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1-[[2-(4-tert-butylphenyl)ethyl]amino]phthalazin-5-ol
-
-
2',6-dihydroxy-2-[phenylmethylene]-3(2H)-benzofuran-3-one
-
-
2,4-dimethoxy-4'-allyloxychalcone
2,4-dimethoxy-4'-butoxychalcone
2-n-heptyl-4-hydroxyquinoline-N-oxide
3',4',6-trihydroxy-2-[phenylmethylene]-3(2H)-benzofuran-3-one
-
-
3',6-dihydroxy-2-[phenylmethylene]-3(2H)-benzofuran-3-one
-
-
4',6-dihydroxy-2-[phenylmethylene]-3(2H)-benzofuran-3-one
-
-
4,6,3'-hydroxy-4'-methoxy-2-[phenylhydroxymethylene]-3(2H)-benzofuran-3-one
-
-
4,6,4'-hydroxy-3'-methoxy-2-[phenylhydroxymethylene]-3(2H)-benzofuran-3-one
-
-
4,6,4'-triacetyl-3',5'-dimethoxy-2-[phenylhydroxymethylene]-3(2H)-benzofuran-3-one
-
i.e. bracteintriacetate
4,6-dihydroxy-2-[phenylhydroxymethylene]-3(2H)-benzofuran-3-ol
-
-
6-benzoyl-2-[phenylhydroxymethylene]-3(2H)-benzofuran-3-ol
-
-
6-hydroxy-2-[(2,3,4-trihydroxyphenyl)-methylene]-3(2H)-benzofuran-3-one-5-beta-D-glucopyranoside
-
i.e. bractein
6-hydroxy-2-[phenylmethylene]-3(2H)-benzofuran-3-one
-
-
6-hydroxy-3',4'-dimethoxy-2-[phenylhydroxymethylene]-3(2H)-benzofuran-3-one
-
-
6-hydroxy-benzofuran-3-one
-
-
6-methoxy-2-[phenylmethylene]-3(2H)-benzofuran-3-one
-
-
Acriflavin
-
specific inhibition of NADH dependent activity
Cinnamic acid
-
preincubation
ClHgSO3H
-
inhibition with all cofactors except the methyl viologen dependent activity
iodoacetate
-
slight inhibition
KCN
-
inhibition with all cofactors except the methyl viologen dependent activity
mesaconic acid
-
strong inhibition with and without preincubation
N-(4-[[2-(4-tert-butylphenyl)ethyl]amino]phthalazin-6-yl)prop-2-enamide
-
-
N-[2-(4-tert-butylphenyl)ethyl]-5-(1-methylethoxy)phthalazin-1-amine
-
-
N-[2-(4-tert-butylphenyl)ethyl]-5-methoxyphthalazin-1-amine
-
-
N-[2-(4-tert-butylphenyl)ethyl]phthalazin-1-amine
-
quinazoline
N1-[2-(4-tert-butylphenyl)ethyl]phthalazine-1,6-diamine
-
-
N1-[2-(4-tert-butylphenyl)ethyl]phthalazine-1,7-diamine
-
-
p-chloromercuribenzoate
-
slight inhibition
Pd(2-mercaptopyridine N-oxide)2
-
Pd-(pyridine-2-thiol N-oxide)2
-
inhibitory effect of metal-pyridine-2-thiol N-oxide complexes, marked increase is obeserved in the inhibitory effect with respect to that of the free ligand, inhibition in a dose-dependent manner, a clear relief of the growth inhibition produced by the metal-mpo complex is observed in the presence of 5 mM succinate
Pt(2-mercaptopyridine N-oxide)2
-
Pt-(pyridine-2-thiol N-oxide)2
-
inhibitory effect of metal-pyridine-2-thiol N-oxide complexes, inhibition observed 2 is similar to that obtained with the ligand alone, a clear relief of the growth inhibition produced by the metal-mpo complex is observed in the presence of 5 mM succinate
pyridine-2-thiol N-oxide
-
2-mercaptopyridine N-oxide (mpo) is a bioactive ligand with a potential as antitrypanosomal agent
sodium pyridine-2-thiol N-oxide
-
inhibitory effect of the sodium salt
trans-, trans muconate
-
slight inhibition
Triton X-100
-
complete loss of NADH dependent activity at concentration of 0.05%, up to 17fold increase in methyl viologen dependent activity
VO(2-mercaptopyridine N-oxide)2
-
2,4-dimethoxy-4'-allyloxychalcone
-
-
2,4-dimethoxy-4'-allyloxychalcone
-
-
2,4-dimethoxy-4'-butoxychalcone
-
-
2,4-dimethoxy-4'-butoxychalcone
-
-
2-n-heptyl-4-hydroxyquinoline-N-oxide
-
strong inhibitor
2-n-heptyl-4-hydroxyquinoline-N-oxide
-
strong inhibitor
citraconate
-
slight inhibition
citraconate
-
preincubation
Cu2+
-
-
licochalcone A
-
lipochalcone A
-
-
malonate
-
slight inhibition
Pd(2-mercaptopyridine N-oxide)2
-
-
Pd(2-mercaptopyridine N-oxide)2
-
-
Pt(2-mercaptopyridine N-oxide)2
-
-
Pt(2-mercaptopyridine N-oxide)2
-
-
pyrvinium pamoate
-
-
pyrvinium pamoate
-
an anthelmintic drug, has an anticancer effect within tumor-mimicking microenvironments, biological mechanism of pyrvinium is the inhibition of the NADH-fumarate reductase system. Under normal conditions, pyrvinium pamoate activates complex II activity and inhibits complex I activity. Pyrvinium pamoate activates the mitochondrial respiratory chain via complex II, despite inhibiting complex I. In cancer cells under hypoxic and glucose-deprived conditions, the activation of SQR by pyrvinium pamoate disappeared and NADH-fumarate reductase activity is inhibited. Pyrvinium pamoate becomes cytotoxic to cancer cells under tumor microenvironmental conditions
pyrvinium pamoate
-
anthelmintic, has an anti-cancer effect within tumour-mimicking microenvironments. Pyrvinium pamoate inhibits NADH-fumarate reductase activities in both parasites and mammalian mitochondria and increases the activity of complex II, succinate-ubiquinone reductase, which is part of fumarate reductase, in mitochondria from human cancer cells cultured under normoxia-normoglycemic conditions but not under hypoxia-hypoglycemic conditions
succinate
-
slight inhibition
succinate
-
preincubation
ukulactone A
-
polyketide isolated from a culture broth of Penicillium sp. FKI-3389, shows potent inhibitory activity
ukulactone B
-
polyketide isolated from a culture broth of Penicillium sp. FKI-3389. Inhibitory activity is 200 times weaker than that of epimer ukulactone A
VO(2-mercaptopyridine N-oxide)2
-
-
VO(2-mercaptopyridine N-oxide)2
-
-
Zn2+
-
strong inhibitor
additional information
-
inhibitory potency of aurones and auronols, overview
-
additional information
-
inactivation by irradiation at 254 nm, can be partially restored by addition of 2,3-dimethyl-1,4-naphthoquinone
-
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Succinic acid production by rumen bacteria: III Enzymatic studies on the formation of succinate by Ruminococcus flavefaciens
Aust. J. Biol. Sci.
22
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1969
Ruminococcus flavefaciens
brenda
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Fumarate reductase activity of Streptococcus faecalis
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Enterococcus faecalis
brenda
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brenda
Hillier, A.J.; Jericho, R.E.; Green, S.M.; Jago, G.R.
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32
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Enterococcus faecalis, Lactococcus lactis
brenda
Wetzstein, H.G.; Gottschalk, G.
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1985
Ruminobacter amylophilus
brenda
Meinhardt, S.W.; Glass, T.L.
Characterization of the NADH dehydrogenase and fumarate reductase of Fibrobacter succinogenes subsp. succinogenes S85
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1994
Fibrobacter succinogenes
-
brenda
Christmas, P.B.; Turrens, J.F.
Separation of NADH-fumarate reductase and succinate dehydrogenase activities in Trypanosoma cruzi
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2000
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brenda
Chen, M.; Zhai, L.; Christensen, S.B.; Theander, T.G.; Kharazmi, A.
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45
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2001
Leishmania donovani, Leishmania major
brenda
Chen, M.; Bennedsen, M.; Zhai, L.; Kharazmi, A.
Purification and enzymatic activity of an NADH-fumarate reductase and other mitochondrial activities of Leishmania parasites
APMIS
109
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2001
Leishmania donovani, Leishmania major
brenda
Besteiro, S.; Biran, M.; Biteau, N.; Coustou, V.; Baltz, T.; Canioni, P.; Bringaud, F.
Succinate secreted by Trypanosoma brucei is produced by a novel and unique glycosomal enzyme: NADH-dependent fumarate reductase
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22
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2002
Trypanosoma brucei (Q8ITL2)
-
brenda
Pankhurst, K.L.; Mowat, C.G.; Miles, C.S.; Leys, D.; Walkinshaw, M.D.; Reid, G.A.; Chapman, S.K.
Role of His505 in the soluble fumarate reductase from Shewanella frigidimarina
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41
8551-8556
2002
Shewanella frigidimarina
brenda
Rothery, E.L.; Mowat, C.G.; Miles, C.S.; Walkinshaw, M.D.; Reid, G.A.; Chapman, S.K.
Histidine 61: an important heme ligand in the soluble fumarate reductase from Shewanella frigidimarina
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42
13160-13169
2003
Shewanella frigidimarina
brenda
Denicola, A.; Rubbo, H.; Haden, L.; Turrens, J.F.
Extramitochondrial localization of NADH-fumarate reductase in trypanosomatids
Comp. Biochem. Physiol. B
133
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2002
Leishmania donovani, Trypanosoma brucei, Trypanosoma cruzi, Leishmania donovani S-2
brenda
Enomoto, K.; Arikawa, Y.; Muratsubaki, H.
Physiological role of soluble fumarate reductase in redox balancing during anaerobiosis in Saccharomyces cerevisiae
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215
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2002
Saccharomyces cerevisiae
brenda
Coustou, V.; Besteiro, S.; Riviere, L.; Biran, M.; Biteau, N.; Franconi, J.M.; Boshart, M.; Baltz, T.; Bringaud, F.
A mitochondrial NADH-dependent fumarate reductase involved in the production of succinate excreted by procyclic Trypanosoma brucei
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280
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2005
Trypanosoma brucei (Q5BU12), Trypanosoma brucei (Q5BU14), Trypanosoma brucei (Q8ITL2), Trypanosoma brucei
brenda
Baughn, A.D.; Malamy, M.H.
The essential role of fumarate reductase in haem-dependent growth stimulation of Bacteroides fragilis
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149
1551-1558
2003
Bacteroides fragilis (Q7X478), Bacteroides fragilis (Q7X479), Bacteroides fragilis (Q7X480), Bacteroides fragilis
brenda
Kayser, O.; Chen, M.; Kharazmi, A.; Kiderlen, A.F.
Aurones interfere with Leishmania major mitochondrial fumarate reductase
Z. Naturforsch. C
57c
717-720
2002
Leishmania major
-
brenda
Hudson, J.M.; Heffron, K.; Kotlyar, V.; Sher, Y.; Maklashina, E.; Cecchini, G.; Armstrong, F.A.
Electron transfer and catalytic control by the iron-sulfur clusters in a respiratory enzyme, E. coli fumarate reductase
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127
6977-6989
2005
Escherichia coli
brenda
Zaunmueller, T.; Kelly, D.J.; Gloeckner, F.O.; Unden, G.
Succinate dehydrogenase functioning by a reverse redox loop mechanism and fumarate reductase in sulphate-reducing bacteria
Microbiology
152
2443-2453
2006
Desulfovibrio desulfuricans
brenda
Matsumoto, J.; Sakamoto, K.; Shinjyo, N.; Kido, Y.; Yamamoto, N.; Yagi, K.; Miyoshi, H.; Nonaka, N.; Katakura, K.; Kita, K.; Oku, Y.
Anaerobic NADH-fumarate reductase system is predominant in the respiratory chain of Echinococcus multilocularis, providing a novel target for the chemotherapy of alveolar echinococcosis
Antimicrob. Agents Chemother.
52
164-170
2008
Echinococcus multilocularis, Echinococcus multilocularis Nemuro
brenda
Mercado-Lubo, R.; Gauger, E.J.; Leatham, M.P.; Conway, T.; Cohen, P.S.
A Salmonella enterica serovar typhimurium succinate dehydrogenase/fumarate reductase double mutant is avirulent and immunogenic in BALB/c mice
Infect. Immun.
76
1128-1134
2008
Salmonella enterica
brenda
Buettner, F.F.; Bendallah, I.M.; Bosse, J.T.; Dreckmann, K.; Nash, J.H.; Langford, P.R.; Gerlach, G.F.
Analysis of the Actinobacillus pleuropneumoniae ArcA regulon identifies fumarate reductase as a determinant of virulence
Infect. Immun.
76
2284-2295
2008
Actinobacillus pleuropneumoniae
brenda
Iwata, F.; Shinjyo, N.; Amino, H.; Sakamoto, K.; Islam, M.K.; Tsuji, N.; Kita, K.
Change of subunit composition of mitochondrial complex II (succinate-ubiquinone reductase/quinol-fumarate reductase) in Ascaris suum during the migration in the experimental host
Parasitol. Int.
57
54-61
2008
Ascaris suum
brenda
Shiomi, K.; Hatano, H.; Morimoto, H.; Ui, H.; Sakamoto, K.; Kita, K.; Tomoda, H.; Lee, E.W.; Heo, T.R.; Kawagishi, H.; Omura, S.
Decursin and decursinol angelate selectively inhibit NADH-fumarate reductase of Ascaris suum
Planta Med.
73
1478-1481
2007
Ascaris suum
brenda
Camarasa, C.; Faucet, V.; Dequin, S.
Role in anaerobiosis of the isoenzymes for Saccharomyces cerevisiae fumarate reductase encoded by OSM1 and FRDS1
Yeast
24
391-401
2007
Saccharomyces cerevisiae
brenda
Osanai, A.; Harada, S.; Sakamoto, K.; Shimizu, H.; Inaoka, D.K.; Kita, K.
Crystallization of mitochondrial rhodoquinol-fumarate reductase from the parasitic nematode Ascaris suum with the specific inhibitor flutolanil
Acta Crystallogr. Sect. F
65
941-944
2009
Ascaris suum
brenda
Pessanha, M.; Rothery, E.L.; Miles, C.S.; Reid, G.A.; Chapman, S.K.; Louro, R.O.; Turner, D.L.; Salgueiro, C.A.; Xavier, A.V.
Tuning of functional heme reduction potentials in Shewanella fumarate reductases
Biochim. Biophys. Acta
1787
113-120
2009
Shewanella oneidensis, Shewanella frigidimarina, Shewanella frigidimarina NCIMB400, Shewanella oneidensis MR-1 / ATCC 700550
brenda
Vieites, M.; Smircich, P.; Parajon-Costa, B.; Rodriguez, J.; Galaz, V.; Olea-Azar, C.; Otero, L.; Aguirre, G.; Cerecetto, H.; Gonzalez, M.; Gomez-Barrio, A.; Garat, B.; Gambino, D.
Potent in vitro anti-Trypanosoma cruzi activity of pyridine-2-thiol N-oxide metal complexes having an inhibitory effect on parasite-specific fumarate reductase
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13
723-735
2008
Trypanosoma cruzi
brenda
Tomitsuka, E.; Kita, K.; Esumi, H.
The NADH-fumarate reductase system, a novel mitochondrial energy metabolism, is a new target for anticancer therapy in tumor microenvironments
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1201
44-49
2010
Homo sapiens
brenda
Weingarten, R.A.; Taveirne, M.E.; Olson, J.W.
The dual-functioning fumarate reductase is the sole succinate:quinone reductase in Campylobacter jejuni and is required for full host colonization
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191
5293-5300
2009
Campylobacter jejuni (Q0PBA0), Campylobacter jejuni (Q0PBA1), Campylobacter jejuni (Q0PBA2), Campylobacter jejuni, Campylobacter jejuni NCTC 11168 (Q0PBA0), Campylobacter jejuni NCTC 11168 (Q0PBA1), Campylobacter jejuni NCTC 11168 (Q0PBA2)
brenda
Tomitsuka, E.; Kita, K.; Esumi, H.
Regulation of succinate-ubiquinone reductase and fumarate reductase activities in human complex II by phosphorylation of its flavoprotein subunit
Proc. Jpn. Acad. Ser. B
85
258-265
2009
Homo sapiens
brenda
Tomitsuka, E.; Kita, K.; Esumi, H.
An anticancer agent, pyrvinium pamoate inhibits the NADH-fumarate reductase system - a unique mitochondrial energy metabolism in tumour microenvironments
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152
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2012
Homo sapiens
brenda
Edwards, C.; Copes, N.; Brito, A.; Canfield, J.; Bradshaw, P.
Malate and fumarate extend lifespan in Caenorhabditis elegans
PLoS ONE
8
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2013
Caenorhabditis elegans
brenda
Mori, M.; Morimoto, H.; Kim, Y.; Ui, H.; Nonaka, K.; Masuma, R.; Sakamoto, K.; Kita, K.; Tomoda, H.; Shiomi, K.; Omura, S.
Ukulactones A and B, new NADH-fumarate reductase inhibitors produced by Penicillium sp. FKI-3389
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67
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2011
Ascaris suum
-
brenda
Yang, L.; Luebeck, M.; Ahring, B.K.; Luebeck, P.S.
Enhanced succinic acid production in Aspergillus saccharolyticus by heterologous expression of fumarate reductase from Trypanosoma brucei
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100
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2016
Trypanosoma brucei (Q8ITL2), Trypanosoma brucei
brenda
Liu, W.C.; Wang, Y.Y.; Liu, J.H.; Ke, A.B.; Zheng, Z.H.; Lu, X.H.; Luan, Y.S.; Xiu, Z.L.; Dong, Y.S.
Wortmannilactones I-L, new NADH-fumarate reductase inhibitors, induced by adding suberoylanilide hydroxamic acid to the culture medium of Talaromyces wortmannii
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26
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2016
Ascaris suum
brenda
Kaifuchi, S.; Mori, M.; Nonaka, K.; Masuma, R.; ?mura, S.; Shiomi, K.
Ukulactone C, a new NADH-fumarate reductase inhibitor produced by Talaromyces sp. FKI-6713
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61
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2015
Ascaris suum
brenda
Salusjaervi, L.; Kaunisto, S.; Holmstroem, S.; Vehkomaeki, M.L.; Koivuranta, K.; Pitkaenen, J.P.; Ruohonen, L.
Overexpression of NADH-dependent fumarate reductase improves D-xylose fermentation in recombinant Saccharomyces cerevisiae
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40
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2013
Trypanosoma brucei (Q8ITL2), Trypanosoma brucei
brenda
Kim, S.H.; Mamuad, L.L.; Kim, D.W.; Kim, S.K.; Lee, S.S.
Fumarate reductase-producing Enterococci reduce methane production in rumen fermentation in vitro
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26
558-566
2016
Enterococcus faecalis, Enterococcus faecalis SROD5, Enterococcus faecium, Enterococcus faecium SROD
brenda
Merlino, A.; Vieites, M.; Gambino, D.; Coitino, E.L.
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48
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2014
Leishmania major (E9AEQ8), Leishmania major, Trypanosoma cruzi (Q4CYX1), Trypanosoma cruzi, Trypanosoma cruzi CL Brener (Q4CYX1)
brenda
Serebryakova, M.V.; Bertsova, Y.V.; Sokolov, S.S.; Kolesnikov, A.A.; Baykov, A.A.; Bogachev, A.V.
Catalytically important flavin linked through a phosphoester bond in a eukaryotic fumarate reductase
Biochimie
149
34-40
2018
Leptomonas pyrrhocoris (A0A0N0E041), Leptomonas pyrrhocoris
brenda
Bertsova, Y.; Oleynikov, I.; Bogachev, A.
A new water-soluble bacterial NADH fumarate oxidoreductase
FEMS Microbiol. Lett.
367
fnaa175
2020
Klebsiella pneumoniae (B5XRB0), Klebsiella pneumoniae, Klebsiella pneumoniae 342 (B5XRB0)
brenda