Synthesis and biological evaluation of mannosyl triazoles and varying the nature of substituents on the terminal phthalimido moiety in the aglycone backbone
In the present study, a facile synthesis of six monovalent α-d-mannoside ligands terminated with phthalimido moiety by Cu(I) catalyzed azide-alkyne cycloaddition reaction (CuAAC) has been achieved. All synthesized ligands were tested for their inhibitory activities against E. coli FimH adhesion usin...
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| Format: | Article |
| Language: | English |
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Elsevier
2022-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715622002673 |
| _version_ | 1811178123243290624 |
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| author | Hussein Al-Mughaid Younis Jaradat Maha Khazaaleh |
| author_facet | Hussein Al-Mughaid Younis Jaradat Maha Khazaaleh |
| author_sort | Hussein Al-Mughaid |
| collection | DOAJ |
| description | In the present study, a facile synthesis of six monovalent α-d-mannoside ligands terminated with phthalimido moiety by Cu(I) catalyzed azide-alkyne cycloaddition reaction (CuAAC) has been achieved. All synthesized ligands were tested for their inhibitory activities against E. coli FimH adhesion using hemagglutination inhibition (HAI) assay and showed inhibitory activity in the range of HAI = 4.8–23.5 µM comparing with 2-azidoethyl α-d-mannopyranoside 17 as the standard ligand (HAI = 135 µM). Among them, ligand 21 (R = NO2), displayed the best activity (HAI = 4.8 µM) which was approximately 28 times more potent than the reference ligand 17. Thus confirming the beneficial effect of lipophilic interactions between the aromatic aglycone and the tyrosine gate of FimH. We feel that our lead ligand will be a good platform for identification of more potent FimH inhibitors. |
| first_indexed | 2024-04-11T06:12:53Z |
| format | Article |
| id | doaj.art-575c0f23e1ce407fafa0656658976e00 |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-04-11T06:12:53Z |
| publishDate | 2022-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-575c0f23e1ce407fafa0656658976e002022-12-22T04:41:09ZengElsevierResults in Chemistry2211-71562022-01-014100548Synthesis and biological evaluation of mannosyl triazoles and varying the nature of substituents on the terminal phthalimido moiety in the aglycone backboneHussein Al-Mughaid0Younis Jaradat1Maha Khazaaleh2Corresponding author.; Department of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, JordanDepartment of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, JordanDepartment of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, JordanIn the present study, a facile synthesis of six monovalent α-d-mannoside ligands terminated with phthalimido moiety by Cu(I) catalyzed azide-alkyne cycloaddition reaction (CuAAC) has been achieved. All synthesized ligands were tested for their inhibitory activities against E. coli FimH adhesion using hemagglutination inhibition (HAI) assay and showed inhibitory activity in the range of HAI = 4.8–23.5 µM comparing with 2-azidoethyl α-d-mannopyranoside 17 as the standard ligand (HAI = 135 µM). Among them, ligand 21 (R = NO2), displayed the best activity (HAI = 4.8 µM) which was approximately 28 times more potent than the reference ligand 17. Thus confirming the beneficial effect of lipophilic interactions between the aromatic aglycone and the tyrosine gate of FimH. We feel that our lead ligand will be a good platform for identification of more potent FimH inhibitors.http://www.sciencedirect.com/science/article/pii/S22117156220026731,2,3-triazoleHemagglutinationMannoconjugateUrinary tract infection |
| spellingShingle | Hussein Al-Mughaid Younis Jaradat Maha Khazaaleh Synthesis and biological evaluation of mannosyl triazoles and varying the nature of substituents on the terminal phthalimido moiety in the aglycone backbone Results in Chemistry 1,2,3-triazole Hemagglutination Mannoconjugate Urinary tract infection |
| title | Synthesis and biological evaluation of mannosyl triazoles and varying the nature of substituents on the terminal phthalimido moiety in the aglycone backbone |
| title_full | Synthesis and biological evaluation of mannosyl triazoles and varying the nature of substituents on the terminal phthalimido moiety in the aglycone backbone |
| title_fullStr | Synthesis and biological evaluation of mannosyl triazoles and varying the nature of substituents on the terminal phthalimido moiety in the aglycone backbone |
| title_full_unstemmed | Synthesis and biological evaluation of mannosyl triazoles and varying the nature of substituents on the terminal phthalimido moiety in the aglycone backbone |
| title_short | Synthesis and biological evaluation of mannosyl triazoles and varying the nature of substituents on the terminal phthalimido moiety in the aglycone backbone |
| title_sort | synthesis and biological evaluation of mannosyl triazoles and varying the nature of substituents on the terminal phthalimido moiety in the aglycone backbone |
| topic | 1,2,3-triazole Hemagglutination Mannoconjugate Urinary tract infection |
| url | http://www.sciencedirect.com/science/article/pii/S2211715622002673 |
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