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Literature summary extracted from

  • Couturier, C.; Silve, S.; Morales, R.; Pessegue, B.; Llopart, S.; Nair, A.; Bauer, A.; Scheiper, B.; Poeverlein, C.; Ganzhorn, A.; Lagrange, S.; Bacque, E.
    Nanomolar inhibitors of Mycobacterium tuberculosis glutamine synthetase 1 synthesis, biological evaluation and X-ray crystallographic studies (2015), Bioorg. Med. Chem. Lett., 25, 1455-1459 .
    View publication on PubMed

Application

EC Number Application Comment Organism
6.3.1.2 drug development GlnA1 may not be a suitable target to find anti-tubercular drugs Mycobacterium tuberculosis

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
6.3.1.2 enzyme complexed with 3, X-ray diffraction structure determination and analysis Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
6.3.1.2 (2S)-2-amino-4-(S-methanesulfonimidoyl)butanoic acid
-
Mycobacterium tuberculosis
6.3.1.2 4-[2-tert-butyl-4-(6-methoxynaphthalen-2-yl)-1H-imidazol-5-yl]pyridin-2-amine
-
Mycobacterium tuberculosis
6.3.1.2 5-(2-methoxyethyl)-9-phenyl-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 5-(3-methylbutyl)-9-(pyridin-3-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 5-(but-3-en-1-yl)-9-(pyridin-3-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 5-benzyl-9-phenyl-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 5-cyclopropyl-9-(pyridin-2-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 5-methyl-9-phenyl-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 5-[3-(dimethylamino)propyl]-9-(3-methoxyphenyl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 5-[3-(dimethylamino)propyl]-9-(pyridin-2-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 5-[3-(dimethylamino)propyl]-9-(pyridin-3-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 9-(3-chlorophenyl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 9-(3-methoxyphenyl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 9-(pyridin-3-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 9-(quinolin-5-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 9-bromo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 9-phenyl-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 9-phenyl-5-(prop-2-en-1-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
-
Mycobacterium tuberculosis
6.3.1.2 additional information high throughput screening of series of imidazo[1,2-a]indeno[1,2-e]pyrazin-4-ones as enzyme inhibitors, overview. None of these compounds is active on whole cell Mycobacterium tuberculosis. Structure activity relationships of 5,10-dihydro-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one derivatives Mycobacterium tuberculosis
6.3.1.2 N-(4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-9-yl)acetamide
-
Mycobacterium tuberculosis

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
6.3.1.2 Mg2+ required Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
6.3.1.2 ATP + L-glutamate + NH3 Mycobacterium tuberculosis
-
ADP + phosphate + L-glutamine
-
r
6.3.1.2 ATP + L-glutamate + NH3 Mycobacterium tuberculosis ATCC 25618 / H37Rv
-
ADP + phosphate + L-glutamine
-
r

Organism

EC Number Organism UniProt Comment Textmining
6.3.1.2 Mycobacterium tuberculosis P9WN39
-
-
6.3.1.2 Mycobacterium tuberculosis ATCC 25618 / H37Rv P9WN39
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
6.3.1.2 ATP + L-glutamate + NH3
-
Mycobacterium tuberculosis ADP + phosphate + L-glutamine
-
r
6.3.1.2 ATP + L-glutamate + NH3
-
Mycobacterium tuberculosis ATCC 25618 / H37Rv ADP + phosphate + L-glutamine
-
r

Subunits

EC Number Subunits Comment Organism
6.3.1.2 dodecamer Mtb-GlnA1 crystallizes in the space group P212121 with 24 monomers in the asymmetric unit to form a dodecamer. The 24 active sites of the dodecamer are found in long grooves between the subunits Mycobacterium tuberculosis

Synonyms

EC Number Synonyms Comment Organism
6.3.1.2 GlnA1
-
Mycobacterium tuberculosis

Cofactor

EC Number Cofactor Comment Organism Structure
6.3.1.2 ATP
-
Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
6.3.1.2 additional information
-
IC50 values of the compounds versus Mycobacterium tuberculosis cells and human Hep-G2 cells Mycobacterium tuberculosis additional information
6.3.1.2 0.000007
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 5-(but-3-en-1-yl)-9-(pyridin-3-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.00003
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 9-bromo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.000031
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 9-(pyridin-3-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.000031
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 9-phenyl-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.000051
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 9-(3-methoxyphenyl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.000066
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 5-(3-methylbutyl)-9-(pyridin-3-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.000084
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 5-[3-(dimethylamino)propyl]-9-(3-methoxyphenyl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.000131
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 5-[3-(dimethylamino)propyl]-9-(pyridin-3-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.00017
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 5-methyl-9-phenyl-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.000219
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 5-(2-methoxyethyl)-9-phenyl-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.000333
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 9-phenyl-5-(prop-2-en-1-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.000456
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 5-cyclopropyl-9-(pyridin-2-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.00061
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 9-(3-chlorophenyl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.000663
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 5-benzyl-9-phenyl-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.000857
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 5-[3-(dimethylamino)propyl]-9-(pyridin-2-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one
6.3.1.2 0.0021
-
pH and temperature not specified in the publication Mycobacterium tuberculosis N-(4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-9-yl)acetamide
6.3.1.2 0.007
-
pH and temperature not specified in the publication Mycobacterium tuberculosis 9-(quinolin-5-yl)-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

General Information

EC Number General Information Comment Organism
6.3.1.2 metabolism the enzyme catalyzes the ATP-dependent synthesis of L-glutamine from glutamate and ammonia. GlnA1 is also involved in the synthesis of poly-L-glutamate/glutamine for the cell wall of pathogenic mycobacteria Mycobacterium tuberculosis
6.3.1.2 physiological function the enzyme catalyzes the ATP-dependent synthesis of L-glutamine from glutamate and ammonia. GlnA1 is also involved in the synthesis of poly-L-glutamate/glutamine for the cell wall of pathogenic mycobacteria Mycobacterium tuberculosis