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 . .

TY  - JOUR
AU  - Mladenović, Milan P.
AU  - Arsić, Biljana
AU  - Stanković, Nevena M.
AU  - Mihović, Nezrina
AU  - Ragno, Rino
AU  - Regan, Andrew C.
AU  - Milićević, Jelena S.
AU  - Trtić-Petrović, Tatjana M.
AU  - Micić, Ružica J.
PY  - 2018
UR  - http://www.mdpi.com/1420-3049/23/9/2192
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7862
AB  - Commercially available pesticides were examined as Mus musculus and Homo sapiens acetylcholinesterase (mAChE and hAChE) inhibitors by means of ligand-based (LB) and structure-based (SB) in silico approaches. Initially, the crystal structures of simazine, monocrotophos, dimethoate, and acetamiprid were reproduced using various force fields. Subsequently, LB alignment rules were assessed and applied to determine the inter synaptic conformations of atrazine, propazine, carbofuran, carbaryl, tebufenozide, imidacloprid, diuron, monuron, and linuron. Afterwards, molecular docking and dynamics SB studies were performed on either mAChE or hAChE, to predict the listed pesticides’ binding modes. Calculated energies of global minima (Eglob_min) and free energies of binding (∆Gbinding) were correlated with the pesticides’ acute toxicities (i.e., the LD50 values) against mice, as well to generate the model that could predict the LD50s against humans. Although for most of the pesticides the low Eglob_min correlates with the high acute toxicity, it is the ∆Gbinding that conditions the LD50 values for all the evaluated pesticides. Derived pLD50 = f(∆Gbinding) mAChE model may predict the pLD50 against hAChE, too. The hAChE inhibition by atrazine, propazine, and simazine (the most toxic pesticides) was elucidated by SB quantum mechanics (QM) DFT mechanistic and concentration-dependent kinetic studies, enriching the knowledge for design of less toxic pesticides.
T2  - Molecules
T1  - The Targeted Pesticides as Acetylcholinesterase Inhibitors: Comprehensive Cross-Organism Molecular Modelling Studies Performed to Anticipate the Pharmacology of Harmfulness to Humans In Vitro
VL  - 23
IS  - 9
SP  - 2192
DO  - 10.3390/molecules23092192
ER  - 

@article{
author = "Mladenović, Milan P. and Arsić, Biljana and Stanković, Nevena M. and Mihović, Nezrina and Ragno, Rino and Regan, Andrew C. and Milićević, Jelena S. and Trtić-Petrović, Tatjana M. and Micić, Ružica J.",
year = "2018",
abstract = "Commercially available pesticides were examined as Mus musculus and Homo sapiens acetylcholinesterase (mAChE and hAChE) inhibitors by means of ligand-based (LB) and structure-based (SB) in silico approaches. Initially, the crystal structures of simazine, monocrotophos, dimethoate, and acetamiprid were reproduced using various force fields. Subsequently, LB alignment rules were assessed and applied to determine the inter synaptic conformations of atrazine, propazine, carbofuran, carbaryl, tebufenozide, imidacloprid, diuron, monuron, and linuron. Afterwards, molecular docking and dynamics SB studies were performed on either mAChE or hAChE, to predict the listed pesticides’ binding modes. Calculated energies of global minima (Eglob_min) and free energies of binding (∆Gbinding) were correlated with the pesticides’ acute toxicities (i.e., the LD50 values) against mice, as well to generate the model that could predict the LD50s against humans. Although for most of the pesticides the low Eglob_min correlates with the high acute toxicity, it is the ∆Gbinding that conditions the LD50 values for all the evaluated pesticides. Derived pLD50 = f(∆Gbinding) mAChE model may predict the pLD50 against hAChE, too. The hAChE inhibition by atrazine, propazine, and simazine (the most toxic pesticides) was elucidated by SB quantum mechanics (QM) DFT mechanistic and concentration-dependent kinetic studies, enriching the knowledge for design of less toxic pesticides.",
journal = "Molecules",
title = "The Targeted Pesticides as Acetylcholinesterase Inhibitors: Comprehensive Cross-Organism Molecular Modelling Studies Performed to Anticipate the Pharmacology of Harmfulness to Humans In Vitro",
volume = "23",
number = "9",
pages = "2192",
doi = "10.3390/molecules23092192"
}

Mladenović, M. P., Arsić, B., Stanković, N. M., Mihović, N., Ragno, R., Regan, A. C., Milićević, J. S., Trtić-Petrović, T. M.,& Micić, R. J.. (2018). The Targeted Pesticides as Acetylcholinesterase Inhibitors: Comprehensive Cross-Organism Molecular Modelling Studies Performed to Anticipate the Pharmacology of Harmfulness to Humans In Vitro. in Molecules, 23(9), 2192.
https://doi.org/10.3390/molecules23092192

Mladenović MP, Arsić B, Stanković NM, Mihović N, Ragno R, Regan AC, Milićević JS, Trtić-Petrović TM, Micić RJ. The Targeted Pesticides as Acetylcholinesterase Inhibitors: Comprehensive Cross-Organism Molecular Modelling Studies Performed to Anticipate the Pharmacology of Harmfulness to Humans In Vitro. in Molecules. 2018;23(9):2192.
doi:10.3390/molecules23092192 .

Mladenović, Milan P., Arsić, Biljana, Stanković, Nevena M., Mihović, Nezrina, Ragno, Rino, Regan, Andrew C., Milićević, Jelena S., Trtić-Petrović, Tatjana M., Micić, Ružica J., "The Targeted Pesticides as Acetylcholinesterase Inhibitors: Comprehensive Cross-Organism Molecular Modelling Studies Performed to Anticipate the Pharmacology of Harmfulness to Humans In Vitro" in Molecules, 23, no. 9 (2018):2192,
https://doi.org/10.3390/molecules23092192 . .