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Literature summary for 2.4.2.36 extracted from

  • Zhang, G.
    Design, synthesis, and evaluation of bisubstrate analog inhibitors of cholera toxin (2008), Bioorg. Med. Chem. Lett., 18, 3724-3727.
    View publication on PubMedView publication on EuropePMC

Inhibitors

Inhibitors Comment Organism Structure
3-((3,3-diethylguanidino)methyl)benzamide 1 mM, 37°C, pH 7, 24% inhibition Vibrio cholerae serotype O1
3-((3,3-diisopropylguanidino)methyl)benzamide 1 mM, 37°C, pH 7, 94% inhibition Vibrio cholerae serotype O1
3-((3-(1-benzylpiperidin-4-yl)guanidino)methyl)benzamide 1 mM, 37°C, pH 7, 96% inhibition Vibrio cholerae serotype O1
3-((3-(1-benzylpyrrolidin-3-yl)guanidino)methyl)benzamide 1 mM, 37°C, pH 7, 68% inhibition Vibrio cholerae serotype O1
3-((3-(2-(ethyl(m-tolyl)amino)ethyl)guanidino)methyl)benzamide 1 mM, 37°C, pH 7, 76% inhibition Vibrio cholerae serotype O1
3-((3-(2-morpholinoethyl)guanidino)methyl)benzamide 1 mM, 37°C, pH 7, 57% inhibition Vibrio cholerae serotype O1
3-((3-(4-bromobenzyl)guanidino)methyl)benzamide 1 mM, 37°C, pH 7, 98% inhibition Vibrio cholerae serotype O1
3-((3-(4-methoxybenzyl)guanidino)methyl)benzamide 1 mM, 37°C, pH 7, 97% inhibition, not sufficient material for IC50 and Ki estimation Vibrio cholerae serotype O1
3-((3-benzylguanidino)methyl)benzamide 1 mM, 37°C, pH 7, 93% inhibition Vibrio cholerae serotype O1
3-((3-phenethylguanidino)methyl)benzamide 1 mM, 37°C, pH 7, 93% inhibition Vibrio cholerae serotype O1
3-((3-phenylguanidino)methyl)benzamide 1 mM, 37°C, pH 7, 57% inhibition Vibrio cholerae serotype O1
3-((3-tert-butylguanidino)methyl)benzamide 1 mM, 37°C, pH 7, 39% inhibition Vibrio cholerae serotype O1
3-(3,3-diisopropylguanidino)benzamide 1 mM, 37°C, pH 7, 15% inhibition Vibrio cholerae serotype O1
3-(3-(1-benzylpiperidin-4-yl)guanidino)benzamide 1 mM, 37°C, pH 7, 58% inhibition Vibrio cholerae serotype O1
3-(3-(4-bromobenzyl)guanidino)benzamide 1 mM, 37°C, pH 7, 22% inhibition Vibrio cholerae serotype O1
3-(3-benzylguanidino)benzamide 1 mM, 37°C, pH 7, 10% inhibition Vibrio cholerae serotype O1
3-(3-phenylguanidino)benzamide 1 mM, 37°C, pH 7, 12% inhibition Vibrio cholerae serotype O1
3-(3-tert-butylguanidino)benzamide 1 mM, 37°C, pH 7, 77% inhibition Vibrio cholerae serotype O1
ethyl 4-(3-(3-carbamoylbenzyl)guanidino)piperidine-1-carboxylate 1 mM, 37°C, pH 7, 34% inhibition Vibrio cholerae serotype O1

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4
-
diethylamino(benzylidine-amino)guanidine
-
Vibrio cholerae serotype O1
14
-
NAD+
-
Vibrio cholerae serotype O1

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
NAD+ + G-protein Vibrio cholerae serotype O1 NAD-dependent ADP-ribosylation of Arg201 of G-protein alpha-subunit, this locks the G-protein in its active state producing cAMP ?
-
?

Organism

Organism UniProt Comment Textmining
Vibrio cholerae serotype O1
-
-
-

Posttranslational Modification

Posttranslational Modification Comment Organism
glycoprotein
-
Vibrio cholerae serotype O1

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
diethylamino(benzylidine-amino)guanidine + NAD+ DEABAG Vibrio cholerae serotype O1 ?
-
?
NAD+ + G-protein NAD-dependent ADP-ribosylation of Arg201 of G-protein alpha-subunit, this locks the G-protein in its active state producing cAMP Vibrio cholerae serotype O1 ?
-
?

Subunits

Subunits Comment Organism
More catalytically active A subunit and five identical B subunits for receptor binding Vibrio cholerae serotype O1

Synonyms

Synonyms Comment Organism
cholera toxin
-
Vibrio cholerae serotype O1

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.008
-
3-((3-(4-bromobenzyl)guanidino)methyl)benzamide 37°C, pH 7, 1400fold more potent than NAD+ and 400fold more potent than diethylamino(benzylidine-amino)guanidine Vibrio cholerae serotype O1
0.013
-
3-((3-(1-benzylpiperidin-4-yl)guanidino)methyl)benzamide 37°C, pH 7 Vibrio cholerae serotype O1
0.03
-
3-((3,3-diisopropylguanidino)methyl)benzamide 37°C, pH 7 Vibrio cholerae serotype O1
0.05
-
3-((3-benzylguanidino)methyl)benzamide 37°C, pH 7 Vibrio cholerae serotype O1
0.071
-
3-((3-phenethylguanidino)methyl)benzamide 37°C, pH 7 Vibrio cholerae serotype O1
0.09
-
3-(3,3-diisopropylguanidino)benzamide 37°C, pH 7 Vibrio cholerae serotype O1
0.5
-
3-((3-tert-butylguanidino)methyl)benzamide 37°C, pH 7 Vibrio cholerae serotype O1
0.5
-
3-(3-phenylguanidino)benzamide 37°C, pH 7 Vibrio cholerae serotype O1

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.031
-
37°C, pH 7 Vibrio cholerae serotype O1 3-((3-(4-bromobenzyl)guanidino)methyl)benzamide
0.049
-
37°C, pH 7 Vibrio cholerae serotype O1 3-((3-(1-benzylpiperidin-4-yl)guanidino)methyl)benzamide
0.115
-
37°C, pH 7 Vibrio cholerae serotype O1 3-((3,3-diisopropylguanidino)methyl)benzamide
0.192
-
37°C, pH 7 Vibrio cholerae serotype O1 3-((3-benzylguanidino)methyl)benzamide
0.272
-
37°C, pH 7 Vibrio cholerae serotype O1 3-((3-phenethylguanidino)methyl)benzamide
0.35
-
37°C, pH 7 Vibrio cholerae serotype O1 3-(3,3-diisopropylguanidino)benzamide
2
-
37°C, pH 7 Vibrio cholerae serotype O1 3-((3-tert-butylguanidino)methyl)benzamide
2
-
37°C, pH 7 Vibrio cholerae serotype O1 3-(3-phenylguanidino)benzamide