2.4.2.4: thymidine phosphorylase
This is an abbreviated version!
For detailed information about thymidine phosphorylase, go to the full flat file.
Word Map on EC 2.4.2.4
-
2.4.2.4
-
5-fluorouracil
-
angiogenic
-
colorectal
-
thymidylate
-
dihydropyrimidine
-
capecitabine
-
microvessels
-
metastasis
-
clinicopathological
-
uridine
-
mngie
-
neurogastrointestinal
-
tumour
-
5'-deoxy-5-fluorouridine
-
fluoropyrimidine
-
thymine
-
5\'-dfur
-
resect
-
encephalomyopathy
-
prodrugs
-
lymph
-
intratumoral
-
deoxyuridine
-
uracil
-
orotate
-
phosphorolysis
-
dysmotility
-
tpi
-
cachexia
-
phosphorylases
-
leukoencephalopathy
-
ophthalmoplegia
-
medicine
-
5-fu-based
-
ptosis
-
taxanes
-
pseudo-obstruction
-
tegafur
-
deoxyribose
-
5-fluoro-2'-deoxyuridine
-
viii-related
-
hand-foot
-
fdump
-
ophthalmoparesis
-
trifluorothymidine
-
analysis
-
5-fluorouridine
-
anti-cd34
-
5-fluorouracil-based
-
tp-induced
-
2'-deoxyuridine
-
synthesis
-
fluoropyrimidine-based
- 2.4.2.4
- 5-fluorouracil
-
angiogenic
- colorectal
- thymidylate
- dihydropyrimidine
- capecitabine
-
microvessels
- metastasis
-
clinicopathological
- uridine
-
mngie
-
neurogastrointestinal
- tumour
- 5'-deoxy-5-fluorouridine
-
fluoropyrimidine
- thymine
-
5\'-dfur
-
resect
-
encephalomyopathy
-
prodrugs
- lymph
-
intratumoral
- deoxyuridine
- uracil
- orotate
-
phosphorolysis
-
dysmotility
- tpi
-
cachexia
- phosphorylases
- leukoencephalopathy
- ophthalmoplegia
- medicine
-
5-fu-based
-
ptosis
-
taxanes
- pseudo-obstruction
-
tegafur
- deoxyribose
- 5-fluoro-2'-deoxyuridine
-
viii-related
-
hand-foot
- fdump
- ophthalmoparesis
- trifluorothymidine
- analysis
- 5-fluorouridine
-
anti-cd34
-
5-fluorouracil-based
-
tp-induced
- 2'-deoxyuridine
- synthesis
-
fluoropyrimidine-based
Reaction
Synonyms
angiogenic factor platelet-derived endothelial cell growth factor/thymidine phosphorylase, animal growth regulators, blood platelet-derived endothelial cell growth factors, blood platelet-derived endothelial cell growth factor, deoA, deoxythymidine phosphorylase, dthdpase, EC 2.4.2.23, gliostatin, gliostatins, GLS, HTP, More, PD-ECGF, PD-ECGF/TP, PD-ECGF/TP platelet-derived endothelial cell growth factor, PDECGF, phosphorylase, thymidine, platelet derived endothelial cell growth factor, platelet derived endothelial cell grwoth factor, platelet derived-endothelial cell growth factor, platelet-derived endothelial cell growth factor, platelet-derived endothelial cell growth factor/thymidine phosphorylase, platelet-derived endotherial cell growth factor, ppnP, pynpase, pyrimidine deoxynucleoside phosphorylase, pyrimidine nucleoside phosphorylase, pyrimidine phosphorylase, pyrimidine/purine nucleoside phosphorylase, TDRPASE, ThdPase, thymidine phosphorylase, thymidine Pi deoxyribosyltransferase, thymidine-orthophosphate deoxyribosyltransferase, thymidine:orthophosphate deoxy-D-ribosyltransferase, Tpase, TYMP
ECTree
2.4.2.4 thymidine phosphorylaseAdvanced search results
results (
results (Inhibitors
Inhibitors on EC 2.4.2.4 - thymidine phosphorylase
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INHIBITOR 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
IMAGE
(2R,3R,4S,5R)-9-(3,4-dihydroxy-5-trityloxymethyl-tetrahydrofuran-2-yl)-1,9-dihydropurin-6-one
(6aS)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
uncompetitive inhibition
(E)-1-((2-fluorophenyl)(hydroxyimino)methyl)-5-iodopyrimidine-2,4(1H,3H)-dione
-
(E)-1-((4-chlorophenyl)(hydroxyimino)methyl)-5-iodopyrimidine-2,4(1H,3H)-dione
-
(E)-1-((4-ethylphenyl)(hydroxyimino)methyl)-5-iodopyrimidine-2,4(1H,3H)-dione
-
(E)-1-((4-fluorophenyl)(hydroxyimino)methyl)-5-iodopyrimidine-2,4(1H,3H)-dione
-
(E)-1-((hydroxyimino)(3-methoxyphenyl)methyl)-5-iodopyrimidine-2,4(1H,3H)-dione
-
(E)-1-((hydroxyimino)(4-methoxyphenyl)methyl)-5-iodopyrimidine-2,4(1H,3H)-dione
-
(E)-1-((hydroxyimino)(p-tolyl)methyl)-5-iodopyrimidine-2,4(1H,3H)-dione
-
(E)-N'-(3,5-dichloro-2-hydroxybenzylidene)isoquinoline-3-carbohydrazide
-
(E)-N'-(3-hydroxy-5-methoxybenzylidene)isoquinoline-3-carbohydrazide
-
(R)-(1-fluoro-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propan-2-yloxy)methylphosphonic phosphoric anhydride
-
strong inhibitory effect
(S)-(1-fluoro-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propan-2-yloxy)methylphosphonic phosphoric anhydride
-
strong inhibitory effect
(Z)-1-((2-fluorophenyl)(hydroxyimino)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((3,4-dichlorophenyl)(hydroxyimino)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((3-fluorophenyl)(hydroxyimino)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((4-bromophenyl)(hydroxyimino)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((4-chlorophenyl)(hydroxyimino)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((4-ethylphenyl)(hydroxyimino)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((4-fluorophenyl)(hydroxyimino)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((hydroxyimino)(3-methoxyphenyl)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((hydroxyimino)(4-methoxyphenyl)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((hydroxyimino)(m-tolyl)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((hydroxyimino)(p-tolyl)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((hydroxyimino)(phenyl)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-1-((hydroxyimino)(thiophen-2-yl)methyl)-6-methylpyrimidine-2,4(1H,3H)-dione
-
(Z)-N'-((4-chloro-2-oxo-4a,8a-dihydro-2H-chromen-3-yl)methylene)-2-oxo-1,2,4a,8a-tetrahydroquinoline-6-carbohydrazide
-
(Z)-N'-(3-chloro-4-hydroxybenzylidene)isoquinoline-3-carbohydrazide
-
(Z)-N'-(4-hydroxy-3,5-dimethoxybenzylidene)isoquinoline-3-carbohydrazide
-
([(1R)-2-fluoro-1-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([(1R)-2-fluoro-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([(1R)-2-fluoro-1-[(5-methyl-2,6-dioxotetrahydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
low inhibitory effect
([(1R)-2-hydroxy-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([(1S)-2-fluoro-1-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([(1S)-2-fluoro-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([(1S)-2-fluoro-1-[(5-methyl-2,6-dioxotetrahydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
low inhibitory effect
([(1S)-2-hydroxy-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([2,2,2-trifluoro-1-[(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl]oxy]methyl)phosphonic acid
-
-
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
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
2-(2-methyl-1H-indol-3-yl)-N'-(2,4,6-trihydroxybenzylidene)acetohydrazide
-
2-(3,4-dichlorophenyl)-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
2-(3-bromophenyl)-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-(3-methylphenyl)-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-(4-bromo-3-methylphenyl)-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-(4-bromophenyl)-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-(4-methylphenyl)-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-(benzylsulfanyl)-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-(diphenylmethyl)-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
2-(furan-2-yl)-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-(methylsulfanyl)-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-(methylsulfanyl)-7-sulfanylidene-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5(4H)-one
-
-
2-(pyridin-2-yl)-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-[(2-phenylethyl)sulfanyl]-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-[(3,4-dichlorophenyl)methyl]-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
2-[(3-phenylpropyl)sulfanyl]-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-[(5-(4-chlorophenyl)-4H-1,2,4-triazol-3-yl)thio]acetic acid
the angiogenic response of 4d is estimated using the chick chorionic allantoic membrane (CAM) assay
2-[[(5-chloro-2-methylidene-6-oxo-1,2,3,6-tetrahydropyrimidin-4-yl)methyl]sulfanyl]-7-phenyl-2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H)-one
-
3-(((4-chlorophenyl)amino)(phenyl)methyl)-5-(2,6-dimethylphenyl)1,3,4-oxadiazole-2(3H)-thione
-
3-(((4-chlorophenyl)amino)methyl)-5-(2-iodophenyl)-1,3,4-oxadiazole-2(3H)-thione
-
3-((4-benzylpiperazin-1-yl)methyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole-2(3H)-thione
-
3-((5-(4-chlorophenyl)-2-thioxo-1,3,4-oxadiazol-3(2H)-yl)methyl)thiazolidine-2,4-dione
-
3-((benzylamino)methyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole-2(3H)-thione
-
3-(3-(quinoxalin-2-yl)thiazolo[2,3-c][1,2,4]triazol-5-yl)benzene-1,2-diol
-
3-([(2-([-(4-oxo-4H-chromen-3-yl)methylidene]amino)ethyl)imino] methyl)-4H-chromen-4-one
-
-
3-[(2,3-dimethylanilino)methyl]-5-(4-methylphenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
3-[(2-chloroanilino)methyl]-5-(2-hydroxyphenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
3-[(2-chloroanilino)methyl]-5-(4-chlorophenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
3-[(2-methoxy-6-nitroanilino)methyl]-5-(4-methylphenyl)-1,3,4-oxadiazole-2(3H)-thione
-
3-[(2-methylanilino)methyl]-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
3-[(3,4-dichloroanilino)methyl]-5-(4-methylphenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
3-[(3,4-dimethylanilino)methyl]-5-(4-methylphenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
3-[(3-methoxyanilino)methyl]-5-(4-methylphenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
3-[(4-bromoanilino)methyl]-5-(2-bromophenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
3-[(4-bromoanilino)methyl]-5-(4-chlorophenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
3-[(4-methylanilino)methyl]-5-(4-methylphenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
3-[3-[(2-methylphenyl)methyl]-2,4,5-trioxoimidazolidin-1-yl]propanamide
-
3-[[(2-phenylethyl)amino]methyl]-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
3-[[(4-methoxy-3'-nitro[1,1'-biphenyl]-3-yl)amino]methyl]-5-(4-methylphenyl)-1,3,4-oxadiazole-2(3H)-thione
-
-
4,4'-[(2R,3S)-2,3-dimethylbutane-1,4-diyl]di(benzene-1,2-diol)
competitive inhibition
4-(2,5-difluorobenzyl)-N-(2-fluorophenyl)piperazine-1-carbothioamide
-
4-(2,5-difluorobenzyl)-N-(2-methoxyphenyl)piperazine-1-carbothioamide
-
4-(2,5-difluorobenzyl)-N-(3-fluorophenyl)piperazine-1-carbothioamide
-
4-(2,5-difluorobenzyl)-N-(3-methoxyphenyl)piperazine-1-carbothioamide
-
4-(2,5-difluorobenzyl)-N-(3-nitrophenyl)piperazine-1-carbothioamide
-
4-(2,5-difluorobenzyl)-N-(4-fluorophenyl)piperazine-1-carbothioamide
-
4-(2,5-difluorobenzyl)-N-(4-methoxyphenyl)piperazine-1-carbothioamide
-
4-(2,5-difluorobenzyl)-N-(4-nitrophenyl)piperazine-1-carbothioamide
-
4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)-N'-(1-(4-nitrophenyl)ethylidene)benzohydrazide
-
4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)-N'-(2,3,4-trihydroxybenzylidene)benzohydrazide
-
4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)-N'-(2,3,4-trimethoxybenzylidene)benzohydrazide
-
4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)-N'-(2-nitrobenzylidene)benzohydrazide
-
4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)-N'-(3,4,5-trimethoxybenzylidene)benzohydrazide
-
4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)-N'-(4-(phenoxymethyl)benzylidene)benzohydrazide
-
4-[(Z)-[(3-hydroxynaphthalen-2-yl)methylidene]amino]-1,5-dimethyl-2-phenylpyrazolidin-3-one
-
5'-O-(2'',4''-dichlorobenzoyl)-thymidine-3'-O-2'',4''-dichlorobenzoate
-
5'-O-(4''-bromobenzoyl)-thymidine-3'-O-4''-bromobenzoate
noncompetitive inhibition
5-(2-bromophenyl)-3-[(2-chloroanilino)methyl]-1,3,4-oxadiazole-2(3H)-thione
-
-
5-(2-bromophenyl)-3-[(2-methoxyanilino)methyl]-1,3,4-oxadiazole-2(3H)-thione
-
-
5-(2-chlorophenyl)-3-(((4-chlorophenyl)amino)(phenyl)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(2-chlorophenyl)-3-((thiazol-2-ylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-(((2-nitrophenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-(((3,3-diphenylpropyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-(((4-fluorophenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-(((4-hydroxyphenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-((2-methyl-1H-imidazol-1-yl)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-((4-cyclohexylpiperazin-1-yl)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-((cyclohexylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-((dicyclohexylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-((naphthalen-1-ylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-((phenylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-((thiazol-2-ylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione
-
5-(4-chlorophenyl)-3-[(2-methoxyanilino)methyl]-1,3,4-oxadiazole-2(3H)-thione
-
-
5-(4-chlorophenyl)-3-[(2-methylanilino)methyl]-1,3,4-oxadiazole-2(3H)-thione
-
-
5-(4-pyridyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
binding mode, modeling
5-(benzylsulfanyl)-2-phenyl-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
5-(methylsulfanyl)-2-phenyl-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
5-bromo-6-(2-imino-pyrrolidin-1-yl)methyl-uracil
-
tightbinding stoichiometric inhibitor of recombinant Escherichia coli thymidine phosphorylase, can be used as active-site titrants for it using either thymidine or 5-nitro-2'-deoxyuridine as substrate
5-bromo-6-amino-uracil
-
enzyme inhibition results in a significant increase in basal and oxidative stress-induced apoptosis, the effect is abrogated by supplementation with 2-deoxy-D-ribose-1-phosphate
5-bromo-6-[[(1,3-dihydroxypropan-2-yl)amino]methyl]pyrimidine-2,4(1H,3H)-dione
-
5-bromo-6-[[(2,3-dihydroxypropyl)amino]methyl]pyrimidine-2,4(1H,3H)-dione
-
5-chloro-6-(2-imino-pyrrolidin-1-yl)methyluracil
-
tightbinding stoichiometric inhibitor of recombinant Escherichia coli thymidine phosphorylase, can be used as active-site titrants for it using either thymidine or 5-nitro-2'-deoxyuridine as substrate
5-chloro-6-(2-iminopyrrolidin-1-yl)methyl-2,4(1H,3H)-pyrimidinedione hydrochloride
-
-
5-chloro-6-[([4-oxo-8-[4-(pentafluoro-lambda6-sulfanyl)phenyl]-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazin-2-yl]sulfanyl)methyl]pyrimidine-2,4(1H,3H)-dione
-
5-chloro-6-[[(1,3-dihydroxypropan-2-yl)amino]methyl]pyrimidine-2,4(1H,3H)-dione
-
5-fluoro-1-(3,6,9,12,15,18,21,24-octaoxahexatriacontan-1-yl)pyrimidine-2,4(1H,3H)-dione
43% competitive inhibition at 0.04 mM
5-fluoro-1-(3,6,9,12,15,18,21-heptaoxatritriacontan-1-yl)pyrimidine-2,4(1H,3H)-dione
40% competitive inhibition at 0.04 mM
5-fluoro-1-(3,6,9,12,15,18-hexaoxatriacontan-1-yl)pyrimidine-2,4(1H,3H)-dione
38% competitive inhibition at 0.04 mM
5-fluoro-6-([[2-hydroxy-1-(hydroxymethyl)ethyl]amino]methyl)pyrimidine-2,4(1H,3H)-dione
-
-
5-fluoro-6-[(4H-1,2,4-triazol-4-ylamino)methyl]pyrimidine-2,4(1H,3H)-dione
-
-
5-Hydroxymethyluracil
-
35% inactivation at 2 mM
5-Iodouracil
His116 directly interacts with the inhibitor via its NE2 group, enzyme binding structure, overview
5-sulfanylidene-2-(thiophen-2-yl)-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
6-(((1,3-dihydroxypropan-2-yl)amino)methyl)-5-iodopyrimidine-2,4(1H,3H)-dione
the inhibitor shows a noncompetitive inhibition mode with both thymidine and inorganic phosphate substrates. Effect of 8g on cell viabilities of different cancer cell lines, overview
6-(2-amino-imidazol-1-yl)methyl-5-bromouracil
-
tightbinding stoichiometric inhibitor of recombinant Escherichia coli thymidine phosphorylase, can be used as active-site titrants for it using either thymidine or 5-nitro-2'-deoxyuridine as substrate
6-(2-amino-imidazol-1-yl)methyl-5-chlorouracil
-
tightbinding stoichiometric inhibitor of recombinant Escherichia coli thymidine phosphorylase, can be used as active-site titrants for it using either thymidine or 5-nitro-2'-deoxyuridine as substrate
6-([[2-hydroxy-1-(hydroxymethyl)ethyl]amino]methyl)pyrimidine-2,4(1H,3H)-dione
-
-
6-methoxy-2-oxo-2H-1-benzopyran-7-yl 6-O-[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]-beta-D-glucopyranoside
uncompetitive inhibition
6-Methyluracil
-
competitive, 86% inhibition at 10 mM and 36% inhibition at 1 mM
6-[[(2,3-dihydroxypropyl)(methyl)amino]methyl]-5-iodopyrimidine-2,4(1H,3H)-dione
-
7-(4-tert-butylphenyl)-2-sulfanylidene-2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H)-one
-
7-(4-tert-butylphenyl)-2-[[(5-chloro-2-methylidene-6-oxo-1,2,3,6-tetrahydropyrimidin-4-yl)methyl]sulfanyl]-2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H)-one
-
7-(methylsulfanyl)-2-phenyl-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5(4H)-one
-
7-phenyl-2-sulfanylidene-2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H)-one
-
8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one
uncompetitive inhibition
8-phenyl-2-sulfanylidene-2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H)-one
-
8-[4-(pentafluoro-lambda6-sulfanyl)phenyl]-2-sulfanylidene-2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H)-one
-
aurothioglucose
-
the expression of tyhmidine phosphorylase mRNA is significantly decreased by stimulation with aurothioglucose
Bromouracil
-
100% inactivation at 1 mM
deoxyadenosine
-
20% inactivation at 1 mM
dexamethasone
-
the expression of tyhmidine phosphorylase mRNA is significantly decreased by stimulation with dexamethasone
diethyl ((2-[(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)(difluoro)methyl)phosphonate
-
-
diethyl ((2-[(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)methyl)phosphonate
-
-
diethyl ((2-[(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)methyl)phosphonate
-
-
diethyl (2-[(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)methyl]benzyl)phosphonate
-
-
diethyl [(Z)-4-(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)but-2-en-1-yl]phosphonate
-
-
disodium ((2-[(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)(difluoro)methyl)phosphonate
-
-
disodium ((2-[(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)methyl)phosphonate
-
-
disodium ((2-[(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)methyl)phosphonate
-
-
disodium (2-[(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)methyl]benzyl)phosphonate
-
-
disodium [(Z)-4-(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)but-2-en-1-yl]phosphonate
-
-
ethyl 4-(4-chlorophenyl)-2-oxo-6-([(pyridin-4-yl)formohydrazido]methyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 4-(4-chlorophenyl)-2-oxo-6-([[(5-phenyl-2-sulfanylidene-1,3,4-oxadiazol-3(2H)-yl)methyl]amino]methyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 4-(4-chlorophenyl)-2-oxo-6-[[(E)-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)amino]methyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 4-(4-chlorophenyl)-6-((3-methyl-5-oxo-2H-pyrazol-1(5H)-yl)methyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 4-(4-chlorophenyl)-6-([(E)-[(4-chlorophenyl)methylidene]amino]methyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 4-(4-chlorophenyl)-6-([(E)-[(4-methoxyphenyl)methylidene]amino]methyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 4-(4-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 4-(4-chlorophenyl)-6-[([[5-(4-chlorophenyl)-2-sulfanylidene-1,3,4-oxadiazol-3(2H)-yl]methyl]amino)methyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 4-(4-chlorophenyl)-6-[([[5-(4-methoxyphenyl)-2-sulfanylidene-1,3,4-oxadiazol-3(2H)-yl]methyl]amino)methyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 4-(4-chlorophenyl)-6-[([[5-(4-methylphenyl)-2-sulfanylidene-1,3,4-oxadiazol-3(2H)-yl]methyl]amino)methyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 6-((1H-imidazol-1-yl)methyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
-
ethyl 6-((2-aminobenzoyloxy)methyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate
-
ethyl 6-((benzylamino)methyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
-
ethyl 6-(benzoyloxymethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
-
ethyl 6-([(E)-[(4-bromophenyl)methylidene]amino]methyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl 6-[([[5-(4-bromophenyl)-2-sulfanylidene-1,3,4-oxadiazol-3(2H)-yl]methyl]amino)methyl]-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ethyl [3-[(2-methylphenyl)methyl]-2,4,5-trioxoimidazolidin-1-yl]acetate
-
hydrogen [[(1R,2S,4S)-2-(hydroxymethyl)-4-(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)pyrrolidinium-1-yl]methyl]phosphonate
-
-
methyl-4-((2-(2-(2-methyl-1H-indol-3-yl)acetyl)hydrazono)methyl)benzoate
-
N'-(2,3-dihydroxybenzylidene)-2-(2-methyl-1H-indol-3-yl)acetohydrazide
-
N'-(2,4-dichlorobenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(2,4-dihydroxybenzylidene)-2-(2-methyl-1H-indol-3-yl)acetohydrazide
-
N'-(2,5-dihydroxybenzylidene)-2-(2-methyl-1H-indol-3-yl)acetohydrazide
-
N'-(2-cyanobenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(2-hydroxy-3-methoxybenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(3,4-dihydroxybenzylidene)-2-(2-methyl-1H-indol-3-yl)acetohydrazide
-
N'-(3,5-dichloro-2-hydroxybenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(3,5-dihydroxybenzylidene)-2-(2-methyl-1H-indol-3-yl)acetohydrazide
-
N'-(3-aminobenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(3-cyanobenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(3-hydroxy-4-methoxybenzylidene)-2-(2-methyl-1H-indol-3-yl)acetohydrazide
-
N'-(3-hydroxy-4-methoxybenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(4-(dimethylamino)benzylidene)-2-(2-methyl-1H-indol-3-yl)acetohydrazide
-
N'-(4-(dimethylamino)benzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(4-chlorobenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(4-cyanobenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(4-hydroxy-3,5-dimethoxybenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(4-hydroxy-3-methoxybenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(5-bromo-2-methoxybenzylidene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N'-(anthracen-9-ylmethylene)-4-(5-(isoquinolin-3-yl)-1,3,4-oxadiazol-2-yl)benzohydrazide
-
N-((5-(4-chlorophenyl)-2-thioxo-1,3,4-oxadiazole-3(2H)-yl)methyl)3(trifluoromethyl) benzamide
-
N-(2-bromophenyl)-4-(2,5-difluorobenzyl)piperazine-1-carbothioamide
-
N-(2-chlorophenyl)-4-(2,5-difluorobenzyl)piperazine-1-carbothioamide
-
N-(3,4-dichlorophenyl)-4-(2,5-difluorobenzyl)piperazine-1-carbothioamide
-
N-(3-bromophenyl)-4-(2,5-difluorobenzyl)piperazine-1-carbothioamide
-
N-(4-bromophenyl)-4-(2,5-difluorobenzyl)piperazine-1-carbothioamide
-
N-(4-oxo-2-sulfanylidene-8-[[4-(trifluoromethyl)phenyl]methyl]-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazin-7-yl)thiourea
-
N-(8-benzyl-4-oxo-2-sulfanylidene-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazin-7-yl)thiourea
-
N-(adamantan-1-yl)-4-(2,5-difluorobenzyl)piperazine-1-carbothioamide
-
TAS-102
is a combination of trifluridine (FTD, a fluorinated thymidine analogue) and tipiracil hydrochloride (TPI, a TP inhibitor) at a 1:0.5 molar ratio. The FTD monophosphate metabolite trifluoromethyl deoxyuridine 5'-monophosphate inhibits TS by binding to its active site, but the inhibition is rapidly reversible. Phosphorylation of trifluoromethyl deoxyuridine 5'-monophosphate results in the formation of trifluoromethyl deoxyuridine 5'-triphosphate that is misincorporated into DNA. Importantly, the concentration of FTD incorporated into DNA is approximately 300fold higher than that of 5FU. FTD is rapidly degraded by TP to its inactive metabolite (5-trifluoromethyl-2,4(1H,3H)-pyrimidinedione). Thus, the main mechanism of action of TAS-102 is its misincorporation into DNA. Tipiracil inhibits the main catabolic pathway of the drug, thus enhancing its half-life and cytotoxicity
trifluridine
FTD, is rapidly degraded by TP to its inactive metabolite, 5-trifluoromethyl-2,4(1H,3H)-pyrimidinedione
[(2S,3aR,4R,6R,6aR)-4-(5-chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-6-(hydroxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]phosphonic acid
-
-
[(2S,4R,5S)-5-(2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxy-1,3-oxazolidin-2-yl]phosphonic acid
-
-
[(3aR,4R,6R,6aR)-4-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-6-(hydroxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]phosphonic acid
-
-
[(3aR,4R,6R,6aR)-4-(hydroxymethyl)-6-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]phosphonic acid
-
-
[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
[5-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy]pentyl]phosphonic acid
-
86% inhibition at 0.01 mM
[6-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy]hexyl]phosphonic acid
-
79% inhibition at 0.01 mM
[[(1R)-2-(5-ethyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-(fluoromethyl)ethoxy]methyl]phosphonic acid
[[(2R,3aR,6aR)-6-(4-amino-5-methyl-2-oxopyrimidin-1(2H)-yl)-4-(hydroxymethyl)hexahydrofuro[3,4-b]furan-2-yl]methyl]phosphonic acid
-
[[(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
[[(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
[[(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
[[(2S,3aR,6aR)-6-(4-amino-5-methyl-2-oxopyrimidin-1(2H)-yl)-4-(hydroxymethyl)hexahydrofuro[3,4-b]furan-2-yl]methyl]phosphonic acid
-
[[(2S,3aR,6aS)-4-(4-amino-5-methyl-2-oxopyrimidin-1(2H)-yl)-6-(hydroxymethyl)hexahydrofuro[3,4-b]furan-2-yl]methyl]phosphonic acid
-
[[(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
[[(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
[[(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
[[(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
[[(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
[[(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
[[(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
[[(3S,4R)-3-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
-
-
[[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
[[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-phenoxyethoxy]methyl]phosphonic acid
-
99% inhibition at 0.01 mM
[[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy](phenyl)methyl]phosphonic acid
-
91% inhibition at 0.01 mM
(2R,3R,4S,5R)-9-(3,4-dihydroxy-5-trityloxymethyl-tetrahydrofuran-2-yl)-1,9-dihydropurin-6-one
KIN59
(2R,3R,4S,5R)-9-(3,4-dihydroxy-5-trityloxymethyl-tetrahydrofuran-2-yl)-1,9-dihydropurin-6-one
KIN59
(R)-1-[3-fluoro-2-(phosphonomethoxy)-propyl]thymine
-
93% inhibition at 0.01 mM
(R)-1-[3-fluoro-2-(phosphonomethoxy)-propyl]thymine
-
at 0.01 mM, 82% inhibition of V79 cell-expressed thymidine phosphorylase, 56% inhibition of thymidine phosphorylase from placenta
(R)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]thymine
-
98% inhibition at 0.01 mM
(R)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]thymine
-
at 0.01 mM, 84% inhibition of V79 cell-expressed thymidine phosphorylase, 84% inhibition of thymidine phosphorylase from placenta
([(1R)-2-fluoro-1-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
-
([(1R)-2-fluoro-1-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
-
([(1R)-2-fluoro-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
98% inhibition at 0.01 mM
([(1R)-2-fluoro-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
at 0.01 mM, complete inhibition of V79 cell-expressed thymidine phosphorylase
([(1R)-2-hydroxy-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
complete inhibition at 0.01 mM
([(1R)-2-hydroxy-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
at 0.01 mM, 91% inhibition of V79 cell-expressed thymidine phosphorylase, 79% inhibition of thymidine phosphorylase from placenta
([(1S)-2-fluoro-1-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
-
([(1S)-2-fluoro-1-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
-
([(1S)-2-fluoro-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
93% inhibition at 0.01 mM
([(1S)-2-fluoro-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
at 0.01 mM, complete inhibition of V79 cell-expressed thymidine phosphorylase
([(1S)-2-hydroxy-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
94% inhibition at 0.01 mM
([(1S)-2-hydroxy-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
at 0.01 mM, complete of V79 cell-expressed thymidine phosphorylase, 95% inhibition of thymidine phosphorylase from placenta
([2,2,2-trifluoro-1-[(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
-
([2,2,2-trifluoro-1-[(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
-
1-[2-(phosphonomethoxy)ethyl]thymine
-
at 0.01 mM, complete inhibition of V79 cell-expressed thymidine phosphorylase, 85% inhibition of thymidine phosphorylase from placenta
2-benzyl-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-benzyl-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
2-deoxy-alpha-D-ribose 1-phosphate
dRib-1-P , a non-competitive product inhibitor of the forward reaction, in the reverse reaction, dRib-1-P enhanced the binding of thymine
2-deoxy-alpha-D-ribose 1-phosphate
dRib-1-P is a competitive product inhibitor of the forward reaction, in the reverse reaction, dRib-1-P enhances the binding of thymine
2-deoxy-D-ribose
-
product inhibition
2-mercapto-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one
-
25% inhibition at 0.045 mM
2-phenyl-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
-
2-phenyl-5-sulfanylidene-5,6-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
-
2-phenyl-7-sulfanylidene-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5(4H)-one
-
-
2-phenyl-7-sulfanylidene-6,7-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazin-5(4H)-one
-
4-(2,5-difluorobenzyl)-N-(4-(trifluoromethyl)phenyl)piperazine-1-carbothioamide
-
4-(2,5-difluorobenzyl)-N-(4-(trifluoromethyl)phenyl)piperazine-1-carbothioamide
-
5'-O-trityl-inosine
-
i.e. KIN59, IC50: 0.044 mM, noncompetitively inhibits, when thymidine or phosphate is the variable substrate. Suppresses thymidine phosphorylase-triggered angiogenesis via a noncompetitive mechanism of action
5'-O-trityl-inosine
-
IC50: 0.044 mM, reversible, noncompetitive inhibition with respect to thymidine and phosphate
5'-O-trityl-inosine
-
i.e. KIN59, IC50: 0.067 mM, noncompetitively inhibits, when thymidine or phosphate is the variable substrate. Suppresses thymidine phosphorylase-triggered angiogenesis via a noncompetitive mechanism of action
5'-O-tritylinosine
i.e. KIN59, noncompetitive. Inhibitor docking and conformational changes, molecular modeling using the crystal structure of the enzyme, molecular dynamics simulations, binding site and mode, overview
5'-O-tritylinosine
-
i.e. KIN59, a small-molecule inhibitor. KIN59 not only prevents the formation of new blood vessels but also promotes the degradation of small pre-existing immature blood vessels, not due to unspecific cell toxicity
5-chloro-6-[1-(2-iminopyrrolidinyl)methyl] uracil hydrochloride
TPI
5-chloro-6-[1-(imminopyrrolidinyl)methyl]uracil hydrochloride
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i.e. TPI, competitive
5-fluoro-6-[(2-aminoimidazol-1-yl)methyl]uracil
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i.e. AIFU, synthesis, overview, uncompetitive with respect to phosphate, acts as transition state analogs, mimicking the anionic thymine leaving group anchored by their protonated side chains to the enzyme-bound phosphate by electrostatic and H-bonding interactions, modeling of ligand binding at the active site, overview
5-fluoro-6-[(2-aminoimidazol-1-yl)methyl]uracil
i.e. AIFU, synthesis, overview, uncompetitive with respect to phosphate, acts as transition state analogs, mimicking the anionic thymine leaving group anchored by their protonated side chains to the enzyme-bound phosphate by electrostatic and H-bonding interactions, modeling of ligand binding at the active site, overview
5-fluorouracil
5-FU, is an anticancer drug, which inhibits human thymidine phosphorylase (hTP) and plays a key role in maintaining the process of DNA replication and repair. It is involved in regulating pyrimidine nucleotide production, by which it inhibits the mechanism of cell proliferation and cancerous tumor growth. In the cell, 80% of 5-FU is metabolized by dihydropyrimidine dehydrogenase (DPD)
5-fluorouracil
5FU, 5-fluorouracil pharmacodynamics, overview. 5FU catabolism is driven by the activity of dihydropyrimidine dehydrogenase (DPD). The expression of the enzymes orotate phosphoribosyl transferase (OPRT), TK, TP, TS and DPD has been demonstrated to influence 5FU activity both in in vitro and in vivo models. 5-Fluoro-2'-deoxyuridine (FUdR), an active antiblastic drug as it can be converted to FdUMP by thymidine kinase (TK), resulting in thymidylate synthase (TS) blockade. FUdR can be hydrolyzed by TP completing the three-step process from capecitabine to 5FU
6-[(2'-aminoimidazol-1'-yl)methyl]-5-chlorouracil
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IC50: below 0.0000206 mM
6-[(2'-aminoimidazol-1'-yl)methyl]-5-chlorouracil
IC50: below 0.000049 mM
7-deazaxanthine
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docking conformation of the standard inhibitor in the active site of thymidine phosphorylase, modeling, overview. Modeling of the three-dimensional structures of piperazine derivatives
ribose 1-phosphate
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20% inactivation at 1.5 mM
thymidine
yields a non-competitive inhibition pattern in agreement with a random mechanism
thymine
thymine is a product activator, but becomes a substrate inhibitor at concentrations eight times higher than its Km. Thymine is an effector rather than a product inhibitor
thymine
thymine is a product activator, but becomes a competitive inhibitor at concentrations eight times higher than its Km
uridine
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competitive 27% inactivation at 1 mM
[8-(2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-1-yl)octyl]phosphonic acid
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[8-(2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-1-yl)octyl]phosphonic acid
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no antitumor activity found with CCRF-CEM T-lymphoblastoid cells, human promyelocytic leukemia HL-60 cells, human cervix carcinoma HeLa S3 cells
[8-(2,4-dioxo-2,3,4,7-tetrahydro-1H-pyrrolo[2,3-d]pyrimidin-1-yl)octyl]phosphonic acid
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[8-(2,4-dioxo-2,3,4,7-tetrahydro-1H-pyrrolo[2,3-d]pyrimidin-1-yl)octyl]phosphonic acid
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no antitumor activity found with CCRF-CEM T-lymphoblastoid cells, human promyelocytic leukemia HL-60 cells, human cervix carcinoma HeLa S3 cells
[[(1R)-2-(5-ethyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-(fluoromethyl)ethoxy]methyl]phosphonic acid
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[[(1R)-2-(5-ethyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-(fluoromethyl)ethoxy]methyl]phosphonic acid
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[[2-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy]methyl]phosphonic acid
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[[2-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy]methyl]phosphonic acid
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[[2-(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethoxy]methyl]phosphonic acid
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complete inhibition at 0.01 mM
[[2-(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethoxy]methyl]phosphonic acid
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at 0.01 mM, complete inhibition of V79 cell-expressed thymidine phosphorylase, 82% inhibition of thymidine phosphorylase from placenta
additional information
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photoinactivation in presence of thymine, thymidine and some halogenated analogs
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additional information
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not inhibited by 5-chloro-6-methyl-3H-pyrimidin-4-one, 5-chloro-6-[1-(2-iminopyrrolidinyl)methyl]-3H-pyrimidin-4-one, 6H-imidazo[1,2-c]pyrimidin-5-one, 7H-pyrrolo[2,3-d]pyrimidin-2(1H)-one, and 7H-pyrrolo[2,3-d]pyrimidine
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additional information
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Schiff bases of 3-formylchromone as thymidine phosphorylase inhibitors, no inhibition by 3-formylchromone and 3-methyl-7-hydroxychromone, and by derivatives 3-[(4-pyridinylimino) methyl]-4H-chromen-4-one, 3-[(3-pyridinylimino) methyl]-4H-chromen-4-one, 3-([(3-methoxyphenyl)imino]methyl)-4H-chromen-4-one, 3-([(2-methoxy-4-nitrophenyl) imino] methyl)-4Hchromen-4-one, 2-([-(4-oxo-4H-chromen-3-yl) methylidene]amino)benzoic acid, 3-([(4-methylphenyl)imino]methyl)-4H-chromen-4-one, 3-([(2,6-dimethylphenyl)imino]methyl)-4H-chromen-4-one, and 3-[bis(tert-butylamino)methyl]-4H-chromen-4-one, overview
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additional information
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design of benzopyrazine analogues as potent inhibitors of thymidine phosphorylase, synthesis of quinoxaline derivatives, overview. No inhibition by (E)-2-(2-(2-nitrobenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(4-nitrobenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(2-methylbenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(3-methylbenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(4-methylbenzylidene)hydrazinyl)quinoxaline, (E)-5-methoxy-2-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol, (E)-2-methoxy-5-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol, (E)-2-(2-(3-methoxybenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(4-methoxybenzylidene)hydrazinyl)quinoxaline, (E)-2-(2-(pyridin-3-ylmethylene)hydrazinyl)quinoxaline, (E)-2-(2-(pyridin-4-ylmethylene)hydrazinyl)quinoxaline, (E)-2-(2-((1H-indol-3-yl)methylene)hydrazinyl)quinoxaline, and (E)-2-((2-(quinoxalin-2-yl)hydrazono)methyl)phenol
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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
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additional information
synthesis and molecular docking study of piperazine derivatives as potent inhibitor of thymidine phosphorylase, overview
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additional information
design, synthesis, in-vitro thymidine phosphorylase inhibition, in-vivo antiangiogenic and in-silico studies of C-6 substituted dihydropyrimidines, molecular docking study, overview. No inhibition by ethyl 4-(4-chlorophenyl)-6-((4-nitrobenzoyloxy)methyl)-2-oxo-1,2,3,4-tetra-hydropyrimidine-5-carboxylate, ethyl 4-(4-chlorophenyl)-6-([(E)-[(4-nitrophenyl)methylidene]amino]methyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate, 5-acetyl-4-(4-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one, ethyl 4-(3,4-dihydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate, 5-acetyl-1,6-dimethyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one, 5-acetyl-1,6-dimethyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one, ethyl 1-benzyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate, ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate, 5-acetyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one, ethyl 4-(3-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate, and 5-acetyl-4-(3-hydroxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one
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additional information
synthesis of 1,2,4-triazoles as thymidine phosphorylase inhibitors and possible future anti-tumor drugs for treatment of human disease. Molecular docking study. Cytoxicity study. No inhibition by 5-(4-methylphenyl)-4H-1,2,4-triazole-3-thiol, 5-(4-nitrophenyl)- 4H-1,2,4-triazole-3-thiol, 5-(4-methylphenyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, 5-(3,4,5-trimethoxyphenyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, 5-(3-chlorophenyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, 5-(4-chlorophenyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, and 2-[(5-phenyl-4H-1,2,4-triazol-3-yl)thio]acetic acid
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additional information
in vitro study of thymidine phosphorylase inhibition, overview. Sixteen analogs of N-benzyliden-isoquinoline-3-carbohydrazide are synthesized and evaluated their inhibitory activity against thymidine phosphorylase enzyme, molecular docking study using structure with PDB ID 4EAD as template. No inhibition by (Z)-N'-(3-methoxy-4-(phenoxymethyl)benzylidene)isoquinoline-3-carbohydrazide
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additional information
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in vitro study of thymidine phosphorylase inhibition, overview. Sixteen analogs of N-benzyliden-isoquinoline-3-carbohydrazide are synthesized and evaluated their inhibitory activity against thymidine phosphorylase enzyme, molecular docking study using structure with PDB ID 4EAD as template. No inhibition by (Z)-N'-(3-methoxy-4-(phenoxymethyl)benzylidene)isoquinoline-3-carbohydrazide
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additional information
synthesis of indole-based acetohydrazide derivatives as inhibitors and molecular docking study using structure with PDB ID 4EAD as template, re-docking of the original ligand 3'-azido-2'-fluoro-dideoxyuridine into the active site. No inhibition by N'-(2,4-dimethoxybenzylidene)-2-(2-methyl-1H-indol-3-yl)acetohydrazide
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additional information
an array of structurally diverse non-nucleobase derivatives has beens designed, synthesized and established as promising TP inhibitors, structure-function analysis, overview
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additional information
natural compounds as angiogenic enzyme thymidine phosphorylase inhibitors, in vitro biochemical inhibition, mechanistic, and in silico modeling and molecular docking studies, enzyme-bound structure modelling, overview. No inhibition by 4',5,7-trihydroxyflavone, 5,7-dihydroxyflavone, 9,10-dimethoxy-5,6,9,12-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium, [(1R,9aR)-octahydro-2H-quinolizin-1-yl]methanol, 3,4,5-trihydroxybenzoic acid, and 4-hydroxy-3-methoxybenzoic acid. Cytotoxicity MTT assay on 3T3 cell line
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additional information
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a specific thymidine phosphorylase inhibitor TPI completely inhibits
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additional information
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iodination reduces activity, 63% inactivation after 5 min and complete inactivation after 20 min
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additional information
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thymidine phosphorylase and its degradation product 2-deoxy-D-ribose suppress hypoxia-induced apoptosis, the upregulation of hypoxia-inducible factor 1alpha and the proapoptotic factor, BNIP3, and caspase 3 activation induced by hypoxia
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additional information
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thymidine phosphorylase promoter methylation is a mechanism for down-regulation of enzyme expression in cancer cells
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additional information
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not inhibited by 1-[(4S,5R)-4-hydroxyisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
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additional information
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capecitabine does not affect enzyme activity and expression
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additional information
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synthesis of 5-alkyl, 5-aryl, or 5-fluoro derivatives of 1-[2-(phosphonomethoxy)-ethyl]thymine inhibitors that mimic the interatomic distance between the incoming phosphate and leaving pyrimidine groups at the transition state for the putative SN2 mechanism of thymidine phosphorylase, structures, the inhibitors are not effective compared to (phosphonomethoxy)-alkyl-pyrimidine inhibitors, overview. Switching the N1-linked side chains found in 1-[2-(phosphonomethoxy)-ethyl]thymine, 1-[(R)-3-hydroxy-2-(phosphonomethoxy)propyl]thymine and 1-[(R)-3-fluoro-2-(phosphonomethoxy)propyl]thymine to the N3-position of the nucleobases resulted in significant loss of activity. Replacement of the iminopyrrolidine ring found in 5-ethyl-1-[(R)-3-hydroxy-2-(phosphonomethoxy)propyl]uracil with a 3-methylimidazol-3-ium ring leads to a series of less active 5-halo-6-[(3-methylimidazol-3-ium-1-yl)methyl]-uracil chlorides. On the other hand, replacement with a 2-aminoimidazole ring, leads to a number of 6-[(2-aminoimidazol-1-yl)methyl]-5-chloro-(and 5-bromo)uracil hydrochlorides with similar inhibitory strength compared to 5-ethyl-1-[(R)-3-hydroxy-2-(phosphonomethoxy)propyl]uracil, computer-modeling simulations, overview
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additional information
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enzyme inhibitors can abrogate the tumorigenic and metastatic properties of the enzyme, e.g. 2-deoxy-L-ribose, which does not inhibit the enzyme but affects its biological functions
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additional information
comparison of binding structures of 5-FU and its derivatives to human thymidine phosphorylase and dihydropyrimidine dehydrogenase (DPD), analysis of strategies to reduce drug binding to DPD to decrease the required dose of 5-FU. hTP can still undergo open-closed conformations in the absence of the ligand, but the presence of a positively charged ligand better stabilizes the closed conformation and rigidifies the core region of the protein more than unliganded or neutral liganded system. Molecular dynamics simulations, overview. One of the three hinge segments linking the two major alpha and alpha/beta domains of the hTP is an important contributing factor to the enzyme's open-close conformational twist during its inactivation-activation process. In addition, the angle between the alpha/beta-domain and the alpha-domain has shown to undergo wide rotations over the course of MD simulation in the absence of a phosphate, suggesting that it contributes to the stabilization of the closed conformation of the hTP
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additional information
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comparison of binding structures of 5-FU and its derivatives to human thymidine phosphorylase and dihydropyrimidine dehydrogenase (DPD), analysis of strategies to reduce drug binding to DPD to decrease the required dose of 5-FU. hTP can still undergo open-closed conformations in the absence of the ligand, but the presence of a positively charged ligand better stabilizes the closed conformation and rigidifies the core region of the protein more than unliganded or neutral liganded system. Molecular dynamics simulations, overview. One of the three hinge segments linking the two major alpha and alpha/beta domains of the hTP is an important contributing factor to the enzyme's open-close conformational twist during its inactivation-activation process. In addition, the angle between the alpha/beta-domain and the alpha-domain has shown to undergo wide rotations over the course of MD simulation in the absence of a phosphate, suggesting that it contributes to the stabilization of the closed conformation of the hTP
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additional information
synthesis, thymidine phosphorylase inhibitory and computational study of 1,3,4-oxadiazole-2-thione derivatives as potential anticancer agents. Determination of growth inhibition of MCF-7 cells, and analysis of toxicity and pharmacokinetics in the human body. Docking study using the ligand-bound TP structure (PDB ID 1UOU). Structure-function analysis. Electron withdrawing groups at R1 position of phenyl ring and less bulky amines group at R2 position have better anticancer activity. Amine groups at R2 position play an important role in binding to the active site residues of enzyme TP
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additional information
an array of structurally diverse non-nucleobase derivatives has been designed, synthesized, and established as promising TP inhibitors, structure-function analysis, docking studies, overview. Analysis of oxadiazole and imidazolidine derivatives, pyrazolone and pyrazolo [1,5-a] [1,3,5]triazine analogues, 1,2,4-triazolo [1,5-a] [1,3,5]triazine analogues, quinazoline and quinoxaline derivatives, chromone and isocoumarin derivatives, and plant glycosides
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additional information
synthesis and biological evaluation of 1-(aryl-aldehyde-oxime)uracil derivatives as a class of thymidine phosphorylase inhibitors, molecular docking and binding energies, overview. The crystal structure of thymidine phosphorylase (PDB ID 1UOU) is used as protein receptor in molecular docking
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additional information
designed as transition-state analogues by mimicking the oxacarbenium ion, the pyrimidine-2,4-diones are synthesized and evaluated as inhibitors of hTP activity, kinetic mechanisms for the most potent molecule and evaluation of the interaction mode using molecular docking, overview
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additional information
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designed as transition-state analogues by mimicking the oxacarbenium ion, the pyrimidine-2,4-diones are synthesized and evaluated as inhibitors of hTP activity, kinetic mechanisms for the most potent molecule and evaluation of the interaction mode using molecular docking, overview
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additional information
synthesis of isoquinoline-base-oxadiazole derivatives as potent inhibitors of thymidine phosphorylase and molecular docking study, overview. Twenty derivatives of isoquinoline bearing oxadiazole are characterized through different spectroscopic techniques such as HREI-MS, 1H-NMR and 13C-NMR and evaluated for thymidine phosphorylase inhibition, structure-activity relationships study
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additional information
not inhibited by pyrimethamine, fludarabine phosphate, lamivudine, adefovir depivoxil, 5-azacytidine, azathioprine, arabinosyl adenine, zalcitabine, caffeine, 7-(2,3-dihydroxypropyl)theophylline, theophylline, allopurinol, 6-mercaptopurine, and valacyclovir
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additional information
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not inhibited by pyrimethamine, fludarabine phosphate, lamivudine, adefovir depivoxil, 5-azacytidine, azathioprine, arabinosyl adenine, zalcitabine, caffeine, 7-(2,3-dihydroxypropyl)theophylline, theophylline, allopurinol, 6-mercaptopurine, and valacyclovir
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