Towards greener and sustainable ionic liquids using naturally occurring and nature-inspired pyridinium structures

Suk, Morten; Kümmerer, Klaus

doi:10.1039/d2gc03178g

Cited by 7 publications

(6 citation statements)

References 56 publications

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“…It should also be mentioned that BIOWIN 7 implies that all the analyzed substances, except NA, do not decompose rapidly under the influence of biotic factors. However, according to ECHA, nicotinamide not only can be considered readily biodegradable (OECD 301F, 99% after 7 days) [ 50 ], but also some of its methylated derivatives ( N -methyl-3-carbamoylpyridinium iodide and hexafluorophosphate) [ 51 ]. Therefore, further practical experiments are crucial in this field, which in the future will allow existing BIOWIN models to develop further.…”

Section: Discussionmentioning

confidence: 99%

“…N -hexyl-3-methylpyridinium bromide was established to be not readily biodegradable but biodegraded over an extended period of time, while N -hexadecylpyridinium, N -octyl-3-methylpyridinium, and N -(2-hydroxy)ethylpyridinium bromides met the criteria for ready and complete biodegradability according to the OECD test guidelines [ 47 , 52 , 53 , 54 , 55 ]. Similarly, pyridinium derivatives with carbonyl group connected to aromatic carbon or nitrogen atom such as 3-(butoxycarbonyl)-1-methylpyridinium and N -methyl-3-carbamoylpyridinium iodides or 1-(2-ethoxy-2-oxoethyl)pyridinium bromide were also assessed as readily biodegradable [ 51 , 56 ]. The literature analysis suggests also that QASs containing long alkyl side chains are more readily biodegradable despite possessing higher antimicrobial activity.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Comprehensive Ecotoxicity Studies on Quaternary Ammonium Salts Synthesized from Vitamin B3 Supported by QSAR Calculations

Nowacka

Olejniczak

Stachowiak

et al. 2023

Plants

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Lately, ionic forms (namely, quaternary ammonium salts, QASs) of nicotinamide, widely known as vitamin B3, are gaining popularity in the sectors developing novel pharmaceuticals and agrochemicals. However, the direct influence of these unique QASs on the development of various terrestrial plants, as well as other organisms, remains unknown. Therefore, three compounds comprising short, medium, and long alkyl chains in N-alkylnicotinamide were selected for phytotoxicity analyses, which were conducted on representative dicotyledonous (white mustard) and monocotyledonous (sorghum) plants. The study allowed the determination of the impact of compounds on the germination capacity as well as on the development of roots and stems of the tested plants. Interestingly, independently of the length of the alkyl chain or plant species, all QASs were established as non-phytotoxic. In addition, QSAR simulations, performed using the EPI Suite™ program pack, allowed the determination of the products’ potential toxicity toward fish, green algae, and daphnids along with the susceptibility to biodegradation. The obtained nicotinamide derivative with the shortest chain (butyl) can be considered practically non-toxic according to GHS criteria, whereas salts with medium (decyl) and longest (hexadecyl) substituent were included in the ‘acute II’ toxicity class. These findings were supported by the results of the toxicity tests performed on the model aquatic plant Lemna minor. It should be stressed that all synthesized salts exhibit not only a lack of potential for bioaccumulation but also lower toxicity than their fully synthetic analogs.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Comprehensive Ecotoxicity Studies on Quaternary Ammonium Salts Synthesized from Vitamin B3 Supported by QSAR Calculations

Nowacka

Olejniczak

Stachowiak

et al. 2023

Plants

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“…Pyridinium-based salts 248 – 250 (Figure 16 ) were synthesized 101 by methylation of ( S )-nicotine and nicotinamide with the aim to study the biodegradability and toxicity of this kind of aromatic cations. Although the authors claimed that these solids were ionic liquids, their very high melting points (from 165–166 °C to 214–215 °C) indicate that they are mere pyridinium iodide salts.…”

Section: Miscellaneous Ionic Liquidsmentioning

confidence: 99%

Recent Advances in the Synthesis and Applications of Ionic Liquids Derived from Natural Products

Ranjbar-Karimi,

Marra,

Khorasani

2024

Synthesis

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Ionic liquids, nonvolatile salts featuring a melting point below 100 °C, are one of the few alternative solvents for environmentally friendly processes. However, like most molecular solvents, they are usually prepared by means of building blocks derived from fossil oil. Fortunately, an increasing number of ionic liquids are synthesized starting from renewable natural products such as sugars and amino acids. In the present review, we describe the detailed synthesis and applications of the biosourced ionic liquids reported in the literature over the last four years.1 Introduction2 Carbohydrate-Based Ionic Liquids3 Amino Acid Based Ionic Liquids4 Terpene-Based Ionic Liquids5 Miscellaneous Ionic Liquids6 Conclusion

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“…Many ILs displayed significant toxicity towards enzymes, microorganisms, and cells, in addition to animals and plants [ 22 , 23 ]; and most are not easily biodegradable [ 24 ]. In addition, recent studies have reported the multiplication and dissemination of antibiotic resistance genes by some persistent imidazolium-based ILs because of enhanced horizontal gene transfer, while other similar structures, such as biocidal quaternary ammonium compounds, have long been found to contribute to the rise of antibiotic resistance [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Cholinium-Based Ionic Liquids as Promising Antimicrobial Agents in Pharmaceutical Applications: Surface Activity, Antibacterial Activity and Ecotoxicological Profile

et al. 2023

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Cholinium-based ionic liquids are compounds increasingly studied in pharmaceutics and biomedicine to enhance bioavailability in drug delivery systems and as bioactive ingredients in pharmaceutical formulations. However, their potential as antimicrobial agents has scarcely been investigated. Herein, we explored the antimicrobial activity of a series of surface-active cholinium-based ionic liquids (Chol-ILs). For this purpose, Chol-ILs with alkyl chains of 10–16 carbon atoms were synthesized and their self-assembly in aqueous medium was investigated. Subsequently, their antimicrobial activity against a panel of clinically relevant bacteria and their ability to eradicate MRSA and P. aeruginosa PAO1 biofilms was evaluated. Finally, we analyzed the ecotoxicological profile of Chol-ILs in terms of susceptibility to aerobic biodegradation and acute aquatic toxicity against D. magna and V. fisheri. Our results reveal that cholinium-based ILs with alkyl chain lengths ≥12 C show a broad spectrum of antibacterial activity. Their antimicrobial efficacy depends on their hydrophobicity, with the C14–C16 homologs being the most effective compounds. These ILs exhibit antimicrobial activity similar to that of imidazolium ILs and quaternary ammonium antiseptics. Moreover, the longer alkyl chain Chol-ILs are able to eradicate established biofilms at concentrations as low as 16–32 µg/mL. The biodegradation rate of cholinium-based ILs decreases with alkyl chain elongation. Our results reinforce the suitability of Chol-ILs as promising multifunctional compounds for application in pharmaceutical and biomedical formulation.

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Towards greener and sustainable ionic liquids using naturally occurring and nature-inspired pyridinium structures

Abstract: The use of naturally occurring and nature-inspired pyridinium molecules can make an important contribution to greener and more sustainable ionic liquids.

Cited by 7 publications

References 56 publications

Comprehensive Ecotoxicity Studies on Quaternary Ammonium Salts Synthesized from Vitamin B3 Supported by QSAR Calculations

Comprehensive Ecotoxicity Studies on Quaternary Ammonium Salts Synthesized from Vitamin B3 Supported by QSAR Calculations

Recent Advances in the Synthesis and Applications of Ionic Liquids Derived from Natural Products

Cholinium-Based Ionic Liquids as Promising Antimicrobial Agents in Pharmaceutical Applications: Surface Activity, Antibacterial Activity and Ecotoxicological Profile

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