Antimicrobial properties of novel ionic liquids derived from imidazolium cation with phenolic functional groups

Guzmán, Luís; Parra-Cid, Cristóbal; Guerrero-Muñoz, Etiennette; Peña-Varas, Carlos; Polo-Cuadrado, Efraín; Duarte, Yorley; Castro, Ricardo I.; Nerio, Luz Stella; Araya‐Maturana, Ramiro; Asefa, Tewodros; Echeverría, Javier; Ramírez, David; Forero-Doria, Oscar

doi:10.1016/j.bioorg.2021.105289

Cited by 14 publications

(7 citation statements)

References 42 publications

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“…91 Compared with other antimicrobials, ILs exhibit multiple modes of action on bacterial cells. They can interact with and destroy bacterial membranes, 83,101 disrupt proteins and enzymes, 102,103 dysregulate bacterial metabolism, 104,105 induce oxidative stress response, 106,107 and cause DNA damage. 108,109 The tunability of ILs, which stems from the free combination of ions, allows for the adjustment of alkyl chain length and the selection of different ions to regulate the strength of antibacterial properties.…”

Section: Ils As Drug Candidatesmentioning

confidence: 99%

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Hu,

Xing,

Yue

et al. 2023

Chem. Soc. Rev.

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Section: Ils As Drug Candidatesmentioning

confidence: 99%

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Hu,

Xing,

Yue

et al. 2023

Chem. Soc. Rev.

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“…aureas, E.coli, and P. aeruginosa under minimal inhibitory concentrations . Ferraz et al prepared active pharmaceutical ingredients containing anions with highly hydrophilic imidazolium/ammonium/phosphonium/pyridinium ionic liquids and studied their antibacterial activity against sensitive and resistant Escherichia coli and Staphylococcus aureus under minimal inhibitory concentrations .…”

Section: Introductionmentioning

confidence: 99%

“…The hydrophobic unit of tert -butyl- N -methyl phenolic imidazolium salt showed excellent efficacy against S. aureas , E.coli , and P. aeruginosa under minimal inhibitory concentrations. 25 Ferraz et al prepared active pharmaceutical ingredients containing anions with highly hydrophilic imidazolium/ammonium/phosphonium/pyridinium ionic liquids and studied their antibacterial activity against sensitive and resistant Escherichia coli and Staphylococcus aureus under minimal inhibitory concentrations. 26 Recently, our laboratory started the synthesis of some novel imidazolium-/pyridinium-type of ionic liquids under conventional 27 /solvent-free silica-supported muffle furnace reaction conditions 28 and reported their antibacterial 29 and catalytic behaviors.…”

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Dimeric Pyridinium Bromide Analogues Inhibits Cancer Cell Growth by Activating Caspases and Downregulating Bcl-2 Protein

et al. 2023

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Flexible dimeric substituted pyridinium bromides with primary and tertiary amines are prepared by conventional and solvent-free methods. The formation of compounds 2 and 4 is much easier than that of compounds 1 and 3 because of the benzyl carbon which is more electropositive than the primary alkyl carbon. The newly synthesized dimeric pyridinium compounds are optimized using p). The in vitro antiproliferative activity is studied in lung (A549) and breast cancer cell lines (MDA-MB 231). Among the four compounds, 1,1′-(1,3-phenylene bis(methylene)bis 2aminopyridinium bromide 4 showed potent anticancer activity when compared to the standard drug 5-fluorouracil. 1,1′-(1,3-Phenylene bis(methylene)bis 2aminopyridinium bromide 4 is not toxic to normal cell lines 3T3-L1 and MRC-5 cell lines. Also, 1,1′-(1,3-phenylene bis(methylene)bis 2-aminopyridinium bromide 4-induced apoptosis in cancer cell lines is examined using AO/EB and Hoechst staining, which is further supported by cell cycle analysis. Western blot analysis showed that 1,1′-(1,3-phenylene bis(methylene)bis 2-aminopyridinium bromide 4 induces apoptosis through the extrinsic apoptotic pathway by upregulating caspase 3 and caspase 9. This compound also downregulates intrinsic apoptotic proteins, including Bcl-2, Bcl-x, and Bad. From the present study results, it is confirmed that 1,1′-(1,3-phenylene bis(methylene)bis 2aminopyridinium bromide 4 has potent anticancer activity when compared to other compounds.

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“…[21][22][23] In relvence to biological studies molecular simulations are gaining importance. [24] The current study aimed at the development of phenyl/ benzothiazole functionalized CÀ C linked pyrazolyl-thiazoles to develop better anti-bacterial and phytotoxic compounds. Synthesis of pyrazolyl-thiazoles has been achieved via reaction of α-tosyloxy pyrazolylketones with thioamide instead of using lachrymatory α-haloketones.…”

Section: Introductionmentioning

confidence: 99%

“…The benzothiazoles have been reported to play a vital role in enhancing the biological properties [21–23] . In relvence to biological studies molecular simulations are gaining importance [24] …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Evaluation of Antimicrobial Activity, Phytotoxicity, Molecular Docking & Dynamic Simulations of Benzothiazole Functionalized C−C Linked Pyrazolyl‐Thiazoles

Kamra,

Rani,

Kiran

et al. 2023

ChemistrySelect

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Synthesis of phenyl/benzothiazole functionalized C−C linked pyrazolyl‐thiazoles has been achieved from non‐lachrymatory α‐tosyloxy pyrazolylketones with different thioamides. The pyrazolyl‐thiazoles were characterized by spectroscopic studies and evaluated for antimicrobial activity and phytotoxicity. Compound 6 n displayed better activity with MIC value of 0.0045 μmol/mL against Gram‐positive bacteria B. cereus in comparison to the standard drug Ciprofloxacin (0.0047 μmol/mL). Compound 6 i displayed better activity against fungal strain C. albicans (MIC=0.0152 μmol/mL) in comparison to the standard drug Fluconazole (0.0204 μmol/mL). Compound 6 o diplayed 95 % cell viability against Mouse Fibroblast cell line and 100 % plant seed germination. Docking studies at the topoisomerase II DNA gyrase B (PDB ID: 1KZN) and C. albicans (PDB ID: 1IYL) were used to investigate potential interactions between the most active compound and the receptor protein. The stability of the compounds with 1KZN and 1IYL by molecular dynamic simulations showed that 6 r, 6 n and 6 i present leading structures for next drug development because of their simple synthesis and useful bioactivity.

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Antimicrobial properties of novel ionic liquids derived from imidazolium cation with phenolic functional groups

Cited by 14 publications

References 42 publications

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Discovery of Novel Dimeric Pyridinium Bromide Analogues Inhibits Cancer Cell Growth by Activating Caspases and Downregulating Bcl-2 Protein

Synthesis, Characterization and Evaluation of Antimicrobial Activity, Phytotoxicity, Molecular Docking & Dynamic Simulations of Benzothiazole Functionalized C−C Linked Pyrazolyl‐Thiazoles

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