1.17.4.1: ribonucleoside-diphosphate reductase
This is an abbreviated version!
For detailed information about ribonucleoside-diphosphate reductase, go to the full flat file.
Word Map on EC 1.17.4.1
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1.17.4.1
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deoxyribonucleotides
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hydroxyurea
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tyrosyl
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reductases
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chlamydia
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trachomatis
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deoxynucleotides
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proton-coupled
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diiron
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deoxycytidine
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diferric
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thiyl
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dntps
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dcdp
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thiosemicarbazone
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diferric-tyrosyl
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nrdabs
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hydroxyurea-resistant
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medicine
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nrdef
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heterodinuclear
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drug development
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antiferromagnetically
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pharmacology
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molecular biology
- 1.17.4.1
- deoxyribonucleotides
- hydroxyurea
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tyrosyl
- reductases
- chlamydia
- trachomatis
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deoxynucleotides
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proton-coupled
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diiron
- deoxycytidine
-
diferric
-
thiyl
- dntps
- dcdp
- thiosemicarbazone
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diferric-tyrosyl
-
nrdabs
-
hydroxyurea-resistant
- medicine
-
nrdef
-
heterodinuclear
- drug development
-
antiferromagnetically
- pharmacology
- molecular biology
Reaction
Synonyms
2'-deoxyribonucleoside-diphosphate:oxidized-thioredoxin 2'-oxidoreductase, ADP reductase, CDP reductase, class I ribonucleotide reductase, class I ribonulceotide reductase, class I RNR, class I RR, class Ia ribonucleotide reductase, class Ia RNR, class Ia RR, class Ib ribonucleotide reductase, class Ib RNR, class Ic ribonucleotide reductase, class II RNR, manganese-ribonucleotide reductase, Mn-RNR, More, mRR, NrdA, NrdB, NrdE, NrdF, nucleoside diphosphate reductase, p53-inducible ribonucleotide reductase, R2F, reductase, ribonucleoside diphosphate, ribonucleoside 5'-diphosphate reductase, ribonucleoside diphosphate reductase, ribonucleoside-diphosphate reductase subunit M2 B, ribonucleotide diphosphate reductase, ribonucleotide reductase, RIR1, RIR2, RNR, RNR1 rRibonucleoside-diphosphate reductase large chain 1, RNR2, UDP reductase
ECTree
1.17.4.1 ribonucleoside-diphosphate reductaseAdvanced search results
results (
results (Inhibitors
Inhibitors on EC 1.17.4.1 - ribonucleoside-diphosphate reductase
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INHIBITOR 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
IMAGE
(2E)-2-(anthracen-9-ylmethylidene)-N-hydroxyhydrazinecarboximidamide
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i.e. ABNM-13, application leads to significant alterations of deoxyribonucleoside triphosphate pool balance and a highly significant decrease of incorporation of radiolabeled cytidine into DNA of HL-60 cells. Diminished ribonucleotide reductase activity causes replication stress which is consistent with activation of Chk1 and Chk2, resulting in downregulation/degradation of Cdc25A. Cdc25B is upregulated, leading to dephosphorylation and activation of Cdk1. The combined disregulation of Cdc25A and Cdc25B is the most likely cause for ABNM-13 induced S-phase arrest
(E)-2'-fluoromethylene-2'-deoxycytidine-5-diphosphate
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i.e. N3dNDP, inhibitor forming a furanone intermediate. Modeling of enzyme-inhibitor complex
1-Formylisoquinoline thiosemicarbazone
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0.0006 mM, 81% inhibition, 0.1 mM desferal reverses inhibition
2',3'-dideoxy-ATP
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less potent inhibitor than dATP, 0.1 mM, 50% inhibition of CDP reduction
2'-methyladenosine 5'-diphosphate
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probably mechanism based inhibition, competitive inhibition vs. ADP and GDP
2'-methyluridine 5'-diphosphate
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probably mechanism based inhibition, competitive inhibition vs. UDP and CDP
2-(diphenylmethylidene)-N,N-dimethylhydrazinecarbothioamide
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metal chelator, significantly decreases ribonucleotide reductase activity, whereas the NADPH/NADP+ total ratio is not reduced
2-acetylpyridine N-pyrrolidinylthiosemicarbazonato-N,N,S-dichlorogallium(III)
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2-[di(pyridin-2-yl)methylidene]-N,N-dimethylhydrazinecarbothioamide
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metal chelator, significantly decreases ribonucleotide reductase activity, whereas the NADPH/NADP+ total ratio is not reduced
3-aminopyridine-2-carboxaldehyde-thiosemicarbazone
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i.e. 3-AP, phase I study in combination with high dose cytarabine in patients with advanced myeloid leukemia, resulting in enhanced cytarabine cytotoxicity with possible methemoglobinemia, overview
5'-O-valproyl-3'-C-methyladenosine
inhibits ribonucleotide reductase activity by competing with ATP as an allosteric effector and concomitantlyreduces the intracellular deoxyribonucleoside triphosphate pools. In contrast to previously used ribonucleotide reductase nucleoside analogs does not require intracellular kinases for its activity and therefore holds promise against drug resistant tumors with downregulated nucleoside kinases
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6-chloro-9H-(3-C-methyl-2,3-di-O-acetyl-5-O-benzoyl-beta-D-ribofuranosyl)purine
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clofarabine
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an adenosine analogue is used in the treatment of refractory leukemias. Its mode of cytotoxicity is associated in part with the triphosphate functioning as an allosteric reversible inhibitor of hRNR, rapid inactivation
clofarabine diphosphate
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ClFDP, a C-site slow-binding, reversible inhibitor, mechanism of inhibition via altering the quaternary structure of the large subunit of RNR, overview. Binds also mutant D57N-alpha subunit. CDP protects against inhibition
clofarabine triphosphate
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ClFTP, an A-site rapidly binding reversible inhibitor, mechanism of inhibition via altering the quaternary structure of the large subunit of RNR, overview. Neither CDP (C site) nor dGTP (A site) had any effect on inhibition by ClFTP
ethyleneglycol-bis-(2-aminoethylether)-N,N,N',N'-tetraacetic acid
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trivial name EGTA
Fmoc(NCH3)PhgLDChaDF
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inhibitor identified by competition with inhibitor N-AcFTLDADF and inhibition of enzyme activity
FmocWFDF
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inhibitor identified by competition with inhibitor N-AcFTLDADF and inhibition of enzyme activity
FmocWVFF
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inhibitor identified by competition with inhibitor N-AcFTLDADF and inhibition of enzyme activity
FTLDADF
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last seven amino acid residues of carboxyl terminus of the R2 subunit of mouse enzyme and its N-alpha-acetyl derivative inhibit thymus enzyme
gamma-L-Glutaminyl-4-hydroxybenzene
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naturally occuring quinol from spores of Agaricus bisporus, 0.76 mM, 50% inhibition
IRBIT
IRBIT is a conserved metazoan protein implicated in diverse functions. IRBIT consists of a putative enzymatic domain that has similarity to S-adenosylhomocysteine hydrolase and an essential N-terminal domain of 104 amino acids. It forms a dATPdependent complex with ribonucleotide reductase, which stabilizes dATP in the activity site of ribonucleotide reductase and thus inhibits the enzyme. Formation of the ribonucleotide reductase-IRBIT complex is regulated through phosphorylation of IRBIT, and ablation of IRBIT expression in HeLa cells causes imbalanced dNTP pools and altered cell cycle progression. Under normal physiological conditions, where ATP levels are high, such inhibition can only be achieved when binding of IRBIT is strengthened by phosphorylation
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L-ADP
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inhibition of D-ADP reduction, competitive inhibition of dGTP-dependent D-ADP reductase
mammalian R2 C-terminal heptapeptide P7
Ac-1FTLDADF7, the inhibitor binds at bind at a contiguous site containing residues that are highly conserved among eukaryotes, binding structure, overview
monoclonal antibody raised against yeast tubulin
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CDP reductase activity is inhibited to a greater extent than ADP, UDP or GDP reductase activity, antibody recognizes a specific sequence in the C-terminal region on the R2 subunit
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N-ethylmaleimide
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0.1 mM, 50% inhibition of intact enzyme, 0.05 mM, 50% inhibition of effector-binding subunit, 0.3 mM, 50% inhibition of non-heme iron subunit
N-[[(3S,5S,7S,7aS)-7-([[3-(9H-fluoren-9-yl)propanoyl]oxy]methyl)-3-hydroxy-5-(2-methylpropoxy)hexahydropyrano[3,4-b]pyrrol-1(2H)-yl]acetyl]-L-alpha-aspartyl-L-phenylalanine
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50% inhibition at 0.04-0.05 mM, bicyclic scaffold is necessary to maintain inhibitory activity
NSFTLDADF
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inhibition of CDP reductase activity, peptide corresponds to the C-terminal region of the R2 subunit and competes with binding of R2 to the R1 subunit
o-ClBzocFc[ELDK]DF
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inhibitor identified by competition with inhibitor N-AcFTLDADF and inhibition of enzyme activity
p-chloromercuribenzoate
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0.35 mM, 50% inhibition of intact enzyme, 0.15 mM, 50% inhibition of effector-binding subunit, 1.5 mM, 50% inhibition of non-heme iron subunit
peptide P6
1Fmoc(Me)PhgLDChaDF7, the inhibitor binds at a contiguous site containing residues that are highly conserved among eukaryotes. The Fmoc group in P6 peptide forms several hydrophobic interactions that contribute to its enhanced potency in binding to ScR1, binding structure, overview
peptide Y-R2C19
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a 20-mer peptide, which is identical to the C-terminal peptide tail of the R2 subunit and is a known competitive inhibitor of binding of the native R2 protein to R1
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quercetin
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i.e. 3,3',4',5,7-pentahydroxyflavone, isolated from air-dried powdered leaves of Vitex negundo, a lipophilic metal chelator, that interferes with the parasite's iron metabolism inhibiting Fe2+ acquisition from an endogenous source, combination of quercetin with serum albumin increases its bioavailability, the inhibitor causes deprivation of the enzyme of iron which in turn destabilized the critical tyrosyl radical required for its catalysing activity
Sml1
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inhibitor protein Sml1 competes with the C-terminal domain of subunit R1 for association with its N-terminal domain to hinder the accessibility of the CX2C motif to the active site for R1 regeneration during the catalytic cycle
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Sml1 protein
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a 104-residue Saccharomyces cerevisiae protein, inhibits ribonucleotide reductase activity by binding to the R1 subunit interacting with the N-terminal domain of R1, R1-NTD, which involves a conserved two-residue sequence motif in the R1-NTD, the Sml1-R1 interaction causes SML1-dependent lethality, overview
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sodium arsenite
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0.025 mM, almost complete inhibition of CDP reduction, 86% inhibition of GDP reduction
Synthetic peptides
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which specifically inhibit the activity of virus-induced enzyme
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YAGAVVNDL
Herpes simplex virus
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peptide may prevent association of the two subunits by competing for the subunit binding site
[bis(2-acetylpyridine N,N-dimethylthiosemicarbazonato)-N,N,S-gallium(III)] hexafluorophosphate
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[bis(2-acetylpyridine N,N-dimethylthiosemicarbazonato)-N,N,S-iron(III)] hexafluorophosphate
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[bis(2-acetylpyridine N,N-dimethylthiosemicarbazonato)-N,N,S-iron(III)] tetrachloroferrate(III)
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[bis(2-acetylpyridine N-pyrrolidinylthiosemicarbazonato)-N,N,S-gallium(III)] hexafluorophosphate
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[bis(2-acetylpyridine N-pyrrolidinylthiosemicarbazonato)-N,N,S-iron(III)] hexafluorophosphate
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[bis(2-acetylpyridine N-pyrrolidinylthiosemicarbazonato)-N,N,S-iron(III)] tetrachloroferrate(III)
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[bis(acetylpyrazine N,N-dimethylthiosemicarbazonato)-N,N,S-gallium(III)] hexafluorophosphate
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[bis(acetylpyrazine N,N-dimethylthiosemicarbazonato)-N,N,S-iron(III)] hexafluorophosphate
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[bis(acetylpyrazine N,N-dimethylthiosemicarbazonato)-N,N,S-iron(III)] tetrachloroferrate(III)
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[bis(acetylpyrazine N-piperidinylthiosemicarbazonato)-N,N,S-gallium(III)] hexafluorophosphate
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[bis(acetylpyrazine N-piperidinylthiosemicarbazonato)-N,N,S-iron(III)] hexafluorophosphate
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[bis(acetylpyrazine N-piperidinylthiosemicarbazonato)-N,N,S-iron(III)] tetrachloroferrate(III)
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[bis(acetylpyrazine N-pyrrolidinylthiosemicarbazonato)-N,N,S-gallium(III)] hexafluorophosphate
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[bis(acetylpyrazine N-pyrrolidinylthiosemicarbazonato)-N,N,S-iron(III)] hexafluorophosphate
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[bis(acetylpyrazine N-pyrrolidinylthiosemicarbazonato)-N,N,S-iron(III)] tetrachloroferrate(III)
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[FeCl4] 2-acetylpyridine N,N-dimethylthiosemicarbazone
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Ga(III) and Fe(III) complexes destroy the tyrosyl radical of the presumed target ribonucleotide reductase
[GalCl2] 2-acetylpyridine N,N-dimethylthiosemicarbazone
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Ga(III) and Fe(III) complexes destroy the tyrosyl radical of the presumed target ribonucleotide reductase
(-)-epicatechin
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interacts with the R2 protein, leading to a loss of the tyrosyl radical EPR signal. Proliferation of cells exposed to (-)-epicatechin is downregulated, and deoxyribonucleotide levels are significantly diminished
(-)-epicatechin
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interacts with the R2 protein, leading to a loss of the tyrosyl radical EPR signal. Proliferation of cells exposed to (-)-epicatechin is downregulated, and deoxyribonucleotide levels are significantly diminished
2,3,4-trihydroxybenzohydroxamic acid
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0.012 mM, 50% inhibition, hydroxyurea-resistant cells
3,5-diamino-1H-1,2,4-triazole
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0.001 mM, 50% inhibition of CDP and UDP reduction, 0.05 mM, 50% inhibition of ADP reduction
3,5-diamino-1H-1,2,4-triazole
Herpes simplex virus
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noncompetitive vs. CDP; trivial name guanazole
3,5-diamino-1H-1,2,4-triazole
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2.3 mM, 50% inhibition of CDP reduction, 2.6 mM, 50% inhibition of ADP reduction
3,5-diamino-1H-1,2,4-triazole
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2 mM, 41% inhibition, presence of 0.1 mM desferal potentiates inhibition; trivial name guanazole
3-aminopyridine-2-carboxaldehyde thiosemicarbazone
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i.e.3-AP or triapine, in combination with the nucleoside analog fludarabine for patients with refractory acute leukemias and aggressive myeloprol, phase I study, detailed overview, the inhibitor inhibits the M2 subunit, and depletes intracellular deoxyribonculeotide pools, especially dATP
4-Methyl-5-amino isoquinoline-1-carboxaldehyde thiosemicarbazone
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inhibits the non-heme iron subunit
4-Methyl-5-amino-1-formylisoquinoline thiosemicarbazone
Herpes simplex virus
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inactivation, half-life: 3 min
4-Methyl-5-amino-1-formylisoquinoline thiosemicarbazone
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0.0003 mM, 93% inhibition, 0.1 mM desferal reverses inhibition
8-hydroxyquinoline 5-sulfonate
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no inhibition in the presence of excess iron
bathophenanthroline sulfonate
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1.5 mM, complete inactivation after 30 min, complete reactivation with FeCl3
bathophenanthroline sulfonate
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5 mM, almost complete inhibition of CDP and GDP reduction
bathophenanthroline sulfonate
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no effect in the presence of excess iron
cisplatin
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more than 90% irreversible inhibition by inhibitor/enzyme ratios smaller than 2 under anaerobic conditions, 0.4 mM, 50% inhibition under aerobic conditions, inhibition of B1 subunit
dATP
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dATP maximally stimulates CDP reduction at 8-10 microM followed by rapid inhibition at higher concentrations
dATP
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0.005 mM, 50% inhibition of CDP and UDP reduction, 0.005 mM, 50% inhibition of GDP and ADP reduction; inhibition of ADP reduction; inhibition of CDP reduction; inhibition of GDP reduction
dATP
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inhibition of ADP reduction; inhibition of CDP reduction; inhibition of GDP reduction
dATP
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inhibition of CDP and UDP reduction is reversed by ATP; inhibition of CDP reduction; inhibition of UDP reduction
dATP
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inhibition of ADP reduction; inhibition of CDP reduction; inhibition of GDP reduction
dATP
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2.1 mM, 50% inhibition; inhibition of CDP reduction; weak inhibition of ADP reduction
dATP
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0.0033 mM, 50% inhibition of CDP reduction, 0.0036 mM, 50% inhibition of GDP reduction; inhibition of CDP reduction
dATP
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inhibition of CDP reduction; inhibition of CDP, UDP, GDP and ADP reduction; noncompetitive inhibition vs. ADP, GDP and CDP
dATP
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0.1 mM, 96% inhibition of CDP reductase activity in dextran sulfate-treated cells, 85% inhibition of GDP reductase activity
dATP
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strong inhibition of the ATP activated enzyme, complete inhibition of GDP reduction, inhibition of ADP reduction
dATP
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inhibition of ADP reduction; inhibition of CDP reduction; inhibition of GDP reduction
dATP
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activation at low concentration with a KL1 value for specificity site binding of 0.0032 mM, inhibition at higher concentration with a KL2 value for activity site binding of 0.0173 mM
dATP
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inhibition of ADP reduction; inhibition of CDP reduction; inhibition of GDP reduction; inhibition of UDP reduction
dATP
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inhibition of ADP reduction; inhibition of CDP reduction; inhibition of GDP reduction
dATP
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0.05 mM, 50% inhibition of CDP reduction in presence of optimum ATP concentration i.e. 6 mM, stimulation in absence of ATP; inhibition of CDP reduction
dATP
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inhibition by dATP has a regulatory function
dATP
Tequatrovirus T4
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inhibition of ADP reduction; inhibition of CDP reduction; inhibition of GDP reduction; inhibition of UDP reduction
dATP
Tequatrovirus T4
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inhibition of ADP reduction; inhibition of CDP reduction; inhibition of GDP reduction
dATP
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3.5 mM, 92% inhibition of activity in extracts; inhibition of CDP reduction
dCTP
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1.2 mM, 50% inhibition of CDP reduction, 0.89 mM, 50% inhibition of ADP reduction
deferoxamine mesylate
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IC50 for subunit p53R2 is 0.00316 mM, IC50 for hRRM2 subunit is 0.5 mM
dGTP
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0.05 mM, 50% inhibition of GDP reduction; 0.1 mM, 50% inhibition of CDP and UDP reduction; inhibition of UDP reduction
dGTP
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1.2 mM, 50% inhibition of CDP reduction, 0.93 mM, 50% inhibition of ADP reduction
dGTP
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0.08 mM, 50% inhibition of CDP reduction, 0.19 mM, 50% inhibition of GDP reduction; inhibition of CDP reduction
dGTP
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inhibition of CDP reduction; inhibition of GDP reduction; inhibition of UDP reduction
EDTA
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reversible stimulation of GDP reduction, irreversible inhibition of CDP reduction
gemcitabine
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i.e. F2dNDP, inhibitor forming a furanone intermediate. Modeling of enzyme-inhibitor complex
Hydroxyurea
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inhibition of the enzyme by the 1-electron donor hydroxyurea produces the Mn(III)Fe(III) state
Hydroxyurea
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inactivates both Ia/b and Ic beta2 subunits by reducing their C oxidants, reacts with the MnIV/FeIII cofactor to give two distinct products: the homogeneous MnIII/FeIII-beta2 complex, which forms only under turnover conditions, in the presence of alpha2 and the substrate, and a distinct, diamagnetic Mn/Fe cluster, which forms about 900fold less rapidly as a second phase in the reaction under turnover conditions and as the sole outcome in the reaction of MnIV/FeIII-beta2 only
Hydroxyurea
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IC50 for subunit p53R2 is 2.48 mM, IC50 for hRRM2 subunit is 0.991 mM
Hydroxyurea
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2 mM, 93% inhibition, presence of 0.1 mM desferal potentiates inhibition
Hydroxyurea
wild-type plants exposed to a low concentration of an RNR inhibitor, hydroxyurea, produce chlorotic leaves without growth retardation, reminiscent of v3 and st1 mutants; wild-type plants exposed to a low concentration of an RNR inhibitor, hydroxyurea, produce chlorotic leaves without growth retardation, reminiscent of v3 and st1 mutants
Hydroxyurea
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approx. 0.5 mM, 50% inhibition
pyrazoloimidazol
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2 mM, 79% inhibition, presence of 0.1 mM desferal potentiates inhibition, inhibits the non-heme iron subunit
Thenoyltrifluoroacetone
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5 mM, almost complete inhibition of CDP and GDP reduction
triapine
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i.e. 3-AP, triapine enhances the cytotoxicity of gemcitabine and arabinoside cytosine in four non-small-cell-lung-cancer cell lines, e.g. in SW1573 cells, but not in H460 cells, multiple-drug-effect analysis, overview
additional information
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overview: naturally occuring inhibitors e.g. proteins and nucleotides
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additional information
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the enzyme is inhibited by radical scavengers
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additional information
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overview: naturally occuring inhibitors e.g. proteins and nucleotides
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additional information
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8-vinyl-ADP is efficiently reduced. The anti-tumoral and anti-viral activity of 8-vinyladenosine can unlikely result from inhibition of ribonucleotide diphosphate reductase
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additional information
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reaction involves formation of a keto-deoxyribonucleotide intermediate. In case of furanone inhibitors, the intermediate dissociates from the active site, depending on the solvation free energy of the 2-substituents, its influence inside the active site, and the charge transfer mechanism from a protein side chain to solution as thermodynamic driving forces. Substrates do not dissociate from the active site but complete the catalytic cycle
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additional information
Herpes simplex virus
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enzyme does not respond to feedbck inhibition by dTTP or dATP
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additional information
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overview: naturally occuring inhibitors e.g. proteins and nucleotides
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additional information
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synthesis, characterization, cytotoxicity in human cell lines, and interaction with ribonucleotide reductase of gallium(III) and iron(III) complexes of alpha-N-heterocyclic thiosemicarbazones, overview, gallium(III) enhances, whereas iron(III) weakens the cytotoxicity of the ligands
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additional information
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construction and synthesis of ribose-modified purine nucleosides as ribonucleotide reductase inhibitors. Synthesis, antitumor activity, and molecular modeling of N6-substituted 3-C-methyladenosine derivatives, an unsubstituted N6-amino group is essential for optimal cytotoxicity of 3'-Me-Ado. The anticancer nucleosides act as antimetabolites after metabolic activation by phosphorylation to the corresponding 5'-di- or 5'-triphosphates, overview
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additional information
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inhibitory mechanisms of heterocyclic carboxaldehyde thiosemicabazones
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additional information
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synthesis and ribonucleotide reductase inhibitory activity of thiosemicarbazones, overview
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additional information
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each ribonucleoside diphosphate substrate is competitively inhibited by reduction of each other substrate
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additional information
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inhibition of reductase by hydroxyurea, guanazole and pyrazolo-imidazole is potentiated by iron-chelating agents e.g. EDTA, desferrioxamine mesylate and 8-hydroxyquinoline, inhibition by 4-methyl-5-amino-1-formylisoquinoline thiosemicarbazone and 1-formylisoquinoline thiosemicarbazone is reversed by iron chelating agents
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additional information
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overview: naturally occuring inhibitors e.g. proteins and nucleotides
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additional information
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L1210 cells with resistance to specific nucleotide reductase inhibitors
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additional information
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comprehensive and quantitative model for allosteric control of mRR enzymatic activity based on molecular mass, ligand binding and enzyme activity studies
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additional information
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synthesis, characterization, and interaction with ribonucleotide reductase subunit R2 of gallium(III) and iron(III) complexes of alpha-N-heterocyclic thiosemicarbazones, overview, gallium(III) enhances, whereas iron(III) weakens the cytotoxicity of the ligands
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additional information
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synthesis and evaluation of peptide inhibitors of RNR derived from the C-terminus of the small subunit of Mycobacterium tuberculosis RNR, based on the heptapeptide Ac-Glu-Asp-Asp-Asp-Trp-Asp-Phe-OH with Trp5 and Phe7 being very important for inhibitory potency, overview
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additional information
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overview: naturally occuring inhibitors e.g. proteins and nucleotides
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additional information
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overview: naturally occuring inhibitors e.g. proteins and nucleotides
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additional information
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overview: naturally occuring inhibitors e.g. proteins and nucleotides
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additional information
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not inhibited by 8-hydroxyquinoline and o-phenanthroline
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additional information
Tequatrovirus T4
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overview: naturally occuring inhibitors e.g. proteins and nucleotides
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additional information
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overview: naturally occuring inhibitors e.g. proteins and nucleotides
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