<meta charset="utf8"></head><body>Synthèse de liquides ioniques à base de quinoléine pour des applications antimicrobiennes

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V., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Applications+of+ionic+liquids+in+electrochemical+sensors+and+biosensors.">Applications of ionic liquids in electrochemical sensors and biosensors.</a> Int J Electrochem. 2012 (9), 112-125 (2012).</li><li>Must, I., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Ionic+liquid-based+actuators+working+in+air:+The+effect+of+ambient+humidity.">Ionic liquid-based actuators working in air: The effect of ambient humidity.</a> Sens Actuat B: Chemical. 202 (3), 114-122 (2014).</li><li>Ray, A., Saruhan, B. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Application+of+ionic+liquids+for+batteries+and+supercapacitors.">Application of ionic liquids for batteries and supercapacitors.</a> Materials. 14 (11), 2942 (2021).</li><li>Alashkar, A., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=A+critical+review+on+the+use+of+ionic+liquids+in+proton+exchange+membrane+fuel+cells.">A critical review on the use of ionic liquids in proton exchange membrane fuel cells.</a> Membranes. 12 (2), 178 (2022).</li><li>Busetti, A., Crawford, R. J., Ivanova, E. P. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Antimicrobial+and+antibiofilm+activities+of+1-alkylquinolinium+bromide+ionic+liquids.">Antimicrobial and antibiofilm activities of 1-alkylquinolinium bromide ionic liquids.</a> Green Chem. 12 (3), 420-425 (2010).</li><li>Sharma, K., Sharma, M. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=In+vitro+anti-biofilm+activity+and+the+artificial+chaperone+activity+of+quinoline-based+ionic+liquids.">In vitro anti-biofilm activity and the artificial chaperone activity of quinoline-based ionic liquids.</a> Colloids Surfaces B: Biointer. 235, 113773 (2024).</li><li>Qashou, E., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Antiproliferative+activities+of+lipophilic+fluoroquinolones-based+scaffold+against+a+panel+of+solid+and+liquid+cancer+cell+lines.">Antiproliferative activities of lipophilic fluoroquinolones-based scaffold against a panel of solid and liquid cancer cell lines.</a> Asian Paci J Cancer Prevent. 23 (5), 1529-1538 (2022).</li><li>Patel, H. M. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Synthesis+of+new+mannich+products+bearing+quinoline+nucleus+using+reusable+ionic+liquid+and+antitubercular+evaluation.">Synthesis of new mannich products bearing quinoline nucleus using reusable ionic liquid and antitubercular evaluation.</a> Green Sust Chem. 5 (4), 137-144 (2015).</li><li>Joshi, D. R., Adhikari, N. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=An+overview+on+common+organic+solvents+and+their+toxicity.">An overview on common organic solvents and their toxicity.</a> J Pharm Res Int. 28 (3), 1-18 (2019).</li><li>Sanchez, J. 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<table border="1" fo:keep-together.within-page="1" fo:keep-with-next.within-page="always">
	<tbody>
		<tr>
			<td>1-bromohexadecane</td>
			<td>Merck</td>
			<td>CAS no.112-82-3</td>
			<td>95% pure (as determined by HPLC analysis)</td>
		</tr>
		<tr>
			<td>Ethyl acetate</td>
			<td>Merck</td>
			<td>CAS no. 205-500-4</td>
			<td>95% pure (as determined by HPLC analysis)</td>
		</tr>
		<tr>
			<td>Nuclear Magnetic Resonance (NMR) spectrometer</td>
			<td>Jeol, Model: JNM-ECZ 400S</td>
			<td>Nil</td>
			<td>Nil</td>
		</tr>
		<tr>
			<td>Quinoline</td>
			<td>Merck</td>
			<td>CAS no.91-22-5</td>
			<td>95% pure (as determined by HPLC analysis)</td>
		</tr>
		<tr>
			<td>Toluene</td>
			<td>Merck</td>
			<td>CAS no. 108-88-3</td>
			<td>95% pure (as determined by HPLC analysis)</td>
		</tr>
	</tbody>
</table>

green synthesis of quinoline-based ionic liquid

The monumental growth in the world population accounts for a tremendous increment in the consumption of a vast array of commodities over the past few years, including food, medicaments, as well as other crucial products for the sustenance of mortal organisms. This has invigorated the quest for novel chemical compounds with exceptionally specialized, ecologically sound, and beneficial properties worldwide. Ionic Liquids (ILs) have proved to be felicitous in this regard. The implication of these compounds in the scientific domain has bolstered new ventures in research in contemporary chemical technologies1. In contrast to the conventional approaches, the utilization of ILs not only facilitates progressive reaction conditions but also promotes a customized strategy to get to grips with various biochemical challenges related to experimental research and development2.
Typically, ILs are stable salts constituting cations (organic) and anions (inorganic), possessing a melting point below 100 &#176;C3. Abiding by the 12 principles of green chemistry, empirically, these are convincing substitutes to the customary organic solvents4. The astounding properties associated with the utilization of these compounds encompass great intrinsic conductivity, polarity, solvating tendency, thermal stability, non-volatility, acidity/basicity, hydrophilicity/ hydrophobicity, and tunability, making ILs best suited for experimental research5.
Apart from the expansive applications of various classes of ILs in modern organic synthesis6, catalysis7, and various electrochemical processes involving sensors8, actuators9, batteries10, and fuel cells11, over the past few years, this class of compounds has been given momentous recognition in the field of biomedicine in light of AMR. Current probations reveal that ILs based on imidazolium, pyridine, choline, and pyrrole are extremely effective as therapeutic agents owing to their high charge and hydrophobicity12. However, quinoline-based counterparts are still considered to be most potent against the pathogenic microbes12. Additional biomedical applications accompanying this class of ILs include artificial chaperone activity13, cytotoxicity against cancerous cells14 as well as an excellent drug-carrying capacity15.
Conventionally, the fabrication of ILs involves the utilization of highly toxic solvent mediums such as dichloromethane, benzene, carbon tetrachloride, dichloroethylene, etc.16, hindering the biocompatibility and elevating the toxicity of the compound, making them undesirable for biological use. Additionally, the use of harmful solvents in the reaction media not only slows down the reaction time but also increases the unintentional production of waste byproducts released into the environment17. Moreover, the dissolvent used in the reaction media also influences the pH of the final product; hence, its removal at the end of the reaction is vital, especially when the desired compound is intended to be used for protein-related biological systems. Hence, keeping away from the usage of such solvent is favorable in the realm of green chemistry.
In this study, we report the one-pot synthesis of a biocompatible and non-toxic13 IL, namely, 1-Hexadecylquinolin-1-ium bromide, using a greener route. The present strategy omits the utilization of a molecular solvent, leveraging the self-solvating ability of the IL formed within the reaction mixture, promoting high reaction efficiency and chemical yield. Menschutkin reaction18forms the basis of the&#160;current synthesis methodology. The purity of the synthesized compound is probed using NMR and IR spectroscopy. The pharmacokinetic profile of the compound and toxicity were investigated through the ADMET studies. Furthermore, the antimicrobial potential of the synthesized IL against the pathogenic Candida albicans strain has also been demonstrated in the study.

<meta charset="utf8"></head><body>Pleins feux sur l’auteur : Faire progresser la recherche sur la résistance aux antimicrobiens grâce à des approches novatrices et à des composés synthétiques

Synthèse verte d’un liquide ionique à base de quinoléine

The ever-growing menace of Antimicrobial Resistance (AMR) jeopardizes the potency of the prevailing antibiotics against the relentlessly sprouting ...

green-synthesis-of-quinoline-based-ionic-liquid

Research

JoVE Journal

Chemistry

Green Synthesis of Quinoline-Based Ionic Liquid

939 vues.  University of Delhi. La résistance aux antimicrobiens est une menace complexe pour la santé mondiale qui nécessite une approche de recherche à multiples facettes. La recherche sur la résistance aux antimicrobiens vise à mieux comprendre le phénomène, à élaborer des interventions efficaces et à atténuer la menace pour la santé mondiale posée par la résistance aux antimicrobiens. Le domaine de la résistance aux antimicrobiens a connu des progrès significatifs ces d...

Vidéo: Pleins feux sur l’auteur : Faire progresser la recherche sur la résistance aux antimicrobiens grâce à des approches novatrices et à des composés synthétiques

The ever-growing menace of Antimicrobial Resistance (AMR) jeopardizes the potency of the prevailing antibiotics against the relentlessly sprouting infections spawned by bacteria, viruses, parasites as well as fungi, posing a great threat to human health and well-being. In this regard, several novel molecules have proved their mettle, with Ionic Liquids (ILs) being one of the most eco-friendly, non-volatile, and thermally stable alternatives to the existing antimicrobials, possessing high solvating potential as well as low vapor pressure. Moreover, the utilization of these entities in both stabilizing as well as destabilizing protein structures and enhancing enzymatic activity has further raised their potential in the biomedical industry. With this in view, we present the green synthesis and characterization of quinoline-based IL, owing to its immense antimicrobial potency, with low cytotoxicity and great artificial chaperone activity. Here, maneuvering the one-pot synthesis approach in solvent-free, greener reaction conditions not only ameliorated the reaction efficiency but also augmented the chemical yield. The purity of the synthesized IL was corroborated using 1H Nuclear Magnetic Resonance (NMR), 13C NMR, and Infrared (IR) spectroscopy. The biological potential of the synthesized compound is further validated by analyzing its Absorption, Distribution, Metabolism, Excretion, and Toxicity (ADMET) properties and authenticated using disc diffusion assay.

In the present work, we elucidate the green synthesis of quinoline-based Ionic Liquid (IL), namely, 1-Hexadecylquinolin-1-ium bromide {[C16quin]Br} by mixing quinoline with an excess of 1-Bromohexadecane, along with its detailed characterization using Nuclear Magnetic Resonance and Infrared spectroscopic measurements.