Assessing toxicity and biodegradation of novel, environmentally benign ionic liquids (1-alkoxymethyl-3-hydroxypyridinium chloride, saccharinate and acesulfamates) on cellular and molecular level

Stasiewicz, Monika; Mulkiewicz, Ewa; Tomczak-Wandzel, Renata; Kumirska, Jolanta; Siedlecka, Ewa Maria; Gołębiowski, Marek; Gajdus, J.; Czerwicka, Małgorzata; Stepnowski, Piotr

doi:10.1016/j.ecoenv.2007.08.011

Cited by 120 publications

(85 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…It was found that shorter alkyl-substituted chains demonstrated lower toxicity compared with the cations with a longer alkyl substituent. This structure-activity relationship (SAR) was also observed for biological enzymes, such as acetylcholine esterase Stasiewicz et al, 2008). Lactic acid production by Lactobacillus, an acid-producing bacterium, was decreased as the alkyl chain length on the imidazolium cations increased (Matsumoto et al, 2004).…”

Section: Introductionmentioning

confidence: 59%

Characterization of the Inhibitory Effects ofN-Butylpyridinium Chloride and Structurally Related Ionic Liquids on Organic Cation Transporters 1/2 and Human Toxic Extrusion Transporters 1/2-K In Vitro and In Vivo

Cheng¹,

Martinez-Guerrero²,

Wright³

et al. 2011

Drug Metab Dispos

View full text Add to dashboard Cite

ABSTRACT:Ionic liquids (ILs) are a class of salts that are expected to be used as a new source of solvents and for many other applications. Our previous studies revealed that selected ILs, structurally related organic cations, are eliminated exclusively in urine as the parent compound, partially mediated by renal transporters. This study investigated the inhibitory effects of N-butylpyridinium chloride (NBuPy-Cl) and structurally related ILs on organic cation transporters (OCTs) and multidrug and toxic extrusion transporters (MATEs) in vitro and in vivo. After Chinese hamster ovary cells expressing rat (r) OCT1, rOCT2, human (h) OCT2, hMATE1, or hMATE2-K were constructed, the ability of NBuPy-Cl, 1-methyl-3-butylimidazolium chloride (Bmim-Cl), N-butyl-N-methylpyrrolidinium chloride (BmPyCl), and alkyl substituted pyridinium ILs to inhibit these transporters was determined in vitro. NBuPy-Cl (0, 0.5, or 2 mg/kg per hour) was also infused into rats to assess its effect on the pharmacokinetics of metformin, a substrate of OCTs and MATEs. NBuPy-Cl, Bmim-Cl, and BmPy-Cl displayed strong inhibitory effects on these transporters (IC 50 ‫؍‬ 0.2-8.5 M). In addition, the inhibitory effects of alkyl-substituted pyridinium ILs on OCTs increased dramatically as the length of the alkyl chain increased. The IC 50 values were 0.1, 3.8, 14, and 671 M (hexyl-, butyl-, and ethyl-pyridinium and pyridinium chloride) for rOCT2-mediated metformin transport. Similar structurally related inhibitory kinetics were also observed for rOCT1 and hOCT2. The in vivo coadministration study revealed that NBuPy-Cl reduced the renal clearance of metformin in rats. These results demonstrate that ILs compete with other substrates of OCTs and MATEs and could alter the in vivo pharmacokinetics of such substrates.

show abstract

Section: Introductionmentioning

confidence: 59%

Characterization of the Inhibitory Effects ofN-Butylpyridinium Chloride and Structurally Related Ionic Liquids on Organic Cation Transporters 1/2 and Human Toxic Extrusion Transporters 1/2-K In Vitro and In Vivo

Cheng¹,

Martinez-Guerrero²,

Wright³

et al. 2011

Drug Metab Dispos

View full text Add to dashboard Cite

show abstract

“…Although the cost of ILs has always been one of the major issues, all ILs are not expensive, particularly, when considered at large scale [51]. Recently, the ILs derived from "low-cost" feedstock or from renewable raw materials may open new pathways for synthesis of cost-effective and competitive ILs for pretreatment of natural fibers and polymers for biocomposite manufacturing [52,53]. The major aspects that should be focused for the future research work in IL-based processing of various biofibers and biopolymers could be summarized as:…”

Section: Future Prospectsmentioning

confidence: 99%

Green Composites from Ionic Liquid-Assisted Processing of Sustainable Resources: A Brief Overview

Mahmood¹,

Moniruzzaman²,

Yusup³

et al. 2017

Progress and Developments in Ionic Liquids

View full text Add to dashboard Cite

The massive use of synthetic, petroleum-based polymeric composites has disturbed the fragile environmental equilibrium of our planet. Composites made solely from polysaccharides can offer unique intrinsic properties such as renewability, biodegradability, easy availability, eco-friendliness, facile processing, flexibility, and exciting physico-mechanical characteristics. The development of green processing of lignocellulosic materials and bio-based polymers such as cellulose, starch, chitin, and chitosan, the most abundant biorenewable materials on earth, is urgent from the perspectives of both environmental protection and sustainability in materials industries. Recently, the enormous potential of ionic liquids (ILs) as an alternative to ecologically harmful conventional organic solvents has been well recognized. Presently, a wide range of pronounced approaches have been explored to further improve the performance of ionic liquid-based processing of polysaccharides for green composite manufacturing. This review presents recent technological developments in which the advantages of ionic liquids as a dissolution medium for polysaccharides for production of plethora of green composites have been gradually realized.

show abstract

“…Für eine Reihe von 1-Alkoxymethyl-3-hydroxypyridinium-Verbindungen konnte ein partieller Abbau nachgewiesen werden (Abb. 7) [24,38]. Zusammenfassend kann festgestellt werden, dass pyridiniumbasierte ILs deutlich besser biologisch abbaubar sind als die Imidazolium-Verbindungen und unter aeroben Bedingungen vollständig mineralisierbar sein können.…”

Section: Pyridinium-verbindungenunclassified

Biodegradability of Ionic Liquids – Test Procedures and Structural Design

Stolte

Arning

Thöming

2011

Chemie Ingenieur Technik

View full text Add to dashboard Cite

Biodegradability of Ionic Liquids -Test Procedures and Structural DesignBiotic and the abiotic degradabilities of organic chemicals are largely influenced by the potential exposure of substances to organisms and, hence, are key parameters in risk assessment for predicting spatio-temporal environmental concentrations and long-term adverse effects. Degradability in particular could be a bottleneck in designing inherently safer and sustainable ILs, because the tendency of certain ILs to be thermally and chemically very stable is often reflected by their great vis-à-vis biological degradation processes. The following review article will provide an introduction to biodegradation test procedures and will present an overview of existing aerobic and anaerobic IL biodegradation data. The discussion of this data should help to improve the future design of inherently safer ILs, thereby reducing the risks they may pose to humans and the environment.

show abstract

Assessing toxicity and biodegradation of novel, environmentally benign ionic liquids (1-alkoxymethyl-3-hydroxypyridinium chloride, saccharinate and acesulfamates) on cellular and molecular level

Cited by 120 publications

References 36 publications

Characterization of the Inhibitory Effects ofN-Butylpyridinium Chloride and Structurally Related Ionic Liquids on Organic Cation Transporters 1/2 and Human Toxic Extrusion Transporters 1/2-K In Vitro and In Vivo

Characterization of the Inhibitory Effects ofN-Butylpyridinium Chloride and Structurally Related Ionic Liquids on Organic Cation Transporters 1/2 and Human Toxic Extrusion Transporters 1/2-K In Vitro and In Vivo

Green Composites from Ionic Liquid-Assisted Processing of Sustainable Resources: A Brief Overview

Biodegradability of Ionic Liquids – Test Procedures and Structural Design

Contact Info

Product

Resources

About