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Literature summary for 1.14.14.18 extracted from

  • Roman, G.; Rahman, M.; Vukomanovic, D.; Jia, Z.; Nakatsu, K.; Szarek, W.
    Heme oxygenase inhibition by 2-oxy-substituted 1-azolyl-4-phenylbutanes: effect of variation of the azole moiety. X-ray crystal structure of human heme oxygenase-1 in complex with 4-phenyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone (2010), Chem. Biol. Drug Des., 75, 68-90.
    View publication on PubMed

Crystallization (Commentary)

Crystallization (Comment) Organism
truncated, soluble hHO-1 variant, consisting of 233 amino acids, in complex with 4-phenyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, sitting-drop vapor diffusion, room temperature, 0.412 mM heme-HO-1 complex in 20 mM potassium phosphate is mixed with inhibitor in a 1:3 molar ratio, the reservoir solution contains100 mM HEPES, pH 7.5, 2.00-2.28 M ammonium sulfate, and 0.8-1.1% 1,6-hexanediol, X-ray diffraction structure determination and analysis Rattus norvegicus

Inhibitors

Inhibitors Comment Organism Structure
(R,S)-1-(1H-imidazol-1-yl)-4-phenyl-2-butanol
-
Rattus norvegicus
(R,S)-1-(4,5-diphenyl-1H-imidazol-1-yl)-4-phenyl-2-butanol
-
Rattus norvegicus
(R,S)-4-phenyl-1-(1H-1,2,3-triazol-1-yl)-2-butanol
-
Rattus norvegicus
(R,S)-4-phenyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol
-
Rattus norvegicus
(R,S)-4-phenyl-1-(1H-tetrazol-1-yl)-2-butanol
-
Rattus norvegicus
(R,S)-4-phenyl-1-(2H-tetrazol-2-yl)-2-butanol
-
Rattus norvegicus
(R,S)-4-phenyl-1-(4-phenyl-1H-imidazol-1-yl)-2-butanol
-
Rattus norvegicus
1-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-1H-1,2,3-triazole
-
Rattus norvegicus
1-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole
-
Rattus norvegicus
1-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-1H-tetrazole
-
Rattus norvegicus
1-((2-phenylethyl)-1,3-dioxolan-2-yl)methyl-1H-imidazole
-
Rattus norvegicus
1-((2-phenylethyl-1,3-dioxolan-2-yl)methyl)-4,5-diphenyl-1H-imidazole
-
Rattus norvegicus
1-((2-phenylethyl-1,3-dioxolan-2-yl)methyl)-4-phenyl-1H-imidazole
-
Rattus norvegicus
1-(1H-benzimidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(1H-benzotriazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(1H-imidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(2-methyl-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(2-methylsulfonyl-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(2-methylthio-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(2-nitro-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(2H-benzotriazol-2-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(3,5-dibromo-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(3,5-diphenyl-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(3-methylsulfonyl-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(3-methylthio-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(3-nitro-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(3-phenyl-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(4,5-dichloro-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(4,5-dicyano-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(4,5-diphenyl-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(4-bromo-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(4-nitro-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(5-bromo-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(5-methylsulfonyl-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(5-methylsulfonyl-1H-tetrazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(5-methylsulfonyl-2H-tetrazol-2-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(5-methylthio-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(5-methylthio-1H-tetrazol-1-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-(5-methylthio-2H-tetrazol-2-yl)-4-phenyl-2-butanone
-
Rattus norvegicus
1-bromo-4-phenyl-2-butanone
-
Rattus norvegicus
2-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-2H-1,2,3-triazole
-
Rattus norvegicus
2-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-2H-tetrazole
-
Rattus norvegicus
2-methylthio-1H-imidazole
-
Rattus norvegicus
3,5-dibromo-1H-1,2,4-triazole
-
Rattus norvegicus
3,5-diphenyl-1H-1,2,4-triazole
-
Rattus norvegicus
3-phenyl-1H-1,2,4-triazole
-
Rattus norvegicus
4-phenyl-1-(1H-1,2,3-triazol-1-yl)-2-butanone
-
Rattus norvegicus
4-phenyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone the inhibitor binds at the distal pocket through the coordination of heme iron by the N4 in the triazole mpiety, whereas the phenyl group is stabilized by hydrophobic interactions from residues within the binding pocket, binding structure, modelling, overview Rattus norvegicus
4-phenyl-1-(1H-pyrazol-1-yl)-2-butanone
-
Rattus norvegicus
4-phenyl-1-(1H-tetrazol-1-yl)-2-butanone
-
Rattus norvegicus
4-phenyl-1-(2-phenyl-1H-imidazol-1-yl)-2-butanone
-
Rattus norvegicus
4-phenyl-1-(2H-1,2,3-triazol-2-yl)-2-butanone
-
Rattus norvegicus
4-phenyl-1-(2H-tetrazol-2-yl)-2-butanone
-
Rattus norvegicus
4-phenyl-1-(4-phenyl-1H-imidazol-1-yl)-2-butanone
-
Rattus norvegicus
4-phenyl-1-(5-phenyl-1H-tetrazol-1-yl)-2-butanone
-
Rattus norvegicus
4-phenyl-1-(5-phenyl-2H-tetrazol-2-yl)-2-butanone
-
Rattus norvegicus
azalanstat
-
Rattus norvegicus
dimethyl 1-(2-oxo-4-phenylbut-1-yl)-1H-imidazole-4,5-dicarboxylate
-
Rattus norvegicus
ethyl (1-(2-oxo-4-phenylbutyl)-1H-tetrazol-5-yl)acetate
-
Rattus norvegicus
ethyl (2-(2-oxo-4-phenylbutyl)-2H-tetrazol-5-yl)acetate
-
Rattus norvegicus
ethyl 1-(2-oxo-4-phenylbut-1-yl)-1H-imidazole-2-carboxylate
-
Rattus norvegicus
methyl 1-(2-oxo-4-phenylbut-1-yl)-1H-1,2,4-triazole-3-carboxylate
-
Rattus norvegicus
methyl 1-(2-oxo-4-phenylbut-1-yl)-1H-1,2,4-triazole-5-carboxylate
-
Rattus norvegicus
methyl 1-(2-oxo-4-phenylbut-1-yl)-1H-imidazole-4-carboxylate
-
Rattus norvegicus
methyl 1-(2-oxo-4-phenylbut-1-yl)-1H-imidazole-5-carboxylate
-
Rattus norvegicus
additional information design and synthesis, and inhibitory potency of a series of 2-oxy-substituted 1-azolyl-4-phenylbutanes, inhibition of heme oxygenase-1 and heme oxygenase-2, overview Rattus norvegicus

Organism

Organism UniProt Comment Textmining
Rattus norvegicus
-
-
-
Rattus norvegicus Sprague-Dawley
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
brain
-
Rattus norvegicus
-
spleen
-
Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information heme oxygenase activity in rat spleen and brain microsomal fractions is determined by the quantitation of CO formed from the degradation of methemalbumin, i.e. heme complexed with albumin Rattus norvegicus ?
-
?
additional information heme oxygenase activity in rat spleen and brain microsomal fractions is determined by the quantitation of CO formed from the degradation of methemalbumin, i.e. heme complexed with albumin Rattus norvegicus Sprague-Dawley ?
-
?

Synonyms

Synonyms Comment Organism
heme oxygenase-1
-
Rattus norvegicus
heme oxygenase-2
-
Rattus norvegicus
HO-1
-
Rattus norvegicus
HO-2
-
Rattus norvegicus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Rattus norvegicus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
assay at Rattus norvegicus