Molecular Sizes and Antibacterial Performance Relationships of Flexible Ionic Liquid Derivatives
Cationic agents, such as ionic liquids (ILs)-based species, have broad-spectrum antibacterial activities. However, the antibacterial mechanisms lack systematic and molecular-level research, especially for Gram-negative bacteria, which have highly organized membrane structures. Here, we designed a se...
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Published in | Journal of the American Chemical Society Vol. 142; no. 47; pp. 20257 - 20269 |
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Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
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WASHINGTON
American Chemical Society
25.11.2020
Amer Chemical Soc |
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Abstract | Cationic agents, such as ionic liquids (ILs)-based species, have broad-spectrum antibacterial activities. However, the antibacterial mechanisms lack systematic and molecular-level research, especially for Gram-negative bacteria, which have highly organized membrane structures. Here, we designed a series of flexible fluorescent diketopyrrolopyrrole-based ionic liquid derivatives (ILDs) with various molecular sizes (1.95–4.2 nm). The structure–antibacterial activity relationships of the ILDs against Escherichia coli (E. coli) were systematically studied thorough antibacterial tests, fluorescent tracing, morphology analysis, molecular biology, and molecular dynamics (MD) simulations. ILD-6, with a relatively small molecular size, could penetrate through the bacterial membrane, leading to membrane thinning and intracellular activities. ILD-6 showed fast and efficient antimicrobial activity. With the increase of molecular sizes, the corresponding ILDs were proven to intercalate into the bacterial membrane, leading to the destabilization of the lipid bilayer and further contributing to the antimicrobial activities. Moreover, the antibacterial activity of ILD-8 was limited, where the size was not large enough to introduce significant membrane disorder. Relative antibacterial experiments using another common Gram-negative bacteria, Pseudomonas aeruginosa (PAO1), further confirmed the proposed structure-antibacterial activity relationships of ILDs. More impressively, both ILD-6 and ILD-12 displayed significant in vivo therapeutic effects on the PAO1-infected rat model, while ILD-8 performed poorly, which confirmed the antibacterial mechanism of ILDs and proved their potentials for future application. This work clarifies the interactions between molecular sizes of ionic liquid-based species and Gram-negative bacteria and will provide useful guidance for the rational design of high-performance antibacterial agents. |
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AbstractList | Cationic agents, such as ionic liquids (ILs)-based species, have broad-spectrum antibacterial activities. However, the antibacterial mechanisms lack systematic and molecular-level research, especially for Gram-negative bacteria, which have highly organized membrane structures. Here, we designed a series of flexible fluorescent diketopyrrolopyrrole-based ionic liquid derivatives (ILDs) with various molecular sizes (1.95–4.2 nm). The structure–antibacterial activity relationships of the ILDs against Escherichia coli (E. coli) were systematically studied thorough antibacterial tests, fluorescent tracing, morphology analysis, molecular biology, and molecular dynamics (MD) simulations. ILD-6, with a relatively small molecular size, could penetrate through the bacterial membrane, leading to membrane thinning and intracellular activities. ILD-6 showed fast and efficient antimicrobial activity. With the increase of molecular sizes, the corresponding ILDs were proven to intercalate into the bacterial membrane, leading to the destabilization of the lipid bilayer and further contributing to the antimicrobial activities. Moreover, the antibacterial activity of ILD-8 was limited, where the size was not large enough to introduce significant membrane disorder. Relative antibacterial experiments using another common Gram-negative bacteria, Pseudomonas aeruginosa (PAO1), further confirmed the proposed structure-antibacterial activity relationships of ILDs. More impressively, both ILD-6 and ILD-12 displayed significant in vivo therapeutic effects on the PAO1-infected rat model, while ILD-8 performed poorly, which confirmed the antibacterial mechanism of ILDs and proved their potentials for future application. This work clarifies the interactions between molecular sizes of ionic liquid-based species and Gram-negative bacteria and will provide useful guidance for the rational design of high-performance antibacterial agents. Cationic agents, such as ionic liquids (ILs)-based species, have broad-spectrum antibacterial activities. However, the antibacterial mechanisms lack systematic and molecular-level research, especially for Gram-negative bacteria, which have highly organized membrane structures. Here, we designed a series of flexible fluorescent diketopyrrolopyrrole-based ionic liquid derivatives (ILDs) with various molecular sizes (1.95-4.2 nm). The structure-antibacterial activity relationships of the ILDs against ( ) were systematically studied thorough antibacterial tests, fluorescent tracing, morphology analysis, molecular biology, and molecular dynamics (MD) simulations. ILD-6, with a relatively small molecular size, could penetrate through the bacterial membrane, leading to membrane thinning and intracellular activities. ILD-6 showed fast and efficient antimicrobial activity. With the increase of molecular sizes, the corresponding ILDs were proven to intercalate into the bacterial membrane, leading to the destabilization of the lipid bilayer and further contributing to the antimicrobial activities. Moreover, the antibacterial activity of ILD-8 was limited, where the size was not large enough to introduce significant membrane disorder. Relative antibacterial experiments using another common Gram-negative bacteria, (PAO1), further confirmed the proposed structure-antibacterial activity relationships of ILDs. More impressively, both ILD-6 and ILD-12 displayed significant in vivo therapeutic effects on the PAO1-infected rat model, while ILD-8 performed poorly, which confirmed the antibacterial mechanism of ILDs and proved their potentials for future application. This work clarifies the interactions between molecular sizes of ionic liquid-based species and Gram-negative bacteria and will provide useful guidance for the rational design of high-performance antibacterial agents. |
Author | Zhang, Xianren Xu, Fu-Jian Duan, Shun Ding, Xiaokang Jia, Weibin Yu, Manman Li, Jing Cao, Dapeng Zheng, Liang Yu, Bingran |
AuthorAffiliation | State Key Laboratory of Chemical Resource Engineering, Laboratory of Biomedical Materials and Key Lab of Biomedical Materials of Natural Macromolecules (Beijing University of Chemical Technology, Ministry of Education) Beijing Advanced Innovation Center for Soft Matter Science and Engineering, and State Key Laboratory of Organic−Inorganic Composites |
AuthorAffiliation_xml | – name: State Key Laboratory of Chemical Resource Engineering, Laboratory of Biomedical Materials and Key Lab of Biomedical Materials of Natural Macromolecules (Beijing University of Chemical Technology, Ministry of Education) – name: Beijing Advanced Innovation Center for Soft Matter Science and Engineering, and State Key Laboratory of Organic−Inorganic Composites |
Author_xml | – sequence: 1 givenname: Liang orcidid: 0000-0001-9992-2440 surname: Zheng fullname: Zheng, Liang organization: State Key Laboratory of Chemical Resource Engineering, Laboratory of Biomedical Materials and Key Lab of Biomedical Materials of Natural Macromolecules (Beijing University of Chemical Technology, Ministry of Education) – sequence: 2 givenname: Jing surname: Li fullname: Li, Jing organization: Beijing Advanced Innovation Center for Soft Matter Science and Engineering, and State Key Laboratory of Organic−Inorganic Composites – sequence: 3 givenname: Manman surname: Yu fullname: Yu, Manman organization: State Key Laboratory of Chemical Resource Engineering, Laboratory of Biomedical Materials and Key Lab of Biomedical Materials of Natural Macromolecules (Beijing University of Chemical Technology, Ministry of Education) – sequence: 4 givenname: Weibin surname: Jia fullname: Jia, Weibin organization: Beijing Advanced Innovation Center for Soft Matter Science and Engineering, and State Key Laboratory of Organic−Inorganic Composites – sequence: 5 givenname: Shun surname: Duan fullname: Duan, Shun organization: State Key Laboratory of Chemical Resource Engineering, Laboratory of Biomedical Materials and Key Lab of Biomedical Materials of Natural Macromolecules (Beijing University of Chemical Technology, Ministry of Education) – sequence: 6 givenname: Dapeng orcidid: 0000-0002-6981-7794 surname: Cao fullname: Cao, Dapeng organization: Beijing Advanced Innovation Center for Soft Matter Science and Engineering, and State Key Laboratory of Organic−Inorganic Composites – sequence: 7 givenname: Xiaokang orcidid: 0000-0002-6705-4148 surname: Ding fullname: Ding, Xiaokang organization: State Key Laboratory of Chemical Resource Engineering, Laboratory of Biomedical Materials and Key Lab of Biomedical Materials of Natural Macromolecules (Beijing University of Chemical Technology, Ministry of Education) – sequence: 8 givenname: Bingran orcidid: 0000-0003-4912-5632 surname: Yu fullname: Yu, Bingran email: yubr@mail.buct.edu.cn organization: State Key Laboratory of Chemical Resource Engineering, Laboratory of Biomedical Materials and Key Lab of Biomedical Materials of Natural Macromolecules (Beijing University of Chemical Technology, Ministry of Education) – sequence: 9 givenname: Xianren orcidid: 0000-0002-8026-9012 surname: Zhang fullname: Zhang, Xianren email: zhangxr@mail.buct.edu.cn organization: Beijing Advanced Innovation Center for Soft Matter Science and Engineering, and State Key Laboratory of Organic−Inorganic Composites – sequence: 10 givenname: Fu-Jian orcidid: 0000-0002-1838-8811 surname: Xu fullname: Xu, Fu-Jian email: xufj@mail.buct.edu.cn organization: State Key Laboratory of Chemical Resource Engineering, Laboratory of Biomedical Materials and Key Lab of Biomedical Materials of Natural Macromolecules (Beijing University of Chemical Technology, Ministry of Education) |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33179921$$D View this record in MEDLINE/PubMed |
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Snippet | Cationic agents, such as ionic liquids (ILs)-based species, have broad-spectrum antibacterial activities. However, the antibacterial mechanisms lack systematic... |
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Title | Molecular Sizes and Antibacterial Performance Relationships of Flexible Ionic Liquid Derivatives |
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