Arsic, Biljana; Barber, Jill; Čikoš, Ana; Kadirvel, Manikandan; Kostic, Emilija; McBain, Andrew J.; Milicevic, Jelena; Oates, Angela; Regan, Andrew (2022) Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform. Molecules, 27 (21). ISSN 1420-3049
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Abstract
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 1H and 13C 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 deuteratedchloroform, other species were also detected in 1D and 2D NMR spectra. We additionally studied theanti-bacterial activity of tylosin A and B against selected Gram-positive and Gram- negative bacteria.
| Item Type: | Article |
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| Uncontrolled Keywords: | macrolides ; bacteria ; 2D ROESY NMR |
| Subjects: | NATURAL SCIENCES > Chemistry NATURAL SCIENCES > Interdisciplinary Natural Sciences BIOMEDICINE AND HEALTHCARE > Pharmacy |
| Divisions: | NMR Center |
| Depositing User: | Sofija Konjević |
| Date Deposited: | 04 Apr 2023 07:59 |
| URI: | http://fulir.irb.hr/id/eprint/7829 |
| DOI: | 10.3390/molecules27217280 |
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