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Volume 27
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10.3390/molecules27217280
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Article

Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform

by
Biljana Arsic
1,2,*,
Jill Barber
1,
Ana Cikos
3,
Manikandan Kadirvel
1,
Emilija Kostic
4,
Andrew J. McBain
1,
Jelena Milicevic
5,
Angela Oates
6 and
Andrew Regan
7
1
Division of Pharmacy and Optometry, School of Health Sciences, University of Manchester, Oxford Road, Manchester M13 9PT, UK
2
Department of Chemistry, Faculty of Sciences and Mathematics, University of Nis, Visegradska 33, 18000 Nis, Serbia
3
NMR Centre, Ruđer Bošković Institute, Bijenička Cesta 54, 10000 Zagreb, Croatia
4
Faculty of Medicine, University of Nis, Bulevar dr Zorana Djindjica 81, 18000 Nis, Serbia
5
Laboratory 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, Serbia
6
Centre for Biomedicine, Hull York Medical School, Faculty of Health Sciences, University of Hull, Hull HU6 7RX, UK
7
Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK
*
Author to whom correspondence should be addressed.
Molecules 2022, 27(21), 7280; https://doi.org/10.3390/molecules27217280
Submission received: 29 August 2022 / Revised: 17 October 2022 / Accepted: 22 October 2022 / Published: 26 October 2022
(This article belongs to the Special Issue Spectroscopic and Spectrometric Techniques for Structural Analysis)
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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 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.
Keywords: macrolides; bacteria; 2D ROESY NMR macrolides; bacteria; 2D ROESY NMR

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MDPI and ACS Style

Arsic, B.; Barber, J.; Cikos, A.; Kadirvel, M.; Kostic, E.; McBain, A.J.; Milicevic, J.; Oates, A.; Regan, A. Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform. Molecules 2022, 27, 7280. https://doi.org/10.3390/molecules27217280

AMA Style

Arsic B, Barber J, Cikos A, Kadirvel M, Kostic E, McBain AJ, Milicevic J, Oates A, Regan A. Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform. Molecules. 2022; 27(21):7280. https://doi.org/10.3390/molecules27217280

Chicago/Turabian Style

Arsic, Biljana, Jill Barber, Ana Cikos, Manikandan Kadirvel, Emilija Kostic, Andrew J. McBain, Jelena Milicevic, Angela Oates, and Andrew Regan. 2022. "Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform" Molecules 27, no. 21: 7280. https://doi.org/10.3390/molecules27217280

APA Style

Arsic, B., Barber, J., Cikos, A., Kadirvel, M., Kostic, E., McBain, A. J., Milicevic, J., Oates, A., & Regan, A. (2022). Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform. Molecules, 27(21), 7280. https://doi.org/10.3390/molecules27217280

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