Computational Studies on Selected Macrolides Active against <i>Escherichia coli</i> Combined with the NMR Study of Tylosin A in Deuterated Chloroform
Although many antibiotics are active against Gram-positive bacteria, fewer also show activity against Gram-negative bacteria. Here, we present a combination of in silico (electron ion-interaction potential, molecular docking, ADMET), NMR, and microbiological investigations of selected macrolides (14...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/21/7280 |
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| author | Biljana Arsic Jill Barber Ana Cikos Manikandan Kadirvel Emilija Kostic Andrew J. McBain Jelena Milicevic Angela Oates Andrew Regan |
| author_facet | Biljana Arsic Jill Barber Ana Cikos Manikandan Kadirvel Emilija Kostic Andrew J. McBain Jelena Milicevic Angela Oates Andrew Regan |
| author_sort | Biljana Arsic |
| collection | DOAJ |
| description | Although many antibiotics are active against Gram-positive bacteria, fewer also show activity against Gram-negative bacteria. Here, we present a combination of in silico (electron ion-interaction potential, molecular docking, ADMET), NMR, and microbiological investigations of selected macrolides (14-membered, 15-membered, and 16-membered), aiming to discover the pattern of design for macrolides active against Gram-negative bacteria. Although the conformational studies of 14-membered and 15-membered macrolides are abundant in the literature, 16-membered macrolides, and their most prominent representative tylosin A, have received relatively little research attention. We therefore report the complete <sup>1</sup>H and <sup>13</sup>C NMR assignment of tylosin A in deuterated chloroform, as well as its 3D solution structure determined through molecular modelling (conformational search) and 2D ROESY NMR. Additionally, due to the degradation of tylosin A in deuterated chloroform, other species were also detected in 1D and 2D NMR spectra. We additionally studied the anti-bacterial activity of tylosin A and B against selected Gram-positive and Gram-negative bacteria. |
| first_indexed | 2024-03-09T18:48:56Z |
| format | Article |
| id | doaj.art-6e59cbb94b5942ef9cc0601635fdd2a8 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T18:48:56Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-6e59cbb94b5942ef9cc0601635fdd2a82023-11-24T06:01:32ZengMDPI AGMolecules1420-30492022-10-012721728010.3390/molecules27217280Computational Studies on Selected Macrolides Active against <i>Escherichia coli</i> Combined with the NMR Study of Tylosin A in Deuterated ChloroformBiljana Arsic0Jill Barber1Ana Cikos2Manikandan Kadirvel3Emilija Kostic4Andrew J. McBain5Jelena Milicevic6Angela Oates7Andrew Regan8Division of Pharmacy and Optometry, School of Health Sciences, University of Manchester, Oxford Road, Manchester M13 9PT, UKDivision of Pharmacy and Optometry, School of Health Sciences, University of Manchester, Oxford Road, Manchester M13 9PT, UKNMR Centre, Ruđer Bošković Institute, Bijenička Cesta 54, 10000 Zagreb, CroatiaDivision of Pharmacy and Optometry, School of Health Sciences, University of Manchester, Oxford Road, Manchester M13 9PT, UKFaculty of Medicine, University of Nis, Bulevar dr Zorana Djindjica 81, 18000 Nis, SerbiaDivision of Pharmacy and Optometry, School of Health Sciences, University of Manchester, Oxford Road, Manchester M13 9PT, UKLaboratory for Bioinformatics and Computational Chemistry, Vinca Institute of Nuclear Sciences, National Institute of the Republic of Serbia, The University of Belgrade, Mike Petrovica Alasa 12-14, 11351 Belgrade, SerbiaCentre for Biomedicine, Hull York Medical School, Faculty of Health Sciences, University of Hull, Hull HU6 7RX, UKDepartment of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UKAlthough many antibiotics are active against Gram-positive bacteria, fewer also show activity against Gram-negative bacteria. Here, we present a combination of in silico (electron ion-interaction potential, molecular docking, ADMET), NMR, and microbiological investigations of selected macrolides (14-membered, 15-membered, and 16-membered), aiming to discover the pattern of design for macrolides active against Gram-negative bacteria. Although the conformational studies of 14-membered and 15-membered macrolides are abundant in the literature, 16-membered macrolides, and their most prominent representative tylosin A, have received relatively little research attention. We therefore report the complete <sup>1</sup>H and <sup>13</sup>C NMR assignment of tylosin A in deuterated chloroform, as well as its 3D solution structure determined through molecular modelling (conformational search) and 2D ROESY NMR. Additionally, due to the degradation of tylosin A in deuterated chloroform, other species were also detected in 1D and 2D NMR spectra. We additionally studied the anti-bacterial activity of tylosin A and B against selected Gram-positive and Gram-negative bacteria.https://www.mdpi.com/1420-3049/27/21/7280macrolidesbacteria2D ROESY NMR |
| spellingShingle | Biljana Arsic Jill Barber Ana Cikos Manikandan Kadirvel Emilija Kostic Andrew J. McBain Jelena Milicevic Angela Oates Andrew Regan Computational Studies on Selected Macrolides Active against <i>Escherichia coli</i> Combined with the NMR Study of Tylosin A in Deuterated Chloroform Molecules macrolides bacteria 2D ROESY NMR |
| title | Computational Studies on Selected Macrolides Active against <i>Escherichia coli</i> Combined with the NMR Study of Tylosin A in Deuterated Chloroform |
| title_full | Computational Studies on Selected Macrolides Active against <i>Escherichia coli</i> Combined with the NMR Study of Tylosin A in Deuterated Chloroform |
| title_fullStr | Computational Studies on Selected Macrolides Active against <i>Escherichia coli</i> Combined with the NMR Study of Tylosin A in Deuterated Chloroform |
| title_full_unstemmed | Computational Studies on Selected Macrolides Active against <i>Escherichia coli</i> Combined with the NMR Study of Tylosin A in Deuterated Chloroform |
| title_short | Computational Studies on Selected Macrolides Active against <i>Escherichia coli</i> Combined with the NMR Study of Tylosin A in Deuterated Chloroform |
| title_sort | computational studies on selected macrolides active against i escherichia coli i combined with the nmr study of tylosin a in deuterated chloroform |
| topic | macrolides bacteria 2D ROESY NMR |
| url | https://www.mdpi.com/1420-3049/27/21/7280 |
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