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Novel Dipyridinium Lipophile-Based Ionic Liquids Tethering Hydrazone Linkage: Design, Synthesis and Antitumorigenic Study

Novel dicationic pyridinium ionic liquids tethering amphiphilic long alkyl side chains and fluorinated counter anions have been successfully synthesized by means of the quaternization of the dipyridinium hydrazone through its alkylation with different alkyl halides. The resulting halogenated di-ioni...

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Autores principales: Al-Sodies, Salsabeel, Rezki, Nadjet, Albelwi, Fawzia Faleh, Messali, Mouslim, Aouad, Mohamed R., Bardaweel, Sanaa K., Hagar, Mohamed
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8508903/
https://www.ncbi.nlm.nih.gov/pubmed/34638826
http://dx.doi.org/10.3390/ijms221910487
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author Al-Sodies, Salsabeel
Rezki, Nadjet
Albelwi, Fawzia Faleh
Messali, Mouslim
Aouad, Mohamed R.
Bardaweel, Sanaa K.
Hagar, Mohamed
author_facet Al-Sodies, Salsabeel
Rezki, Nadjet
Albelwi, Fawzia Faleh
Messali, Mouslim
Aouad, Mohamed R.
Bardaweel, Sanaa K.
Hagar, Mohamed
author_sort Al-Sodies, Salsabeel
collection PubMed
description Novel dicationic pyridinium ionic liquids tethering amphiphilic long alkyl side chains and fluorinated counter anions have been successfully synthesized by means of the quaternization of the dipyridinium hydrazone through its alkylation with different alkyl halides. The resulting halogenated di-ionic liquids underwent a metathesis reaction in order to incorporate some fluorinated counter anions in their structures. The structures of all the resulting di-ionic liquids were characterized by several spectroscopic experiments. The antitumorigenic activities of the investigated compounds were further studied against three different human lung cancer cell lines. Compared to the standard chemotherapeutic agent, cisplatin, the synthesized di-ionic liquids exerted equal, even more active, moderate, or weak anticancer activities against the various lung cancer cell lines under investigation. The observed anticancer activity appears to be enhanced by increasing the length of the aliphatic side chains. Moreover, dicationic pyridinium bearing a nine carbon chain as counter cation and hexafluoro phosphate and/or tetrafluoro bororate as counter anion were selected for further evaluation and demonstrated effective and significant antimetastatic effects and suppressed the colonization ability of the lung cancer cells, suggesting a therapeutic potential for the synthesized compounds in lung cancer treatment.
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spelling pubmed-85089032021-10-13 Novel Dipyridinium Lipophile-Based Ionic Liquids Tethering Hydrazone Linkage: Design, Synthesis and Antitumorigenic Study Al-Sodies, Salsabeel Rezki, Nadjet Albelwi, Fawzia Faleh Messali, Mouslim Aouad, Mohamed R. Bardaweel, Sanaa K. Hagar, Mohamed Int J Mol Sci Article Novel dicationic pyridinium ionic liquids tethering amphiphilic long alkyl side chains and fluorinated counter anions have been successfully synthesized by means of the quaternization of the dipyridinium hydrazone through its alkylation with different alkyl halides. The resulting halogenated di-ionic liquids underwent a metathesis reaction in order to incorporate some fluorinated counter anions in their structures. The structures of all the resulting di-ionic liquids were characterized by several spectroscopic experiments. The antitumorigenic activities of the investigated compounds were further studied against three different human lung cancer cell lines. Compared to the standard chemotherapeutic agent, cisplatin, the synthesized di-ionic liquids exerted equal, even more active, moderate, or weak anticancer activities against the various lung cancer cell lines under investigation. The observed anticancer activity appears to be enhanced by increasing the length of the aliphatic side chains. Moreover, dicationic pyridinium bearing a nine carbon chain as counter cation and hexafluoro phosphate and/or tetrafluoro bororate as counter anion were selected for further evaluation and demonstrated effective and significant antimetastatic effects and suppressed the colonization ability of the lung cancer cells, suggesting a therapeutic potential for the synthesized compounds in lung cancer treatment. MDPI 2021-09-28 /pmc/articles/PMC8508903/ /pubmed/34638826 http://dx.doi.org/10.3390/ijms221910487 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Al-Sodies, Salsabeel
Rezki, Nadjet
Albelwi, Fawzia Faleh
Messali, Mouslim
Aouad, Mohamed R.
Bardaweel, Sanaa K.
Hagar, Mohamed
Novel Dipyridinium Lipophile-Based Ionic Liquids Tethering Hydrazone Linkage: Design, Synthesis and Antitumorigenic Study
title Novel Dipyridinium Lipophile-Based Ionic Liquids Tethering Hydrazone Linkage: Design, Synthesis and Antitumorigenic Study
title_full Novel Dipyridinium Lipophile-Based Ionic Liquids Tethering Hydrazone Linkage: Design, Synthesis and Antitumorigenic Study
title_fullStr Novel Dipyridinium Lipophile-Based Ionic Liquids Tethering Hydrazone Linkage: Design, Synthesis and Antitumorigenic Study
title_full_unstemmed Novel Dipyridinium Lipophile-Based Ionic Liquids Tethering Hydrazone Linkage: Design, Synthesis and Antitumorigenic Study
title_short Novel Dipyridinium Lipophile-Based Ionic Liquids Tethering Hydrazone Linkage: Design, Synthesis and Antitumorigenic Study
title_sort novel dipyridinium lipophile-based ionic liquids tethering hydrazone linkage: design, synthesis and antitumorigenic study
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8508903/
https://www.ncbi.nlm.nih.gov/pubmed/34638826
http://dx.doi.org/10.3390/ijms221910487
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