Synthesis, self-assembly, bacterial and fungal toxicity, and preliminary biodegradation studies of a series of<scp>l</scp>-phenylalanine-derived surface-active ionic liquids

Капитанов, И. В.; Jordan, Andrew; Karpichev, Yevgen; Špulák, Marcel; Pérez, Lourdes; Kellett, Andrew; Kümmerer, Klaus; Gathergood, Nicholas

doi:10.1039/c9gc00030e

Cited by 59 publications

(50 citation statements)

References 93 publications

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“…Consequently, monoimidazolium [22][23][24] and bisimidazolium [25][26][27][28] salts have been explored as a new generation of antibacterial agents. In this context, amino acid-based monoimidazolium salts with good bacterial toxicity have been reported in the literature [29]. Our research group has an ongoing interest in the biomimetic and bioactive capacity of imidazole or imidazolium amino acid derivatives [30][31][32][33].…”

Section: Synthesismentioning

confidence: 99%

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Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids

et al. 2020

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The antibacterial activity of imidazole and imidazolium salts is highly dependent upon their lipophilicity, which can be tuned through the introduction of different hydrophobic substituents on the nitrogen atoms of the imidazole or imidazolium ring of the molecule. Taking this into consideration, we have synthesized and characterized a series of imidazole and imidazolium salts derived from L-valine and L-phenylalanine containing different hydrophobic groups and tested their antibacterial activity against two model bacterial strains, Gram-negative E. coli and Gram-positive B. subtilis. Importantly, the results demonstrate that the minimum bactericidal concentration (MBC) of these derivatives can be tuned to fall close to the cytotoxicity values in eukaryotic cell lines. The MBC value of one of these compounds toward B. subtilis was found to be lower than the IC50 cytotoxicity value for the control cell line, HEK-293. Furthermore, the aggregation behavior of these compounds has been studied in pure water, in cell culture media, and in mixtures thereof, in order to determine if the compounds formed self-assembled aggregates at their bioactive concentrations with the aim of determining whether the monomeric species were in fact responsible for the observed antibacterial activity. Overall, these results indicate that imidazole and imidazolium compounds derived from L-valine and L-phenylalanine—with different alkyl lengths in the amide substitution—can serve as potent antibacterial agents with low cytotoxicity to human cell lines.

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Section: Synthesismentioning

confidence: 99%

“…Consequently, monoimidazolium [ 22 , 23 , 24 ] and bisimidazolium [ 25 , 26 , 27 , 28 ] salts have been explored as a new generation of antibacterial agents. In this context, amino acid-based monoimidazolium salts with good bacterial toxicity have been reported in the literature [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids

et al. 2020

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“…One of the promising approaches in the design of building blocks for biomedical applications, which include formulations for drug delivery, is the creation of new multifunctional environmentally friendly, cleavable, green, and less toxic cationic surfactant systems answering the biotechnological criteria and improving biocompatibility, solubility, bioavailability, and biodegradability of therapeutics [35,36,37]. The promising strategy in this way is the design of cationic systems containing several covalently bound hydrophobic, hydrophilic groups, and various spacers to decrease surfactant concentration thresholds.…”

Section: Structural Diversity Of Biocompatible and Ecologically Frmentioning

confidence: 99%

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Zakharova

Pashirova

Doktorovová

et al. 2019

IJMS

108

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The development of biotechnological protocols based on cationic surfactants is a modern trend focusing on the fabrication of antimicrobial and bioimaging agents, supramolecular catalysts, stabilizers of nanoparticles, and especially drug and gene nanocarriers. The main emphasis given to the design of novel ecologically friendly and biocompatible cationic surfactants makes it possible to avoid the drawbacks of nanoformulations preventing their entry to clinical trials. To solve the problem of toxicity various ways are proposed, including the use of mixed composition with nontoxic nonionic surfactants and/or hydrotropic agents, design of amphiphilic compounds bearing natural or cleavable fragments. Essential advantages of cationic surfactants are the structural diversity of their head groups allowing of chemical modification and introduction of desirable moiety to answer the green chemistry criteria. The latter can be exemplified by the design of novel families of ecological friendly cleavable surfactants, with improved biodegradability, amphiphiles with natural fragments, and geminis with low aggregation threshold. Importantly, the development of amphiphilic nanocarriers for drug delivery allows understanding the correlation between the chemical structure of surfactants, their aggregation behavior, and their functional activity. This review focuses on several aspects related to the synthesis of innovative cationic surfactants and their broad biological applications including antimicrobial activity, solubilization of hydrophobic drugs, complexation with DNA, and catalytic effect toward important biochemical reaction.

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“…Zebrafish, green algae, brine shrimp [90] 7 Amino acid Aspartic acid, cysteine, valine, phenylalanine, glycine, histidine, proline Bacteria [125] 8 Surface active 24 L-phenylalanine Bacteria [126] could enhance the bioprocessing of materials to biofuels and biochemicals. Hopefully, a number of studies have investigated the toxicity of ILs toward various microorganisms, and evaluated their performances in biocatalysis and biotransformation ( Table 3).…”

Section: Ionic Liquid Tolerant Microorganisms For Biocatalysis/biotramentioning

confidence: 99%

An Overview on the Toxicological Properties of Ionic Liquids toward Microorganisms

Sivapragasam

Moniruzzaman

Goto

2020

Biotechnology Journal

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Ionic liquids (ILs), a class of materials with unique physicochemical properties, have been used extensively in the fields of chemical engineering, biotechnology, material sciences, pharmaceutics, and many others. Because ILs are very polar by nature, they can migrate into the environment with the possibility of inclusion in the food chain and bioaccumulation in living organisms. However, the chemical natures of ILs are not quintessentially biocompatible. Therefore, the practical uses of ILs must be preceded by suitable toxicological assessments. Among different methods, the use of microorganisms to evaluate IL toxicity provides many advantages including short generation time, rapid growth, and environmental and industrial relevance. This article reviews the recent research progress on the toxicological properties of ILs toward microorganisms and highlights the computational prediction of various toxicity models.

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Synthesis, self-assembly, bacterial and fungal toxicity, and preliminary biodegradation studies of a series ofl-phenylalanine-derived surface-active ionic liquids

Abstract: A comprehensive study devoted to designing green surface-active ionic liquids (SAILs) based on the “benign-of-design” approach results in finding greener alternatives.

Cited by 59 publications

References 93 publications

Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids

Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

An Overview on the Toxicological Properties of Ionic Liquids toward Microorganisms

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