Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions

Pharmaceutics

TássiaL.da Silveira¹  FélixA. A. Soares¹  ClarissaP. Frizzo²  BrunaL. Kuhn²  Nilo Zanatta²  TaísF. A. Kaminski³  ÂndersonR. Carvalho³  AlexandreM. Fuentefria³  BiancaM. B. C. Johann⁴  GustavoP. Silveira⁴  EdilmaE.da Silva⁵ 

[1] Departament of Biochemistry and Molecular Biology, Federal University of Santa Maria, Avenida Roraima 1000, Santa Maria 97105-900, Brazil;Department of Chemistry, Federal University of Santa Maria, Santa Maria 97105-900, Brazil;Laboratory of Applied Mycology, School of Pharmacy, Federal University of Rio Grande do Sul, Porto Alegre 90470-440, Brazil;Postgraduate Program in Agricultural Microbiology and the Environment, Instituto de Ciências Básicas da Saúde-Campus Centro, Rua Sarmento Leite 500, Porto Alegre 90050-170, Brazil;Postgraduate Program in Chemistry, Instituto de Química-Campus Vale, Av. Bento Gonçalves 9500, Porto Alegre 91501-970, Brazil;

关键词: dicationic ionic liquid;    dicarboxylate anion;    antimicrobial activity;    C. elegans;    cytotoxicity;    ESKAPE panel;   

DOI  :  10.3390/pharmaceutics13050639

来源: DOAJ

【 摘 要 】

Imidazolium-based dicationic ILs (DILs) presenting antimicrobial activity and relatively low toxicity are highly desirable and are envisioned for use in live tissue to prevent bacterial or fungal infections. In this context, we present here DILs with dicarboxylate anions [C_n(MIM)₂[C_n(MIM)₂][CO₂-(CH₂)_mCO₂], in which n = 4, 6, 8, and 10, and m = 0, 1, 2 3, 4, and 5. The results showed that DILs with an alkyl chain spacer of ten carbons were active against yeasts and the bacterial strains tested. However, most of the DILs were cytotoxic and toxic at 1 mM. By contrast, DILs with alkyl chains possessing less than ten carbons were active against some specific Candidas and bacteria (mainly S. aureus), and they showed moderate cytotoxicity. The best activity against Gram-positive bacteria was observed for [C₄(MIM)₂][Pim] toward MRSA. For the DILs described herein, their level of toxicity against C. elegans was lower than that of most of the mono- and dicationic IL analogs with other anions. Our results showed that the presence of carboxylate anions reduces the toxicity of DILs compared to DILs containing halide anions, which is particularly significant to the means of designing biologically active compounds in antimicrobial formulations.

【 授权许可】

Unknown