitors, using the crystal structure of Streptococcus pneumoniae Hyal, overview. Except for N-(3-phenylpropionyl)benzoxazole-2-thione, other N-acylated benzimidazoles and benzoxazoles are just as active at pH 7.4, but not at pH 5.0. The compounds show a binding mode characterized by interactions with residues in the catalytic site and with a hydrophobic patch, overview. No inhibition by 3-hexanoylbenzo[d]oxazol-2(3H)-one. Inhibition at pH 5.0, structure-activity relationships, overview
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additional information
not inhibited by ascorbic acid at concentration up to 20 mM
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additional information
no inhibition and conformational change induced by NaCl
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additional information
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no inhibition and conformational change induced by NaCl
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additional information
IC50 for 1,3-diacetylbenzimidazole-2-thione is above 0.1 mM
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additional information
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IC50 for 1,3-diacetylbenzimidazole-2-thione is above 0.1 mM
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additional information
Streptomyces hyalurolyticus
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poor inhibitors are alpha-D-glucoheptonic-gamma-lactone, L-gulonic-gamma-lactone, D-ribonic-gamma-lactone, and D-gluconic-gamma-lactone
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