TY  - JOUR
AU  - Jovanović, Milan
AU  - Radan, Milica
AU  - Čarapić, Marija
AU  - Filipović, Nenad
AU  - Nikolić, Katarina
AU  - Crevar, Milkica
PY  - 2024
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/13287
AB  - Aim: This study aims to investigate the passive diffusion of protein kinase inhibitors through the blood–brain barrier (BBB) and to develop a model for their permeability prediction. Materials & methods: We used the parallel artificial membrane permeability assay to obtain logPe values of each of 34 compounds and calculated descriptors for these structures to perform quantitative structure–property relationship modeling, creating different regression models. Results: The logPe values have been calculated for all 34 compounds. Support vector machine regression was considered the most reliable, and CATS2D_09_DA, CATS2D_04_AA, B04[N-S] and F07[C-N] descriptors were identified as the most influential to passive BBB permeability. Conclusion: The quantitative structure–property relationship-support vector machine regression model that has been generated can serve as an efficient method for preliminary screening of BBB permeability of new analogs.
T2  - Future Medicinal Chemistry
T1  - Application of parallel artificial membrane permeability assay technique and chemometric modeling for blood–brain barrier permeability prediction of protein kinase inhibitors
SP  - 1
EP  - 13
DO  - 10.4155/fmc-2023-0390
ER  - 

@article{
author = "Jovanović, Milan and Radan, Milica and Čarapić, Marija and Filipović, Nenad and Nikolić, Katarina and Crevar, Milkica",
year = "2024",
abstract = "Aim: This study aims to investigate the passive diffusion of protein kinase inhibitors through the blood–brain barrier (BBB) and to develop a model for their permeability prediction. Materials & methods: We used the parallel artificial membrane permeability assay to obtain logPe values of each of 34 compounds and calculated descriptors for these structures to perform quantitative structure–property relationship modeling, creating different regression models. Results: The logPe values have been calculated for all 34 compounds. Support vector machine regression was considered the most reliable, and CATS2D_09_DA, CATS2D_04_AA, B04[N-S] and F07[C-N] descriptors were identified as the most influential to passive BBB permeability. Conclusion: The quantitative structure–property relationship-support vector machine regression model that has been generated can serve as an efficient method for preliminary screening of BBB permeability of new analogs.",
journal = "Future Medicinal Chemistry",
title = "Application of parallel artificial membrane permeability assay technique and chemometric modeling for blood–brain barrier permeability prediction of protein kinase inhibitors",
pages = "1-13",
doi = "10.4155/fmc-2023-0390"
}

Jovanović, M., Radan, M., Čarapić, M., Filipović, N., Nikolić, K.,& Crevar, M.. (2024). Application of parallel artificial membrane permeability assay technique and chemometric modeling for blood–brain barrier permeability prediction of protein kinase inhibitors. in Future Medicinal Chemistry, 1-13.
https://doi.org/10.4155/fmc-2023-0390

Jovanović M, Radan M, Čarapić M, Filipović N, Nikolić K, Crevar M. Application of parallel artificial membrane permeability assay technique and chemometric modeling for blood–brain barrier permeability prediction of protein kinase inhibitors. in Future Medicinal Chemistry. 2024;:1-13.
doi:10.4155/fmc-2023-0390 .

Jovanović, Milan, Radan, Milica, Čarapić, Marija, Filipović, Nenad, Nikolić, Katarina, Crevar, Milkica, "Application of parallel artificial membrane permeability assay technique and chemometric modeling for blood–brain barrier permeability prediction of protein kinase inhibitors" in Future Medicinal Chemistry (2024):1-13,
https://doi.org/10.4155/fmc-2023-0390 . .

TY  - JOUR
AU  - Jovanović, Milan T.
AU  - Nikolić, Katarina
AU  - Čarapić, Marija
AU  - Aleksić, Mara M.
PY  - 2023
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/11362
AB  - A comprehensive investigation of tyrosine kinase inhibitor erlotinib (ERL) electrochemical behavior and interaction with DNA was performed with the aim to clarify its redox mechanism and to determine the mode of binding. Irreversible oxidation and reduction processes of ERL on glassy carbon electrode were investigated using three voltammetric techniques CV, DPV, SWV in pH range between 2.0 and 9.0. Oxidation was established as an adsorption-controlled process, while the reduction manifested diffusion-adsorption mixed controlled process in acidic medium and adsorption became predominant in the neutral solutions. According to the determined number of transferred electrons and protons, oxidation and reduction mechanism of ERL are proposed. To follow the interaction between ERL and DNA, the multilayer ct-DNA electrochemical biosensor was incubated in ERL solutions concentrations ranged from 2 × 10–7 M to 5 × 10–5 M (pH 4.6) for 30 min. SWV measurements have shown the decrease in deoxyadenosine peak current as a consequence of ERL increased concentration and binding to ct-DNA. The calculated value of binding constant was K = 8.25 × 104 M−1. Molecular docking showed that ERL forms hydrophobic interactions when docked into minor groove, as well as when intercalated, and molecular dynamics analysis predicted the stability of obtained complexes. These results together with voltammetric studies imply that the intercalation could be more dominant way ERL binding to DNA compared to minor groove binding. © 2023 Elsevier B.V.
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Electrochemical and theoretical study on interaction between erlotinib and DNA
VL  - 234
SP  - 115560
DO  - 10.1016/j.jpba.2023.115560
ER  - 

@article{
author = "Jovanović, Milan T. and Nikolić, Katarina and Čarapić, Marija and Aleksić, Mara M.",
year = "2023",
abstract = "A comprehensive investigation of tyrosine kinase inhibitor erlotinib (ERL) electrochemical behavior and interaction with DNA was performed with the aim to clarify its redox mechanism and to determine the mode of binding. Irreversible oxidation and reduction processes of ERL on glassy carbon electrode were investigated using three voltammetric techniques CV, DPV, SWV in pH range between 2.0 and 9.0. Oxidation was established as an adsorption-controlled process, while the reduction manifested diffusion-adsorption mixed controlled process in acidic medium and adsorption became predominant in the neutral solutions. According to the determined number of transferred electrons and protons, oxidation and reduction mechanism of ERL are proposed. To follow the interaction between ERL and DNA, the multilayer ct-DNA electrochemical biosensor was incubated in ERL solutions concentrations ranged from 2 × 10–7 M to 5 × 10–5 M (pH 4.6) for 30 min. SWV measurements have shown the decrease in deoxyadenosine peak current as a consequence of ERL increased concentration and binding to ct-DNA. The calculated value of binding constant was K = 8.25 × 104 M−1. Molecular docking showed that ERL forms hydrophobic interactions when docked into minor groove, as well as when intercalated, and molecular dynamics analysis predicted the stability of obtained complexes. These results together with voltammetric studies imply that the intercalation could be more dominant way ERL binding to DNA compared to minor groove binding. © 2023 Elsevier B.V.",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Electrochemical and theoretical study on interaction between erlotinib and DNA",
volume = "234",
pages = "115560",
doi = "10.1016/j.jpba.2023.115560"
}

Jovanović, M. T., Nikolić, K., Čarapić, M.,& Aleksić, M. M.. (2023). Electrochemical and theoretical study on interaction between erlotinib and DNA. in Journal of Pharmaceutical and Biomedical Analysis, 234, 115560.
https://doi.org/10.1016/j.jpba.2023.115560

Jovanović MT, Nikolić K, Čarapić M, Aleksić MM. Electrochemical and theoretical study on interaction between erlotinib and DNA. in Journal of Pharmaceutical and Biomedical Analysis. 2023;234:115560.
doi:10.1016/j.jpba.2023.115560 .

Jovanović, Milan T., Nikolić, Katarina, Čarapić, Marija, Aleksić, Mara M., "Electrochemical and theoretical study on interaction between erlotinib and DNA" in Journal of Pharmaceutical and Biomedical Analysis, 234 (2023):115560,
https://doi.org/10.1016/j.jpba.2023.115560 . .