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Literature summary extracted from

  • Javaid, S.; Ishtiaq, M.; Shaikh, M.; Hameed, A.; Choudhary, M.I.
    Thymidine esters as substrate analogue inhibitors of angiogenic enzyme thymidine phosphorylase in vitro (2017), Bioorg. Chem., 70, 44-56 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.4.2.4 5'-O-(2'',4''-dichlorobenzoyl)-thymidine-3'-O-2'',4''-dichlorobenzoate
-
 Escherichia coli
2.4.2.4 5'-O-(2''-methoxybenzoyl)-thymidine
-
 Escherichia coli
2.4.2.4 5'-O-(3''-bromobenzoyl)-thymidine competitive inhibition Escherichia coli
2.4.2.4 5'-O-(4''-bromobenzoyl)-thymidine-3'-O-4''-bromobenzoate noncompetitive inhibition Escherichia coli
2.4.2.4 5'-O-(4''-methoxybenzoyl)-thymidine competitive inhibition Escherichia coli
2.4.2.4 5'-O-(4''-methylbenzoyl)-thymidine competitive inhibition Escherichia coli
2.4.2.4 7-deazaxanthine noncompetitive inhibition Escherichia coli
2.4.2.4 additional information thymidine esters as substrate analogue inhibitors of angiogenic enzyme thymidine phosphorylase (TP) in vitro, molecular docking studies, erview. Thymidine is functionalized to develop TP inhibitors, derivatization of thymidine at C-5'/3' hydroxyl groups by reacting with different substituted benzoyl chlorides to produce corresponding esters for biological evaluation against TP activity. The pyrimidine moiety makes hydrogen bonds with Thr123, Gln156 and the bound water molecule while one of the bromobenzyl substitutions shows Pi-cation interaction with Arg171. No inhibition by 5'-O-(benzoyl)-thymidine-3'-O-benzoate, 5'-O-(4''-methyl-3''-nitrobenzoyl)-thymidine-3'-O-4''-methyl-3''-nitrobenzoate, 5'-O-(4''-methylbenzoyl)-thymidine-3'-O-4''-methylbenzoate, 5'-O-(3''-methylbenzoyl)-thymidine-3'-O-3''-methylbenzoate, 5'-O-(2''-methylbenzoyl)-thymidine-3'-O-2''-methylbenzoate, 5'-O-(3''-methoxybenzoyl)-thymidine-3'-O-3''-methoxybenzoate, 5'-O-(4''-fluorobenzoyl)-thymidine-3'-O-3''-fluorobenzoate, 5'-O-(4''-nitrobenzoyl)-thymidine-3'-O-4''-nitrobenzoate Escherichia coli

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.4.2.4 thymine + 2-deoxy-alpha-D-ribose 1-phosphate Escherichia coli
-
 thymidine + phosphate
-
 r

Organism

EC Number Organism UniProt Comment Textmining
2.4.2.4 Escherichia coli P0C037
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.4.2.4 commercial preparation
-
 Escherichia coli
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.4.2.4 additional information the pyrimidine moiety of thymidine is involved in making hydrogen bonds with the side chains of residues Arg171, Ser186, Lys190, while the deoxyribose moiety form hydrogen bond with a co-crystallized water molecule. The phosphate ion shows hydrogen bonding with Lys84, Ser95, Ser113, and a water molecule Escherichia coli ?
-
-
2.4.2.4 thymine + 2-deoxy-alpha-D-ribose 1-phosphate
-
 Escherichia coli thymidine + phosphate
-
 r

Synonyms

EC Number Synonyms Comment Organism
2.4.2.4 dthdpase
-
 Escherichia coli

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.4.2.4 30
-
 assay at Escherichia coli

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.4.2.4 additional information
-
 additional information inhibition kinetics, Lineweaver-Burk plots Escherichia coli
2.4.2.4 0.0078
-
 5'-O-(4''-bromobenzoyl)-thymidine-3'-O-4''-bromobenzoate pH not specified in the publication, 30°C Escherichia coli
2.4.2.4 0.0114
-
 5'-O-(3''-bromobenzoyl)-thymidine pH not specified in the publication, 30°C Escherichia coli
2.4.2.4 0.0125
-
 5'-O-(4''-methylbenzoyl)-thymidine pH not specified in the publication, 30°C Escherichia coli
2.4.2.4 0.0128
-
 5'-O-(4''-methoxybenzoyl)-thymidine pH not specified in the publication, 30°C Escherichia coli

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.4.2.4 0.0075
-
 pH not specified in the publication, 30°C Escherichia coli 5'-O-(4''-bromobenzoyl)-thymidine-3'-O-4''-bromobenzoate
2.4.2.4 0.0185
-
 pH not specified in the publication, 30°C Escherichia coli 5'-O-(4''-methylbenzoyl)-thymidine
2.4.2.4 0.0188
-
 pH not specified in the publication, 30°C Escherichia coli 5'-O-(4''-methoxybenzoyl)-thymidine
2.4.2.4 0.0333
-
 pH not specified in the publication, 30°C Escherichia coli 5'-O-(3''-bromobenzoyl)-thymidine
2.4.2.4 0.041
-
 pH not specified in the publication, 30°C Escherichia coli 7-deazaxanthine
2.4.2.4 0.09
-
 pH not specified in the publication, 30°C Escherichia coli 5'-O-(2''-methoxybenzoyl)-thymidine
2.4.2.4 0.146
-
 pH not specified in the publication, 30°C Escherichia coli 5'-O-(2'',4''-dichlorobenzoyl)-thymidine-3'-O-2'',4''-dichlorobenzoate