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Literature summary for 1.14.14.137 extracted from

  • Takeuchi, J.; Okamoto, M.; Mega, R.; Kanno, Y.; Ohnishi, T.; Seo, M.; Todoroki, Y.
    Abscinazole-E3M, a practical inhibitor of abscisic acid 8'-hydroxylase for improving drought tolerance (2016), Sci. Rep., 6, 37060 .
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

Cloned (Comment) Organism
gene CYP707A3, recombinant expression in Escherichia coli Arabidopsis thaliana

Inhibitors

Inhibitors Comment Organism Structure
(1E,3R)-1-(3-[3-[2-(2-butoxyethoxy)ethoxy]prop-1-yn-1-yl]phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
Arabidopsis thaliana
(1E,3R)-1-(4-[3-[2-(2-butoxyethoxy)ethoxy]prop-1-yn-1-yl]phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
Arabidopsis thaliana
(1E,3R)-1-[4-(4-[[2-(2-butoxyethoxy)ethoxy]methyl]-1H-1,2,3-triazol-1-yl)phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (-)-Abz-E2B, selective inhibitor Arabidopsis thaliana
(1E,3R)-4,4-dimethyl-1-[3-[4-(2,5,8,11-tetraoxadodecan-1-yl)-1H-1,2,3-triazol-1-yl]phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol strong and selective inhibitor, effects of the inhibitor on stomatal closure and drought tolerance, overview Arabidopsis thaliana
(1E,3R)-4,4-dimethyl-1-[4-(2,5,8,11-tetraoxatetradec-13-yn-14-yl)phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
Arabidopsis thaliana
(1E,3S)-1-(3-[3-[2-(2-butoxyethoxy)ethoxy]prop-1-yn-1-yl]phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
Arabidopsis thaliana
(1E,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol i.e. S-uniconazole Arabidopsis thaliana
(1E,3S)-1-(4-[3-[2-(2-butoxyethoxy)ethoxy]prop-1-yn-1-yl]phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
Arabidopsis thaliana
(1E,3S)-1-[4-(4-[[2-(2-butoxyethoxy)ethoxy]methyl]-1H-1,2,3-triazol-1-yl)phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (+)-Abz-E2B Arabidopsis thaliana
(1E,3S)-4,4-dimethyl-1-[3-(2,5,8,11-tetraoxatetradec-13-yn-14-yl)phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
Arabidopsis thaliana
(1E,3S)-4,4-dimethyl-1-[4-(2,5,8,11-tetraoxatetradec-13-yn-14-yl)phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
-
Arabidopsis thaliana
additional information development of a selective inhibitor of CYP707A, (1E,3R)-1-[4-(4-[[2-(2-butoxyethoxy)ethoxy]methyl]-1H-1,2,3-triazol-1-yl)phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol, by structurally modifying S-uniconazole, which functions as an inhibitor of CYP707A and as a gibberellin biosynthetic enzyme, but with low yield. Design of CYP707A inhibitors, Abz-T compounds, that have simpler structures in which the 1,2,3-triazolyl ring of (1E,3R)-1-[4-(4-[[2-(2-butoxyethoxy)ethoxy]methyl]-1H-1,2,3-triazol-1-yl)phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol has been replaced with a triple bond, by successful synthesis in shorter steps, resulting in greater yields than that of (1E,3R)-1-[4-(4-[[2-(2-butoxyethoxy)ethoxy]methyl]-1H-1,2,3-triazol-1-yl)phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol. In the enzymatic assays, Abz-T compound (1E,3R)-4,4-dimethyl-1-[3-[4-(2,5,8,11-tetraoxadodecan-1-yl)-1H-1,2,3-triazol-1-yl]phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol acts as a strong and selective inhibitor and is a more practical and effective inhibitor of CYP707A than (-)-Abz-E2B. Analysis of the biological effects in Arabidopsis thaliana reveals that (1E,3R)-4,4-dimethyl-1-[3-[4-(2,5,8,11-tetraoxadodecan-1-yl)-1H-1,2,3-triazol-1-yl]phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol enhances abscisic acid effects more than (1E,3R)-1-[4-(4-[[2-(2-butoxyethoxy)ethoxy]methyl]-1H-1,2,3-triazol-1-yl)phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol in seed germination and in the expression of ABA-responsive genes. Treatment with (1E,3R)-4,4-dimethyl-1-[3-[4-(2,5,8,11-tetraoxadodecan-1-yl)-1H-1,2,3-triazol-1-yl]phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol induces stomatal closure and improves drought tolerance in Arabidopsis thaliana Arabidopsis thaliana

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(+)-abscisate + [reduced NADPH-hemoprotein reductase] + O2 Arabidopsis thaliana
-
8'-hydroxyabscisate + [oxidized NADPH-hemoprotein reductase] + H2O
-
?

Organism

Organism UniProt Comment Textmining
Arabidopsis thaliana Q9FH76
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(+)-abscisate + [reduced NADPH-hemoprotein reductase] + O2
-
Arabidopsis thaliana 8'-hydroxyabscisate + [oxidized NADPH-hemoprotein reductase] + H2O
-
?

Synonyms

Synonyms Comment Organism
abscisic acid 8'-hydroxylase
-
Arabidopsis thaliana
CYP707A
-
Arabidopsis thaliana
CYP707A3
-
Arabidopsis thaliana

Cofactor

Cofactor Comment Organism Structure
cytochrome P-450
-
Arabidopsis thaliana
NADPH-hemoprotein reductase A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._ Arabidopsis thaliana

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000035
-
(1E,3R)-4,4-dimethyl-1-[3-[4-(2,5,8,11-tetraoxadodecan-1-yl)-1H-1,2,3-triazol-1-yl]phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol pH 7.6, 22°C, recombinant isozyme CYP707A12 Arabidopsis thaliana

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000012
-
pH 7.6, 22°C, recombinant isozyme CYP707A8 Arabidopsis thaliana (1E,3R)-1-(3-[3-[2-(2-butoxyethoxy)ethoxy]prop-1-yn-1-yl]phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.000054
-
pH 7.6, 22°C, recombinant isozyme CYP707A4 Arabidopsis thaliana (1E,3R)-1-[4-(4-[[2-(2-butoxyethoxy)ethoxy]methyl]-1H-1,2,3-triazol-1-yl)phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.000064
-
pH 7.6, 22°C, recombinant isozyme CYP707A12 Arabidopsis thaliana (1E,3R)-4,4-dimethyl-1-[3-[4-(2,5,8,11-tetraoxadodecan-1-yl)-1H-1,2,3-triazol-1-yl]phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.0002
-
pH 7.6, 22°C, recombinant isozyme CYP707A6 Arabidopsis thaliana (1E,3R)-1-(4-[3-[2-(2-butoxyethoxy)ethoxy]prop-1-yn-1-yl]phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.00024
-
pH 7.6, 22°C, recombinant isozyme CYP707A7 Arabidopsis thaliana (1E,3S)-1-(3-[3-[2-(2-butoxyethoxy)ethoxy]prop-1-yn-1-yl]phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.001
-
pH 7.6, 22°C, recombinant isozyme CYP707A5 Arabidopsis thaliana (1E,3S)-1-(4-[3-[2-(2-butoxyethoxy)ethoxy]prop-1-yn-1-yl]phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.0011
-
pH 7.6, 22°C, recombinant isozyme CYP707A3 Arabidopsis thaliana (1E,3S)-1-[4-(4-[[2-(2-butoxyethoxy)ethoxy]methyl]-1H-1,2,3-triazol-1-yl)phenyl]-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.0012
-
pH 7.6, 22°C, recombinant isozyme CYP707A11 Arabidopsis thaliana (1E,3S)-4,4-dimethyl-1-[3-(2,5,8,11-tetraoxatetradec-13-yn-14-yl)phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.0015
-
pH 7.6, 22°C, recombinant isozyme CYP707A10 Arabidopsis thaliana (1E,3R)-4,4-dimethyl-1-[4-(2,5,8,11-tetraoxatetradec-13-yn-14-yl)phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
0.0077
-
pH 7.6, 22°C, recombinant isozyme CYP707A9 Arabidopsis thaliana (1E,3S)-4,4-dimethyl-1-[4-(2,5,8,11-tetraoxatetradec-13-yn-14-yl)phenyl]-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol