Information on EC 1.5.1.33 - pteridine reductase

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LmPTR1

NADPH-dependent short-chain dehydrogenase/reductase pteridine reductase

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NADPH-dihydropteridine reductase

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pteridine reductase

P42556

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654075

pteridine reductase 1

12 entries

PTR1

15 entries

reductase, dihydropteridine (reduced nicotinamide adenine dinucleotide phosphate)

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TbPTR1

5,6,7,8-tetrahydrobiopterin + 2 NADP+ = biopterin + 2 NADPH + 2 H+

5 entries

oxidation

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reduction

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KEGG

Folate biosynthesis

5,6,7,8-tetrahydrobiopterin:NADP+ oxidoreductase

The enzyme from Leishmania (both amastigote and promastigote forms) catalyses the reduction by NADPH of folate and a wide variety of unconjugated pterins, including biopterin, to their tetrahydro forms. It also catalyses the reduction of 7,8-dihydropterins and 7,8-dihydrofolate to their tetrahydro forms. In contrast to EC 1.5.1.3 (dihydrofolate reductase) and EC 1.5.1.34 (6,7-dihydropteridine reductase), pteridine reductase will not catalyse the reduction of the quinonoid form of dihydrobiopterin. The enzyme is specific for NADPH; no activity has been detected with NADH. It also differs from EC 1.5.1.3 (dihydrofolate reductase) in being specific for the Si-face of NADPH.

131384-61-7

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2 biopterin + 3 NADPH + 3 H+

dihydrobiopterin + tetrahydrobiopterin + 3 NADP+

6-biopterin + NADPH + H+

5,6,7,8-tetrahydrobiopterin + NADP+

biopterin + 2 NADPH + 2 H+

5,6,7,8-tetrahydrobiopterin + 2 NADP+

9 entries

Biopterin + NADPH

5,6,7,8-Tetrahydrobiopterin + NADP+

biopterin + NADPH + H+

5,6,7,8-tetrahydrobiopterin + NADP+

biopterin + NADPH + H+

dihydrobiopterin + NADP+

dihydrobiopterin + NADPH

5,6,7,8-tetrahydrobiopterin + NADP+

Dihydrobiopterin + NADPH

?

4 entries

dihydrobiopterin + NADPH + H+

5,6,7,8-tetrahydrobiopterin + NADP+

Dihydrofolate + NADPH

5,6,7,8-Tetrahydrofolate + NADP+

5 entries

Dihydroneopterin + NADPH

?

dihydrosepiapterin + NADPH

?

folate + NADPH

5,6,7,8-tetrahydrofolate + NADP+

folate + NADPH + H+

7,8-dihydrofolate + tetrahydrofolate + NADP+

quinonoid 6,7-dimethyl-7,8-dihydropterin + NADPH + H+

?

quinonoid dihydrobiopterin + NADPH + H+

tetrahydrobiopterin + NADP+

additional information

?

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16 entries

2 biopterin + 3 NADPH + 3 H+

dihydrobiopterin + tetrahydrobiopterin + 3 NADP+

6-biopterin + NADPH + H+

5,6,7,8-tetrahydrobiopterin + NADP+

biopterin + 2 NADPH + 2 H+

5,6,7,8-tetrahydrobiopterin + 2 NADP+

biopterin + NADPH + H+

5,6,7,8-tetrahydrobiopterin + NADP+

folate + NADPH + H+

7,8-dihydrofolate + tetrahydrofolate + NADP+

additional information

?

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12 entries

NADPH

21 entries

(2-amino-2,3-dihydro-1H-benzimidazol-1-yl)(phenyl)methanone

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(2E,4E)-N-(2-methylpropyl)dodeca-2,4-dienamide

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(2E,4E)-N-(2-methylpropyl)octadeca-2,4-dienamide

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(2E,4E,12E)-13-(benzo[d][1,3]dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide

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(4-fluoro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester

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(4-fluoro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester

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treatment with 98 microM resulted in reduction of viable cells from 96.5% (control) to 9.86% after 5 h

700560

(4S)-4-[[(4-[[(2,4-diaminopteridin-6-yl)methyl](methyl)amino]phenyl)carbonyl]amino]-5-oxohexanoic acid

(Z)-5-(2,4-dichlorobenzylidene)-thiazolidine-2,4-dione

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(Z)-5-(2-bromo-5-methoxybenzylidene)-thiazolidine-2,4-dione

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(Z)-5-(2-bromo-6-fluorobenzylidene)-thiazolidine-2,4-dione

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(Z)-5-(2-hydroxy-3-bromo-5-chlorobenzylidene)-thiazolidine-2,4-dione

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a noncompetitive inhibitor that binds in the same site as the cofactor

(Z)-5-(2-hydroxy-5-chlorobenzylidene)-thiazolidine-2,4-dione

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1-(2,5-dichlorobenzyl)-2,3-dihydro-1H-benzimidazol-2-amine

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1-(2-chlorobenzyl)-2,3-dihydro-1H-benzimidazol-2-amine

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1-(2-fluorobenzyl)-1H-benzimidazol-2-amine

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1-(2-methylbenzyl)-1H-benzimidazol-2-amine

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1-(2-phenylethyl)-2,3-dihydro-1H-benzimidazol-2-amine

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1-(3,4-dichlorobenzyl)-1H-benzimidazol-2-amine

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1-(3,4-dichlorobenzyl)-2,3-dihydro-1H-benzimidazol-2-amine

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1-(3,4-dichlorobenzyl)-4-methoxy-1H-benzimidazol-2-amine

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1-(3,4-dichlorobenzyl)-4-phenyl-1H-benzimidazol-2-amine

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1-(3,4-dichlorobenzyl)-4-propoxy-1H-benzimidazol-2-amine

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1-(3,4-dichlorobenzyl)-5,6-dimethyl-1H-benzimidazol-2-amine

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1-(3,4-dichlorobenzyl)-7-methoxy-1H-benzimidazol-2-amine

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1-(3,4-dichlorobenzyl)-7-phenyl-1H-benzimidazol-2-amine

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1-(3,4-dichlorobenzyl)-7-propoxy-1H-benzimidazol-2-amine

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1-(3,4-methylenedioxyphenyl)-(1E)-tetradecene

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1-(3,5-dichlorobenzyl)-1H-benzimidazol-2-amine

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1-(3-chlorobenzyl)-2,3-dihydro-1H-benzimidazol-2-amine

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1-(4-bromobenzyl)-1H-benzimidazol-2-amine

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1-(4-chlorobenzyl)-2,3-dihydro-1H-benzimidazol-2-amine

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1-(4-methylbenzyl)-1H-benzimidazol-2-amine

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1-(4-tert-butylbenzyl)-1H-benzimidazol-2-amine

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1-(naphthalen-1-ylmethyl)-1H-benzimidazol-2-amine

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1-(naphthalen-2-ylmethyl)-1H-benzimidazol-2-amine

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1-(pyridin-2-yl)-1H-benzimidazol-2-amine

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1-(pyridin-3-yl)-1H-benzimidazol-2-amine

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1-benzyl-2,3-dihydro-1H-benzimidazol-2-amine

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1-ethyl-2,3-dihydro-1H-benzimidazol-2-amine

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1-[(4-[[6-(trifluoromethyl)quinoxalin-2-yl]amino]phenyl)carbonyl]piperidine-4-carboxylic acid

1-[(4-[[8-amino-3-phenyl-6-(trifluoromethyl)quinoxalin-2-yl]amino]phenyl)carbonyl]piperidine-4-carboxylic acid

1-[3-(trifluoromethyl)benzyl]-1H-benzimidazol-2-amine

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1H-benzimidazol-2-amine

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2,4,6-triaminoquinazoline

i.e. TAQ, mimics the pterin head group of methotrexate, binds to the active site, binding structure and inhibition mechanism

654109

2,4-diamino-6-bromo-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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2,4-diamino-6-[(E)-2-phenylethenyl]-7H-pyrrolo[2,3-d]-pyrimidine-5-carbonitrile

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2,4-diamino-6-[(Z)-2-(4-methylphenyl)ethenyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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2,4-diamino-6-[(Z)-2-phenylethenyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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2,4-diamino-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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2,4-Diaminopteridines

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overview

484953

2,4-diaminopyrimidines

2,4-Diaminoquinazolines

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overview

484953

2,6-dimethyl [3-O-benzyl-1,2-O isopropylidene-beta-L-threo-pentofuronose-4-yl]-1-phenyl-1,4-dihydro pyridine-3,5-dicarboxylic acid diethyl ether

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2,6-dimethyl-4-(3-O-benzyl-1,2-O-isopropylidene-beta-L-threo pentofuranos-4-yl)-1-phenyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

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oral therapy shows apoptosis like phenotypes targeting pteridine reductase 1 in intracellular amastigotes

711946

2,6-dimethyl-4-(3-O-benzyl-1,2-ortho-isopropylidene-beta-L-threopentofuranos-4-yl)-1-phenyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

treatment with 90 microM GDA resulted in reduction of viable cells from 94.2% (control) to 77.1%, 76.8%, 74.9%, 35.3% and 24.9% at 18, 24, 48, 72 and 96 h, respectively

697820

2-(3,4-dihydroxyphenyl)-3,6-dihydroxy-4H-1-benzopyran-4-one

2-(3,4-dihydroxyphenyl)-6-hydroxy-2,3-dihydro-4H-1-benzopyran-4-one

2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidine-4-thione

2-amino-4-(1-pyrrolidinyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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2-amino-4-(cyclopentyloxy)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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2-amino-4-(thiomorpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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2-amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

2-amino-4-oxo-6-phenyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

2-amino-4-oxo-6-[(E)-2-phenylethenyl]-4,7-dihydro-3Hpyrrolo[2,3-d]pyrimidine-5-carbonitrile

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2-amino-4-[(propan-2-yl)oxy]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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2-amino-5,6-bis(4-chlorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-5,6-bis(4-fluorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-5,6-bis(4-methylphenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-5,6-diphenyl-3,7-dihydro-4H-pyrrolo[2,3-d]-pyrimidin-4-one

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2-amino-5-(2-phenylethyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

2-amino-5-(3-chlorophenyl)-6-(4-fluorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-5-(4-fluorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-5-(4-methylphenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-5-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-5-methyl-6-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-6-(1,3-benzodioxol-5-yl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

2-amino-6-(3-formylphenyl)-4-(1-pyrrolidinyl)-7H-pyrrolo-[2,3-d]pyrimidine-5-carbonitrile

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2-amino-6-(3-formylphenyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

2-amino-6-(4-bromophenyl)-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-6-(4-ethylphenyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

2-amino-6-(4-fluorophenyl)-5-(4-methoxyphenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-6-(4-fluorophenyl)-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-6-(4-methoxyphenyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

2-amino-6-bromo-4-(1-pyrrolidinyl)-7H-pyrrolo[2,3-d]-pyrimidine-5-carbonitrile

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2-amino-6-bromo-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

2-amino-6-phenyl-5-(2-phenylethyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-6-[3-(methanesulfonyl)phenyl]-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

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2-amino-6-[4-(2-methylpropyl)phenyl]-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-6-[4-(methanesulfonyl)phenyl]-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

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2-amino-6-[4-[3-(4-morpholinyl)propyl]phenyl]-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one trifluoroacetate

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3,6-dihydroxy-2-(3-hydroxyphenyl)-4H-1-benzopyran-4-one

4-(1-pyrrolidinyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

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4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-4H-pyrimidin-5-carboxylic acid ethyl ester

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both monastrol (R) and (S) enantiomers fit well in the ligand-binding pocket of LdPTR1. Monastrol is a potent inhibitor of PTR1 in Leishmania, it inhibits proliferation of amastigotes in macrophage cultures infected with an Leishmania donovani clinical isolate, with no host cytotoxicity

4-(benzyloxy)-1-(3,4-dichlorobenzyl)-1H-benzimidazol-2-amine

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4-(thiomorpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

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4-chloro-1-(3,4-dichlorobenzyl)-1H-benzimidazol-2-amine

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5,6-bis(4-chlorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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5,6-bis(4-chlorophenyl)-N~4~,N~4~-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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5,6-bis(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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5,6-bis(4-fluorophenyl)-N~4~,N~4~-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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5,6-bis(4-methylphenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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5-(2-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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5-(3,4-dichlorobenzylidene)-thiazolidine-2,4-dione

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5-(3-chlorophenyl)-6-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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5-(4-fluorophenyl)-4-(2-methylpropoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

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5-(4-fluorophenyl)-4-isopropyloxy-7H-pyrrolo[2,3-d]-pyrimidin-2-amine

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5-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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5-(4-methylphenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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5-(phenylethynyl)-4-(1-pyrrolidinyl)-7H-pyrrolo[2,3-d]-pyrimidin-2-amine

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5-Deaza-5,6,7,8-tetrahydrofolate

-

484957

5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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6,7-di(propan-2-yl)pteridine-2,4-diamine

6-(4-bromophenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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6-(4-fluorophenyl)-5-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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6-(4-fluorophenyl)-5-(4-methoxyphenyl)-N4,N4-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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6-(4-fluorophenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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6-(4-fluorophenyl)-N~4~,N~4~-dimethyl-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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6-(benzylsulfanyl)pyrimidine-2,4-diamine

6-hydroxy-2-(3-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

6-methyl-7-(propan-2-yl)pteridine-2,4-diamine

6-phenylpteridine-2,4,7-triamine

6-[(4-methoxybenzyl)sulfanyl]pyrimidine-2,4-diamine

6-[(4-methylphenyl)sulfanyl]pyrimidine-2,4-diamine

6-[4-(2-methylpropyl)phenyl]-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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6-[4-(methanesulfonyl)phenyl]-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

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7-(benzyloxy)-1-(3,4-dichlorobenzyl)-1H-benzimidazol-2-amine

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7-chloro-1-(3,4-dichlorobenzyl)-1H-benzimidazol-2-amine

-

CB3717

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dihydrobiopterin

dihydrofolate

dihydroneopterin

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substrate inhibition

Dihydrosepiapterin

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substrate inhibition

dimethyl 1-[(4-[[3-(ethoxycarbonyl)quinoxalin-2-yl]amino]phenyl)carbonyl]piperidine-2,4-dicarboxylate

-

dimethyl 1-[(4-[[3-phenyl-7-(trifluoromethyl)quinoxalin-2-yl]amino]phenyl)carbonyl]piperidine-2,4-dicarboxylate

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ethyl 1-[(4-[[7-(trifluoromethyl)quinoxalin-2-yl]amino]phenyl)carbonyl]piperidine-2-carboxylate

methotrexate

5 entries

methyl 1-[(4-[[(2,4-diaminopteridin-6-yl)methyl](methyl)amino]phenyl)carbonyl]piperidine-4-carboxylate

methyl 1-[(4-[[(2,4-diaminopteridin-6-yl)methyl]amino]phenyl)carbonyl]piperidine-4-carboxylate

miltefosine

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N-isobutyl-19-(3',4'-methylenedioxyphenyl)-(2E,4E)-nonadecadienamide

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N-[3-(2,4-diamino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl]methanesulfonamide

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N-[3-(2-amino-5-cyano-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl]methanesulfonamide

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N4,N4-dimethyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

N4-cyclohexyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

N4-cyclohexyl-5-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

N4-cyclopropylpyrimidine-2,4,6-triamine

NADP+

-

piperlongimin A

-

i.e. (2E)-N-isobutyl-hexadecenamide

piperlongimin B

-

i.e. (2E)-octadecenoylpiperidine

Pteridines

-

and analogs, overview

484953

-

pyrimethamine

pyrimidine-2,4,6-triamine

quinonoid 6,7-dimethyl-7,8-dihydropterin

quinonoid dihydrobiopterin

sodium antimony gluconate

-

trimethoprim

-

additional information

-

0.0032 - 0.0399

biopterin

0.0000294 - 0.033

dihydrobiopterin

0.0034 - 0.0067

dihydrofolate

0.001 - 0.085

folate

0.0014 - 0.0169

NADPH

0.0166 - 0.021

quinonoid 6,7-dimethyl-7,8-dihydropterin

0.0036 - 0.0103

quinonoid dihydrobiopterin

additional information

-

kinetics, thermal shift assay

-

0.22 - 0.23

biopterin

0.05 - 4.7

dihydrobiopterin

0.43 - 0.44

quinonoid 6,7-dimethyl-7,8-dihydropterin

0.54 - 1.84

quinonoid dihydrobiopterin

170 - 1700

dihydrobiopterin

21 - 26

quinonoid 6,7-dimethyl-7,8-dihydropterin

160 - 180

quinonoid dihydrobiopterin

0.06

(2-amino-2,3-dihydro-1H-benzimidazol-1-yl)(phenyl)methanone

-

Ki above 0.06 mM, pH and temperature not specified in the publication

0.00011 - 0.00018

(4S)-4-[[(4-[[(2,4-diaminopteridin-6-yl)methyl](methyl)amino]phenyl)carbonyl]amino]-5-oxohexanoic acid

0.0037

1-(2,5-dichlorobenzyl)-2,3-dihydro-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.01

1-(2-chlorobenzyl)-2,3-dihydro-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.021

1-(2-fluorobenzyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.015

1-(2-methylbenzyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.024

1-(2-phenylethyl)-2,3-dihydro-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.06

1-(3,4-dichlorobenzyl)-1H-benzimidazol-2-amine

-

Ki above 0.06 mM, pH and temperature not specified in the publication

0.0004

1-(3,4-dichlorobenzyl)-2,3-dihydro-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.00046

1-(3,4-dichlorobenzyl)-4-methoxy-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.06

1-(3,4-dichlorobenzyl)-4-phenyl-1H-benzimidazol-2-amine

-

Ki above 0.06 mM, pH and temperature not specified in the publication

0.00031

1-(3,4-dichlorobenzyl)-4-propoxy-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.0039

1-(3,4-dichlorobenzyl)-5,6-dimethyl-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.00065

1-(3,4-dichlorobenzyl)-7-methoxy-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.000007

1-(3,4-dichlorobenzyl)-7-phenyl-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.000047

1-(3,4-dichlorobenzyl)-7-propoxy-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.0088

1-(3,5-dichlorobenzyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.0075

1-(3-chlorobenzyl)-2,3-dihydro-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.0031

1-(4-bromobenzyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.0054

1-(4-chlorobenzyl)-2,3-dihydro-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.015

1-(4-methylbenzyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.0042

1-(4-tert-butylbenzyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.0061

1-(naphthalen-1-ylmethyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.0028

1-(naphthalen-2-ylmethyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.053

1-(pyridin-2-yl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.054

1-(pyridin-3-yl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.016

1-benzyl-2,3-dihydro-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.2

1-ethyl-2,3-dihydro-1H-benzimidazol-2-amine

-

Ki above 0.2 mM, pH and temperature not specified in the publication

0.007 - 0.075

1-[(4-[[6-(trifluoromethyl)quinoxalin-2-yl]amino]phenyl)carbonyl]piperidine-4-carboxylic acid

0.02

1-[(4-[[8-amino-3-phenyl-6-(trifluoromethyl)quinoxalin-2-yl]amino]phenyl)carbonyl]piperidine-4-carboxylic acid

-

0.0063

1-[3-(trifluoromethyl)benzyl]-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.228

1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.003317

2,4-diamino-6-bromo-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

-

pH and temperature not specified in the publication

0.00016

2,4-diamino-6-[(E)-2-phenylethenyl]-7H-pyrrolo[2,3-d]-pyrimidine-5-carbonitrile

-

pH and temperature not specified in the publication

0.00035

2,4-diamino-6-[(Z)-2-(4-methylphenyl)ethenyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

-

pH and temperature not specified in the publication

0.00024

2,4-diamino-6-[(Z)-2-phenylethenyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

-

pH and temperature not specified in the publication

0.0049

2,4-diamino-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

-

pH and temperature not specified in the publication

0.141

2,4-diaminopyrimidine

called compound 3

699467

0.021

2,4-diaminoquinazoline

called compound 2

699467

0.027 - 0.035

2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

0.027 - 0.035

2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidine-4-thione

0.1

2-amino-4-(cyclopentyloxy)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

-

above, pH and temperature not specified in the publication

0.0088

2-amino-4-(thiomorpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

-

pH and temperature not specified in the publication

0.075

2-amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

-

above, pH and temperature not specified in the publication

0.0058 - 0.027

2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

0.00071 - 0.027

2-amino-4-oxo-6-phenyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

0.000137

2-amino-4-oxo-6-[(E)-2-phenylethenyl]-4,7-dihydro-3Hpyrrolo[2,3-d]pyrimidine-5-carbonitrile

-

pH and temperature not specified in the publication

0.1

2-amino-4-[(propan-2-yl)oxy]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

-

above, pH and temperature not specified in the publication

0.00025

2-amino-5,6-bis(4-chlorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.00076

2-amino-5,6-bis(4-fluorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.002 - 0.01

2-amino-5,6-bis(4-methylphenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.00117

2-amino-5,6-diphenyl-3,7-dihydro-4H-pyrrolo[2,3-d]-pyrimidin-4-one

-

pH and temperature not specified in the publication

0.00027 - 0.027

2-amino-5-(2-phenylethyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

0.00047

2-amino-5-(3-chlorophenyl)-6-(4-fluorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.0013

2-amino-5-(4-fluorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.0012

2-amino-5-(4-methylphenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.0073

2-amino-5-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.00106

2-amino-5-methyl-6-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.0012

2-amino-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.0004 - 0.0026

2-amino-6-(1,3-benzodioxol-5-yl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

0.0002

2-amino-6-(3-formylphenyl)-4-(1-pyrrolidinyl)-7H-pyrrolo-[2,3-d]pyrimidine-5-carbonitrile

-

pH and temperature not specified in the publication

0.00029 - 0.0042

2-amino-6-(3-formylphenyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

0.00023

2-amino-6-(4-bromophenyl)-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.0005 - 0.0164

2-amino-6-(4-ethylphenyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

0.0005

2-amino-6-(4-fluorophenyl)-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.00036 - 0.0034

2-amino-6-(4-methoxyphenyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

0.0008

2-amino-6-bromo-4-(1-pyrrolidinyl)-7H-pyrrolo[2,3-d]-pyrimidine-5-carbonitrile

-

pH and temperature not specified in the publication

0.0039 - 0.027

2-amino-6-bromo-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

0.01

2-amino-6-chloro-benzimidazole

-

699467

0.00095

2-amino-6-phenyl-5-(2-phenylethyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

pH and temperature not specified in the publication

0.000731

2-amino-6-[3-(methanesulfonyl)phenyl]-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

-

pH and temperature not specified in the publication

0.01

2-amino-6-[4-(2-methylpropyl)phenyl]-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

-

above, pH and temperature not specified in the publication

0.01

2-amino-6-[4-[3-(4-morpholinyl)propyl]phenyl]-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one trifluoroacetate

-

above, in Creek's minimal medium, pH and temperature not specified in the publication

0.0042

4-(1-pyrrolidinyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

-

pH and temperature not specified in the publication

0.000428

4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-4H-pyrimidin-5-carboxylic acid ethyl ester

-

pH 4.8, 30°C

0.016

4-(benzyloxy)-1-(3,4-dichlorobenzyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.0086

4-(thiomorpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

-

pH and temperature not specified in the publication

0.0023

4-chloro-1-(3,4-dichlorobenzyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.0003

5,6-bis(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.00059

5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.00026

5-(2-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.00029

5-(3-chlorophenyl)-6-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.05

5-(4-fluorophenyl)-4-(2-methylpropoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

-

above, pH and temperature not specified in the publication

0.00048

5-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.00032

5-(4-methylphenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.00019

5-(phenylethynyl)-4-(1-pyrrolidinyl)-7H-pyrrolo[2,3-d]-pyrimidin-2-amine

-

pH and temperature not specified in the publication

0.0004

5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.00024 - 0.0033

6,7-di(propan-2-yl)pteridine-2,4-diamine

0.000135

6-(4-bromophenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.00058

6-(4-fluorophenyl)-5-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.0003

6-(4-fluorophenyl)-5-(4-methoxyphenyl)-N4,N4-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

in Creek's minimal medium, pH and temperature not specified in the publication

0.00024

6-(4-fluorophenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.0006 - 0.0032

6-(benzylsulfanyl)pyrimidine-2,4-diamine

0.0012 - 0.035

6-methyl-7-(propan-2-yl)pteridine-2,4-diamine

0.0012 - 0.0034

6-phenylpteridine-2,4,7-triamine

0.0027 - 0.018

6-[(4-methoxybenzyl)sulfanyl]pyrimidine-2,4-diamine

0.0054 - 0.027

6-[(4-methylphenyl)sulfanyl]pyrimidine-2,4-diamine

0.00058

6-[4-(2-methylpropyl)phenyl]-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.00128

6-[4-(methanesulfonyl)phenyl]-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.000098

7-(benzyloxy)-1-(3,4-dichlorobenzyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.00051

7-chloro-1-(3,4-dichlorobenzyl)-1H-benzimidazol-2-amine

-

pH and temperature not specified in the publication

0.00015 - 0.0038

dihydrobiopterin

0.038

dimethyl 1-[(4-[[3-(ethoxycarbonyl)quinoxalin-2-yl]amino]phenyl)carbonyl]piperidine-2,4-dicarboxylate

-

0.04

dimethyl 1-[(4-[[3-phenyl-7-(trifluoromethyl)quinoxalin-2-yl]amino]phenyl)carbonyl]piperidine-2,4-dicarboxylate

-

0.006 - 0.106

ethyl 1-[(4-[[7-(trifluoromethyl)quinoxalin-2-yl]amino]phenyl)carbonyl]piperidine-2-carboxylate

0.0000111 - 0.000152

methotrexate

0.000037

methyl 1-[(4-[[(2,4-diaminopteridin-6-yl)methyl](methyl)amino]phenyl)carbonyl]piperidine-4-carboxylate

-

0.0001 - 0.007

methyl 1-[(4-[[(2,4-diaminopteridin-6-yl)methyl]amino]phenyl)carbonyl]piperidine-4-carboxylate

0.00023

N-[3-(2,4-diamino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl]methanesulfonamide

-

pH and temperature not specified in the publication

0.00035

N-[3-(2-amino-5-cyano-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl]methanesulfonamide

-

pH and temperature not specified in the publication

0.00029

N4,N4-dimethyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

in Creek's minimal medium, pH and temperature not specified in the publication

0.0002

N4-cyclohexyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

in Creek's minimal medium, pH and temperature not specified in the publication

0.00056

N4-cyclohexyl-5-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

-

pH and temperature not specified in the publication

0.027 - 0.035

N4-cyclopropylpyrimidine-2,4,6-triamine

0.027 - 0.035

pyrimidine-2,4,6-triamine

0.0922 - 0.475

quinonoid 6,7-dimethyl-7,8-dihydropterin

0.00122 - 0.00314

quinonoid dihydrobiopterin

additional information

-

inhibition kinetics, thermal shift assay

-

23.1 - 101

(4-fluoro-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester

0.0624

2,4-diamino-6-bromo-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.07252

2,4-diamino-6-[(E)-2-phenylethenyl]-7H-pyrrolo[2,3-d]-pyrimidine-5-carbonitrile

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.01708

2,4-diamino-6-[(Z)-2-(4-methylphenyl)ethenyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.17

2,4-diamino-6-[(Z)-2-phenylethenyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Trypanosoma brucei

-

pH and temperature not specified in the publication

2.44

2,4-diamino-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Trypanosoma brucei

-

pH and temperature not specified in the publication

18.3 - 90.8

2,6-dimethyl [3-O-benzyl-1,2-O isopropylidene-beta-L-threo-pentofuronose-4-yl]-1-phenyl-1,4-dihydro pyridine-3,5-dicarboxylic acid diethyl ether

0.035 - 0.038

2-(3,4-dihydroxyphenyl)-3,6-dihydroxy-4H-1-benzopyran-4-one

0.036 - 0.082

2-(3,4-dihydroxyphenyl)-6-hydroxy-2,3-dihydro-4H-1-benzopyran-4-one

0.34

2-amino-4-(1-pyrrolidinyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00104

2-amino-4-(cyclopentyloxy)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Trypanosoma brucei

-

above, pH and temperature not specified in the publication

0.01433

2-amino-4-(thiomorpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.0073

2-amino-4-[(propan-2-yl)oxy]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Trypanosoma brucei

-

above, pH and temperature not specified in the publication

0.00156

2-amino-5,6-bis(4-chlorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00074

2-amino-5,6-bis(4-fluorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00043

2-amino-5,6-bis(4-methylphenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00041

2-amino-5,6-diphenyl-3,7-dihydro-4H-pyrrolo[2,3-d]-pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

7.62

2-amino-5-(2-phenylethyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00077

2-amino-5-(3-chlorophenyl)-6-(4-fluorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.02511

2-amino-5-(4-fluorophenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.125

2-amino-5-(4-methylphenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.0104

2-amino-5-methyl-6-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.05334

2-amino-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00775

2-amino-6-(3-formylphenyl)-4-(1-pyrrolidinyl)-7H-pyrrolo-[2,3-d]pyrimidine-5-carbonitrile

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.0032

2-amino-6-(4-bromophenyl)-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00103

2-amino-6-(4-fluorophenyl)-5-(4-methoxyphenyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00061

2-amino-6-(4-fluorophenyl)-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.139

2-amino-6-bromo-4-(1-pyrrolidinyl)-7H-pyrrolo[2,3-d]-pyrimidine-5-carbonitrile

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00014

2-amino-6-phenyl-5-(2-phenylethyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00213

2-amino-6-[4-(2-methylpropyl)phenyl]-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

above, pH and temperature not specified in the publication

0.1

2-amino-6-[4-(methanesulfonyl)phenyl]-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Trypanosoma brucei

-

above, pH and temperature not specified in the publication

0.0201

2-amino-6-[4-[3-(4-morpholinyl)propyl]phenyl]-5-phenyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one trifluoroacetate

Trypanosoma brucei

-

above, in Creek's minimal medium, pH and temperature not specified in the publication

0.0043 - 0.0125

3,6-dihydroxy-2-(3-hydroxyphenyl)-4H-1-benzopyran-4-one

0.01

4-(3-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-4H-pyrimidin-5-carboxylic acid ethyl ester

Leishmania donovani

-

pH 4.8, 30°C

0.08006

4-(thiomorpholin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00202

5,6-bis(4-chlorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00308

5,6-bis(4-chlorophenyl)-N~4~,N~4~-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

in Creek's minimal medium, pH and temperature not specified in the publication

0.00015

5,6-bis(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00131

5,6-bis(4-fluorophenyl)-N~4~,N~4~-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00019

5,6-bis(4-methylphenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00058

5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.09352

5-(2-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00019

5-(3-chlorophenyl)-6-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00253

5-(4-fluorophenyl)-4-(2-methylpropoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Trypanosoma brucei

-

above, pH and temperature not specified in the publication

0.00142

5-(4-fluorophenyl)-4-isopropyloxy-7H-pyrrolo[2,3-d]-pyrimidin-2-amine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.01447

5-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.17

5-(4-methylphenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00065

5-(phenylethynyl)-4-(1-pyrrolidinyl)-7H-pyrrolo[2,3-d]-pyrimidin-2-amine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.04101

5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00025

6-(4-bromophenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.000083

6-(4-fluorophenyl)-5-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00343

6-(4-fluorophenyl)-5-(4-methoxyphenyl)-N4,N4-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

in Creek's minimal medium, pH and temperature not specified in the publication

0.00008

6-(4-fluorophenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00134

6-(4-fluorophenyl)-N~4~,N~4~-dimethyl-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

in Creek's minimal medium, pH and temperature not specified in the publication

0.031 - 0.057

6-hydroxy-2-(3-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

0.035 - 0.133

6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

0.00139

6-[4-(2-methylpropyl)phenyl]-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00616

6-[4-(methanesulfonyl)phenyl]-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00603

N-[3-(2,4-diamino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl]methanesulfonamide

Trypanosoma brucei

-

pH and temperature not specified in the publication

0.00611

N4,N4-dimethyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

in Creek's minimal medium, pH and temperature not specified in the publication

0.00178

N4-cyclohexyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

in Creek's minimal medium, pH and temperature not specified in the publication

0.0115

N~4~-cyclohexyl-5-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

Trypanosoma brucei

-

pH and temperature not specified in the publication

12.1

sodium antimony gluconate

Leishmania donovani

-

amastigote

0.1

2

-

pH 3.7, substrate biopterin

676067

2.3

-

pH 3.7, substrate dihydrobiopterin

3.7

-

4.7

5 - 7

-

dihydrofolate as substrate

5.5 - 8

6

7.5

4 - 9

4.5 - 7

-

pH 4.5: about 50% of maximal activity, pH 7.0: about 30% of maximal activity with biopterin

484956

4.7 - 7

-

significant decline of activity at pH 7 and 4.7

484951

30

Leishmania amazonensis

wild-type (WTS) and SbIII-resistant (SbR) lines

O09352

UniProt

Leishmania braziliensis

wild-type (WTS) and SbIII-resistant (SbR) lines

UniProt

Leishmania guyanensis

wild-type (WTS) and SbIII-resistant (SbR) lines

A0A1E1IZ95

UniProt

Leishmania infantum

wild-type (WTS) and SbIII-resistant (SbR) lines

UniProt

-

UniProt

Leishmania sp. BK-2007

-

725166

A2TEY0

UniProt

no activity in Homo sapiens

-

-

Y strain

-

-

-

-

in stationary phase promastigotes

-

686606

malfunction

physiological function

9 entries

additional information

-

organization of the TbPTR1 active site, overview

Trypanosoma brucei brucei

2xox, download, 3D-view

116000

-

recombinant enzyme, gel filtration

116800

-

gel filtration

484956

117000

-

native enzyme, gel filtration

134000

recombinant enzyme, gel filtration

25700

4 * 25700, crystal structure

654109

29000

4 * 33500, recombinant enzyme, SDS-PAGE, 4 * 29000, native enzyme, SDS-PAGE

30000

4 entries

31000

-

2 * 31000, SDS-PAGE

484956

33500

4 * 33500, recombinant enzyme, SDS-PAGE, 4 * 29000, native enzyme, SDS-PAGE

51000

x * 51000, SDS-PAGE

57000

x * 57000, SDS-PAGE, GFP-fusion protein

?

homotetramer

x-ray crystallography

tetramer

11 entries

additional information

sitting drop vapor diffusion method, using 0.1 M MES pH 6.5, 10%(v/v) dioxane and 1.6 M ammonium sulfate

crystallized in complex with reduced cofactor and two different inhibitors

enzyme in ternary complex with NADPH and inhibitor 2,4,6-triaminoquinazoline in protein solution containing 10 mg/ml protein, 20 mM sodium acetate, pH 5.3, 1 mM NADPH, 1 mM 2,4,6-triaminoquinazoline, 20 mM DTT, and 1% DMSO, hanging drop vapour diffusion method, against equal volume of 0.002 ml of reservoir solution containing 11-14% PEG 5000, 100 mM sodium acetate, pH 5.5, and 40-140 mM calcium acetate, 20°C, thin grew clumps of thin fragile rods, cryopreservation in a solution of 0% reservoir solution and 30% glycerol, X-ray diffraction structure determination and analysis at 2.6 A resolution, molecular replacement

654109

in complex with NADPH, and with NADPH and biopterin, 5,6-dihydrobiopterin, or 5,6,7,8-tetrahydrobiopterin as well as in complex with NADPH and inhibitors CB3717 or trimethoprim. Enzyme does not undergo major conformational changes to accomplish binding and processing of substrates. Quinazoline moiety of inhibotr CB3717 binds similarly to pterin of substrate

-

675351

purified enzyme LmPtr1 in ternary complex with compounds 6-hydroxy-2-(3-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one and 2-(3,4-dihydroxyphenyl)-6-hydroxy-2,3-dihydro-4H-1-benzopyran-4-one, hanging drop vapour diffusion method, mixing of 0.002 ml of 12.5 mg/ml protein in 20 mM sodium acetate, pH 5.3, containing 1 mM NADPH, and 20 mM DTT, with 0.002 ml of reservoir solution containing 12% PEG 4600, 100 mM sodium acetate buffer pH 5.5 and 120-160 mM calcium acetate, equilibration against reservoir solution, at 20°C, for complex crystals the preformed crystals are soaked in a 2 mM inhibitor solution (dissolved in a 1:1 mixture of 1,4-dioxane and water) for 4.5 h, X-ray diffraction structure determination and analysis at 2.10-2.35 A resolution

743328

purified recombinant enzyme in binary complex with NADPH and in ternary complex with NADPH and methotrexate, 0.02 ml of protein solution containing 20 mg/ml protein, 20 mM Tris-HCl, pH 7.0, mixed with 0.01 ml of a solution containing 4 mM NADPH, 4 mM methotrexate on ice for 1 h, then mixed with 0.01 ml of reservoir solution containing 28% 1,4-butanediol, 12.5 mM cetyl trimethyl ammonium chloride and 100 mM HEPES, pH 7.0, 5 days, 14°C, X-ray diffraction structure determination and analysis of flash frozen crystals at 2.8 A resolution, molecular replacement technique

P42556

654075

-

purified enzyme TbPtr1 in ternary complex with compound 6-hydroxy-2-(3-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one, sitting drop vapor diffusion method, mixing of equal volumes of protein solution containing 6-10 mg/ml protein in 20 mM Tris-HCl, pH 7.5, and 10 mM DTT, with precipitant solution containing 1.5-2.5 M sodium acetate and 0.1 M sodium citrate, pH 5.0, equilibration against 0.6 ml of reservoir solution, at room temperature, several days, for complexed crystals are soaked in a 2 mM solution of the inhibitor (dissolved in a 1:1 mixture of 1,4-dioxane and water) for 4 h, X-ray diffraction structure determination and analysis at 1.70 A resolution

743328

K199E

-

The mutant enzymes Y38D, Y195F, Y195W, and K199R are inactive even if they are purified as tetramers

Y175D

-

mutant enzyme Y175D shows properties similar to wild type enzyme. The mutant enzymes Y38D, Y195F, Y195W, and K199R are inactive even if they are purified as tetramers

Y195F

-

The mutant enzymes Y38D, Y195F, Y195W, and K199R are inactive even if they are purified as tetramers

Y195W

-

The mutant enzymes Y38D, Y195F, Y195W, and K199R are inactive even if they are purified as tetramers

Y38D

-

The mutant enzymes Y38D, Y195F, Y195W, and K199R are inactive even if they are purified as tetramers

4.5 - 7.5

-

enzyme LmPTR1 is stable either in pH 4.5 or pH 7.5, since Tm values does not vary significantly between these conditions

742445

additional information

-

midpoint temperatures of the LmPTR1-unfolding transition (Tm) at different pHs, DMSO concentrations, and inhibitor concentrations, thermal shift enzyme assay optimization, overview

-80°C, 20% glycerol, 20 mM beta-mercaptoethanol, stable

-

-

HisTrap nickel-chelating column chromatography

native and recombinant enzyme

-

recombinant enzyme

recombinant enzyme from Escherichia coli

P42556

654075

recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3)by nickel affinity chromatography

T7 Tag antibody agarose column chromatography

Leishmania sp.

A2TEY0

725166

using Ni-NTA chromatography

-

-

expressed as a His-tagged fusion protein

-

expressed as N-terminal His6-tagged protein in Spodoptera frugiperda 21 cells

695556

expressed in Escherichia coli BL21 (DE3) GOLD cells

expressed in Escherichia coli strain JM109

Leishmania sp.

A2TEY0

725166

expression in Escherichia coli

expression of GFP-tagged enzyme in Leishmania donovani

-

gene ptr1 from wild-type and SbIII-resistant lines, DNA and amino acid sequenc determination, analysis, and comparison, chromosomal localization, enzyme expression analysis. PTR1 protein is more expressed in the Sb-resistant lines compared to their respective wild-type counterparts

gene ptr1 from wild-type and SbIII-resistant lines, DNA and amino acid sequenc determination, analysis, and comparison, chromosomal localization, enzyme expression analysis. PTR1 protein is more expressed in the Sb-resistant lines compared to their respective wild-type counterparts. Overexpression of ptr1 gene in the wild-type Leishmania braziliensis lines increases 2fold the SbIII-resistance phenotype compared to the non-transfected counterpart

Leishmania braziliensis

A4HCP1

gene ptr1 from wild-type and SbIII-resistant lines, DNA and amino acid sequenc determination, analysis, and comparison, chromosomal localization, enzyme expression analysis. PTR1 protein is more expressed in the Sb-resistant lines compared to their respective wild-type counterparts. Overexpression of ptr1 gene in the wild-type Leishmania infantum lines does not change the SbIII-resistance phenotype

Leishmania infantum

A4I067

gene PTR1, recombinant expression of His6-tagged enzyme in Escherichia coli strain BL21(DE3)

-

overexpressed in transgenic Leishmania parasites as N-terminal GFP-tagged PTR1-green fluorescent protein

-

700560

overexpression of the N-terminally His-tagged enzyme in Escherichia coli strain BL21(DE3)

promastigote form of Leishmania donovani transfected with GFP and GFP-PTR1 chimera

686606

recombinantly expressed

transgenic parasites overexpress a PTR1-GFP chimera (PTR1 tagged at the N-terminal with GFP)