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 i...n 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.
TY - JOUR
AU - Arsić, Biljana
AU - Barber, Jill
AU - Čikoš, Ana
AU - Kadirvel, Manikandan
AU - Kostić, Emilija
AU - McBain, Andrew J.
AU - Milićević, Jelena S.
AU - Oates, Angela
AU - Regan, Andrew
PY - 2022
UR - https://vinar.vin.bg.ac.rs/handle/123456789/10502
AB - 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.
T2 - Molecules
T1 - Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform
VL - 27
IS - 21
SP - 7280
DO - 10.3390/molecules27217280
ER -
@article{
author = "Arsić, Biljana and Barber, Jill and Čikoš, Ana and Kadirvel, Manikandan and Kostić, Emilija and McBain, Andrew J. and Milićević, Jelena S. and Oates, Angela and Regan, Andrew",
year = "2022",
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.",
journal = "Molecules",
title = "Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform",
volume = "27",
number = "21",
pages = "7280",
doi = "10.3390/molecules27217280"
}
Arsić, B., Barber, J., Čikoš, A., Kadirvel, M., Kostić, E., McBain, A. J., Milićević, J. S., 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. in Molecules, 27(21), 7280.
https://doi.org/10.3390/molecules27217280
Arsić B, Barber J, Čikoš A, Kadirvel M, Kostić E, McBain AJ, Milićević JS, Oates A, Regan A. Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform. in Molecules. 2022;27(21):7280.
doi:10.3390/molecules27217280 .
Arsić, Biljana, Barber, Jill, Čikoš, Ana, Kadirvel, Manikandan, Kostić, Emilija, McBain, Andrew J., Milićević, Jelena S., Oates, Angela, Regan, Andrew, "Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform" in Molecules, 27, no. 21 (2022):7280,
https://doi.org/10.3390/molecules27217280 . .
