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IUBMB CommentsThe enzyme, found in mycobacteria, is a member of a family of heterocyclic toxin methyltransferases. It is involved in defense against several antimicrobial natural compounds and drugs. 4-Hydroxyquinolin-2(1H)-one, 2-heptylquinolin-4(1H)-one, 2-heptyl-3-hydroxyquinolin-4(1H)-one (the "Pseudomonas quinolone signal", PQS) and the flavonol quercetin are also O-methylated, albeit with lower activity . The enzyme also N-methylates the bactericidal compound 3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile .
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S-adenosyl-L-methionine:2-heptyl-1-hydroxyquinolin-4(1H)-one methyltransferase
The enzyme, found in mycobacteria, is a member of a family of heterocyclic toxin methyltransferases. It is involved in defense against several antimicrobial natural compounds and drugs. 4-Hydroxyquinolin-2(1H)-one, 2-heptylquinolin-4(1H)-one, 2-heptyl-3-hydroxyquinolin-4(1H)-one (the "Pseudomonas quinolone signal", PQS) and the flavonol quercetin are also O-methylated, albeit with lower activity [2]. The enzyme also N-methylates the bactericidal compound 3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile [1].
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S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
S-adenosyl-L-methionine + 2-heptyl-3-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-3-methoxyquinolin-4(1H)-one
S-adenosyl-L-methionine + 2-heptylquinolin-4(1H)-one
S-adenosyl-L-homocysteine + ?
S-adenosyl-L-methionine + 3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + 4-hydroxyisoquinolin-1(2H)-one
S-adenosyl-L-homocysteine + 4-methoxyisoquinolin-1(2H)-one
S-adenosyl-L-methionine + 4-hydroxyquinolin-2(1H)-one
S-adenosyl-L-homocysteine + 4-methoxyquinolin-2(1H)-one
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + ?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
preferred substrate
-
-
?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
preferred substrate
-
-
?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
preferred substrate
-
-
?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
preferred substrate
-
-
?
S-adenosyl-L-methionine + 2-heptyl-3-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-3-methoxyquinolin-4(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 2-heptyl-3-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-3-methoxyquinolin-4(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 2-heptyl-3-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-3-methoxyquinolin-4(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 2-heptyl-3-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-3-methoxyquinolin-4(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 2-heptylquinolin-4(1H)-one
S-adenosyl-L-homocysteine + ?
-
-
-
?
S-adenosyl-L-methionine + 2-heptylquinolin-4(1H)-one
S-adenosyl-L-homocysteine + ?
-
-
-
?
S-adenosyl-L-methionine + 2-heptylquinolin-4(1H)-one
S-adenosyl-L-homocysteine + ?
-
-
-
?
S-adenosyl-L-methionine + 2-heptylquinolin-4(1H)-one
S-adenosyl-L-homocysteine + ?
-
-
-
?
S-adenosyl-L-methionine + 4-hydroxyisoquinolin-1(2H)-one
S-adenosyl-L-homocysteine + 4-methoxyisoquinolin-1(2H)-one
-
-
-
?
S-adenosyl-L-methionine + 4-hydroxyisoquinolin-1(2H)-one
S-adenosyl-L-homocysteine + 4-methoxyisoquinolin-1(2H)-one
-
-
-
?
S-adenosyl-L-methionine + 4-hydroxyquinolin-2(1H)-one
S-adenosyl-L-homocysteine + 4-methoxyquinolin-2(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 4-hydroxyquinolin-2(1H)-one
S-adenosyl-L-homocysteine + 4-methoxyquinolin-2(1H)-one
-
-
-
?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + ?
methylation sites not assigned
-
-
?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + ?
methylation sites not assigned
-
-
?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + ?
methylation sites not assigned
-
-
?
S-adenosyl-L-methionine + quercetin
S-adenosyl-L-homocysteine + ?
methylation sites not assigned
-
-
?
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S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
S-adenosyl-L-methionine + 3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile
S-adenosyl-L-homocysteine + ?
-
-
-
-
?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
-
-
-
?
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one
S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one
-
-
-
?
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Tuberculosis
A comparison of Rv0559c and Rv0560c expression in drug-resistant Mycobacterium tuberculosis in response to first-line antituberculosis drugs.
Tuberculosis
Co-induction of methyltransferase Rv0560c by naphthoquinones and fibric acids suggests attenuation of isoprenoid quinone action in Mycobacterium tuberculosis.
Tuberculosis
Mycobacterium tuberculosis Rv0560c is not essential for growth in vitro or in macrophages.
Tuberculosis
Structural basis of O-methylation of (2-heptyl-)1-hydroxyquinolin-4(1H)-one and related compounds by the heterocyclic toxin methyltransferase Rv0560c of Mycobacterium tuberculosis.
Tuberculosis
The Inhibitory Effect of GlmU Acetyltransferase Inhibitor TPSA on Mycobacterium tuberculosis May Be Affected Due to Its Methylation by Methyltransferase Rv0560c.
Tuberculosis
The promoter of Rv0560c is induced by salicylate and structurally-related compounds in Mycobacterium tuberculosis.
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0.0094 - 0.0098
2-heptyl-1-hydroxyquinolin-4(1H)-one
-
0.0014 - 0.004
3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile
0.0094
2-heptyl-1-hydroxyquinolin-4(1H)-one
pH 7.0 30°C
-
0.0098
2-heptyl-1-hydroxyquinolin-4(1H)-one
pH 7.0 30°C
-
0.0014
3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile
-
pH 7.4, 37°C, mutant enzyme S140A
0.004
3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile
-
pH 7.4, 37°C, wild-type enzyme
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0.09
2-heptyl-1-hydroxyquinolin-4(1H)-one
-
0.00123 - 0.0028
3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile
0.09
2-heptyl-1-hydroxyquinolin-4(1H)-one
pH 7.0 30°C
-
0.09
2-heptyl-1-hydroxyquinolin-4(1H)-one
pH 7.0 30°C
-
0.00123
3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile
-
pH 7.4, 37°C, wild-type enzyme
0.0028
3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile
-
pH 7.4, 37°C, mutant enzyme S140A
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85.1 - 204.1
2-heptyl-1-hydroxyquinolin-4(1H)-one
-
0.3075 - 2
3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile
85.1
2-heptyl-1-hydroxyquinolin-4(1H)-one
pH 7.0 30°C
-
204.1
2-heptyl-1-hydroxyquinolin-4(1H)-one
pH 7.0 30°C
-
0.3075
3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile
-
pH 7.4, 37°C, wild-type enzyme
2
3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile
-
pH 7.4, 37°C, mutant enzyme S140A
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drug target
the enzyme is involved in cellular response to chemical stress and possibly contributes to resistance of mycobacteria toward antimicrobial natural compounds as well as drugs.Synthetic antimycobacterial agents may be designed to be unamenable to methyl transfer
drug target
the enzyme is involved in cellular response to chemical stress and possibly contributes to resistance of mycobacteria toward antimicrobial natural compounds as well as drugs.Synthetic antimycobacterial agents may be designed to be unamenable to methyl transfer
drug target
-
the enzyme is involved in cellular response to chemical stress and possibly contributes to resistance of mycobacteria toward antimicrobial natural compounds as well as drugs.Synthetic antimycobacterial agents may be designed to be unamenable to methyl transfer
-
drug target
-
the enzyme is involved in cellular response to chemical stress and possibly contributes to resistance of mycobacteria toward antimicrobial natural compounds as well as drugs.Synthetic antimycobacterial agents may be designed to be unamenable to methyl transfer
-
physiological function
the enzyme is involved in cellular response to chemical stress and possibly contributes to resistance of mycobacteria toward antimicrobial natural compounds as well as drugs
physiological function
the enzyme is involved in cellular response to chemical stress and possibly contributes to resistance of mycobacteria toward antimicrobial natural compounds as well as drugs
physiological function
-
the enzyme N-methylates N-methylates the bactericidal compound 3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile, abrogating its bactericidal activity. Methylation of an antibacterial compound is a mode of antimicrobial resistance
physiological function
-
the enzyme is involved in cellular response to chemical stress and possibly contributes to resistance of mycobacteria toward antimicrobial natural compounds as well as drugs
-
physiological function
-
the enzyme is involved in cellular response to chemical stress and possibly contributes to resistance of mycobacteria toward antimicrobial natural compounds as well as drugs
-
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Sartor, P.; Bock, J.; Hennecke, U.; Thierbach, S.; Fetzner, S.
Modification of the Pseudomonasxa0aeruginosa toxin 2-heptyl-1-hydroxyquinolin-4(1H)-one and other secondary metabolites by methyltransferases from mycobacteria
FEBS J.
288
2360-2376
2020
Mycobacteroides abscessus (B1MCE2), Mycobacterium tuberculosis (P9WKL5), Mycobacteroides abscessus ATCC 19977 (B1MCE2), Mycobacterium tuberculosis ATCC 25618 (P9WKL5)
brenda
Warrier, T.; Kapilashrami, K.; Argyrou, A.; Ioerger, T.; Little, D.; Murphye, K.; Nandakumar, M.; Park, S.; Gold, B.; Mi, J.; Zhang, T.; Meiler, E.; Rees, M.; Somersan-Karakaya, S.; Francisco, E.; Martinez-Hoyos, M.; Burns-Huang, K.; Roberts, J.; Ling, Y.
N-Methylation of a bactericidal compound as a resistance mechanism in Mycobacterium tuberculosis
Proc. Natl. Acad. Sci. USA
113
E4523-E4530
2016
Mycobacterium tuberculosis
brenda