Computational Studies on Selected Macrolides Active against Escherichia coli Combined with the NMR Study of Tylosin A in Deuterated Chloroform
Аутори
Arsić, BiljanaBarber, Jill
Čikoš, Ana
Kadirvel, Manikandan
Kostić, Emilija
McBain, Andrew J.
Milićević, Jelena S.
Oates, Angela
Regan, Andrew
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
2D ROESY NMR / bacteria / macrolidesИзвор:
Molecules, 2022, 27, 21, 7280-Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200124 (Универзитет у Нишу, Природно-математички факултет) (RS-MESTD-inst-2020-200124)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200017 (Универзитет у Београду, Институт за нуклеарне науке Винча, Београд-Винча) (RS-MESTD-inst-2020-200017)
DOI: 10.3390/molecules27217280
ISSN: 1420-3049
PubMed: 36364103
Scopus: 2-s2.0-85141563511
Институција/група
VinčaTY - 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 . .