Synthesis, anti-microbial activities and anti-electrostatic properties of phosphonium-based ionic liquids

Cieniecka‐Rosłonkiewicz, Anna; Pernak, Juliusz; Kubis-Feder, Joanna; Ramani, Alwar; Robertson, Allan J.; Seddon, Kenneth R.

doi:10.1039/b508499g

Cited by 193 publications

(107 citation statements)

References 56 publications

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“…In fact only recently, have specific ILs with biologically active ions been prepared and shown to retain their biological activity; specifically, IL salts of anti-bacterial quaternary ammonium cations were shown to be active against various types of bacteria and in some cases, an increased anti-bacterial effect was observed. [63][64][65][66] But ILs are composed of a minimum of two ions (a cation and an anion) and both may impart biological activity to the resulting salt. This dual functionality inherent in ILs is rarely exploited, 67,68 and we have only recently published our first paper with the designed incorporation of two biologically active ions into an IL.…”

Section: Ionic Liquids As Active Pharmaceutical Ingredients (Apis)mentioning

confidence: 99%

Ionic Liquids Then and Now: From Solvents to Materials to Active Pharmaceutical Ingredients

Hough¹,

Rogers²

2007

Bulletin of the Chemical Society of Japan

323

219

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Ionic liquids (ILs) have evolved from salts studied primarily for their physical properties (low melting salts which could be used as solvents) to tunable materials based upon the physical, chemical, and now even biological properties that can be introduced through either ion. In this perspective, we follow this interesting evolution with respect to our work in this growing field, and discuss possible future directions, such as the use of ILs as active pharmaceutical ingredients (APIs).

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Section: Ionic Liquids As Active Pharmaceutical Ingredients (Apis)mentioning

confidence: 99%

Ionic Liquids Then and Now: From Solvents to Materials to Active Pharmaceutical Ingredients

Hough¹,

Rogers²

2007

Bulletin of the Chemical Society of Japan

323

219

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“…The significance of side-chain length on toxicity of ILs has been previously indicated and a general trend of increasing toxicity with increasing chain length, and consequently lipophilicity, was observed . However, some studies reported limited toxicity for various ILs with long side chains, containing fourteen, sixteen and more carbon atoms (García et al 2001;Pernak and Branicka 2003;Pernak and Chwała 2003;Cieniecka-Rosłonkiewicz et al 2005). Although not always raised by the authors, this was probably an artifact from limited solubility of these compounds, which were not bioavailable for microorganisms to cause toxic effect.…”

Section: Introductionmentioning

confidence: 86%

Biodegradation of diesel fuel by a microbial consortium in the presence of 1-alkoxymethyl-2-methyl-5-hydroxypyridinium chloride homologues

et al. 2009

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Fast development of ionic liquids as gaining more and more attention valuable chemicals will undoubtedly lead to environmental pollution. New formulations and application of ionic liquids may result in contamination in the presence of hydrophobic compounds, such as petroleum mixtures. We hypothesize that in the presence of diesel fuel low-water-soluble ionic liquids may become more toxic to hydrocarbon-degrading microorganisms. In this study the influence of 1-alkoxymethyl-2-methyl-5-hydroxypyridinium chloride homologues (side-chain length from C(3) to C(18)) on biodegradation of diesel fuel by a bacterial consortium was investigated. Whereas test performed for the consortium cultivated on disodium succinate showed that toxicity of the investigated ionic liquids decreased with increase in side-chain length, only higher homologues (C(8)-C(18)) caused a decrease in diesel fuel biodegradation. As a result of exposure to toxic compounds also modification in cell surface hydrophobicity was observed (MATH). Disulphine blue active substances method was employed to determine partitioning index of ionic liquids between water and diesel fuel phase, which varied from 1.1 to 51% for C(3) and C(18) homologues, respectively. We conclude that in the presence of hydrocarbons acting as a solvent, the increased bioavailability of hydrophobic homologues is responsible for the decrease in biodegradation efficiency of diesel fuel.

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“…All ILs' were synthesized according to established methods (Bradaric et al, 2003;Cieniecka-Roslonkiewicz et al, 2005). An equivalent of tertiary phosphine was added dropwise to the appropriate alkylating reagent under nitrogen and stirred at a temperature rising from 30 to 200°C.…”

Section: Chemicalsmentioning

confidence: 99%

Toxicity Assessment of Phosphonium Based Ionic Liquids Towards Female Guppy Fish

El-Harbawi¹

2013

American Journal of Environmental Sciences

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In this study, two phosphonium based ionic liquids (butyl triphenyl phosphonium chloride and hexyl triphenyl phosphonium bromide) have been synthesized using quarternisation process. The toxicities of these Ionic Liquids (ILs) are unknown and may be harmful to humans and the environment. Therefore, the toxicity assessment of these ILs was carried out according to the Organization for Economic Cooperation and Development (OECD) 203 guideline using female guppy fish (Poecilia reticulata). The median Lethal Concentrations (LC 50 ) have been estimated for butyl triphenyl phosphonium chloride and for hexyl triphenyl phosphonium bromide to be 73.35 and 61.36 mg L −1 respectively. Both LC 50 obtained can be identified as slightly toxic ILs based on Acute Toxicity Rating Scale by Fish and Wildlife Service (FWS). The findings from this study can be used for better design of phosphonium-based ILs with consideration of their aquatic toxicities.

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Synthesis, anti-microbial activities and anti-electrostatic properties of phosphonium-based ionic liquids

Cited by 193 publications

References 56 publications

Ionic Liquids Then and Now: From Solvents to Materials to Active Pharmaceutical Ingredients

Ionic Liquids Then and Now: From Solvents to Materials to Active Pharmaceutical Ingredients

Biodegradation of diesel fuel by a microbial consortium in the presence of 1-alkoxymethyl-2-methyl-5-hydroxypyridinium chloride homologues

Toxicity Assessment of Phosphonium Based Ionic Liquids Towards Female Guppy Fish

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