Reduced ecotoxicity and improved biodegradability of cationic biocides based on ester-functionalized pyridinium ionic liquids

Trush, Maria M.; Metelytsia, Larysa; Semenyuta, Ivan; Kalashnikova, L. E.; Papeykin, O; Venger, Irina; Tarasyuk, Oksana; Bodachivska, Larysa; Blagodatnyi, Volodymyr; Rogalsky, Sergiy

doi:10.1007/s11356-018-3924-8

Cited by 24 publications

(18 citation statements)

References 53 publications

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“…In contrast, pyridinium ILs attack a different target in fungi. Trush et al demonstrated that ILs containing decyl and dodecyl side chains with and without ester groups are effective inhibitors of myristoyl CoA:protein-N-myristoyltransferase (NMT), again in accordance with the established mechanism of pyridine antifungal agents. , Studies of pyridinium ILs docking to NMT revealed three decisive structural characteristics for the interaction with the enzyme: the pyridinium moiety itself, hydrophobic interactions with the alkyl chain, and hydrogen bonding of esters, if available . Extending the alkyl chain from decyl to dodecyl slightly reduced the inhibitory effect, which was explained by steric hindrance.…”

Section: Structural Design For Less-(eco)toxic Ilsmentioning

confidence: 95%

“…Notably, the specific modes of IL toxicity toward fungi have already been studied quite comprehensively. The antifungal activity of ILs is strongly related to interference with several biosynthetic pathways, which ultimately leads to cell wall and membrane damage. ,, One of the major targets in this context is ergosterol biosynthesis, but the modes of action of certain groups of ILs differ. While imidazolium ILs inhibit the cytochrome P450 enzyme lanosterol 14α-demethylase in several Candida and Trichosporon species, which is in accordance with the established mechanism of action of other imidazole and azole antifungal agents, the target of morpholinium ILs is probably sterol Δ 14 reductase .…”

Section: Structural Design For Less-(eco)toxic Ilsmentioning

confidence: 99%

“…259,260 Studies of pyridinium ILs docking to NMT revealed three decisive structural characteristics for the interaction with the enzyme: the pyridinium moiety itself, hydrophobic interactions with the alkyl chain, and hydrogen bonding of esters, if available. 257 Extending the alkyl chain from decyl to dodecyl slightly reduced the inhibitory effect, which was explained by steric hindrance. Some ILs, e.g., alkyltributylphosphonium chlorides, lead to membrane permeabilization and cell wall damage in A. nidulans.…”

Section: Specific Toxic Effects Of Ionic Liquids and Species Sensitivitymentioning

confidence: 99%

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Toward the Proactive Design of Sustainable Chemicals: Ionic Liquids as a Prime Example

et al. 2021

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The tailorable and often unique properties of ionic liquids (ILs) drive their implementation into a broad variety of seminal technologies. The modular design of ILs allows in this context a proactive selection of structures that favor environmental sustainabilityideally without compromising their technological performance. To achieve this objective, the whole life cycle must be taken into account and various aspects considered simultaneously. In this review, we discuss how the structural design of ILs affects their environmental impacts throughout all stages of their life cycles and scrutinize the available data in order to point out knowledge gaps that need further research activities. The design of more sustainable ILs starts with the selection of the most beneficial precursors and synthesis routes, takes their technical properties and application specific performance into due account, and considers its environmental fate particularly in terms of their (eco)toxicity, biotic and abiotic degradability, mobility, and bioaccumulation potential. Special emphasis is placed on reported structure−activity relationships and suggested mechanisms on a molecular level that might rationalize the empirically found design criteria.

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Section: Structural Design For Less-(eco)toxic Ilsmentioning

confidence: 95%

Section: Structural Design For Less-(eco)toxic Ilsmentioning

confidence: 99%

Section: Specific Toxic Effects Of Ionic Liquids and Species Sensitivitymentioning

confidence: 99%

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Toward the Proactive Design of Sustainable Chemicals: Ionic Liquids as a Prime Example

et al. 2021

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“…Functionalizing of long alkyl chains could be susceptibility to the degradation of ionic liquids. The introduction of ether, ester, ester, and ether groups (simultaneously), into long had alkyl chains improved the ecotoxicity of the ionic liquids as well as nitrile, hydroxyl, and ether groups on the alkyl chain and the double bond [34,[51][52][53][54][55].…”

Section: Hplc Analysismentioning

confidence: 99%

Biodegradation of L-Valine Alkyl Ester Ibuprofenates by Bacterial Cultures

et al. 2021

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Nowadays, we consume very large amounts of medicinal substances. Medicines are used to cure, halt, or prevent disease, ease symptoms, or help in the diagnosis of illnesses. Some medications are used to treat pain. Ibuprofen is one of the most popular drugs in the world (it ranks third). This drug enters our water system through human pharmaceutical use. In this article, we describe and compare the biodegradation of ibuprofen and ibuprofen derivatives—salts of L-valine alkyl esters. Biodegradation studies of ibuprofen and its derivatives have been carried out with activated sludge. The structure modifications we received were aimed at increasing the biodegradation of the drug used. The influence of the alkyl chain length of the ester used in the biodegradation of the compound was also verified. The biodegradation results correlated with the lipophilic properties (log P).

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“…However, the relatively high viscosity of ILs is a barrier to further practical applications. Inserting ether groups into the cations of ILs has been shown to substantially reduce their viscosity without lowering thermal stability, while also reducing their toxicity [ 7 , 8 , 9 , 10 ]. Ether-functionalized ILs (EFILs) have demonstrated remarkable performance in many fields.…”

Section: Introductionmentioning

confidence: 99%

A New Compartmentalized Scale (PN) for Measuring Polarity Applied to Novel Ether-Functionalized Amino Acid Ionic Liquids

Guo

et al. 2022

Molecules

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Functionalized and environmentally friendly ionic liquids are required in many fields, but convenient methods for measuring their polarity are lacking. Two novel ether-functionalized amino acid ionic liquids, 1-(2-methoxyethyl)-3-methylimidazolium alanine ([C1OC2mim][Ala]) and 1-(2-ethoxyethyl)-3-methylimidazolium alanine ([C2OC2mim][Ala]), were synthesized by a neutralization method and their structures confirmed by NMR spectroscopy. Density, surface tension, and refractive index were determined using the standard addition method. The strength of intermolecular interactions within these ionic liquids was examined in terms of standard entropy, lattice energy, and association enthalpy. A new polarity scale, PN, is now proposed, which divides polarity into two compartments: the surface and the body of the liquid. Surface tension is predicted via an improved Lorentz-Lorenz equation, and molar surface entropy is used to determine the polarity of the surface. This new PN scale is based on easily measured physicochemical parameters, is validated against alternative polarity scales, and is applicable to both ionic and molecular liquids.

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Reduced ecotoxicity and improved biodegradability of cationic biocides based on ester-functionalized pyridinium ionic liquids

Cited by 24 publications

References 53 publications

Toward the Proactive Design of Sustainable Chemicals: Ionic Liquids as a Prime Example

Toward the Proactive Design of Sustainable Chemicals: Ionic Liquids as a Prime Example

Biodegradation of L-Valine Alkyl Ester Ibuprofenates by Bacterial Cultures

A New Compartmentalized Scale (PN) for Measuring Polarity Applied to Novel Ether-Functionalized Amino Acid Ionic Liquids

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