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Literature summary for 2.4.2.4 extracted from

  • Kocalka, P.; Rejman, D.; Vanek, V.; Rinnova, M.; Tomeckova, I.; Kralikova, S.; Petrova, M.; Pav, O.; Pohl, R.; Budesinsky, M.; Liboska, R.; Tocik, Z.; Panova, N.; Votruba, I.; Rosenberg, I.
    Structural diversity of nucleoside phosphonic acids as a key factor in the discovery of potent inhibitors of rat T-cell lymphoma thymidine phosphorylase (2010), Bioorg. Med. Chem. Lett., 20, 862-865.
    View publication on PubMed
Search for more literature for 2.4.2.4

Inhibitors

Inhibitors Comment Organism Structure
1-[2-deoxy-3,5-O-[phenyl(phosphono)methylidene]-b-L-erythro-pentofuranosyl]-5-methylpyrimidine-2,4(1H,3H)-dione 53% inhibition at 0.01 mM; 96% inhibition at 0.01 mM Rattus norvegicus
1-[3,5-O-(2-bromo-1-phosphonoethylidene)-2-deoxy-b-L-erythro-pentofuranosyl]-5-methylpyrimidine-2,4(1H,3H)-dione 74% inhibition at 0.01 mM; 80% inhibition at 0.01 mM Rattus norvegicus
[2-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]-2-oxoethyl]phosphonic acid 41% inhibition at 0.01 mM Rattus norvegicus
[5-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy]pentyl]phosphonic acid 86% inhibition at 0.01 mM Rattus norvegicus
[6-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy]hexyl]phosphonic acid 79% inhibition at 0.01 mM Rattus norvegicus
[[(2R,4R)-2-(hydroxymethyl)-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid 83% inhibition at 0.01 mM Rattus norvegicus
[[(2R,4S)-2-(hydroxymethyl)-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid 98% inhibition at 0.01 mM Rattus norvegicus
[[(2R,4S)-2-(hydroxymethyl)-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid complete inhibition at 0.01 mM Rattus norvegicus
[[(2S,4S)-2-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonothioyl]phosphonic acid complete inhibition at 0.01 mM Rattus norvegicus
[[(2S,4S)-2-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid complete inhibition at 0.01 mM Rattus norvegicus
[[(3R,4R)-3-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid 96% inhibition at 0.01 mM Rattus norvegicus
[[(3R,4R)-3-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid 99% inhibition at 0.01 mM Rattus norvegicus
[[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonothioyl]phosphonic acid 91% inhibition at 0.01 mM Rattus norvegicus
[[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid 97% inhibition at 0.01 mM Rattus norvegicus
[[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid 71% inhibition at 0.01 mM Rattus norvegicus
[[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-(prop-2-en-1-yloxy)ethoxy]methyl]phosphonic acid 90% inhibition at 0.01 mM Rattus norvegicus
[[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-phenoxyethoxy]methyl]phosphonic acid 99% inhibition at 0.01 mM Rattus norvegicus
[[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy](phenyl)methyl]phosphonic acid 91% inhibition at 0.01 mM Rattus norvegicus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0832
-
 thymine pH 6.7 Rattus norvegicus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
thymidine + phosphate Rattus norvegicus
-
 thymine + 2-deoxy-alpha-D-ribose 1-phosphate
-
 ?

Organism

Organism UniProt Comment Textmining
Rattus norvegicus
-
 Sprague-Dawley rats
-

Source Tissue

Source Tissue Comment Organism Textmining
T-cell lymphoma cell
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
thymidine + phosphate
-
 Rattus norvegicus thymine + 2-deoxy-alpha-D-ribose 1-phosphate
-
 ?

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.7
-
 assay at Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000011
-
 pH 6.7 Rattus norvegicus [[(2S,4S)-2-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
0.000015
-
 pH 6.7 Rattus norvegicus [[(2S,4S)-2-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonothioyl]phosphonic acid
0.000045
-
 pH 6.7 Rattus norvegicus [[(2R,4S)-2-(hydroxymethyl)-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
0.000045
-
 pH 6.7 Rattus norvegicus [[(3R,4R)-3-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid
0.00019
-
 pH 6.7 Rattus norvegicus [[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonothioyl]phosphonic acid
0.00022
-
 pH 6.7 Rattus norvegicus [[(3R,4R)-3-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
0.00025
-
 pH 6.7 Rattus norvegicus [[(2R,4S)-2-(hydroxymethyl)-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid
0.0003
-
 about, pH 6.7 Rattus norvegicus [[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-(prop-2-en-1-yloxy)ethoxy]methyl]phosphonic acid
0.00035
-
 pH 6.7 Rattus norvegicus [[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
0.00075
-
 pH 6.7 Rattus norvegicus [[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-phenoxyethoxy]methyl]phosphonic acid