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Literature summary for 1.5.1.3 extracted from

  • Srinivasan, B.; Tonddast-Navaei, S.; Skolnick, J.
    Ligand binding studies, preliminary structure-activity relationship and detailed mechanistic characterization of 1-phenyl-6,6-dimethyl-1,3,5-triazine-2,4-diamine derivatives as inhibitors of Escherichia coli dihydrofolate reductase (2015), Eur. J. Med. Chem., 103, 600-614 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.5.1.3

Inhibitors

Inhibitors Comment Organism Structure
1-(3-ethoxyphenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
 Escherichia coli
1-(4-chlorophenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
 Escherichia coli
1-(4-ethoxyphenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
 Escherichia coli
1-[3-(aminomethyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
 Escherichia coli
1-[3-chloro-4-(5-phenylpentyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine uncompetitive versus NADPH, competitive versus 7,8-dihydrofolate Escherichia coli
1-[4-(aminomethyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
 Escherichia coli
1-[4-(dimethylamino)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
 Escherichia coli
1-[4-[4-(2,4-dichlorophenyl)butyl]phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
 Escherichia coli
3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)benzonitrile
-
 Escherichia coli
4-[3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)benzamido]benzene-1-sulfonyl fluoride contains a fluorosulfonylphenylaminocarbonyl substitution at R2 on 1-phenyl-6,6-dimethyl-1,3,5-triazine-2,4-diamine ring, and shows the unique behavior of tight-binding and average inhibition, uncompetitive versus NADPH, competitive versus 7,8-dihydrofolate Escherichia coli
4-[4,6-diamino-2-(4-chlorophenyl)-1,3,5-triazin-1(2H)-yl]benzene-1-sulfonamide
-
 Escherichia coli
4-[4-[3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1-yl)phenyl]butyl]benzenesulfonyl fluoride uncompetitive versus NADPH, competitive versus 7,8-dihydrofolate Escherichia coli
4-[6-[4-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1-yl)phenyl]hexyl]benzenesulfonyl fluoride uncompetitive versus NADPH, competitive versus 7,8-dihydrofolate Escherichia coli
6,6-dimethyl-1-(4-methylphenyl)-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
 Escherichia coli
6,6-dimethyl-1-[3-(4-phenylbutyl)phenyl]-1,6-dihydro-1,3,5-triazine-2,4-diamine uncompetitive versus NADPH, competitive versus 7,8-dihydrofolate Escherichia coli
lamotrigine
-
 Escherichia coli
additional information analysis of 1,3,5-triazine-2,4-diamine and 1,2,4-triazine-2,4-diamine group-containing compounds as potential inhibitors of Escherichia coli DHFR. Fifteen derivatives of 1,3,5-triazine-2,4-diamine are assessed for their ability to bind to the apo form of enzyme EcDHFR. Quantitative structure-activity relationship analysis and macromolecular docking of the diaminotriazine series of compounds, overview. Effects of 1,3,5-triazine-2,4-diamine derivatives on the cofactor NADPH binding Escherichia coli

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information Michaelis-Menten kinetics Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
7,8-dihydrofolate + NADPH + H+ Escherichia coli
-
 5,6,7,8-tetrahydrofolate + NADP+
-
 r

Organism

Organism UniProt Comment Textmining
Escherichia coli P0ABQ4
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
7,8-dihydrofolate + NADPH + H+
-
 Escherichia coli 5,6,7,8-tetrahydrofolate + NADP+
-
 r

Synonyms

Synonyms Comment Organism
DHFR
-
 Escherichia coli

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
22
-
 assay at room temperature Escherichia coli

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.3
-
 assay at Escherichia coli

Cofactor

Cofactor Comment Organism Structure
NADP+
-
 Escherichia coli
NADPH effects of 1,3,5-triazine-2,4-diamine derivatives on the cofactor NADPH binding, overview Escherichia coli

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
additional information
-
 additional information inhibition kinetics, overview Escherichia coli
0.0000497
-
 4-[4-[3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1-yl)phenyl]butyl]benzenesulfonyl fluoride pH 7.3, 22°C Escherichia coli
0.0000926
-
 4-[6-[4-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1-yl)phenyl]hexyl]benzenesulfonyl fluoride pH 7.3, 22°C Escherichia coli
0.0003591
-
 6,6-dimethyl-1-[3-(4-phenylbutyl)phenyl]-1,6-dihydro-1,3,5-triazine-2,4-diamine pH 7.3, 22°C Escherichia coli
0.0008802
-
 1-[3-chloro-4-(5-phenylpentyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine pH 7.3, 22°C Escherichia coli
0.000958
-
 3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)benzonitrile pH 7.3, 22°C Escherichia coli
0.00102
-
 1-(4-chlorophenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine pH 7.3, 22°C Escherichia coli
0.00155
-
 6,6-dimethyl-1-(4-methylphenyl)-1,6-dihydro-1,3,5-triazine-2,4-diamine pH 7.3, 22°C Escherichia coli
0.00289
-
 4-[3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)benzamido]benzene-1-sulfonyl fluoride pH 7.3, 22°C Escherichia coli
0.00402
-
 1-(4-ethoxyphenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine pH 7.3, 22°C Escherichia coli
0.01116
-
 1-(3-ethoxyphenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine pH 7.3, 22°C Escherichia coli
0.02022
-
 1-[3-(aminomethyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine pH 7.3, 22°C Escherichia coli
0.0393
-
 1-[4-(aminomethyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine pH 7.3, 22°C Escherichia coli
0.105
-
 4-[4,6-diamino-2-(4-chlorophenyl)-1,3,5-triazin-1(2H)-yl]benzene-1-sulfonamide pH 7.3, 22°C Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00115
-
 pH 7.3, 22°C Escherichia coli 4-[4-[3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1-yl)phenyl]butyl]benzenesulfonyl fluoride
0.00184
-
 pH 7.3, 22°C Escherichia coli 4-[6-[4-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1-yl)phenyl]hexyl]benzenesulfonyl fluoride
0.00759
-
 pH 7.3, 22°C Escherichia coli 6,6-dimethyl-1-[3-(4-phenylbutyl)phenyl]-1,6-dihydro-1,3,5-triazine-2,4-diamine
0.01845
-
 pH 7.3, 22°C Escherichia coli 1-[3-chloro-4-(5-phenylpentyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
0.02019
-
 pH 7.3, 22°C Escherichia coli 3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)benzonitrile
0.02091
-
 pH 7.3, 22°C Escherichia coli 1-(4-chlorophenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
0.03227
-
 pH 7.3, 22°C Escherichia coli 6,6-dimethyl-1-(4-methylphenyl)-1,6-dihydro-1,3,5-triazine-2,4-diamine
0.06283
-
 pH 7.3, 22°C Escherichia coli 4-[3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)benzamido]benzene-1-sulfonyl fluoride
0.0891
-
 pH 7.3, 22°C Escherichia coli 1-(4-ethoxyphenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
0.263
-
 pH 7.3, 22°C Escherichia coli 1-(3-ethoxyphenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
0.478
-
 pH 7.3, 22°C Escherichia coli 1-[3-(aminomethyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
0.722
-
 pH 7.3, 22°C Escherichia coli 1-[4-(aminomethyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
1.548
-
 pH 7.3, 22°C Escherichia coli 4-[4,6-diamino-2-(4-chlorophenyl)-1,3,5-triazin-1(2H)-yl]benzene-1-sulfonamide

General Information

General Information Comment Organism
metabolism enzyme DHFR is a pivotal enzyme in the thymidine and purine synthesis pathway Escherichia coli