Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary 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

Application

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

Inhibitors

EC Number Inhibitors Comment Organism Structure
6.3.2.4 1,4-dimethyl-9H-carbazole
-
 Escherichia coli
6.3.2.4 1,4-dimethyl-9H-carbazole-3-carbaldehyde
-
 Escherichia coli
6.3.2.4 1-(3-chloro-8-methoxy-11H-indolo[3,2-c]quinolin-9-yl)-N,N-dimethylmethanamine
-
 Escherichia coli
6.3.2.4 1-[4-[(6-chloro-2-methoxyacridin-9-yl)amino]phenyl]-3-(dimethylamino)propan-1-ol
-
 Escherichia coli
6.3.2.4 1H-indole
-
 Escherichia coli
6.3.2.4 2,2-diethoxy-N-[(6-methoxy-1,4-dimethyl-9H-carbazol-3-yl)methyl]ethanamine
-
 Escherichia coli
6.3.2.4 2,2-diethoxy-N-[(7-fluoro-1,4-dimethyl-9H-carbazol-3-yl)methyl]ethanamine
-
 Escherichia coli
6.3.2.4 2,2-diethoxy-N-[(8-ethyl-1,4-dimethyl-9H-carbazol-3-yl)methyl]ethanamine
-
 Escherichia coli
6.3.2.4 2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
6.3.2.4 3-(9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazol-6-yl)propan-1-amine
-
 Escherichia coli
6.3.2.4 3-[(1,6-dichloro-4-methoxyacridin-9-yl)amino]-2-[(diethylamino)methyl]phenol
-
 Escherichia coli
6.3.2.4 3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-(pyrrolidin-1-ylmethyl)phenol
-
 Escherichia coli
6.3.2.4 3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-[(4-methylpiperazin-1-yl)methyl]phenol
-
 Escherichia coli
6.3.2.4 3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-[(diethylamino)methyl]-6-(prop-2-en-1-yl)phenol
-
 Escherichia coli
6.3.2.4 3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-[(diethylamino)methyl]phenol
-
 Escherichia coli
6.3.2.4 5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
6.3.2.4 5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
6.3.2.4 5-bromo-1H-indole
-
 Escherichia coli
6.3.2.4 5-methoxy-1H-indole
-
 Escherichia coli
6.3.2.4 6-bromo-1,4-dimethyl-9H-carbazole
-
 Escherichia coli
6.3.2.4 6-bromo-1,4-dimethyl-9H-carbazole-3-carbaldehyde
-
 Escherichia coli
6.3.2.4 6-chloro-2-methoxy-N-(6-methoxyquinolin-8-yl)acridin-9-amine
-
 Escherichia coli
6.3.2.4 6-fluoro-1H-indole
-
 Escherichia coli
6.3.2.4 6-methoxy-1,4-dimethyl-9H-carbazole
-
 Escherichia coli
6.3.2.4 6-methoxy-1,4-dimethyl-9H-carbazole-3-carbaldehyde
-
 Escherichia coli
6.3.2.4 7-ethyl-1H-indole
-
 Escherichia coli
6.3.2.4 7-ethyl-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
6.3.2.4 7-fluoro-1,4-dimethyl-9H-carbazole
-
 Escherichia coli
6.3.2.4 7-fluoro-1,4-dimethyl-9H-carbazole-3-carbaldehyde
-
 Escherichia coli
6.3.2.4 8-ethyl-1,4-dimethyl-9H-carbazole
-
 Escherichia coli
6.3.2.4 8-ethyl-1,4-dimethyl-9H-carbazole-3-carbaldehyde
-
 Escherichia coli
6.3.2.4 8-fluoro-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
6.3.2.4 8-fluoro-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
6.3.2.4 8-fluoro-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
6.3.2.4 9-bromo-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
6.3.2.4 9-bromo-2,5,6,11-tetramethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
6.3.2.4 9-bromo-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
6.3.2.4 9-bromo-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
6.3.2.4 9-methoxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium acetate
-
 Escherichia coli
6.3.2.4 9-methoxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
6.3.2.4 9-methoxy-2,5,6,11-tetramethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
-
 Escherichia coli
6.3.2.4 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
6.3.2.4 9-methoxy-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
-
 Escherichia coli
6.3.2.4 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
6.3.2.4 N-[(1,4-dimethyl-9H-carbazol-3-yl)methyl]-2,2-diethoxyethanamine
-
 Escherichia coli
6.3.2.4 N-[(3-chloro-8-methoxy-11H-indolo[3,2-c]quinolin-9-yl)methyl]-N-ethylethanamine
-
 Escherichia coli
6.3.2.4 N-[(6-bromo-1,4-dimethyl-9H-carbazol-3-yl)methyl]-2,2-diethoxyethanamine
-
 Escherichia coli

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
6.3.2.4 Mg2+ required Escherichia coli

Natural Substrates/ Products (Substrates)

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

Organism

EC Number Organism UniProt Comment Textmining
6.3.2.4 Escherichia coli
-
-
-

Substrates and Products (Substrate)

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

Synonyms

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

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
6.3.2.4 37
-
 assay at Escherichia coli

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
6.3.2.4 8
-
 assay at Escherichia coli

Cofactor

EC Number Cofactor Comment Organism Structure
6.3.2.4 ATP
-
 Escherichia coli

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
6.3.2.4 0.023
-
 pH 8.0, 37°C Escherichia coli 9-bromo-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
6.3.2.4 0.032
-
 pH 8.0, 37°C Escherichia coli 6-chloro-2-methoxy-N-(6-methoxyquinolin-8-yl)acridin-9-amine
6.3.2.4 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
6.3.2.4 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
6.3.2.4 0.046
-
 pH 8.0, 37°C Escherichia coli 2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
6.3.2.4 0.06
-
 pH 8.0, 37°C Escherichia coli 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
6.3.2.4 0.064
-
 pH 8.0, 37°C Escherichia coli 8-fluoro-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
6.3.2.4 0.065
-
 pH 8.0, 37°C Escherichia coli 9-methoxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium iodide
6.3.2.4 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
6.3.2.4 0.086
-
 pH 8.0, 37°C Escherichia coli 9-bromo-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
6.3.2.4 0.089
-
 pH 8.0, 37°C Escherichia coli 9-methoxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazol-2-ium acetate
6.3.2.4 0.09
-
 pH 8.0, 37°C Escherichia coli 6-chloro-2-methoxy-N-(6-methoxyquinolin-8-yl)acridin-9-amine
6.3.2.4 0.09
-
 pH 8.0, 37°C Escherichia coli 8-fluoro-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
6.3.2.4 0.102
-
 pH 8.0, 37°C Escherichia coli 3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-(pyrrolidin-1-ylmethyl)phenol
6.3.2.4 0.103
-
 pH 8.0, 37°C Escherichia coli 8-fluoro-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
6.3.2.4 0.119
-
 pH 8.0, 37°C Escherichia coli 3-[(1,6-dichloro-4-methoxyacridin-9-yl)amino]-2-[(diethylamino)methyl]phenol
6.3.2.4 0.125
-
 pH 8.0, 37°C Escherichia coli 7-ethyl-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
6.3.2.4 0.135
-
 pH 8.0, 37°C Escherichia coli 1-[4-[(6-chloro-2-methoxyacridin-9-yl)amino]phenyl]-3-(dimethylamino)propan-1-ol
6.3.2.4 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
6.3.2.4 0.162
-
 pH 8.0, 37°C Escherichia coli 3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-[(4-methylpiperazin-1-yl)methyl]phenol
6.3.2.4 0.184
-
 pH 8.0, 37°C Escherichia coli 9-methoxy-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
6.3.2.4 0.192
-
 pH 8.0, 37°C Escherichia coli 5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
6.3.2.4 0.297
-
 pH 8.0, 37°C Escherichia coli 9-bromo-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole
6.3.2.4 0.32
-
 pH 8.0, 37°C Escherichia coli 3-[(6-chloro-2-methoxyacridin-9-yl)amino]-2-[(diethylamino)methyl]phenol
6.3.2.4 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
6.3.2.4 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

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