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Substituted N-phenylitaconamides as inhibitors of mycobacteria and mycobacterial isocitrate lyase Context Sensitive Links 1 of 2 Substituted N-phenylitaconamides as inhibitors of mycobacteria and mycobacterial isocitrate lyase

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F71009396%3A_____%2F22%3AN0000010" target="_blank" >RIV/71009396:_____/22:N0000010 - isvavai.cz</a>

  • Result on the web

    <a href="https://www.sciencedirect.com/science/article/pii/S0928098722001373?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0928098722001373?via%3Dihub</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1016/j.ejps.2022.106252" target="_blank" >10.1016/j.ejps.2022.106252</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Substituted N-phenylitaconamides as inhibitors of mycobacteria and mycobacterial isocitrate lyase Context Sensitive Links 1 of 2 Substituted N-phenylitaconamides as inhibitors of mycobacteria and mycobacterial isocitrate lyase

  • Original language description

    Novel antimycobacterial drugs are needed, especially those with dual activity against both actively growing and non-replicating subpopulations of mycobacteria. Isocitrate lyase (ICL) is one of proposed targets and this enzyme is inhibited by itaconic acid. That is why we have designed and prepared sixteen amides of itaconic acid and various anilines and amine antimicrobial drugs to evaluate them as potential inhibitors of ICL and antimycobacterial agents. N-Phenylitaconamides were prepared from itaconic anhydride and substituted anilines (yields 57-99%). They were characterized and evaluated against mycobacterial ICL and against actively growing mycobacteria (M. tuberculosis H37Rv, M. avium, two strains of M. kansasii). All derivatives showed antimycobacterial efficacy with minimum inhibitory concentrations starting from 125 mu M. M. kansasii was the most susceptible species. Itaconamides derived from sulfonamides or p-aminosalicylic acid were optimal for activity against extracellular mycobacteria. ICL1 was significantly inhibited by two compounds, with 2-methylene-4-[(4nitrophenyl)amino]-4-oxobutanoic acid 1k being the most potent (36% inhibition at 10 mu M), which was also more efficient than two comparators. Molecular docking revealed its mode of binding to the enzyme. Using in silico tools, physicochemical properties and structural features for drug-likeness and gastrointestinal absorption were evaluated.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    30104 - Pharmacology and pharmacy

Result continuities

  • Project

    <a href="/en/project/GJ20-19638Y" target="_blank" >GJ20-19638Y: Design and investigation of novel antimicrobial agents active against drug-resistant and biofilm-forming gram-positive bacteria</a><br>

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2022

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    European Journal of Pharmaceutical Sciences

  • ISSN

    0928-0987

  • e-ISSN

    1879-0720

  • Volume of the periodical

    176

  • Issue of the periodical within the volume

    106252

  • Country of publishing house

    NL - THE KINGDOM OF THE NETHERLANDS

  • Number of pages

    8

  • Pages from-to

    1-8

  • UT code for WoS article

    000839196000010

  • EID of the result in the Scopus database

    2-s2.0-85134358236