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505893 Mycobacterium Bactericide, TCA1 - Calbiochem

MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: Ethyl-(2-(benzo[d]thiazole-2-carboxamido)thiophene-3-carbonyl)carbamate, Ethyl-((2-((1,3-benzothiazol-2-ylcarbonyl)amino)-3-thienyl)carbonyl)carbamate, Mycobacteria MoeW Inhibitor, Mtb Inhibitor, Mycobacteria DprE1 Inhibitor

505893
  
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Overview

Replacement Information

Key Spec Table

Empirical Formula
C₁₆H₁₃N₃O₄S₂
Description
OverviewA cell-permeable benzothiazolylthiophene that exhibits bactericidal activity against mycobacteria, including M. smegmatis, M. bovis GCG, and M. tuberculosis (MIC50 = 30, 40, and 10 ng/mL, respectively, in biofilm medium; MIC50 = 4.5, 3, 0.19 µg/mL, respectively, in 7H9 medium), but not E. coli, Staphylococcus aureus, or Pseudomonas aeruginosa, by simultaneously targeting DprE1 FAD-binding domain of DprE1/DprE2 required for Mycobacterium cell wall arabinan biosynthesis and the Mtb MoeW protein involved in the biosynthesis of MoCo, molybdenum cofactor indispensable for nitrate assimilation via MoCo-dependent enzymes. Either alone or used in combination, TCA1 is shown to greatly complement INH (Isoniazid) and RIF (Rifampicin) against both wt and drug-resistant Mtb cultures in vitro (1-7.5 µg/mL) and in treating acute and chronic Mtb H37Rv infections in mice in vivo (10-100 mg/kg p.o.) with no apparent host toxicity.
Catalogue Number505893
Brand Family Calbiochem®
SynonymsEthyl-(2-(benzo[d]thiazole-2-carboxamido)thiophene-3-carbonyl)carbamate, Ethyl-((2-((1,3-benzothiazol-2-ylcarbonyl)amino)-3-thienyl)carbonyl)carbamate, Mycobacteria MoeW Inhibitor, Mtb Inhibitor, Mycobacteria DprE1 Inhibitor
References
ReferencesWang, F., et al. 2013. Proc. Natl. Acad. Sci. USA 110, E2510.
Product Information
FormYellow solid
Hill FormulaC₁₆H₁₃N₃O₄S₂
Chemical formulaC₁₆H₁₃N₃O₄S₂
ReversibleY
Structure formula ImageStructure formula Image
Quality LevelMQ200
Applications
Biological Information
Primary TargetDprE1
Secondary targetMoeW
Purity≥97% by HPLC
Physicochemical Information
Cell permeableY
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Safety Information
Product Usage Statements
Storage and Shipping Information
Ship Code Ambient Temperature Only
Toxicity Standard Handling
Storage +2°C to +8°C
Protect from Light Protect from light
Do not freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Packaging Information
Packaged under inert gas Packaged under inert gas
Transport Information
Supplemental Information
Specifications
Global Trade Item Number
Catalogue Number GTIN
505893 0

Documentation

Mycobacterium Bactericide, TCA1 - Calbiochem SDS

Title

Safety Data Sheet (SDS) 

References

Reference overview
Wang, F., et al. 2013. Proc. Natl. Acad. Sci. USA 110, E2510.
Data Sheet

Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

Revision14-January-2014 JSW
SynonymsEthyl-(2-(benzo[d]thiazole-2-carboxamido)thiophene-3-carbonyl)carbamate, Ethyl-((2-((1,3-benzothiazol-2-ylcarbonyl)amino)-3-thienyl)carbonyl)carbamate, Mycobacteria MoeW Inhibitor, Mtb Inhibitor, Mycobacteria DprE1 Inhibitor
DescriptionA cell-permeable benzothiazolylthiophene that exhibits bactericidal activity against mycobacteria, including M. smegmatis, M. bovis GCG, and M. tuberculosis (MIC50 = 30, 40, and 10 ng/mL, respectively, in biofilm medium; MIC50 = 4.5, 3, 0.19 µg/mL, respectively, in 7H9 medium), but not E. coli, Staphylococcus aureus, or Pseudomonas aeruginosa, by simultaneously targeting DprE1 FAD-binding domain of the decaprenylphosphoryl-β-D-ribofuranose 2'-epimerase DprE1/DprE2 required for Mycobacterium cell wall arabinan biosynthesis and the Mtb MoeW protein (M. smegmatis MoeB homolog) involved in the biosynthesis of MoCo, molybdenum cofactor indispensable for nitrate assimilation via MoCo-dependent enzymes. Either alone or used in combination, TCA1 is shown to greatly complement INH (Isoniazid) and RIF (Rifampicin) against both wt and drug-resistant Mtb cultures in vitro (3.75-7.5 µg/mL, 1 µg/mL, and 2 µg/mL, respectively), including the XDR (extensively drug resistant) TF275 (strain# mc28013) that is resistant to 10 TB drugs, and in treating acute and chronic Mtb H37Rv infections in mice in vivo (40-100 mg/kg, 25 mg/kg, and 10 mg/kg, respectively; p.o.). TCA1 exhibits no host toxicity (≥25 µM in cultures and 100 mg/kg in mice) and no activity toward hERG or four CTP enzymes.
FormYellow solid
Intert gas (Yes/No) Packaged under inert gas
Chemical formulaC₁₆H₁₃N₃O₄S₂
Structure formulaStructure formula
Purity≥97% by HPLC
SolubilityDMSO (50 mg/ml)
Storage Protect from light
+2°C to +8°C
Do Not Freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Toxicity Standard Handling
ReferencesWang, F., et al. 2013. Proc. Natl. Acad. Sci. USA 110, E2510.