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Literature summary for 4.1.2.13 extracted from

  • Han, X.; Zhu, X.; Hong, Z.; Wei, L.; Ren, Y.; Wan, F.; Zhu, S.; Peng, H.; Guo, L.; Rao, L.; Feng, L.; Wan, J.
    Structure-based rational design of novel inhibitors against fructose-1,6-bisphosphate aldolase from Candida albicans (2017), J. Chem. Inf. Model., 57, 1426-1438 .
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli BL21(DE3) cells Candida albicans

Protein Variants

Protein Variants Comment Organism
D289A the mutant enzyme exhibits higher resistance against inhibitor (2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine compared to the wild type Candida albicans
D289A compound 3g exhibits similar inhibitory activities to the mutant enzyme (0.0031 mM) as compared to wild-type enzyme Candida albicans
R332A the mutant enzyme exhibits higher resistance against inhibitor (2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine compared to the wild type Candida albicans
R332A mutation results in 60fold (0.101 mM) increase of Ki value for compound 3g compared with wild-type enzyme Ca-FBA-II (0.0017 mM) Candida albicans
S62A the mutant enzyme exhibits higher resistance against inhibitor (2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine compared to the wild type Candida albicans
S62A mutation results in about 15fold increase of the Ki value of S62A (0.0315 mM) as compared to wild-type enzyme Candida albicans
T290A the mutant enzyme exhibits higher resistance against inhibitor (2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine compared to the wild type Candida albicans
T290A mutation results in 130fold (0.230 mM) increase of Ki value for compound 3g as compared with wild-type enzyme Ca-FBA-II (0.0017 mM) Candida albicans

Inhibitors

Inhibitors Comment Organism Structure
(1E)-1-benzylidene-2-(4-nitrophenyl)hydrazine 0.05 mM, 43% inhibition; 43% inhibition at 0.05 mM Candida albicans
(1E)-1-[(4-chlorophenyl)methylidene]-2-(4-nitrophenyl)hydrazine 0.05 mM, 91% inhibition; 91% inhibition at 0.05 mM Candida albicans
(1E)-1-[(4-fluorophenyl)methylidene]-2-(4-nitrophenyl)hydrazine 0.05 mM, 94% inhibition; 94% inhibition at 0.05 mM Candida albicans
(1E)-1-[(4-methylphenyl)methylidene]-2-(4-nitrophenyl)hydrazine 0.05 mM, 80% inhibition; 80% inhibition at 0.05 mM Candida albicans
(1E)-1-[([1,1'-biphenyl]-4-yl)methylidene]-2-(4-nitrophenyl)hydrazine 0.05 mM, 92% inhibition; 92% inhibition at 0.05 mM Candida albicans
(1E)-1-[1-(4-bromophenyl)ethylidene]-2-(4-nitrophenyl)hydrazine 0.05 mM, 99% inhibition; 99% inhibition at 0.05 mM Candida albicans
(1E)-1-[1-([1,1'-biphenyl]-4-yl)ethylidene]-2-(4-nitrophenyl)hydrazine 62% inhibition at 0.05 mM Candida albicans
(1E)-1-[2-(4-nitrophenyl)hydrazinylidene]propan-2-one 0.05 mM, 6% inhibition; 6% inhibition at 0.05 mM Candida albicans
(2E)-1-(4-nitrophenyl)-2-(1-phenylethylidene)hydrazine 0.05 mM, 62% inhibition Candida albicans
(2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine 0.05 mM, 100% inhibition; complete inhibition at 0.05 mM Candida albicans
(2E)-1-(4-nitrophenyl)-2-[(5-nitrothiophen-2-yl)methylidene]hydrazine 0.05 mM, 97% inhibition; 97% inhibition at 0.05 mM Candida albicans
(2E)-1-(4-nitrophenyl)-2-[[4-(trifluoromethyl)phenyl]methylidene]hydrazine 0.05 mM, 60% inhibition; 60% inhibition at 0.05 mM Candida albicans
(2E)-2-[2-(2-hydroxy-4-nitrophenyl)hydrazinylidene]-3-oxobutanamide 94% inhibition at 0.05 mM Candida albicans
(2E)-2-[2-(4-nitrophenyl)hydrazinylidene]-1-phenylethan-1-one 0.05 mM, 91% inhibition; 91% inhibition at 0.05 mM Candida albicans
1-(4-[(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl]phenyl)-1H-1,2,4-triazole 0.05 mM, 83% inhibition; 83% inhibition at 0.05 mM Candida albicans
2-[2-(2,4-dioxopentan-3-ylidene)hydrazinyl]-5-nitrobenzoic acid 0.05 mM, 10% inhibition; 10% inhibition at 0.05 mM Candida albicans
2-[2-(2,4-dioxopentan-3-ylidene)hydrazinyl]benzonitrile 0.05 mM, 16% inhibition; 16% inhibition at 0.05 mM Candida albicans
3-(2-phenylhydrazinylidene)pentane-2,4-dione 0.05 mM, 10% inhibition; 10% inhibition at 0.05 mM Candida albicans
3-[2-(2,4-dinitrophenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 1% inhibition; 1% inhibition at 0.05 mM Candida albicans
3-[2-(2-chloro-4-nitrophenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 68% inhibition; 68% inhibition at 0.05 mM Candida albicans
3-[2-(2-fluorophenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 3% inhibition; 3% inhibition at 0.05 mM Candida albicans
3-[2-(2-hydroxy-4-nitrophenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 94% inhibition; 0.05 mM, 96% inhibition; 96% inhibition at 0.05 mM Candida albicans
3-[2-(2-hydroxy-5-nitrophenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 14% inhibition; 14% inhibition at 0.05 mM Candida albicans
3-[2-(2-hydroxyphenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 73% inhibition; 73% inhibition at 0.05 mM Candida albicans
3-[2-(2-methyl-4-nitrophenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 65% inhibition; 65% inhibition at 0.05 mM Candida albicans
3-[2-(2-methylphenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 9% inhibition; 9% inhibition at 0.05 mM Candida albicans
3-[2-(4-bromophenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 27% inhibition; 27% inhibition at 0.05 mM Candida albicans
3-[2-(4-chlorophenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 20% inhibition; 20% inhibition at 0.05 mM Candida albicans
3-[2-(4-fluorophenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 7% inhibition; 7% inhibition at 0.05 mM Candida albicans
3-[2-(4-hydroxyphenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 5% inhibition; 5% inhibition at 0.05 mM Candida albicans
3-[2-(4-nitrophenyl)hydrazinylidene]pentane-2,4-dione 0.05 mM, 92% inhibition; 92% inhibition at 0.05 mM Candida albicans
4-nitro-N'-[(E)-(4-nitrophenyl)methylidene]benzohydrazide 0.05 mM, 59% inhibition; 59% inhibition at 0.05 mM Candida albicans
4-[(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl]benzonitrile 0.05 mM, 100% inhibition; complete inhibition at 0.05 mM Candida albicans
4-[2-(2,4-dioxopentan-3-ylidene)hydrazinyl]benzene-1-sulfonic acid 0.05 mM, 14% inhibition; 14% inhibition at 0.05 mM Candida albicans
5-bromo-3-[(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl]-1H-indole 0.05 mM, 97% inhibition; 97% inhibition at 0.05 mM Candida albicans
N'-[(E)-(4-cyanophenyl)methylidene]-4-nitrobenzohydrazide 0.05 mM, 21% inhibition; 21% inhibition at 0.05 mM Candida albicans

Metals/Ions

Metals/Ions Comment Organism Structure
Zn2+ required Candida albicans

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
D-fructose 1,6-bisphosphate Candida albicans
-
glycerone phosphate + D-glyceraldehyde 3-phosphate
-
?
D-fructose 1,6-bisphosphate Candida albicans ATCC MYA-2876
-
glycerone phosphate + D-glyceraldehyde 3-phosphate
-
?

Organism

Organism UniProt Comment Textmining
Candida albicans Q9URB4
-
-
Candida albicans ATCC MYA-2876 Q9URB4
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
D-fructose 1,6-bisphosphate
-
Candida albicans glycerone phosphate + D-glyceraldehyde 3-phosphate
-
?
D-fructose 1,6-bisphosphate
-
Candida albicans ATCC MYA-2876 glycerone phosphate + D-glyceraldehyde 3-phosphate
-
?

Synonyms

Synonyms Comment Organism
Ca-FBA-II
-
Candida albicans
class II fructose-1,6-bisphosphate aldolase
-
Candida albicans
FBA-II
-
Candida albicans
fructose-1,6-bisphosphate aldolase
-
Candida albicans

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0017
-
(2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine at pH 7.4 and 30°C Candida albicans
0.0017
-
(2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine pH and temperature not specified in the publication, wild-type enzyme Candida albicans
0.0031
-
(2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine pH and temperature not specified in the publication, mutant enzyme D289A Candida albicans
0.0315
-
(2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine pH and temperature not specified in the publication, mutant enzyme S62A Candida albicans
0.101
-
(2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine pH and temperature not specified in the publication, mutant enzyme R332A Candida albicans
0.23
-
(2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine pH and temperature not specified in the publication, mutant enzyme T290A Candida albicans

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0027
-
at pH 7.4 and 30°C Candida albicans (2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine
0.00276
-
pH and temperature not specified in the publication, wild-type enzyme Candida albicans (2E)-1-(4-nitrophenyl)-2-[(4-nitrophenyl)methylidene]hydrazine
0.0041
-
pH and temperature not specified in the publication Candida albicans (1E)-1-[([1,1'-biphenyl]-4-yl)methylidene]-2-(4-nitrophenyl)hydrazine
0.0041
-
at pH 7.4 and 30°C Candida albicans (1E)-1-[([1,1'-biphenyl]-4-yl)methylidene]-2-(4-nitrophenyl)hydrazine
0.00564
-
pH and temperature not specified in the publication Candida albicans (1E)-1-[(4-chlorophenyl)methylidene]-2-(4-nitrophenyl)hydrazine
0.006
-
at pH 7.4 and 30°C Candida albicans 5-bromo-3-[(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl]-1H-indole
0.0064
-
at pH 7.4 and 30°C Candida albicans (1E)-1-[(4-chlorophenyl)methylidene]-2-(4-nitrophenyl)hydrazine
0.00643
-
pH and temperature not specified in the publication Candida albicans 5-bromo-3-[(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl]-1H-indole
0.0075
-
pH and temperature not specified in the publication Candida albicans (1E)-1-[1-(4-bromophenyl)ethylidene]-2-(4-nitrophenyl)hydrazine
0.0075
-
at pH 7.4 and 30°C Candida albicans (1E)-1-[1-(4-bromophenyl)ethylidene]-2-(4-nitrophenyl)hydrazine
0.0094
-
pH and temperature not specified in the publication Candida albicans 4-[(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl]benzonitrile
0.0094
-
at pH 7.4 and 30°C Candida albicans 4-[(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl]benzonitrile
0.0126
-
pH and temperature not specified in the publication Candida albicans (1E)-1-[(4-fluorophenyl)methylidene]-2-(4-nitrophenyl)hydrazine
0.0126
-
at pH 7.4 and 30°C Candida albicans (1E)-1-[(4-fluorophenyl)methylidene]-2-(4-nitrophenyl)hydrazine
0.017
-
pH and temperature not specified in the publication Candida albicans 3-[2-(2-hydroxy-4-nitrophenyl)hydrazinylidene]pentane-2,4-dione
0.017
-
at pH 7.4 and 30°C Candida albicans 3-[2-(2-hydroxy-4-nitrophenyl)hydrazinylidene]pentane-2,4-dione
0.02
-
pH and temperature not specified in the publication Candida albicans (1E)-1-[(4-methylphenyl)methylidene]-2-(4-nitrophenyl)hydrazine
0.02
-
pH and temperature not specified in the publication Candida albicans (2E)-1-(4-nitrophenyl)-2-[(5-nitrothiophen-2-yl)methylidene]hydrazine
0.02
-
pH and temperature not specified in the publication Candida albicans 3-[2-(2-hydroxy-4-nitrophenyl)hydrazinylidene]pentane-2,4-dione
0.02
-
pH and temperature not specified in the publication Candida albicans 3-[2-(4-nitrophenyl)hydrazinylidene]pentane-2,4-dione
0.02
-
at pH 7.4 and 30°C Candida albicans (1E)-1-[(4-methylphenyl)methylidene]-2-(4-nitrophenyl)hydrazine
0.02
-
at pH 7.4 and 30°C Candida albicans (2E)-1-(4-nitrophenyl)-2-[(5-nitrothiophen-2-yl)methylidene]hydrazine
0.02
-
at pH 7.4 and 30°C Candida albicans (2E)-2-[2-(2-hydroxy-4-nitrophenyl)hydrazinylidene]-3-oxobutanamide
0.02
-
at pH 7.4 and 30°C Candida albicans 3-[2-(4-nitrophenyl)hydrazinylidene]pentane-2,4-dione
0.025
-
pH and temperature not specified in the publication Candida albicans 1-(4-[(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl]phenyl)-1H-1,2,4-triazole
0.025
-
at pH 7.4 and 30°C Candida albicans 1-(4-[(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl]phenyl)-1H-1,2,4-triazole
0.026
-
pH and temperature not specified in the publication Candida albicans (2E)-2-[2-(4-nitrophenyl)hydrazinylidene]-1-phenylethan-1-one
0.026
-
at pH 7.4 and 30°C Candida albicans (2E)-2-[2-(4-nitrophenyl)hydrazinylidene]-1-phenylethan-1-one
0.038
-
pH and temperature not specified in the publication Candida albicans 3-[2-(2-hydroxyphenyl)hydrazinylidene]pentane-2,4-dione
0.038
-
at pH 7.4 and 30°C Candida albicans 3-[2-(2-hydroxyphenyl)hydrazinylidene]pentane-2,4-dione
0.043
-
pH and temperature not specified in the publication Candida albicans 3-[2-(2-methyl-4-nitrophenyl)hydrazinylidene]pentane-2,4-dione
0.043
-
at pH 7.4 and 30°C Candida albicans 3-[2-(2-methyl-4-nitrophenyl)hydrazinylidene]pentane-2,4-dione

General Information

General Information Comment Organism
drug target the enzyme is an attractive targets for the discovery of drugs to combat invasive fungal infection, because it is absent in animals and higher plants. It is a promising target for the discovery of drugs against azole-resistant fungal pathogens in the future Candida albicans