Morita-Baylis-Hillman Adduct 2-(3-Hydroxy-2-oxoindolin-3-yl)acrylonitrile (ISACN) Modulates Inflammatory Process In vitro and In vivo

França, Juliane Santos de; Sales-Neto, José Marreiro de; Carvalho, Deyse Cristina Madruga; Lima, Éssia de Almeida; Olegário, Tayná Rodrigues; Mendes, Rhuan Karlos Santos; Lima-Júnior, Cláudio Gabriel; Vasconcellos, Mário Luiz Araújo de Almeida; Rodrigues‐Mascarenhas, Sandra

doi:10.1007/s10753-020-01385-9

Cited by 4 publications

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“…Morita–Baylis–Hillman adducts (MBHA) derived from isatin derivatives and acrylonitrile has showed bactericidal and fungicidal properties by preventing the growth of the majority of microorganism species utilized in biological experiments 14 . The adduct 2-(3-hydroxy-2-oxoindolin-3-yl)acrylonitrile (ISACN) has shown as a promising anti-inflammatory agent 15 . MBHA obtained using acrylonitrile as Michael acceptor inhibited the growth of various species of bacteria and fungi showing minimum inhibitory concentration of 32 µg/ml which reflects the antimicrobial effectiveness of acrylonitrile adducts 14 .…”

Section: Introductionmentioning

confidence: 99%

Acrylonitrile adducts: design, synthesis and biological evaluation as antimicrobial, haemolytic and thrombolytic agent

Das

Devi

Gaur

et al. 2023

Sci Rep

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In this work, five acrylonitrile adducts were screened for antibacterial activity against Gram-positive Bacillus subtilis, Microbial Type Culture Collection and Gene Bank (MTCC 1305) and Gram-negative Escherichia coli (MTCC 443). Synthesis was followed by aza-Michael addition reaction, where the acrylonitrile accepts an electron pair from the respective amines and results in the formation of n-alkyliminobis-propionitrile and n-alkyliminopropionitrile under microwave irradiation. Characterization of the compounds were performed using Fourier Transform Infrared (FTIR), Proton Nuclear Magnetic Resonance (1H NMR) and Electrospray Ionisation Mass Spectrometry (ESI–MS). The particle size characterization was done by Dynamic Light Scattering (DLS) technique. The antibacterial study showed higher inhibition rate for both Gram-positive and Gram-negative bacteria. The antibacterial ability was found to be dose dependent. The minimum inhibitory concentration against both bacteria were found to be 1, 3, 0.4, 1, 3 µl/ml for E. coli and 6, 6, 0.9, 0.5, 5 µl/ml for B. subtilis. Time-kill kinetics evaluation showed that the adducts possess bacteriostatic action. Further it was evaluated for high-throughput in vitro assays to determine the compatibility of the adducts for drug delivery. The haemolytic and thrombolytic activity was analysed against normal mouse erythrocytes. The haemolytic activity showed prominent results, and thereby projecting this acrylonitrile adducts as potent antimicrobial and haemolytic agent.

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Section: Introductionmentioning

confidence: 99%