Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions
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<sub>n</sub>(M...
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| Format: | Article |
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MDPI AG
2021-04-01
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| Series: | Pharmaceutics |
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| Online Access: | https://www.mdpi.com/1999-4923/13/5/639 |
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| author | Bruna L. Kuhn Taís F. A. Kaminski Ânderson R. Carvalho Alexandre M. Fuentefria Bianca M. B. C. Johann Edilma E. da Silva Gustavo P. Silveira Tássia L. da Silveira Félix A. A. Soares Nilo Zanatta Clarissa P. Frizzo |
| author_facet | Bruna L. Kuhn Taís F. A. Kaminski Ânderson R. Carvalho Alexandre M. Fuentefria Bianca M. B. C. Johann Edilma E. da Silva Gustavo P. Silveira Tássia L. da Silveira Félix A. A. Soares Nilo Zanatta Clarissa P. Frizzo |
| author_sort | Bruna L. Kuhn |
| collection | DOAJ |
| description | 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<sub>n</sub>(MIM)<sub>2</sub>[C<sub>n</sub>(MIM)<sub>2</sub>][CO<sub>2</sub>-(CH<sub>2</sub>)<sub>m</sub>CO<sub>2</sub>], in which <i>n</i> = 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 <i>Candidas</i> and bacteria (mainly <i>S. aureus</i>), and they showed moderate cytotoxicity. The best activity against Gram-positive bacteria was observed for [C<sub>4</sub>(MIM)<sub>2</sub>][Pim] toward MRSA. For the DILs described herein, their level of toxicity against <i>C. elegans</i> 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. |
| first_indexed | 2024-03-10T11:49:31Z |
| format | Article |
| id | doaj.art-bdb686eda0a84ebc9641618d7a80109c |
| institution | Directory Open Access Journal |
| issn | 1999-4923 |
| language | English |
| last_indexed | 2024-03-10T11:49:31Z |
| publishDate | 2021-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceutics |
| spelling | doaj.art-bdb686eda0a84ebc9641618d7a80109c2023-11-21T17:51:22ZengMDPI AGPharmaceutics1999-49232021-04-0113563910.3390/pharmaceutics13050639Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate AnionsBruna L. Kuhn0Taís F. A. Kaminski1Ânderson R. Carvalho2Alexandre M. Fuentefria3Bianca M. B. C. Johann4Edilma E. da Silva5Gustavo P. Silveira6Tássia L. da Silveira7Félix A. A. Soares8Nilo Zanatta9Clarissa P. Frizzo10Department of Chemistry, Federal University of Santa Maria, Santa Maria 97105-900, BrazilLaboratory of Applied Mycology, School of Pharmacy, Federal University of Rio Grande do Sul, Porto Alegre 90470-440, BrazilLaboratory of Applied Mycology, School of Pharmacy, Federal University of Rio Grande do Sul, Porto Alegre 90470-440, BrazilLaboratory of Applied Mycology, School of Pharmacy, Federal University of Rio Grande do Sul, Porto Alegre 90470-440, BrazilPostgraduate Program in Agricultural Microbiology and the Environment, Instituto de Ciências Básicas da Saúde-Campus Centro, Rua Sarmento Leite 500, Porto Alegre 90050-170, BrazilPostgraduate Program in Chemistry, Instituto de Química-Campus Vale, Av. Bento Gonçalves 9500, Porto Alegre 91501-970, BrazilPostgraduate Program in Agricultural Microbiology and the Environment, Instituto de Ciências Básicas da Saúde-Campus Centro, Rua Sarmento Leite 500, Porto Alegre 90050-170, BrazilDepartament of Biochemistry and Molecular Biology, Federal University of Santa Maria, Avenida Roraima 1000, Santa Maria 97105-900, BrazilDepartament of Biochemistry and Molecular Biology, Federal University of Santa Maria, Avenida Roraima 1000, Santa Maria 97105-900, BrazilDepartment of Chemistry, Federal University of Santa Maria, Santa Maria 97105-900, BrazilDepartment of Chemistry, Federal University of Santa Maria, Santa Maria 97105-900, BrazilImidazolium-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<sub>n</sub>(MIM)<sub>2</sub>[C<sub>n</sub>(MIM)<sub>2</sub>][CO<sub>2</sub>-(CH<sub>2</sub>)<sub>m</sub>CO<sub>2</sub>], in which <i>n</i> = 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 <i>Candidas</i> and bacteria (mainly <i>S. aureus</i>), and they showed moderate cytotoxicity. The best activity against Gram-positive bacteria was observed for [C<sub>4</sub>(MIM)<sub>2</sub>][Pim] toward MRSA. For the DILs described herein, their level of toxicity against <i>C. elegans</i> 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.https://www.mdpi.com/1999-4923/13/5/639dicationic ionic liquiddicarboxylate anionantimicrobial activity<i>C. elegans</i>cytotoxicityESKAPE panel |
| spellingShingle | Bruna L. Kuhn Taís F. A. Kaminski Ânderson R. Carvalho Alexandre M. Fuentefria Bianca M. B. C. Johann Edilma E. da Silva Gustavo P. Silveira Tássia L. da Silveira Félix A. A. Soares Nilo Zanatta Clarissa P. Frizzo Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions Pharmaceutics dicationic ionic liquid dicarboxylate anion antimicrobial activity <i>C. elegans</i> cytotoxicity ESKAPE panel |
| title | Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions |
| title_full | Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions |
| title_fullStr | Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions |
| title_full_unstemmed | Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions |
| title_short | Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions |
| title_sort | antimicrobial and toxicity evaluation of imidazolium based dicationic ionic liquids with dicarboxylate anions |
| topic | dicationic ionic liquid dicarboxylate anion antimicrobial activity <i>C. elegans</i> cytotoxicity ESKAPE panel |
| url | https://www.mdpi.com/1999-4923/13/5/639 |
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