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3.5.3.15: protein-arginine deiminase

This is an abbreviated version!
For detailed information about protein-arginine deiminase, go to the full flat file.

Word Map on EC 3.5.3.15

Reaction

protein L-arginine
+
H2O
=
protein L-citrulline
 +
NH3

Synonyms

deiminase, protein (arginine), HL-60 PAD, hPADI2, hPADI4, hPADVI, PAD, PAD 1, PAD 2, PAD 3, PAD 4, PAD II, PAD IV, PAD type 2, PAD-4, PAD-H19, PAD-R11, PAD-R4, PAD1, PAD2, PAD3, PAD4, PAD6, PADI1, Padi2, PADI3, PADI4, peptidyl arginine deiminas 4, peptidyl arginine deiminase, peptidyl arginine deiminase 2, peptidyl-arginine deiminase, peptidylarginine deiminase, peptidylarginine deiminase 1, peptidylarginine deiminase 2, peptidylarginine deiminase 3, peptidylarginine deiminase 4, peptidylarginine deiminase 6, peptidylarginine deiminase isoform VI, peptidylarginine deiminase IV, peptidylarginine deiminase type 4, Peptidylarginine deiminase type alpha, peptidylarginine deiminase type I, peptidylarginine deiminase type II, peptidylarginine deiminase type III, peptidylarginine deiminase type VI, peptidylarginine deiminase-4, PPAD, protein arginine deiminase, protein arginine deiminase 2, protein arginine deiminase 3, protein arginine deiminase 4

ECTree

     3 Hydrolases
         3.5 Acting on carbon-nitrogen bonds, other than peptide bonds
             3.5.3 In linear amidines
                3.5.3.15 protein-arginine deiminase

Inhibitors

Inhibitors on EC 3.5.3.15 - protein-arginine deiminase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(3R)-3-[2-[4-(2-carbamimidamidoethyl)-1H-1,2,3-triazol-1-yl]acetamido]-3-(4-fluorophenyl)propanoic acid
1,2,3-triazole peptidomimetic-based compound, 39% inhibition at 1 microM, 99% inhibition at 10 microM
(3S)-3-[2-[4-(2-carbamimidamidoethyl)-1H-1,2,3-triazol-1-yl]acetamido]-3-phenylpropanoic acid
1,2,3-triazole peptidomimetic-based compound, 26% inhibition at 1 microM, 69% inhibition at 10 microM
1-(2-{4-[(aminooxy)sulfinyl]phenyl}ethyl)guanidine hydrochloride
5% inhibition at 0.01 mM
1-[3-(1H-imidazol-4-yl)propyl]-3-{2-[(4-phenyl-1,2,5-oxadiazol-3-yl)oxy]ethyl}guanidine hydrochloride
34% inhibition at 0.01 mM
1-[[4-(benzoylamino)-5-(ethylamino)-5-oxopentyl]amino]-2-chloroethaniminium
-
-
1-[[4-(benzoylamino)-5-(ethylamino)-5-oxopentyl]amino]-2-fluoroethaniminium
-
-
1-[[6-amino-5-(benzoylamino)-6-oxohexyl]amino]-2-chloroethaniminium
-
potent, irreversible and specific PAD3 inhibitor
1-[[6-amino-5-(benzoylamino)-6-oxohexyl]amino]-2-fluoroethaniminium
-
potent, irreversible and specific PAD3 inhibitor
2-({(1S)-1-(2-tert-butyl-2H-tetrazol-5-yl)-4-[(2-chloroethanimidoyl)amino]butyl}carbamoyl)benzoic acid
-
2-({(1S)-1-(2-tert-butyl-2H-tetrazol-5-yl)-4-[(2-fluoroethanimidoyl)amino]butyl}carbamoyl)benzoic acid
-
2-chloro-N-[3-(2,5-dioxo-1-phenylimidazolidin-4-yl)propyl]ethanimidamide
-
2-chloro-N-[3-(2,5-dioxoimidazolidin-4-yl)propyl]ethanimidamide
-
2-chloroacetamidine
2-cyano-1-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
1% inhibition at 0.01 mM
2-cyano-1-{2-[({2-[(diaminomethylidene)amino]-1,3-thiazol-5-yl}methyl)sulfanyl]ethyl}-3-(2-hydroxyethyl)guanidine ethanedioate
3% inhibition at 0.01 mM
2-{[(1S)-4-[(2-chloroethanimidoyl)amino]-1-(2H-tetrazol-5-yl)butyl]carbamoyl}benzoic acid
15fold selectivity versus PAD2 and PAD3; 15fold selectivity versus PAD2 and PAD3; 15fold selectivity versus PAD2 and PAD3; 15fold selectivity versus PAD2 and PAD3
2-{[(1S)-4-[(2-fluoroethanimidoyl)amino]-1-(2H-tetrazol-5-yl)butyl]carbamoyl}benzoic acid
exhibits 20 to 30fold selectivity over isoform PAD2 and PAD3 when compared to PAD1; exhibits 20 to 30fold selectivity over isoform PAD2 and PAD3 when compared to PAD1; exhibits 20 to 30fold selectivity over isoform PAD2 and PAD3 when compared to PAD1; exhibits 20 to 30fold selectivity over isoform PAD2 and PAD3 when compared to PAD1
4-(4-{3-[(2-chloroethanimidoyl)amino]propyl}-2,5-dioxoimidazolidin-1-yl)-2-ethoxy-N-(4-methoxyphenyl)benzamide
-
4-(4-{3-[(2-chloroethanimidoyl)amino]propyl}-2,5-dioxoimidazolidin-1-yl)-2-methoxy-N-(4-methoxyphenyl)benzamide
-
4-(4-{3-[(2-chloroethanimidoyl)amino]propyl}-2,5-dioxoimidazolidin-1-yl)-N-(4-methoxyphenyl)benzamide
-
4-(4-{3-[(2-chloroethanimidoyl)amino]propyl}-2,5-dioxoimidazolidin-1-yl)-N-phenylbenzamide
-
4-chloromercuribenzoate
inhibits PAD3
4-[(2-chloroethanimidoyl)amino]-N-(diphenylmethyl)butanamide
-
5-aminosalicylic acid
-
-
antipain
-
8 mM, 41% inhibition
Azathioprine
-
-
azithromycin
-
-
BAPTA-AM
inhibits PAD2; inhibits PAD2
benzoyl-N-dimethyl-Arg
inhibits PAD4
benzoyl-N-methyl-Arg
inhibits PAD4
benzoyl-Ngamma,Ngamma-dimethyl-Arg
IC50: 0.4 mM
benzoyl-Ngamma-methyl-Arg
-
chloro-N-(3-{1-[(2'-chloro-3'-fluoro[1,1'-biphenyl]-3-yl)methyl]-2,5-dioxoimidazolidin-4-yl}propyl)ethanimidamide
-
chloro-N-(3-{1-[(2'-chloro[1,1'-biphenyl]-3-yl)methyl]-2,5-dioxoimidazolidin-4-yl}propyl)ethanimidamide
-
chloro-N-(3-{1-[(3'-fluoro[1,1'-biphenyl]-3-yl)methyl]-2,5-dioxoimidazolidin-4-yl}propyl)ethanimidamide
-
chloroamidine
chlortetracycline
-
-
Cl-amidine
clindamycin
-
-
Cys
-
25 mM, complete inhibition
F-amidine
H2O2
in vitro inhibitory to isoform Pad2 above 0.04 mM, peptidylarginine deiminase released from stimulated leukocytes is unaffected by exogenously added H2O2 at concentrations up to 1000 microM; in vitro inhibitory to isoform Pad4 above 0.04 mM, peptidylarginine deiminase released from stimulated leukocytes is unaffected by exogenously added H2O2 at concentrations up to 1000 microM
interferon beta
inhibits PAD2
-
iodoacetamide
iodoacetate
L-canavanine
-
suicide substrate
leflunomide
-
-
leupeptin
-
5 mM, complete inhibition
lipid vesicle
binding of substrate myelin basic protein to lipid vesicles, consisting of 7.8% phosphatidylserine and 92.2% phosphatidylcholine, increases deimination activity, but in the 40 mino acid C-terminal region, where the arginyl residues are no longer deiminated, while they are deiminated in aqueous solution; binding of substrate myelin basic protein to lipid vesicles, consisting of 7.8% phosphatidylserine and 92.2% phosphatidylcholine, increases deimination activity, but in the 40 mino acid C-terminal region, where the arginyl residues are no longer deiminated, while they are deiminated in aqueous solution
-
methotrexate
-
-
minocycline
-
a mixed type inhibitor
monoiodoacetate
-
-
N-(3-{1-[([1,1'-biphenyl]-3-yl)methyl]-2,5-dioxoimidazolidin-4-yl}propyl)(chloro)ethanimidamide
-
N-(biphenyl-3-ylmethyl)-4-[(2-chloroethanimidoyl)amino]butanamide
-
N-alpha-benzoyl-N5-(2-chloro-1-iminoethyl)-L-ornithine amide
N-alpha-benzoyl-N5-(2-chloro-1-iminoethyl)-L-ornithine ethyl ester
N-alpha-benzoyl-N5-(2-fluoro-1-iminoethyl)-L-ornithine amide
i.e. F-amidine, a potent and bioavailable irreversible inactivator of PAD4, structure of the PAD4-F-amidine-calcium complex, overview
N-[(1R)-1-(biphenyl-3-yl)ethyl]-4-[(2-chloroethanimidoyl)amino]butanamide
-
N-[(1S)-1-(2-tert-butyl-2H-tetrazol-5-yl)-4-[(2-fluoroethanimidoyl)amino]butyl]benzamide
preferentially inhibits protein-arginine deiminase 2 by 3fold with the highest selectivity being observed for PAD2 over PAD4. Highly selective protein-arginine deiminase 2 inhibitor relative to the other protein-arginine deiminases
N-[(1S)-1-(2-tert-butyl-2H-tetrazol-5-yl)-4-[(2-fluoroethanimidoyl)amino]butyl][1,1'-biphenyl]-4-carboxamide
preferentially inhibits protein-arginine deiminase 2 by 25fold with the highest selectivity being observed for PAD2 over PAD4. Highly selective protein-arginine deiminase 2 inhibitor relative to the other protein-arginine deiminases
N-[(1S)-1-(biphenyl-3-yl)ethyl]-4-[(2-chloroethanimidoyl)amino]butanamide
-
N-[(1S)-4-[(2-chloroethanimidoyl)amino]-1-(2H-tetrazol-5-yl)butyl]benzamide
-
N-[(1S)-4-[(2-chloroethanimidoyl)amino]-1-(2H-tetrazol-5-yl)butyl][1,1'-biphenyl]-4-carboxamide
-
N-[(1S)-4-[(2-fluoroethanimidoyl)amino]-1-(2H-tetrazol-5-yl)butyl]benzamide
-
N-[(1S)-4-[(2-fluoroethanimidoyl)amino]-1-(2H-tetrazol-5-yl)butyl][1,1'-biphenyl]-4-carboxamide
-
N-[(3'-bromobiphenyl-3-yl)methyl]-4-[(2-chloroethanimidoyl)amino]butanamide
-
N-[([1,1'-biphenyl]-3-yl)methyl]-4-[(2-chloroethanimidoyl)amino]butanamide
inhibitor at at 10 microM rescues thapsigargin-induced cell death in HEK293T cells
N-[3-(1H-imidazol-4-yl)propyl]-N'-{3-[(5-oxo-4-phenyl-1,2lambda~5~,5-oxadiazol-3-yl)oxy]propyl}guanidine hydrochloride
36% inhibition at 0.01 mM
N-[3-[5-([1,1'-biphenyl]-3-yl)-1H-imidazol-2-yl]propyl](chloro)ethanimidamide
inhibitor at at 10 microM rescues thapsigargin-induced cell death in HEK293T cells
N-{(1S)-1-(2-tert-butyl-2H-tetrazol-5-yl)-4-[(2-chloroethanimidoyl)amino]butyl}benzamide
-
N-{(1S)-1-(2-tert-butyl-2H-tetrazol-5-yl)-4-[(2-chloroethanimidoyl)amino]butyl}[1,1'-biphenyl]-4-carboxamide
-
N-{(1S)-1-(2-tert-butyl-2H-tetrazol-5-yl)-4-[(2-fluoroethanimidoyl)amino]butyl}benzamide
highly selective isoform PAD2 inhibitor; highly selective isoform PAD2 inhibitor; highly selective isoform PAD2 inhibitor; highly selective isoform PAD2 inhibitor
N-{(1S)-1-(2-tert-butyl-2H-tetrazol-5-yl)-4-[(2-fluoroethanimidoyl)amino]butyl}[1,1'-biphenyl]-4-carboxamide
preferentially inhibits isoform PAD2 by 3 to 25fold with the highest selectivity being observed for PAD2 over PAD4; preferentially inhibits isoform PAD2 by 3 to 25fold with the highest selectivity being observed for PAD2 over PAD4; preferentially inhibits isoform PAD2 by 3 to 25fold with the highest selectivity being observed for PAD2 over PAD4; preferentially inhibits isoform PAD2 by 3 to 25fold with the highest selectivity being observed for PAD2 over PAD4
N-{(2S)-1-amino-5-[(2-chloroethanimidoyl)amino]-1-oxopentan-2-yl}benzamide
-
-
N-{(2S)-1-amino-5-[(2-fluoroethanimidoyl)amino]-1-oxopentan-2-yl}benzamide
-
-
N2-benzoyl-N5-(N,N-dimethylcarbamimidoyl)-L-ornithine
-
inhibits PAD4 at high micromolar to millimolar concentrations
Nalpha-L-Arg methyl ester
-
12.5 mM, 48% inhibition
oxalic acid 3-(N''-cyano-N'-{2-[({2-[(diaminomethylidene)amino]-1,3-thiazol-5-yl}methyl)sulfanyl]ethyl}carbamimidamido)propane-1,2-diyl dinitrate
8% inhibition at 0.01 mM
oxalic acid 3-(N''-cyano-N'-{2-[({2-[(diaminomethylidene)amino]-1,3-thiazol-5-yl}methyl)sulfanyl]ethyl}carbamimidamido)propyl nitrate
10% inhibition at 0.01 mM
oxalic acid 3-({2-[({5-[(dimethylamino)methyl]furan-2-yl}methyl)sulfanyl]ethyl}amino)-4-(methylamino)-1H-1lambda~4~,2,5-thiadiazol-1-one
9% inhibition at 0.01 mM
paclitaxel
streptomycin
-
a competitive inhibitor of PAD4
sulfamethoxazole
-
-
sulfapyridine
-
-
tetracycline
-
-
thiocitrulline
-
12.5 mM, complete inhibition
Thiourea
-
50 mM, complete inhibition
tosyl-L-leucinechloromethyl ketone
-
12.5 mM, 98% inhibition
trimethoprim
-
-
additional information
-