2.4.2.8: hypoxanthine phosphoribosyltransferase
This is an abbreviated version!
For detailed information about hypoxanthine phosphoribosyltransferase, go to the full flat file.
Word Map on EC 2.4.2.8
-
2.4.2.8
-
hamster
-
lymphocyte
-
genotoxic
-
lesch-nyhan
-
6-thioguanine
-
salvage
-
x-linked
-
ovary
-
gapdh
-
adduct
-
erythrocyte
-
normfinder
-
nucleoside
-
genorm
-
thymidine
-
housekeeping
-
t-lymphocytes
-
uric
-
x-chromosome
-
lymphoblast
-
lymphoblastoid
-
tbp
-
micronuclei
-
bestkeeper
-
transversions
-
chromatid
-
hyperuricemia
-
gout
-
benzoapyrene
-
cytogenetic
-
phosphoribosylpyrophosphate
-
ywhaz
-
comet
-
allopurinol
-
clastogenic
-
n-ethyl-n-nitrosourea
-
aminopterin
-
mutable
-
non-transcribed
-
1,3-butadiene
-
lns
-
repair-deficient
-
sister-chromatid
-
32p-postlabeling
-
x-ray-induced
-
repair-proficient
-
analysis
-
pharmacology
-
o6-methylguanine
-
micronucleated
-
synthesis
-
drug development
-
diagnostics
-
biotechnology
-
molecular biology
-
butadiene
-
x-inactivation
-
medicine
- 2.4.2.8
- hamster
- lymphocyte
-
genotoxic
- lesch-nyhan
- 6-thioguanine
-
salvage
-
x-linked
- ovary
- gapdh
- adduct
- erythrocyte
-
normfinder
- nucleoside
-
genorm
- thymidine
-
housekeeping
- t-lymphocytes
-
uric
-
x-chromosome
- lymphoblast
-
lymphoblastoid
- tbp
-
micronuclei
-
bestkeeper
-
transversions
-
chromatid
- hyperuricemia
- gout
-
benzoapyrene
-
cytogenetic
-
phosphoribosylpyrophosphate
-
ywhaz
- comet
- allopurinol
-
clastogenic
-
n-ethyl-n-nitrosourea
- aminopterin
-
mutable
-
non-transcribed
- 1,3-butadiene
- lns
-
repair-deficient
-
sister-chromatid
-
32p-postlabeling
-
x-ray-induced
-
repair-proficient
- analysis
- pharmacology
- o6-methylguanine
-
micronucleated
- synthesis
- drug development
- diagnostics
- biotechnology
- molecular biology
- butadiene
-
x-inactivation
- medicine
Reaction
Synonyms
6-hydroxypurine phosphoribosyltransferase, 6-mercaptopurine phosphoribosyltransferase, 6-oxo PRTase, 6-oxopurine phosphoribosyltransferase, 6-oxopurine PRTase, Cthe_2254, EcHPRT, GMP pyrophosphorylase, GPRT, gpT-2, guanine phosphoribosyltransferase, guanine PRTase, guanine-hypoxanthine phosphoribosyltransferase, guanosine 5'-phosphate pyrophosphorylase, guanosine phosphoribosyltransferase, guanylate pyrophosphorylase, guanylic pyrophosphorylase, HGPRT, HGPRT-1, HGPRTase, HGXPRT, HGXPRTase, HG[X]PRT, HPRT, HPRT1, HPRTJerusalem, HPT, HXGPRT, hypoxanthine guanine phosphoribosyltransferase, hypoxanthine guanine xanthine phosphoribosyltransferase, hypoxanthine phosphoribosyl transferase, hypoxanthine phosphoribosyltransferase, hypoxanthine phosphoribosyltransferase 1, hypoxanthine PRTase, hypoxanthine-guanine phosphoribosyl transferase, hypoxanthine-guanine phosphoribosyltransferase, hypoxanthine-guanine phosphoribosyltransferase/adenylate kinase, hypoxanthine-guanine-(xanthine) phosphoribosyltransferase, hypoxanthine-guanine-xanthine phosphoribosyltransferase, hypoxanthine-guanine-[xanthine]-phosphoribosyltransferase, hypoxanthine-xanthine-guanine phosphoribosyltransferase, IMP pyrophosphorylase, IMP-GMP pyrophosphorylase, inosinate pyrophosphorylase, inosine 5'-phosphate pyrophosphorylase, inosine monophosphate:pyrophosphate phosphoribosyltransferase, inosinic acid pyrophosphorylase, inosinic pyrophosphorylase, More, MSMEG_6110, MtHGPRT, Pf HGXPRT, PF3D7_1012400, PfHGXPRT, PhHGXPRT, phosphoribosyltransferase, 6-mercaptopurine, phosphoribosyltransferase, hypoxanthine, PhPRT, plasma hypoxanthine-guanine phosphoribosyl transferase, PRT, purine-6-thiol phosphoribosyltransferase, PvHGPRT, SmHGPRT1, SSO2424, Tb927.10.1400, TcHPRT, transphosphoribosidase, TthHPRT, TT_C1766, ZgHGPRT/AMPK
ECTree
2.4.2.8 hypoxanthine phosphoribosyltransferaseAdvanced search results
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results (Inhibitors
Inhibitors on EC 2.4.2.8 - hypoxanthine phosphoribosyltransferase
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INHIBITOR 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
IMAGE
(2-[(2,3-dihydroxypropyl)[2-(6-oxo-1,6-dihydro-9H-purin-9-yl)ethyl]amino]ethyl)phosphonic acid
-
(2-[(3R,4R)-3-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-4-[(2R)-2-hydroxy-2-phosphonoethoxy]pyrrolidin-1-yl]-2-oxoethyl)phosphonic acid
(2-[3-(8-bromoguanin-9-yl)-2-(2-(bishydroxyphosphoryl)-ethoxy)propoxy]ethyl)phosphonic acid
(2-[[(3R,4R)-4-(6-oxo-1,6-dihydro-9H-purin-9-yl)-1-(phosphonoacetyl)pyrrolidin-3-yl]oxy]ethyl)phosphonic acid
(2-[[2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)ethyl][2-(2-phosphonoethoxy)ethyl]amino]ethyl)phosphonic acid
-
(3-hydroxy-2-[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]methyl]propyl)phosphonic acid
(3-[[(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]propyl)phosphonic acid
-
competitive. 466fold lower affinity for human enzyme. Treatment of cultured parasites with the bis-pavalate of the inhibitor as a prodrug inhibits growth with an IC50 of 45 microM
([2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-3-(2-phosphonoethoxy)propoxy]methyl)phosphonic acid
([2-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-3-(2-phosphonoethoxy)propoxy]methyl)phosphonic acid
([3-(7-deazahypoxanthine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
([3-(8-bromohypoxanthine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
2-((2,3-dihydroxypropyl)(2-(hypoxanthin-9-yl)ethyl)-amino)ethyl phosphonate
weak inhibition
2-((2-(guanin-9-yl)ethyl)(2-((2-hydroxyethyl)((2-phosphonoethyl)amino)ethyl)amino)ethyl)phosphonic acid
-
2-(2-((2-(hypoxanthine-9-yl)ethyl)((2-phosphonoethyl)amino)ethyl)((2-phosphonoethyl)amino)ethyl)phosphonic acid
-
2-([3-(guanin-9-yl)-2-(2-bis(hydroxyphosphoryl)ethoxy)propoxy]ethyl)phosphonic acid
-
4-(2-methyl-4-oxo-(3H) quinazolin-3-yl)-benzoic acid (4-formyl-benzylidene) hydrazide
-
78.12% inhibition at 0.25 mg/ml
4-(2-methyl-6,8-dibromo-4-oxo-(3H)quinazolin-3-yl)-benzoic acid (4-formyl-benzylidene) hydrazide
-
79.07% inhibition at 0.25 mg/ml
4-(2-methyl-6-bromo-4-oxo-(3H) quinazolin-3-yl)-benzoic acid (4-formyl-benzylidene) hydrazide
-
77.06% inhibition at 0.25 mg/ml
4-(2-phenyl-4-oxo-(3H) quinazolin-3-yl)-benzoic acid (4-formyl-benzylidene) hydrazide
-
79.42% inhibition at 0.25 mg/ml
4-(2-phenyl-6,8-dibromo-4-oxo-(3H)quinazolin-3-yl)-benzoic acid (4-formyl-benzylidene) hydrazide
-
79.71% inhibition at 0.25 mg/ml
4-(2-phenyl-6-bromo-4-oxo-(3H) quinazolin-3-yl)-benzoic acid (4-formyl-benzylidene) hydrazide
-
79.55% inhibition at 0.25 mg/ml
6-methylheptyl hydrogen {[2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)ethoxy]methyl}phosphonate
9-[(N-phosphonoethyl-N-phosphonoethoxyethyl)-2-aminoethyl]-hypoxanthine
-
9-[(N-phosphonoethyl-N-phosphonomethoxyethyl)-2-aminoethyl]hypoxanthine
-
diethyl (2S,15S)-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-8-[(4-oxo-3,4-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl]-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
diethyl (2S,15S)-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-8-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
diethyl (2S,15S)-2,15-dibenzyl-8-[(8-bromo-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
diethyl (2S,15S)-4,13-bis[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-4,13-dioxo-8-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-bis(2-phenylethyl)-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
diethyl (2S,15S)-8-[(2-amino-4-oxo-3,4-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
diethyl (2S,15S)-8-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
diethyl (2S,15S)-8-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-7,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
diethyl (2S,15S)-8-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-4,13-bis[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-4,13-dioxo-2,15-bis(2-phenylethyl)-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
diethyl (2S,15S)-8-[(2-amino-8-bromo-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-7,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
diethyl dicarbonate
-
alkylation of Arg155, complete inactivation at pH 9.0, pH dependent
immucillin-G 5'-phosphate
active site contacts in the HGPRT/immucillin-G 5'-phosphate/diphosphate complex, overview
immucillin-H
-
transition state analogue, binds tightly to the active site, inhibition mechanism and kinetics
Mg2+
-
inhibitory effects are noncompetitive against 5-phosphoribose 1-diphosphate
Phenylglyoxal
-
irreversible, complete inactivation, alkylation of Arg155, GMP protects, no alkylation of mutant R155K
propan-2-yl hydrogen {[2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)ethoxy]methyl}phosphonate
Tetranitromethane
-
complete inactivation at pH 9.0, pH dependent, modifies Tyr96 in the active site
[(+/-)-2(R/S)-3-hydroxy-2-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]propoxy]phosphonic acid
[(+/-)-2(R/S)-[([2-chloro-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-3-hydroxypropoxy]phosphonic acid
[(1S)-1-hydroxy-2-[[(3R,4R)-4-(6-oxo-1,6-dihydro-9H-purin-9-yl)-1-(phosphonoacetyl)pyrrolidin-3-yl]oxy]ethyl]phosphonic acid
[(2R)-2-[([2-amino-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-3-hydroxypropoxy]phosphonic acid
[(2R)-3-hydroxy-2-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]propoxy]phosphonic acid
[(2S)-2-[([2-amino-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-3-hydroxypropoxy]phosphonic acid
[(2S,3R)-2,4-dihydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butoxy]phosphonic acid
[(3R)-4-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butyl]phosphonic acid
[(3S)-1,1-difluoro-4-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butyl]phosphonic acid
[(3S)-3-[([2-amino-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-1,1-difluoro-4-hydroxybutyl]phosphonic acid
[(3S)-4-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butyl]phosphonic acid
[(3S)-4-hydroxy-3-[[(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]amino]butyl]phosphonic acid
-
competitive. 592fold lower affinity for human enzyme
[2-([2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)ethyl][2-[(2-hydroxyethyl)(2-phosphonoethyl)amino]ethyl]amino)ethyl]phosphonic acid
-
[2-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]propyl] phosphonic acid
[2-[(2-hydroxyethyl)(2-[[2-(6-oxo-1,6-dihydro-9H-purin-9-yl)ethyl](2-phosphonoethyl)amino]ethyl)amino]ethyl]phosphonic acid
-
[3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propyl]phosphonic acid
a competitive inhibitor
[3-hydroxy-2-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-2-(hydroxymethyl)propoxy]phosphonic acid
[3R,4R]-4-guanin-9-yl-3-((S)-2-hydroxy-2-phosphonoethyl)oxy-1-N-(phosphonopropionyl)pyrrolidine
[4-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)butyl]phosphonic acid
a competitive inhibitor
[4-(6-oxo-1,6-dihydro-9H-purin-9-yl)butyl]phosphonic acid
a competitive inhibitor, enzyme binding structure analysis, crystal structure, overview. In the complex with the inhibitor there is no association with K145 located away from the purine base and the base itself rotated slightly compared to when GMP is bound, such that the distance between the 6-oxo group and this lysine is 3.9 A at its closest approach. A sulfate ion is also observed in the active site, and is located in the diphosphate binding pocket where it interacts with the amide nitrogen of G55, the side-chain of R179 and one magnesium ion. A second magnesium is located between E113 and D114, which is a Mg2+ binding site in the 6-oxopurine PRTs
[5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)pentyl]phosphonic acid
a competitive inhibitor
[5-(6-oxo-1,6-dihydro-9H-purin-9-yl)pentyl]phosphonic acid
a competitive inhibitor, enzyme binding structure analysis, crystal structure, overview
[6-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)hexyl]phosphonic acid
a competitive inhibitor, enzyme binding structure analysis, crystal structure, overview
[6-(6-oxo-1,6-dihydro-9H-purin-9-yl)hexyl]phosphonic acid
a competitive inhibitor
[[2-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]propane-1,3-diyl]bis(oxymethylene)]bis(phosphonic acid)
[[[(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]azanediyl]di(propane-3,1-diyl)]bis(phosphonic acid)
-
(1S)-1-(9-deazaguanin-9-yl)-1,4-dideoxy-1,4-imino-D-ribitol 5-phosphate
-
(1S)-1-(9-deazaguanin-9-yl)-1,4-dideoxy-1,4-imino-D-ribitol 5-phosphate
-
-
(1S)-1-(9-deazahypoxanthin-9-yl)-1,4-dideoxy-1,4-imino-D-ribitol 5-phosphate
-
(1S)-1-(9-deazahypoxanthin-9-yl)-1,4-dideoxy-1,4-imino-D-ribitol 5-phosphate
-
-
(2-[(3R,4R)-3-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-4-[(2R)-2-hydroxy-2-phosphonoethoxy]pyrrolidin-1-yl]-2-oxoethyl)phosphonic acid
enzyme-bound crystal structure analysis
(2-[(3R,4R)-3-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-4-[(2R)-2-hydroxy-2-phosphonoethoxy]pyrrolidin-1-yl]-2-oxoethyl)phosphonic acid
enzyme-bound crystal structure analysis; enzyme-bound crystal structure analysis
(2-[3-(8-bromoguanin-9-yl)-2-(2-(bishydroxyphosphoryl)-ethoxy)propoxy]ethyl)phosphonic acid
-
(2-[3-(8-bromoguanin-9-yl)-2-(2-(bishydroxyphosphoryl)-ethoxy)propoxy]ethyl)phosphonic acid
-
(2-[[(3R,4R)-4-(6-oxo-1,6-dihydro-9H-purin-9-yl)-1-(phosphonoacetyl)pyrrolidin-3-yl]oxy]ethyl)phosphonic acid
-
(2-[[(3R,4R)-4-(6-oxo-1,6-dihydro-9H-purin-9-yl)-1-(phosphonoacetyl)pyrrolidin-3-yl]oxy]ethyl)phosphonic acid
-
(3-hydroxy-2-[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]methyl]propyl)phosphonic acid
-
-
(3-hydroxy-2-[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]methyl]propyl)phosphonic acid
-
(R)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]guanine
is toxic to cells and arrests cell growth
(R)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]guanine
-
is toxic to cells and arrests cell growth
(S)-3-(guanin-9-yl)-pyrrolidin-N-ylacetylphosphonic acid
-
(S)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]guanine
is toxic to cells and arrests cell growth
(S)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]guanine
-
is toxic to cells and arrests cell growth
([2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-3-(2-phosphonoethoxy)propoxy]methyl)phosphonic acid
-
([2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-3-(2-phosphonoethoxy)propoxy]methyl)phosphonic acid
-
([2-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-3-(2-phosphonoethoxy)propoxy]methyl)phosphonic acid
-
([2-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-3-(2-phosphonoethoxy)propoxy]methyl)phosphonic acid
-
([3-(7-deazaguanine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
sodium salt
([3-(7-deazaguanine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
sodium salt
([3-(7-deazahypoxanthine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
sodium salt
([3-(7-deazahypoxanthine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
sodium salt
([3-(8-bromoguanine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
sodium salt
([3-(8-bromoguanine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
sodium salt
([3-(8-bromohypoxanthine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
sodium salt
([3-(8-bromohypoxanthine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
sodium salt
([3-(guanine-9-yl)-2-((2-phosphonoethoxy)-methyl)propoxy]methyl)phosphonic acid
sodium salt
([3-(guanine-9-yl)-2-((2-phosphonoethoxy)-methyl)propoxy]methyl)phosphonic acid
sodium salt
([3-(hypoxanthine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
sodium salt
([3-(hypoxanthine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methyl)phosphonic acid
sodium salt
3-((7-hydroxy-1H-pyrazolo[4,3-d]pyrimidin-3-yl)methylamino)propylphosphonate
-
-
3-((7-hydroxy-1H-pyrazolo[4,3-d]pyrimidin-3-yl)methylamino)propylphosphonate
-
5-phospho-alpha-D-ribose 1-diphosphate
-
competitive against GMP; product inhibition
5-phospho-alpha-D-ribose 1-diphosphate
-
competitive versus diphosphate and GMP or IMP
6-methylheptyl hydrogen {[2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)ethoxy]methyl}phosphonate
-
6-methylheptyl hydrogen {[2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)ethoxy]methyl}phosphonate
-
-
9-[2-(phosphonomethoxy)ethyl]guanine
is toxic to cells and arrests cell growth
9-[2-(phosphonomethoxy)ethyl]guanine
-
is toxic to cells and arrests cell growth
acyclic nucleoside phosphonates
analogues of the nucleotide reaction product, comprising a purine base joined by a linker to a phosphonate moiety, inhibitor design and potencies, overview. The inhibitors are selectivity for the enzyme of the human parasite Plasmodium falciparum, up to factor 58, compared to the human enzyme, overview
acyclic nucleoside phosphonates
-
analogues of the nucleotide reaction product, comprising a purine base joined by a linker to a phosphonate moiety, inhibitor design and potencies, overview. Selectivity for the parasite enzyme of up to 58 compared to the Homo sapiens enzyme, overview, design of potent and selective acyclic nucleoside phosphonates inhibitors of Plasmodium falciparum HGXPRT as antimalarial drug leads
cyclic (R)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]guanine
is toxic to cells and arrests cell growth
cyclic (R)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]guanine
-
is toxic to cells and arrests cell growth
cyclic (S)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]guanine
is toxic to cells and arrests cell growth
cyclic (S)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]guanine
-
is toxic to cells and arrests cell growth
diethyl (2S,15S)-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-8-[(4-oxo-3,4-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl]-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-8-[(4-oxo-3,4-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl]-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-8-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-8-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-2,15-dibenzyl-8-[(8-bromo-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-2,15-dibenzyl-8-[(8-bromo-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-4,13-bis[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-4,13-dioxo-8-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-bis(2-phenylethyl)-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
-
diethyl (2S,15S)-4,13-bis[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-4,13-dioxo-8-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-bis(2-phenylethyl)-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
-
diethyl (2S,15S)-8-[(2-amino-4-oxo-3,4-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-8-[(2-amino-4-oxo-3,4-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-8-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-8-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-8-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-7,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-8-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-7,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-8-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-4,13-bis[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-4,13-dioxo-2,15-bis(2-phenylethyl)-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
-
diethyl (2S,15S)-8-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-4,13-bis[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-4,13-dioxo-2,15-bis(2-phenylethyl)-6,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
-
diethyl (2S,15S)-8-[(2-amino-8-bromo-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-7,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diethyl (2S,15S)-8-[(2-amino-8-bromo-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-2,15-dibenzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-4,13-dioxo-7,10-dioxa-3,14-diaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate
prodrug
diphosphate
-
competitive versus 5-phospho-alpha-D-ribose 1-diphosphate, uncompetitive versus hypoxanthine or guanine
GMP
-
competitive against 5-phospho-alpha-D-ribose 1-diphosphate; product inhibition
GMP
-
0.3 mM, 50% inhibition of guanine phosphoribosyltransferase activity
GMP
competitive inhibitor with respect to guanine, xanthine, and 5-phospho-alpha-D-ribose 1-diphosphate
GMP
-
competitive versus 5-phospho-alpha-D-ribose 1-diphosphate, noncompetitive versus guanine
guanine
-
0.06 mM, 50% inhibition of hypoxanthine phosphoribosyltransferase activity
hypoxanthine
-
0.16 mM, 50% inhibition of guanine phosphoribosyltransferase activity
immucillin-H 5'-phosphate
5'-phosphate binding structure on HGPRT, overview
immucillin-H 5'-phosphate
-
transition state analogue, binds tightly to the active site, inhibition mechanism and kinetics
IMP
-
feedback inhibition, competitive versus 5-phospho-alpha-D-ribose 1-diphosphate, binding mode
IMP
-
competitive versus 5-phospho-alpha-D-ribose 1-diphosphate, noncompetitive versus hypoxanthine
nucleotides
-
all free 5'-nucleotides are inhibitory, 6-OH purine nucleotides are most inhibitory, while 6-NH2 purine only at high concentrations
-
nucleotides
-
all free 5'-nucleotides are inhibitory, 6-OH purine nucleotides are most inhibitory, while 6-NH2 purine only at high concentrations
-
Pb2+
-
inhibits the enzyme in erythrocytes about 20% at 0.0005 mM and about 12% at 0.0001 mM, and participates in hemolysis, the intensity of which negatively correlates with the activity of phosphoribosyltransferases, HPRT inhibition as one of the mechanisms of lead toxicity
Pb2+
-
moderately inhibits both the enzyme in erythrocytes even at very low concentrations, and participates in hemolysis, the intensity of which negatively correlates with the activity of phosphoribosyltransferases, HPRT inhibition as one of the mechanisms of lead toxicity
propan-2-yl hydrogen {[2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)ethoxy]methyl}phosphonate
-
propan-2-yl hydrogen {[2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)ethoxy]methyl}phosphonate
-
-
[(+/-)-2(R/S)-3-hydroxy-2-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]propoxy]phosphonic acid
-
-
[(+/-)-2(R/S)-3-hydroxy-2-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]propoxy]phosphonic acid
-
[(+/-)-2(R/S)-[([2-chloro-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-3-hydroxypropoxy]phosphonic acid
-
-
[(+/-)-2(R/S)-[([2-chloro-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-3-hydroxypropoxy]phosphonic acid
-
[(1S)-1-hydroxy-2-[[(3R,4R)-4-(6-oxo-1,6-dihydro-9H-purin-9-yl)-1-(phosphonoacetyl)pyrrolidin-3-yl]oxy]ethyl]phosphonic acid
-
[(1S)-1-hydroxy-2-[[(3R,4R)-4-(6-oxo-1,6-dihydro-9H-purin-9-yl)-1-(phosphonoacetyl)pyrrolidin-3-yl]oxy]ethyl]phosphonic acid
-
[(2R)-2-[([2-amino-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-3-hydroxypropoxy]phosphonic acid
-
-
[(2R)-2-[([2-amino-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-3-hydroxypropoxy]phosphonic acid
-
[(2R)-3-hydroxy-2-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]propoxy]phosphonic acid
-
-
[(2R)-3-hydroxy-2-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]propoxy]phosphonic acid
-
[(2S)-2-[([2-amino-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-3-hydroxypropoxy]phosphonic acid
-
-
[(2S)-2-[([2-amino-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-3-hydroxypropoxy]phosphonic acid
-
[(2S,3R)-2,4-dihydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butoxy]phosphonic acid
-
-
[(2S,3R)-2,4-dihydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butoxy]phosphonic acid
-
[(3R)-4-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butyl]phosphonic acid
-
-
[(3R)-4-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butyl]phosphonic acid
-
[(3S)-1,1-difluoro-4-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butyl]phosphonic acid
-
-
[(3S)-1,1-difluoro-4-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butyl]phosphonic acid
-
[(3S)-3-[([2-amino-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-1,1-difluoro-4-hydroxybutyl]phosphonic acid
-
-
[(3S)-3-[([2-amino-4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-1,1-difluoro-4-hydroxybutyl]phosphonic acid
-
[(3S)-4-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butyl]phosphonic acid
-
-
[(3S)-4-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butyl]phosphonic acid
-
[2-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]propyl] phosphonic acid
-
-
[2-hydroxy-3-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]propyl] phosphonic acid
-
[2-[(2-[4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]ethyl)amino]ethyl]phosphonic acid
-
-
[2-[(2-[4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]ethyl)amino]ethyl]phosphonic acid
-
[2-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]ethoxy]phosphonic acid
-
-
[2-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]ethoxy]phosphonic acid
-
[3-(guanine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methylphosphonic acid
structure bound in the active site of human HGPRT (PDB ID 4IJQ), molecular docking. The crystal structure shows that a magnesium ion is coordinated to one of the sulfate oxygen atoms and one of the phosphonate oxygen atoms of the inhibitor
[3-(guanine-9-yl)-2-((2-phosphonoethoxy)methyl)propoxy]methylphosphonic acid
-
[3-hydroxy-2-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-2-(hydroxymethyl)propoxy]phosphonic acid
-
-
[3-hydroxy-2-[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]-2-(hydroxymethyl)propoxy]phosphonic acid
-
[3-[(2-[4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]ethyl)amino]propyl]phosphonic acid
-
-
[3-[(2-[4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]ethyl)amino]propyl]phosphonic acid
-
[3R,4R]-4-guanin-9-yl-3-((S)-2-hydroxy-2-phosphonoethyl)oxy-1-N-(phosphonopropionyl)pyrrolidine
-
[3R,4R]-4-guanin-9-yl-3-((S)-2-hydroxy-2-phosphonoethyl)oxy-1-N-(phosphonopropionyl)pyrrolidine
-
[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butyl]phosphonic acid
-
-
[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]butyl]phosphonic acid
-
[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]ethyl]phosphonic acid
-
-
[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]ethyl]phosphonic acid
-
[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]methyl]phosphonic acid
-
-
[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]methyl]phosphonic acid
-
[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]pentyl]phosphonic acid
-
-
[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]pentyl]phosphonic acid
-
[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]propyl]phosphonic acid
-
-
[[([4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl)amino]propyl]phosphonic acid
-
[[2-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]propane-1,3-diyl]bis(oxymethylene)]bis(phosphonic acid)
-
[[2-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]propane-1,3-diyl]bis(oxymethylene)]bis(phosphonic acid)
-
[[2-[(6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]propane-1,3-diyl]bis(oxymethylene)]bis(phosphonic acid)
-
additional information
-
overview: inhibition constant of purines and purine analogs
-
additional information
EcHPRT inhibitor design, synthesis and optimization. Several acyclic nucleoside phosphonates (ANPs) have previously been identified as inhibitors of EcXGPRT and EcHPRT, and the most potent of these have Ki values as low as 10 nM for EcXGPRT and 0.8 mM for EcHPRT. Inhibitors binding structures, detailed overview
-
additional information
cytotoxicity studies using human lung carcinoma A549 cells at 37°C. The binding site for the 5'-phosphate is located at residues 132-141. No inhibition by (R)-9-[2-(phosphonomethoxy)propyl]hypoxanthine
-
additional information
-
cytotoxicity studies using human lung carcinoma A549 cells at 37°C. The binding site for the 5'-phosphate is located at residues 132-141. No inhibition by (R)-9-[2-(phosphonomethoxy)propyl]hypoxanthine
-
additional information
design of Plasmodium vivax hypoxanthine-guanine phosphoribosyltransferase inhibitors as potential antimalarial therapeutics, rational structure-based methods, binding structure and comparison to the human enzyme, overview
-
additional information
synthesis and evaluation of asymmetric acyclic nucleoside bisphosphonates as inhibitors of human hypoxanthine-guanine phosphoribosyltransferase
-
additional information
-
synthesis and evaluation of asymmetric acyclic nucleoside bisphosphonates as inhibitors of human hypoxanthine-guanine phosphoribosyltransferase
-
additional information
-
no effect of iodoacetate, phenylglyoxal, p-chloromercuribenzoate, acetic anhydride, ethyl dimethylaminopropylcarbodiimide/ammonium acetate, and diisopropyl fluorophosphate
-
additional information
-
guanine phosphoribosyltransferase activity: IMP and AMP are not inhibitory at concentrations up to 0.6 mM, adenine and xanthine are not inhibitory at concentrations up to 0.5 mM. Adenine and xanthine do not inhibit hypoxanthine phosphoribosyltransferase activity
-
additional information
the antimicrobial activity of acyclic nucleoside phosphonates (ANP) prodrugs diethyl (2R,15S)-7-[2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)ethyl]-2-benzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-10-(2-hydroxyethyl)-4,13-dioxo-15-(2-phenylethyl)-3,7,10,14-tetraaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate and diethyl (2R,15S)-2-benzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-10-(2-hydroxyethyl)-4,13-dioxo-7-[2-(6-oxo-1,6-dihydro-9H-purin-9-yl)ethyl]-15-(2-phenylethyl)-3,7,10,14-tetraaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate is not attributable to inhibition of HGPRT
-
additional information
-
the antimicrobial activity of acyclic nucleoside phosphonates (ANP) prodrugs diethyl (2R,15S)-7-[2-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)ethyl]-2-benzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-10-(2-hydroxyethyl)-4,13-dioxo-15-(2-phenylethyl)-3,7,10,14-tetraaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate and diethyl (2R,15S)-2-benzyl-4,13-bis[[(2S)-1-ethoxy-1-oxo-3-phenylpropan-2-yl]amino]-10-(2-hydroxyethyl)-4,13-dioxo-7-[2-(6-oxo-1,6-dihydro-9H-purin-9-yl)ethyl]-15-(2-phenylethyl)-3,7,10,14-tetraaza-4lambda5,13lambda5-diphosphahexadecane-1,16-dioate is not attributable to inhibition of HGPRT
-
additional information
design of Plasmodium vivax hypoxanthine-guanine phosphoribosyltransferase inhibitors as potential antimalarial therapeutics, rational structure-based methods, overview; design of Plasmodium vivax hypoxanthine-guanine phosphoribosyltransferase inhibitors as potential antimalarial therapeutics, rational structure-based methods, overview
-
additional information
design of Plasmodium vivax hypoxanthine-guanine phosphoribosyltransferase inhibitors as potential antimalarial therapeutics, rational structure-based methods, overview; design of Plasmodium vivax hypoxanthine-guanine phosphoribosyltransferase inhibitors as potential antimalarial therapeutics, rational structure-based methods, overview
-
additional information
-
design of Plasmodium vivax hypoxanthine-guanine phosphoribosyltransferase inhibitors as potential antimalarial therapeutics, rational structure-based methods, overview; design of Plasmodium vivax hypoxanthine-guanine phosphoribosyltransferase inhibitors as potential antimalarial therapeutics, rational structure-based methods, overview
-
additional information
spectrometric enzyme-inhibitor binding analysis, molecular docking and molecular dynamics studies, computational binding affinity analysis, binding mode and kinetics, overview. Iso-mukaadial acetate and ursolic acid acetate ligands are docked into the binding sites of Plasmodium falciparum and human hypoxanthine-guanine phosphoribosyl transferases protein using the glide docking module, binding structure comparisons
-
additional information
synthesis and evaluation of asymmetric acyclic nucleoside bisphosphonates as inhibitors of Plasmodium falciparum hypoxanthine-guanine-(xanthine) phosphoribosyltransferase. Low Ki values are achieved by inserting an extra carbon atom in the linker connecting the N9 atom of guanine to one of the phosphonate groups
-
additional information
-
synthesis and evaluation of asymmetric acyclic nucleoside bisphosphonates as inhibitors of Plasmodium falciparum hypoxanthine-guanine-(xanthine) phosphoribosyltransferase. Low Ki values are achieved by inserting an extra carbon atom in the linker connecting the N9 atom of guanine to one of the phosphonate groups
-
additional information
the activity of HGXPRTase was unaffected by the triphosphates ATP, GTP, CTP or UTP
-
additional information
-
the activity of HGXPRTase was unaffected by the triphosphates ATP, GTP, CTP or UTP
-
additional information
-
mechanism of product inhibition; no inhibition by ADP, ATP, dAMP, UMP, and UTP
-
additional information
structural differences between the Tbr and human enzymes suggest that selective inhibitors for the Tbr enzyme can be designed. Crystal structures of the enzyme in complex with GMP and IMP and with three acyclic nucleoside phosphonate (ANP) inhibitors are determined. Evaluation of acyclic nucleoside phosphonate inhibitors, overview
-
additional information
-
product inhibition study, the substrates/products protect the enzyme against digestion by trypsin, especially hypoxanthine with diphosphate
-
