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Information on EC 1.7.1.B2 - aromatic nitroreductase [NAD(P)H]
for references in articles please use BRENDA:EC1.7.1.B2preliminary BRENDA-supplied EC number
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EC Tree
1.7.1.B2 aromatic nitroreductase [NAD(P)H]Specify your search results
The enzyme appears in viruses and cellular organisms
Reaction Schemes
+
3
+
2
=
+
3
+
3
Synonyms
nfsb_ec, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
NfsB
NprA
-
-
ambiguous
-
oxygen-insensitive nitroreductase (NAD(P)H)
-
-
-
-
YfkO
NfsB
-
-
ambiguous
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an aromatic amine + NAD(P)+ + H2O = an aromatic hydroxylamine + NAD(P)H + H+
(1a)
-
-
-
an aromatic hydroxylamine + NAD(P)+ = an aromatic nitric oxide + NAD(P)H + H+
(1b)
-
-
-
an aromatic nitric oxide + NAD(P)+ + H2O = an aromatic nitrate + NAD(P)H + H+
(1c)
-
-
-
an aromatic amine + 3 NAD(P)+ + 2 H2O = an aromatic nitrate + 3 NAD(P)H + 3 H+
(overall reaction)
-
-
-
an aromatic amine + 3 NAD(P)+ + 2 H2O = an aromatic nitrate + 3 NAD(P)H + 3 H+
in vivo the reaction is obseverved in the opposite direction from that shown in the equation
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
aromatic nitrate:NAD(P)H oxidoreductase
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2,4,6-trinitrotoluene + NADH + H+
4-hydroxyamino-2,6-dinitrotoluene + NAD+ + H2O
-
-
-
?
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide + NADPH + H+
?
the wild type enzyme is largely inactive with 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide (SN33623) as a substrate
-
-
?
2-(2-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)-acetamide + NADPH + H+
?
-
-
-
?
2-amino-4,6-dinitrotoluene + NADH + H+
4-hydroxyamino-2-aminotoluene + NAD+ + H2O
-
-
-
?
2-[(2-bromoethyl)(2-[(2-hydroxyethyl)carbamoyl]-4,6-dinitrophenyl)amino]ethyl methanesulfonate + NADPH + H+
?
-
-
-
?
4-amino-2,6-dinitrotoluene + NADH + H+
2-hydroxyamino-4-aminotoluene + NAD+ + H2O
-
-
-
?
methyl (6-nitro-4-oxoquinolin-1(4H)-yl)acetate + NADPH + H+
?
-
-
-
?
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxyamino-2,6-dinitrotoluene + NADP+ + H2O
-
-
-
?
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxyamino-2,6-dinitrotoluene + NADP+ + H2O
-
-
-
-
?
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxyamino-2,6-dinitrotoluene + NADP+ + H2O
i.e. TNT, NfsB reduces TNT to the para isomer 4-hydroxyamino-2,6-dinitrotoluene more easily than the ortho isomer 2-hydroxyamino-4,6-dinitrotoluene
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H + H+
? + NAD(P)+
i.e. CB1954, an aziridinyl dinitrobenzamide prodrug
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H + H+
? + NAD(P)+
i.e. CB1954, an aziridinyl dinitrobenzamide prodrug, low activity
-
-
?
nitro-CBI-5-[(dimethylamino)ethoxy]indole + NAD(P)H + H+
? + NAD(P)+
a nitro-CBI prodrug, low activity
-
-
?
nitro-CBI-5-[(dimethylamino)ethoxy]indole + NAD(P)H + H+
? + NAD(P)+
a nitro-CBI prodrug, high activity
-
-
?
additional information
?
-
Escherichia coli nitroreductase NfsB can reduce nitrochloromethylbenzindolines, i.e. nitro-CBIs, in an oxygen-independent fashion, generating highly cytotoxic metabolites that alkylate the N3 of adenine in the minor groove of DNA
-
-
?
additional information
?
-
an intrinsically oxygen-insensitive nature of the two-electron reduction mechanism
-
-
?
additional information
?
-
no activity with 2,4-diamino-6-nitrotoluene and 2,6-diamino-4-nitrotoluene
-
-
?
additional information
?
-
Pseudomonas aeruginosa nitroreductase NfsB can reduce nitrochloromethylbenzindolines, i.e. nitro-CBIs, in an oxygen-independent fashion, generating highly cytotoxic metabolites that alkylate the N3 of adenine in the minor groove of DNA
-
-
?
additional information
?
-
an intrinsically oxygen-insensitive nature of the two-electron reduction mechanism
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2,4,6-trinitrotoluene + NADH + H+
4-hydroxyamino-2,6-dinitrotoluene + NAD+ + H2O
-
-
-
?
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxyamino-2,6-dinitrotoluene + NADP+ + H2O
-
-
-
?
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxyamino-2,6-dinitrotoluene + NADP+ + H2O
-
-
-
-
?
additional information
?
-
Escherichia coli nitroreductase NfsB can reduce nitrochloromethylbenzindolines, i.e. nitro-CBIs, in an oxygen-independent fashion, generating highly cytotoxic metabolites that alkylate the N3 of adenine in the minor groove of DNA
-
-
?
additional information
?
-
Pseudomonas aeruginosa nitroreductase NfsB can reduce nitrochloromethylbenzindolines, i.e. nitro-CBIs, in an oxygen-independent fashion, generating highly cytotoxic metabolites that alkylate the N3 of adenine in the minor groove of DNA
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
NfsB is capable of utilizing bothNADH and NADPH as cofactor
-
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
-
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.5 - 3.7
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
-
additional information
additional information
Michaelis-Menten steady-state kinetics of recombinant His6-tagged wild-type and mutant enzymes
-
0.0023
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant N71S, with NADH
0.0057
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124W, with NADH
0.0072
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A/F124W, with NADH
0.0091
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A, with NADH
0.0174
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged wild-type enzyme, with NADH
0.0534
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant T41L, with NADH
0.0928
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124N, with NADH
0.0997
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124A, with NADH
1.5
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
mutant enzyme F70A/F108Y, at pH 7.0 and 23°C
-
3.3
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
mutant enzyme F70A, at pH 7.0 and 23°C
-
3.7
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
mutant enzyme F108Y, at pH 7.0 and 23°C
-
0.0398
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant N71S, with NADH
0.0881
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A, with NADH
0.0996
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A/F124W, with NADH
0.163
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124W, with NADH
0.339
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged wild-type enzyme, with NADH
0.411
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant T41L, with NADH
0.575
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124N, with NADH
1.495
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124A, with NADH
0.172
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant N71S, with NADH
0.265
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A/F124W, with NADH
0.306
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124W, with NADH
0.38
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A, with NADH
0.518
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged wild-type enzyme, with NADH
0.732
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124A, with NADH
1.069
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124N, with NADH
1.168
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant T41L, with NADH
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.19 - 0.27
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
-
1.51
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant N71S, with NADH
14.38
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124W, with NADH
26.9
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124N, with NADH
37.65
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged wild-type enzyme, with NADH
38.88
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A/F124W, with NADH
46.67
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A, with NADH
54.52
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124A, with NADH
62.87
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant T41L, with NADH
0.19
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
mutant enzyme F70A, at pH 7.0 and 23°C
-
0.2
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
mutant enzyme F108Y, at pH 7.0 and 23°C
-
0.27
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
mutant enzyme F70A/F108Y, at pH 7.0 and 23°C
-
1.03
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant N71S, with NADH
9.28
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124W, with NADH
15.27
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124N, with NADH
15.31
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged wild-type enzyme, with NADH
18.02
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A/F124W, with NADH
18.2
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A, with NADH
26.84
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant T41L, with NADH
69.26
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124A, with NADH
0.76
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant N71S, with NADH
3.25
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged wild-type enzyme, with NADH
4.74
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124A, with NADH
8.06
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A/F124W, with NADH
9.4
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124W, with NADH
11.29
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124N, with NADH
11.48
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A, with NADH
14.01
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant T41L, with NADH
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.055 - 0.31
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
-
290
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124N, with NADH
547
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124A, with NADH
653
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant N71S, with NADH
1177
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant T41L, with NADH
2170
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged wild-type enzyme, with NADH
2526
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124W, with NADH
5111
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A, with NADH
5389
2,4,6-trinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A/F124W, with NADH
0.055
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
mutant enzyme F108Y, at pH 7.0 and 23°C
-
0.058
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
mutant enzyme F70A, at pH 7.0 and 23°C
-
0.31
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
mutant enzyme F70A/F108Y, at pH 7.0 and 23°C
-
26
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant N71S, with NADH
27
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124N, with NADH
45
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged wild-type enzyme, with NADH
46
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124A, with NADH
57
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124W, with NADH
65
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant T41L, with NADH
181
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A/F124W, with NADH
206
2-amino-4,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A, with NADH
4
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant N71S, with NADH
6
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124A, with NADH
6
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged wild-type enzyme, with NADH
11
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124N, with NADH
12
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant T41L, with NADH
30
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A, with NADH
31
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F123A/F124W, with NADH
31
4-amino-2,6-dinitrotoluene
pH 7.0, 37°C, recombinant His6-tagged mutant F124W, with NADH
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.038 - 0.4
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
-
0.038
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme F70A/E72Q/F108Y, at pH 7.0 and 23°C
-
0.041
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme F70A/F108Y, at pH 7.0 and 23°C
-
0.045
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme F70A/F108Y, at pH 7.0 and 23°C
-
0.07
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme T41L/F70A/F108Y, at pH 7.0 and 23°C
-
0.15
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme F70A/E72Q, at pH 7.0 and 23°C
-
0.17
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme T41L/F70A/N71S/F108Y, at pH 7.0 and 23°C
-
0.19
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme F70A, at pH 7.0 and 23°C
-
0.2
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme T41L/F70A, at pH 7.0 and 23°C
-
0.23
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme E72Q/F108Y, at pH 7.0 and 23°C
-
0.26
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme F108Y, at pH 7.0 and 23°C
-
0.31
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme T41L/F70A/N71S, at pH 7.0 and 23°C
-
0.4
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme E72Q, IC50 above 0.4 mM, at pH 7.0 and 23°C
-
0.4
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme T41L, IC50 above 0.4 mM, at pH 7.0 and 23°C
-
0.4
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
mutant enzyme T41L/N71S, IC50 above 0.4 mM, at pH 7.0 and 23°C
-
0.4
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Escherichia coli
wild type enzyme, IC50 above 0.4 mM, at pH 7.0 and 23°C
-
0.11
5-(aziridin-1-yl)-2,4-dinitrobenzamide
Escherichia coli
mutant enzyme F70A/F108Y, at pH 7.0 and 23°C
0.19
5-(aziridin-1-yl)-2,4-dinitrobenzamide
Escherichia coli
mutant enzyme T41L/N71S, at pH 7.0 and 23°C
0.2
5-(aziridin-1-yl)-2,4-dinitrobenzamide
Escherichia coli
mutant enzyme T41L/F70A/F108Y, at pH 7.0 and 23°C
0.23
5-(aziridin-1-yl)-2,4-dinitrobenzamide
Escherichia coli
mutant enzyme T41L/F70A, at pH 7.0 and 23°C
0.25
5-(aziridin-1-yl)-2,4-dinitrobenzamide
Escherichia coli
mutant enzyme T41L/F70A/N71S, at pH 7.0 and 23°C
0.29
5-(aziridin-1-yl)-2,4-dinitrobenzamide
Escherichia coli
mutant enzyme T41L, at pH 7.0 and 23°C
0.32
5-(aziridin-1-yl)-2,4-dinitrobenzamide
Escherichia coli
mutant enzyme T41L/F70A/N71S/F108Y, at pH 7.0 and 23°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
nitroreductases are a family of flavoproteins that catalyze the NAD(P)H-dependent reduction of nitro groups to hydroxyamino and/or amino groups on vari-ous nitro-substituted compounds
physiological function
additional information
the enzyme crystal structure of NfsB, PDB ID 1DS7, is used for molecular ligand docking studies
physiological function
Escherichia coli NfsB expressing HCT-116 cells are 23.5fold more sensitive to prodrug nitro-CBI-DEI than pure cultures of untransfected cells, monolayer cytotoxicity assays using human colon carcinoma HCT-116 cells. The discrepancy in the fold-sensitivity to nitro-CBI-DEI between the two and three dimensional cytotoxicity assays stems from loss of activated drug into the media in the monolayer cultures
physiological function
Pseudomonas aeruginosa NfsB expressing HCT-116 cells are 540fold more sensitive to prodrug nitro-CBI-DEI than pure cultures of untransfected cells, the activated drug that they generate also displays an unprecedented local bystander effect, monolayer cytotoxicity assays using human colon carcinoma HCT-116 cells. The discrepancy in the fold-sensitivity to nitro-CBI-DEI between the two and three dimensional cytotoxicity assays stems from loss of activated drug into the media in the monolayer cultures
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). NFSB_ECOLI
Escherichia coli (strain K12)
217
0
23905
Swiss-Prot
other Location (Reliability: 2)
Q9HTZ9_PSEAE
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
200
0
22450
TrEMBL
Mitochondrion (Reliability: 4)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
E72Q
the mutation does not increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
E72Q/F108Y
the mutations substantially increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
F108Y
the mutation substantially increases the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
F123A
site-directed mutagenesis, residue F123 is located in helix alpha6 constituting the substrate entry site, the mutant enzyme kinetics are altered compared to the wild-type enzyme
F124A
site-directed mutagenesis, residue F124 is located in helix alpha6 constituting the substrate entry site, the mutant enzyme kinetics are altered compared to the wild-type enzyme
F124N
site-directed mutagenesis, residue F124 is located in helix alpha6 constituting the substrate entry site, the mutant enzyme kinetics are altered compared to the wild-type enzyme
F124W
site-directed mutagenesis, residue F124 is located in helix alpha6 constituting the substrate entry site, the mutant enzyme kinetics are altered compared to the wild-type enzyme
F70A
the mutation substantially increases the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
F70A/E72Q
the mutations substantially increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
F70A/E72Q/F108Y
the mutations substantially increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
F70A/F108Y
N71S
site-directed mutagenesis, active site residue mutation, the mutant shows increased activity with prodrug 5-[aziridin-1-yl]-2,4-dinitrobenzamide (CB1954) and nitrofurazone compared to the wild-type enzyme
T41L
T41L/F70A
the mutations substantially increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
T41L/F70A/F108Y
the mutations substantially increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
T41L/F70A/N71S
the mutations substantially increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
T41L/F70A/N71S/F108Y
the mutations substantially increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
T41L/N71S
the mutations do not increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
F70A/F108Y
the mutations confer high levels of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide activity and also substantially improve activity with 5-(aziridin-1-yl)-2,4-dinitrobenzamide and metronidazole. The mutations substantially increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
F70A/F108Y
the mutations substantially increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
T41L
site-directed mutagenesis, active site residue mutation, the mutant shows increased activity with prodrug 5-[aziridin-1-yl]-2,4-dinitrobenzamide (CB1954) and nitrofurazone compared to the wild-type enzyme
T41L
the mutation does not increase the sensitivity of the Escherichia coli host cell to 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Ni-NTA resin column chromatography
recombinant wild-type and mutant N-terminally His6-tagged enzymes from Escherichia coli strain BL21(DE3) by nickel affinity chromatography to over 95% purity
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
gene nfsB, recombinant expression of wild-type and mutant N-terminally His6-tagged enzymes in Escherichia coli strain BL21(DE3)
gene nfsB, recombinant overexpression in Escherichia coli reporter strain SOS-R2, which contains a lacZ reporter gene under control of the SOS responsive promoter sfiA, functional nitroreductase NfsB expression in human HCT-116 cells
gene nfsB, recombinant overexpression in Escherichia coli reporter strain SOS-R2, which contains a lacZ reporter gene under control of the SOS responsive promoter sfiA, functional nitroreductase NfsB expression in human HCT-116 cells
gene nfsB, recombinant overexpression in Escherichia coli reporter strain SOS-R2, which contains a lacZ reporter gene under control of the SOS responsive promoter sfiA, functional nitroreductase NfsB expression in human HCT-116 cells
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pharmacology
Pseudomonas aeruginosa NfsB and nitro-CBI-DEI is a promising enzyme/prodrug combination for gene directed enzyme prodrug therapy
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Green, L.K.; Syddall, S.P.; Carlin, K.M.; Bell, G.D.; Guise, C.P.; Mowday, A.M.; Hay, M.P.; Smaill, J.B.; Patterson, A.V.; Ackerley, D.F.
Pseudomonas aeruginosa NfsB and nitro-CBI-DEI - a promising enzyme/prodrug combination for gene directed enzyme prodrug therapy
Mol. Cancer
12
58
2013
Escherichia coli (P38489), Pseudomonas aeruginosa (Q9HTZ9)
brenda
Bai, J.; Yang, J.; Liu, P.; Yang, Q.
Transformation pathway of 2,4,6-trinitrotoluene by Escherichia coli nitroreductases and improvement of activity using structure-based mutagenesis
Process Biochem.
50
705-711
2015
Escherichia coli (P38489)
brenda
Van Hung Le, V.; Davies, I.; Moon, C.; Wheeler, D.; Biggs, P.; Rakonjac, J.
Novel 5-nitrofuran-activating reductase in Escherichia coli
Antimicrob. Agents Chemother.
63
e00868-19
2019
Escherichia coli
brenda
Toogood, H.; Scrutton, N.
Flavin oxidation state impacts on nitrofuran antibiotic binding orientation in nitroreductases
Biochem. J.
478
3423-3428
2021
Escherichia coli
brenda
Williams, E.M.; Rich, M.H.; Mowday, A.M.; Ashoorzadeh, A.; Copp, J.N.; Guise, C.P.; Anderson, R.F.; Flanagan, J.U.; Smaill, J.B.; Patterson, A.V.; Ackerley, D.F.
Engineering Escherichia coli NfsB To activate a hypoxia-resistant analogue of the PET probe EF5 to enable non-invasive imaging during enzyme prodrug therapy
Biochemistry
58
3700-3710
2019
Escherichia coli (P38489), Escherichia coli
brenda
Hyde, E.; Chau, A.; Smith, L.
Backbone assignment of E. coli NfsB and the effects of addition of the cofactor analogue nicotinic acid
Biomol. NMR Assign.
15
143-151
2021
Escherichia coli
brenda
Williams, E.; Sharrock, A.; Rylott, E.; Bruce, N.; MacKichan, J.; Ackerley, D.
A cofactor consumption screen identifies promising NfsB family nitroreductases for dinitrotoluene remediation
Biotechnol. Lett.
41
1155-1162
2019
Bacillus subtilis (O34475), Vibrio vulnificus (Q7MCD2), Vibrio vulnificus ATCC 27562 (Q7MCD2), Bacillus subtilis 168 (O34475)
brenda
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Release 2023.1 (January 2023)
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