Steroid-Functionalized Imidazolium Salts with an Extended Spectrum of Antifungal and Antibacterial Activity

It is established that high rates of morbidity and mortality caused by fungal infections are related to the current limited number of antifungal drugs and the toxicity of these agents. Imidazolium salts as azole derivatives can be successfully used in the treatment of fungal infections in humans. St...

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Autores principales:	Marta Malinowska, Diana Sawicka, Katarzyna Niemirowicz-Laskowska, Przemysław Wielgat, Halina Car, Tomasz Hauschild, Agnieszka Hryniewicka
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	imidazolium salts steroid antifungal activity antibacterial activity Biology (General) QH301-705.5 Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/c2c2266f9a34455e9ff8d00efba92a14
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spelling	oai:doaj.org-article:c2c2266f9a34455e9ff8d00efba92a142021-11-25T17:54:04ZSteroid-Functionalized Imidazolium Salts with an Extended Spectrum of Antifungal and Antibacterial Activity10.3390/ijms2222121801422-00671661-6596https://doaj.org/article/c2c2266f9a34455e9ff8d00efba92a142021-11-01T00:00:00Zhttps://www.mdpi.com/1422-0067/22/22/12180https://doaj.org/toc/1661-6596https://doaj.org/toc/1422-0067It is established that high rates of morbidity and mortality caused by fungal infections are related to the current limited number of antifungal drugs and the toxicity of these agents. Imidazolium salts as azole derivatives can be successfully used in the treatment of fungal infections in humans. Steroid-functionalized imidazolium salts were synthesized using a new, more efficient method. As a result, 20 salts were obtained with high yields, 12 of which were synthesized and characterized for the first time. They were derivatives of lithocholic acid and 3-oxo-23,24-dinorchol-4-ene-22-al and were fully characterized by <sup>1</sup>H and <sup>13</sup>C nuclear magnetic resonance (NMR), infrared spectroscopy (IR), and high resolution mass spectrometry (HRMS). Due to the excellent activity against bacteria and <i>Candida albicans</i>, new research was extended to include tests on five species of pathogenic fungi and molds: <i>Aspergillus niger</i> ATCC 16888, <i>Aspergillus fumigatus</i> ATCC 204305, <i>Trichophyton mentagrophytes</i> ATCC 9533, <i>Cryptococcus neoformans</i> ATCC 14116, and <i>Microsporum canis</i> ATCC 11621. The results showed that the new salts are almost universal antifungal agents and have a broad spectrum of activity against other human pathogens. To initially assess the safety of the synthesized salts, hemocompatibility with host cells and cytotoxicity were also examined. No toxicity was observed at the concentration at which the compounds were active against pathogens.Marta MalinowskaDiana SawickaKatarzyna Niemirowicz-LaskowskaPrzemysław WielgatHalina CarTomasz HauschildAgnieszka HryniewickaMDPI AGarticleimidazolium saltssteroidantifungal activityantibacterial activityBiology (General)QH301-705.5ChemistryQD1-999ENInternational Journal of Molecular Sciences, Vol 22, Iss 12180, p 12180 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	imidazolium salts steroid antifungal activity antibacterial activity Biology (General) QH301-705.5 Chemistry QD1-999
spellingShingle	imidazolium salts steroid antifungal activity antibacterial activity Biology (General) QH301-705.5 Chemistry QD1-999 Marta Malinowska Diana Sawicka Katarzyna Niemirowicz-Laskowska Przemysław Wielgat Halina Car Tomasz Hauschild Agnieszka Hryniewicka Steroid-Functionalized Imidazolium Salts with an Extended Spectrum of Antifungal and Antibacterial Activity
description	It is established that high rates of morbidity and mortality caused by fungal infections are related to the current limited number of antifungal drugs and the toxicity of these agents. Imidazolium salts as azole derivatives can be successfully used in the treatment of fungal infections in humans. Steroid-functionalized imidazolium salts were synthesized using a new, more efficient method. As a result, 20 salts were obtained with high yields, 12 of which were synthesized and characterized for the first time. They were derivatives of lithocholic acid and 3-oxo-23,24-dinorchol-4-ene-22-al and were fully characterized by <sup>1</sup>H and <sup>13</sup>C nuclear magnetic resonance (NMR), infrared spectroscopy (IR), and high resolution mass spectrometry (HRMS). Due to the excellent activity against bacteria and <i>Candida albicans</i>, new research was extended to include tests on five species of pathogenic fungi and molds: <i>Aspergillus niger</i> ATCC 16888, <i>Aspergillus fumigatus</i> ATCC 204305, <i>Trichophyton mentagrophytes</i> ATCC 9533, <i>Cryptococcus neoformans</i> ATCC 14116, and <i>Microsporum canis</i> ATCC 11621. The results showed that the new salts are almost universal antifungal agents and have a broad spectrum of activity against other human pathogens. To initially assess the safety of the synthesized salts, hemocompatibility with host cells and cytotoxicity were also examined. No toxicity was observed at the concentration at which the compounds were active against pathogens.
format	article
author	Marta Malinowska Diana Sawicka Katarzyna Niemirowicz-Laskowska Przemysław Wielgat Halina Car Tomasz Hauschild Agnieszka Hryniewicka
author_facet	Marta Malinowska Diana Sawicka Katarzyna Niemirowicz-Laskowska Przemysław Wielgat Halina Car Tomasz Hauschild Agnieszka Hryniewicka
author_sort	Marta Malinowska
title	Steroid-Functionalized Imidazolium Salts with an Extended Spectrum of Antifungal and Antibacterial Activity
title_short	Steroid-Functionalized Imidazolium Salts with an Extended Spectrum of Antifungal and Antibacterial Activity
title_full	Steroid-Functionalized Imidazolium Salts with an Extended Spectrum of Antifungal and Antibacterial Activity
title_fullStr	Steroid-Functionalized Imidazolium Salts with an Extended Spectrum of Antifungal and Antibacterial Activity
title_full_unstemmed	Steroid-Functionalized Imidazolium Salts with an Extended Spectrum of Antifungal and Antibacterial Activity
title_sort	steroid-functionalized imidazolium salts with an extended spectrum of antifungal and antibacterial activity
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/c2c2266f9a34455e9ff8d00efba92a14
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Steroid-Functionalized Imidazolium Salts with an Extended Spectrum of Antifungal and Antibacterial Activity

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