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Literature summary for 6.3.2.4 extracted from

  • Vehar, B.; Hrast, M.; Kovac, A.; Konc, J.; Mariner, K.; Chopra, I.; O'Neill, A.; Janezic, D.; Gobec, S.
    Ellipticines and 9-acridinylamines as inhibitors of D-alanine:D-alanine ligase (2011), Bioorg. Med. Chem., 19, 5137-5146.
    View publication on PubMed
Search for more literature for 6.3.2.4

Application

Application Comment Organism
drug development the enzyme is an attractive target for development of antimicrobial drugs Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
1,4-dimethyl-9H-carbazole
-
 Escherichia coli
1,4-dimethyl-9H-carbazole-3-carbaldehyde
-
 Escherichia coli
1-(3-chloro-8-methoxy-11H-indolo[3,2-c]quinolin-9-yl)-N,N-dimethylmethanamine
-
 Escherichia coli
1-[4-[(6-chloro-2-methoxyacridin-9-yl)amino]phenyl]-3-(dimethylamino)propan-1-ol
-
 Escherichia coli
1H-indole
-
 Escherichia coli
2,2-diethoxy-N-[(6-methoxy-1,4-dimethyl-9H-carbazol-3-yl)methyl]ethanamine
-
 Escherichia coli
2,2-diethoxy-N-[(7-fluoro-1,4-dimethyl-9H-carbazol-3-yl)methyl]ethanamine
-
 Escherichia coli
2,2-diethoxy-N-[(8-ethyl-1,4-dimethyl-9H-carbazol-3-yl)methyl]ethanamine
-
 Escherichia coli
2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
3-(9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazol-6-yl)propan-1-amine
-
 Escherichia coli
3-[(1,6-dichloro-4-methoxyacridin-9-yl)amino]-2-[(diethylamino)methyl]phenol
-
 Escherichia coli
3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-(pyrrolidin-1-ylmethyl)phenol
-
 Escherichia coli
3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-[(4-methylpiperazin-1-yl)methyl]phenol
-
 Escherichia coli
3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-[(diethylamino)methyl]-6-(prop-2-en-1-yl)phenol
-
 Escherichia coli
3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-[(diethylamino)methyl]phenol
-
 Escherichia coli
5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
5-bromo-1H-indole
-
 Escherichia coli
5-methoxy-1H-indole
-
 Escherichia coli
6-bromo-1,4-dimethyl-9H-carbazole
-
 Escherichia coli
6-bromo-1,4-dimethyl-9H-carbazole-3-carbaldehyde
-
 Escherichia coli
6-chloro-2-methoxy-N-(6-methoxyquinolin-8-yl)acridin-9-amine
-
 Escherichia coli
6-fluoro-1H-indole
-
 Escherichia coli
6-methoxy-1,4-dimethyl-9H-carbazole
-
 Escherichia coli
6-methoxy-1,4-dimethyl-9H-carbazole-3-carbaldehyde
-
 Escherichia coli
7-ethyl-1H-indole
-
 Escherichia coli
7-ethyl-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
7-fluoro-1,4-dimethyl-9H-carbazole
-
 Escherichia coli
7-fluoro-1,4-dimethyl-9H-carbazole-3-carbaldehyde
-
 Escherichia coli
8-ethyl-1,4-dimethyl-9H-carbazole
-
 Escherichia coli
8-ethyl-1,4-dimethyl-9H-carbazole-3-carbaldehyde
-
 Escherichia coli
8-fluoro-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
8-fluoro-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
8-fluoro-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
9-bromo-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
9-bromo-2,5,6,11-tetramethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
9-bromo-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
9-bromo-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
9-methoxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium acetate
-
 Escherichia coli
9-methoxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
9-methoxy-2,5,6,11-tetramethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
9-methoxy-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
additional information evaluation of ellipticines and 9-acridinylamines as enzyme inhibitors. Ellipticines with a quaternary methylpyridinium moiety are the most potent among all studied compounds, with MIC values as low as 2 mg/l in strains with intact efflux mechanisms. The compounds cause membrane damage. Inhibitor MIC values, overview Escherichia coli
N-[(1,4-dimethyl-9H-carbazol-3-yl)methyl]-2,2-diethoxyethanamine
-
 Escherichia coli
N-[(3-chloro-8-methoxy-11H-indolo[3,2-c]quinolin-9-yl)methyl]-N-ethylethanamine
-
 Escherichia coli
N-[(6-bromo-1,4-dimethyl-9H-carbazol-3-yl)methyl]-2,2-diethoxyethanamine
-
 Escherichia coli

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
ATP + 2 D-alanine Escherichia coli
-
 ADP + phosphate + D-alanyl-D-alanine
-
 ?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
ATP + 2 D-alanine
-
 Escherichia coli ADP + phosphate + D-alanyl-D-alanine
-
 ?

Synonyms

Synonyms Comment Organism
D-Alanine:D-alanine ligase
-
 Escherichia coli
Ddl
-
 Escherichia coli

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Escherichia coli

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8
-
 assay at Escherichia coli

Cofactor

Cofactor Comment Organism Structure
ATP
-
 Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.023
-
 pH 8.0, 37°C Escherichia coli 9-bromo-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
0.032
-
 pH 8.0, 37°C Escherichia coli 6-chloro-2-methoxy-N-(6-methoxyquinolin-8-yl)acridin-9-amine
0.036
-
 pH 8.0, 37°C Escherichia coli 9-bromo-2,5,6,11-tetramethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
0.043
-
 pH 8.0, 37°C Escherichia coli 9-methoxy-2,5,6,11-tetramethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
0.046
-
 pH 8.0, 37°C Escherichia coli 2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
0.06
-
 pH 8.0, 37°C Escherichia coli 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
0.064
-
 pH 8.0, 37°C Escherichia coli 8-fluoro-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
0.065
-
 pH 8.0, 37°C Escherichia coli 9-methoxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
0.07
-
 pH 8.0, 37°C Escherichia coli 3-(9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazol-6-yl)propan-1-amine
0.086
-
 pH 8.0, 37°C Escherichia coli 9-bromo-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
0.089
-
 pH 8.0, 37°C Escherichia coli 9-methoxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium acetate
0.09
-
 pH 8.0, 37°C Escherichia coli 6-chloro-2-methoxy-N-(6-methoxyquinolin-8-yl)acridin-9-amine
0.09
-
 pH 8.0, 37°C Escherichia coli 8-fluoro-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
0.102
-
 pH 8.0, 37°C Escherichia coli 3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-(pyrrolidin-1-ylmethyl)phenol
0.103
-
 pH 8.0, 37°C Escherichia coli 8-fluoro-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
0.119
-
 pH 8.0, 37°C Escherichia coli 3-[(1,6-dichloro-4-methoxyacridin-9-yl)amino]-2-[(diethylamino)methyl]phenol
0.125
-
 pH 8.0, 37°C Escherichia coli 7-ethyl-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
0.135
-
 pH 8.0, 37°C Escherichia coli 1-[4-[(6-chloro-2-methoxyacridin-9-yl)amino]phenyl]-3-(dimethylamino)propan-1-ol
0.161
-
 pH 8.0, 37°C Escherichia coli 3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-[(diethylamino)methyl]-6-(prop-2-en-1-yl)phenol
0.162
-
 pH 8.0, 37°C Escherichia coli 3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-[(4-methylpiperazin-1-yl)methyl]phenol
0.184
-
 pH 8.0, 37°C Escherichia coli 9-methoxy-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
0.192
-
 pH 8.0, 37°C Escherichia coli 5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
0.297
-
 pH 8.0, 37°C Escherichia coli 9-bromo-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
0.32
-
 pH 8.0, 37°C Escherichia coli 3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-[(diethylamino)methyl]phenol
0.33
-
 pH 8.0, 37°C Escherichia coli N-[(3-chloro-8-methoxy-11H-indolo[3,2-c]quinolin-9-yl)methyl]-N-ethylethanamine
0.623
-
 pH 8.0, 37°C Escherichia coli N-[(3-chloro-8-methoxy-11H-indolo[3,2-c]quinolin-9-yl)methyl]-N-ethylethanamine

General Information

General Information Comment Organism
physiological function D-alanine:D-alanine ligase is an intracellular bacterial enzyme essential for cell wall biosynthesis Escherichia coli