Antimicrobial, Cytotoxic and Mutagenic Activity of Gemini QAS Derivatives of 1,4:3,6-Dianhydro-<span style="font-variant: small-caps">l</span>-iditol
A series of quaternary diammonium salts derivatives of 1,4:3,6-dianhydro-<span style="font-variant: small-caps;">l</span>-iditol were synthesized, using isommanide (1,4:3,6-dianhydro-<span style="font-variant: small-caps;">d</span>-mannitol) as a starting...
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MDPI AG
2022-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/3/757 |
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| author | Karol Sikora Andrzej Nowacki Piotr Szweda Anna Woziwodzka Sylwia Bartoszewska Jacek Piosik Barbara Dmochowska |
| author_facet | Karol Sikora Andrzej Nowacki Piotr Szweda Anna Woziwodzka Sylwia Bartoszewska Jacek Piosik Barbara Dmochowska |
| author_sort | Karol Sikora |
| collection | DOAJ |
| description | A series of quaternary diammonium salts derivatives of 1,4:3,6-dianhydro-<span style="font-variant: small-caps;">l</span>-iditol were synthesized, using isommanide (1,4:3,6-dianhydro-<span style="font-variant: small-caps;">d</span>-mannitol) as a starting material. Both aromatic (pyridine, 4-(<i>N</i>,<i>N</i>-dimethylamino)pyridine (DMAP), (3-carboxamide)pyridine; <i>N</i>-methylimidazole) and aliphatic (trimethylamine, <i>N</i>,<i>N</i>-dimethylhexylamine, <i>N</i>,<i>N</i>-dimethyloctylamine, <i>N</i>,<i>N</i>-dimethyldecylamine) amines were used, giving eight gemini quaternary ammonium salts (QAS). All salts were tested for their antimicrobial activity against yeasts, <i>Candida albicans</i> and <i>Candida glabrata</i>, as well as bacterial <i>Staphylococcus aureus</i> and <i>Escherichia coli</i> reference strains. Moreover, antibacterial activity against 20 isolates of <i>S. aureus</i> collected from patients with skin and soft tissue infections (<i>n</i> = 8) and strains derived from subclinical bovine mastitis milk samples (<i>n</i> = 12) were evaluated. Two QAS with octyl and decyl residues exhibited antimicrobial activity, whereas those with two decyl residues proved to be the most active against the tested pathogens, with MIC of 16–32, 32, and 8 µg/mL for yeast, <i>E. coli,</i> and <i>S. aureus</i> reference and clinical strains, respectively. Only QAS with decyl residues proved to be cytotoxic in MTT assay against human keratinocytes (HaCaT), IC<sub>50</sub> 12.8 ± 1.2 μg/mL. Ames test was used to assess the mutagenic potential of QAS, and none of them showed mutagenic activity in the concentration range 4–2000 µg/plate. |
| first_indexed | 2024-03-09T23:29:22Z |
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| id | doaj.art-916cc52fa1d54fce8ab2f1422d6b260b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
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| last_indexed | 2024-03-09T23:29:22Z |
| publishDate | 2022-01-01 |
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| spelling | doaj.art-916cc52fa1d54fce8ab2f1422d6b260b2023-11-23T17:12:00ZengMDPI AGMolecules1420-30492022-01-0127375710.3390/molecules27030757Antimicrobial, Cytotoxic and Mutagenic Activity of Gemini QAS Derivatives of 1,4:3,6-Dianhydro-<span style="font-variant: small-caps">l</span>-iditolKarol Sikora0Andrzej Nowacki1Piotr Szweda2Anna Woziwodzka3Sylwia Bartoszewska4Jacek Piosik5Barbara Dmochowska6Department of Inorganic Chemistry, Faculty of Pharmacy, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, PolandFaculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, PolandDepartment of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdańsk University of Technology, ul. G. Narutowicza 11/12, 80-233 Gdańsk, PolandLaboratory of Biophysics, Intercollegiate Faculty of Biotechnology, University of Gdańsk and Medical University of Gdańsk, Abrahama 58, 80-307 Gdańsk, PolandDepartment of Inorganic Chemistry, Faculty of Pharmacy, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, PolandLaboratory of Biophysics, Intercollegiate Faculty of Biotechnology, University of Gdańsk and Medical University of Gdańsk, Abrahama 58, 80-307 Gdańsk, PolandFaculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, PolandA series of quaternary diammonium salts derivatives of 1,4:3,6-dianhydro-<span style="font-variant: small-caps;">l</span>-iditol were synthesized, using isommanide (1,4:3,6-dianhydro-<span style="font-variant: small-caps;">d</span>-mannitol) as a starting material. Both aromatic (pyridine, 4-(<i>N</i>,<i>N</i>-dimethylamino)pyridine (DMAP), (3-carboxamide)pyridine; <i>N</i>-methylimidazole) and aliphatic (trimethylamine, <i>N</i>,<i>N</i>-dimethylhexylamine, <i>N</i>,<i>N</i>-dimethyloctylamine, <i>N</i>,<i>N</i>-dimethyldecylamine) amines were used, giving eight gemini quaternary ammonium salts (QAS). All salts were tested for their antimicrobial activity against yeasts, <i>Candida albicans</i> and <i>Candida glabrata</i>, as well as bacterial <i>Staphylococcus aureus</i> and <i>Escherichia coli</i> reference strains. Moreover, antibacterial activity against 20 isolates of <i>S. aureus</i> collected from patients with skin and soft tissue infections (<i>n</i> = 8) and strains derived from subclinical bovine mastitis milk samples (<i>n</i> = 12) were evaluated. Two QAS with octyl and decyl residues exhibited antimicrobial activity, whereas those with two decyl residues proved to be the most active against the tested pathogens, with MIC of 16–32, 32, and 8 µg/mL for yeast, <i>E. coli,</i> and <i>S. aureus</i> reference and clinical strains, respectively. Only QAS with decyl residues proved to be cytotoxic in MTT assay against human keratinocytes (HaCaT), IC<sub>50</sub> 12.8 ± 1.2 μg/mL. Ames test was used to assess the mutagenic potential of QAS, and none of them showed mutagenic activity in the concentration range 4–2000 µg/plate.https://www.mdpi.com/1420-3049/27/3/757quaternary ammonium saltsgemini1,4:3,6-dianhydro-<span style="font-variant: small-caps">d</span>-mannitolantimicrobial activitymutagenicity |
| spellingShingle | Karol Sikora Andrzej Nowacki Piotr Szweda Anna Woziwodzka Sylwia Bartoszewska Jacek Piosik Barbara Dmochowska Antimicrobial, Cytotoxic and Mutagenic Activity of Gemini QAS Derivatives of 1,4:3,6-Dianhydro-<span style="font-variant: small-caps">l</span>-iditol Molecules quaternary ammonium salts gemini 1,4:3,6-dianhydro-<span style="font-variant: small-caps">d</span>-mannitol antimicrobial activity mutagenicity |
| title | Antimicrobial, Cytotoxic and Mutagenic Activity of Gemini QAS Derivatives of 1,4:3,6-Dianhydro-<span style="font-variant: small-caps">l</span>-iditol |
| title_full | Antimicrobial, Cytotoxic and Mutagenic Activity of Gemini QAS Derivatives of 1,4:3,6-Dianhydro-<span style="font-variant: small-caps">l</span>-iditol |
| title_fullStr | Antimicrobial, Cytotoxic and Mutagenic Activity of Gemini QAS Derivatives of 1,4:3,6-Dianhydro-<span style="font-variant: small-caps">l</span>-iditol |
| title_full_unstemmed | Antimicrobial, Cytotoxic and Mutagenic Activity of Gemini QAS Derivatives of 1,4:3,6-Dianhydro-<span style="font-variant: small-caps">l</span>-iditol |
| title_short | Antimicrobial, Cytotoxic and Mutagenic Activity of Gemini QAS Derivatives of 1,4:3,6-Dianhydro-<span style="font-variant: small-caps">l</span>-iditol |
| title_sort | antimicrobial cytotoxic and mutagenic activity of gemini qas derivatives of 1 4 3 6 dianhydro span style font variant small caps l span iditol |
| topic | quaternary ammonium salts gemini 1,4:3,6-dianhydro-<span style="font-variant: small-caps">d</span>-mannitol antimicrobial activity mutagenicity |
| url | https://www.mdpi.com/1420-3049/27/3/757 |
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