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Literature summary for 1.14.14.137 extracted from

  • Todoroki, Y.; Kobayashi, K.; Shirakura, M.; Aoyama, H.; Takatori, K.; Nimitkeatkai, H.; Jin, M.H.; Hiramatsu, S.; Ueno, K.; Kondo, S.; Mizutani, M.; Hirai, N.
    Abscinazole-F1, a conformationally restricted analogue of the plant growth retardant uniconazole and an inhibitor of ABA 8-hydroxylase CYP707A with no growth-retardant effect (2009), Bioorg. Med. Chem., 17, 6620-6630.
    View publication on PubMed

Application

Application Comment Organism
agriculture introduction of drought tolerance in apple seedlings, the 3R-isomer of the abscisic acid 8'-hydroxylase inhibitor abscinazole-F1 (3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol) has no growth-retardant effect on apple seedlings but induces stomatal closure and drought tolerance during dehydration at concentrations of 10, 50, and 100 microM (spray treatment) Malus sylvestris

Cloned(Commentary)

Cloned (Comment) Organism
recombinant truncated Arabidopsis enzyme (707A3d28, lack of putative membrane spanning segment at N-terminus), expressed in Escherichia coli BL21 Arabidopsis thaliana
truncated CYP707A3 (707A3d28), which lacks the putative membrane-spanning segment of the N-terminus, residues 3-28, coexpressed in Escherichia coli BL21 with Arabidopsis P450 reductase Arabidopsis thaliana

Inhibitors

Inhibitors Comment Organism Structure
(1E,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol 27% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
(1E,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol 27% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
(1E,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol 10% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
(1E,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol 10% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol 14% inhibition of recombinant enzyme with 10 microM inhibitor; inhibitory activity is much weaker than that of S-UNI Arabidopsis thaliana
(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol 14% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[2,1-c][1,4]oxazin-8(6H)-one 35% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[2,1-c][1,4]oxazin-8(6H)-one 35% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[5,1-c][1,4]oxazin-8(6H)-one 52% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[5,1-c][1,4]oxazin-8(6H)-one 52% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5Himidazo[2,1-c][1,4]oxazin-8(6H)-one
-
Arabidopsis thaliana
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5Himidazo[5,1-c][1,4]oxazin-8(6H)-one
-
Arabidopsis thaliana
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol abscinazole-F1, 91% inhibition of recombinant enzyme with 10 microM inhibitor; abscinazole-F1, more than 50% inhibition at 0.01 mM, competitive inhibitor, is the most specific inhibitor against ABA 8'-hydroxylase, although it is not the strongest Arabidopsis thaliana
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol abscinazole-F1, 91% inhibition of recombinant enzyme with 10 microM inhibitor Malus sylvestris
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol abscinazole-F1, 91% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine 13% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine 13% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine 100% inhibition of recombinant enzyme with 10 microM inhibitor; competitive inhibitor Arabidopsis thaliana
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine 100% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-8-ol 69% inhibition of recombinant enzyme with 10 microM inhibitor; more than 50% inhibition at 0.01 mM Arabidopsis thaliana
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-8-ol 69% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazine 31% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazine 31% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol abscinazole-F1, 95% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol abscinazole-F1, 95% inhibition of recombinant enzyme with 10 microM inhibitor Malus sylvestris
3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol abscinazole-F1, 95% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
3S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol abscinazole-F1, 96% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
3S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol abscinazole-F1, 96% inhibition of recombinant enzyme with 10 microM inhibitor Malus sylvestris
3S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol abscinazole-F1, 96% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
R-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol R-(+)-uniconazole, 79% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
R-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol R-(+)-uniconazole, 79% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine 87% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine 87% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol S-(+)-uniconazole, 100% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol S-(+)-uniconazole, 100% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Malus sylvestris
S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol S-(+)-uniconazole, 100% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine 100% inhibition of recombinant enzyme with 10 microM inhibitor Arabidopsis thaliana
S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine 100% inhibition of recombinant Arabidopsis enzyme with 10 microM inhibitor Oryza sativa
uniconazole
-
Arabidopsis thaliana

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0034
-
(+)-abscisic acid 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C Arabidopsis thaliana

Localization

Localization Comment Organism GeneOntology No. Textmining
microsome
-
Arabidopsis thaliana
-
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2 Arabidopsis thaliana
-
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2 Oryza sativa
-
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2 Malus sylvestris
-
8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
?

Organism

Organism UniProt Comment Textmining
Arabidopsis thaliana
-
-
-
Arabidopsis thaliana
-
enzyme from recombinant Escherichia coli
-
Malus sylvestris
-
apple variant domestica, 90 days old seedlings
-
Oryza sativa
-
rice cultivar Nipponbare, length of second leaf sheath of 7 days old seedlings grown in test solution
-

Purification (Commentary)

Purification (Comment) Organism
recombinant enzyme production is induced, cells centrifuged, pellets resuspended in buffer A (50 mM potassium phosphate buffer, pH 7.25, 20% glycerol, 1 mM EDTA, 0.1 mM dithiothreitol), sonicated, centrifuged, supernatants collected Arabidopsis thaliana

Source Tissue

Source Tissue Comment Organism Textmining

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(+)-S-abscisate + [reduced NADPH-hemoprotein reductase] + O2
-
Arabidopsis thaliana 8'-hydroxyabscisate + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
Arabidopsis thaliana 8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
Oryza sativa 8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
Malus sylvestris 8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
S-(+)-abscisic acid + [reduced NADPH-hemoprotein reductase] + O2
-
Arabidopsis thaliana 8'-hydroxyabscisic acid + [oxidized NADPH-hemoprotein reductase] + H2O for inhibitor studies the decrease in production of phaseic acid is measured ?

Synonyms

Synonyms Comment Organism
ABA 8'-hydroxylase
-
Arabidopsis thaliana
ABA 8'-hydroxylase
-
Oryza sativa
ABA 8'-hydroxylase
-
Malus sylvestris
abscisic acid 8'-hydroxylase
-
Arabidopsis thaliana
abscisic acid 8'-hydroxylase
-
Oryza sativa
abscisic acid 8'-hydroxylase
-
Malus sylvestris
CYP707A
-
Arabidopsis thaliana
CYP707A3
-
Arabidopsis thaliana

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00001
-
S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C, recombinant enzyme Arabidopsis thaliana
0.00016
-
S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C, recombinant enzyme Arabidopsis thaliana
0.00042
-
3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C, recombinant enzyme Arabidopsis thaliana
0.00042
-
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol 3R-enantiomer, pH 7.25, 30°C Arabidopsis thaliana
0.00052
-
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[5,1-c][1,4]oxazin-8(6H)-one 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C, recombinant enzyme Arabidopsis thaliana
0.00097
-
3S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C, recombinant enzyme Arabidopsis thaliana
0.00097
-
(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol 3S-enantiomer, pH 7.25, 30°C Arabidopsis thaliana
0.00145
-
R-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol 10 microM inhibitor in 50 mM potassium phosphate buffer, pH 7.25, 50 microM NADPH, 30°C Arabidopsis thaliana

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
additional information
-
3R-isomer abscinazole-F1 (3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol) has no growth-retardant effect on apple seedlings but induces stomatal closure and drought tolerance during dehydration at concentrations of 10, 50, and 100 microM (spray treatment) in contrast to uniconazole (S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol) which has growth-retardant effects Malus sylvestris additional information
additional information
-
no inhibition of rice seedling growth (second leaf sheath length) with (E)-6-tert-butyl-5-(4-chlorobenzylidene)-5Himidazo[2,1-c][1,4]oxazin-8(6H)-one, (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol, 3S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol, 3R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-ol Oryza sativa additional information
0.00018
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa S-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol
0.0013
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa (1E,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.0023
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa (E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.0032
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-8-ol
0.0078
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa R-(+)-E-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazo-1-yl)-1-penten-3-ol
0.0082
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa S-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine
0.009
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine
0.012
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa R-(E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[5,1-c][1,4]oxazine
0.028
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine
0.046
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa (1E,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.058
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazine
0.078
-
rice seedling, growth of second leaf sheath after 7 days in inhibitor medium Oryza sativa (E)-6-tert-butyl-5-(4-chlorobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazine

General Information

General Information Comment Organism
metabolism key enzyme in the catabolism of abscisic acid (plant hormone involved in stress tolerance, seed dormancy, and other physiological events) Arabidopsis thaliana
metabolism key enzyme in the catabolism of abscisic acid (plant hormone involved in stress tolerance, seed dormancy, and other physiological events) Oryza sativa
metabolism key enzyme in the catabolism of abscisic acid (plant hormone involved in stress tolerance, seed dormancy, and other physiological events) Malus sylvestris