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Literature summary for 3.1.3.48 extracted from

  • Noeren-Mueller, A.; Wilk, W.; Saxena, K.; Schwalbe, H.; Kaiser, M.; Waldmann, H.
    Discovery of a new class of inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B by biology-oriented synthesis (2008), Angew. Chem., 47, 5973-5977.
    View publication on PubMed

Application

Application Comment Organism
drug development inhibition of MptpA and MptpB represents a promising strategy for the development of selective antibiotics against this severe pathogen Mycobacterium tuberculosis

Inhibitors

Inhibitors Comment Organism Structure
methyl (6S,10S)-12-(2-chloro-3-hydroxybenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
-
Mycobacterium tuberculosis
methyl (6S,10S)-12-(2-fluoro-5-iodobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
-
Mycobacterium tuberculosis
methyl (6S,10S)-12-(2-hydroxybenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate absolutely specific for MptpB, no inhibition of MptpA Mycobacterium tuberculosis
methyl (6S,10S)-12-(3,4-dichlorobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate absolutely specific for MptpB, no inhibition of MptpA Mycobacterium tuberculosis
methyl (6S,10S)-12-(3,4-difluorobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
-
Mycobacterium tuberculosis
methyl (6S,10S)-12-(3-bromo-4-fluorobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate absolutely specific for MptpB, no inhibition of MptpA Mycobacterium tuberculosis
methyl (6S,10S)-12-(3-hydroxybenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate absolutely specific for MptpB, no inhibition of MptpA Mycobacterium tuberculosis
methyl (6S,10S)-12-benzyl-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
-
Mycobacterium tuberculosis
methyl (6S,10S)-12-[(4,6-dichloro-2H-chromen-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate absolutely specific for MptpB, no inhibition of MptpA Mycobacterium tuberculosis
methyl (6S,10S)-12-[(4-chloro-6-fluoro-2H-chromen-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate absolutely specific for MptpB, no inhibition of MptpA, inhibition kinetics, overview Mycobacterium tuberculosis
methyl (6S,10S)-12-[(5-chloro-1H-indol-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate absolutely specific for MptpB, no inhibition of MptpA Mycobacterium tuberculosis
methyl (6S,10S)-12-[(5-methylfuran-2-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate absolutely specific for MptpB, no inhibition of MptpA Mycobacterium tuberculosis
methyl (6S,10S)-9-hydroxy-12-(3-hydroxybenzyl)-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
-
Mycobacterium tuberculosis
methyl (6S,10S)-9-oxo-12-(pyridin-3-ylmethyl)-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
-
Mycobacterium tuberculosis

Localization

Localization Comment Organism GeneOntology No. Textmining
extracellular MptpA and MptpB are secreted in host lung Mycobacterium tuberculosis
-
-

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-nitrophenyl phosphate + H2O
-
Mycobacterium tuberculosis 4-nitrophenol + phosphate
-
?

Synonyms

Synonyms Comment Organism
MPtpA
-
Mycobacterium tuberculosis
MPtpB
-
Mycobacterium tuberculosis
protein tyrosine phosphatase B
-
Mycobacterium tuberculosis

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00134
-
methyl (6S,10S)-12-[(4-chloro-6-fluoro-2H-chromen-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate inhibition of MptpB Mycobacterium tuberculosis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00471
-
inhibition of MptpB Mycobacterium tuberculosis methyl (6S,10S)-12-[(4,6-dichloro-2H-chromen-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
0.00595
-
inhibition of MptpB Mycobacterium tuberculosis methyl (6S,10S)-12-[(5-methylfuran-2-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
0.0061
-
inhibition of MptpB Mycobacterium tuberculosis methyl (6S,10S)-12-(3-hydroxybenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
0.00704
-
inhibition of MptpB Mycobacterium tuberculosis methyl (6S,10S)-12-[(4-chloro-6-fluoro-2H-chromen-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
0.00826
-
inhibition of MptpB Mycobacterium tuberculosis methyl (6S,10S)-12-(3,4-dichlorobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
0.00964
-
inhibition of MptpB Mycobacterium tuberculosis methyl (6S,10S)-12-(2-hydroxybenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
0.0107
-
inhibition of MptpB Mycobacterium tuberculosis methyl (6S,10S)-12-(3-bromo-4-fluorobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate
0.0116
-
inhibition of MptpB Mycobacterium tuberculosis methyl (6S,10S)-12-[(5-chloro-1H-indol-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate

General Information

General Information Comment Organism
physiological function MptpA and MptpB selectively dephosphorylate human host proteins involved in interferon-gamma signaling pathways, thereby preventing the initiation of host defense mechanisms, overview Mycobacterium tuberculosis