Novel cinnamic acid-based PET derivatives as quorum sensing modulators
Само за регистроване кориснике
2024
Аутори
Škaro Bogojević, SanjaPerminova, D
Jakšić, Jovana
Milčić, Miloš K.
Medaković, Vesna
Milovanović, Jelena
Nikodinović-Runić, Jasmina
Maslak, V
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Poly(ethylene terephthalate) (PET) is widely used material in the healthcare due to its mechanical properties including resistance to chemicals and abrasion. However, it is susceptible to bacterial attachment and contamination. This study addresses some newly designed model compounds of PET with antimicrobial properties that could potentially be incorporated into PET materials. All compounds were synthesized for the first time by labeling an integral part of PET with chromophores in the form of esters of cinnamic and ferulic acids. After complete structural characterization, the effect of new compounds on microbial growth and communication (quorum sensing, QS) was analyzed and further investigated using molecular docking. The obtained results indicate that the introduction of chromophores that have one part of cinnamic acid enriched with a methoxy functional group in them acts as QS modulators. Moreover, compounds exhibited dose-dependent selectivity toward QS signaling pathways and th...e highest tested concentration of compounds showed Pseudomonas Quinolone Signal (PQS) inhibitory activity suggesting that these compounds have a potential effect on pyocyanin production. Docking studies demonstrated that compounds hold binding power to all four QS protein targets (LuxP, periplasmatic protein that binds AI-2 inducer and forms a complex able to transduce the autoinducer signal, RhIR protein that is a key QS transcriptional regulator that activates the genes involved in the synthesis of rhamnolipids and pyocyanin, AbaI protein that has a role in QS signal transduction, and LasR protein which is a key QS transcriptional regulator that activates transcription of genes coding for some virulence-associated traits) while the highest binding strength is observed with compounds 2 and 6 containing single cinnamic acid fragment, suggesting their further biomedical application.
Кључне речи:
Cinnamic acid / Molecular docking / PET derivatives synthesis / Quorum sensingИзвор:
Journal of Molecular Structure, 2024, 1300, 137291-Издавач:
- Elsevier
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Škaro Bogojević, Sanja AU - Perminova, D AU - Jakšić, Jovana AU - Milčić, Miloš K. AU - Medaković, Vesna AU - Milovanović, Jelena AU - Nikodinović-Runić, Jasmina AU - Maslak, V PY - 2024 UR - http://cherry.chem.bg.ac.rs/handle/123456789/6476 AB - Poly(ethylene terephthalate) (PET) is widely used material in the healthcare due to its mechanical properties including resistance to chemicals and abrasion. However, it is susceptible to bacterial attachment and contamination. This study addresses some newly designed model compounds of PET with antimicrobial properties that could potentially be incorporated into PET materials. All compounds were synthesized for the first time by labeling an integral part of PET with chromophores in the form of esters of cinnamic and ferulic acids. After complete structural characterization, the effect of new compounds on microbial growth and communication (quorum sensing, QS) was analyzed and further investigated using molecular docking. The obtained results indicate that the introduction of chromophores that have one part of cinnamic acid enriched with a methoxy functional group in them acts as QS modulators. Moreover, compounds exhibited dose-dependent selectivity toward QS signaling pathways and the highest tested concentration of compounds showed Pseudomonas Quinolone Signal (PQS) inhibitory activity suggesting that these compounds have a potential effect on pyocyanin production. Docking studies demonstrated that compounds hold binding power to all four QS protein targets (LuxP, periplasmatic protein that binds AI-2 inducer and forms a complex able to transduce the autoinducer signal, RhIR protein that is a key QS transcriptional regulator that activates the genes involved in the synthesis of rhamnolipids and pyocyanin, AbaI protein that has a role in QS signal transduction, and LasR protein which is a key QS transcriptional regulator that activates transcription of genes coding for some virulence-associated traits) while the highest binding strength is observed with compounds 2 and 6 containing single cinnamic acid fragment, suggesting their further biomedical application. PB - Elsevier T2 - Journal of Molecular Structure T1 - Novel cinnamic acid-based PET derivatives as quorum sensing modulators VL - 1300 SP - 137291 DO - 10.1016/j.molstruc.2023.137291 ER -
@article{ author = "Škaro Bogojević, Sanja and Perminova, D and Jakšić, Jovana and Milčić, Miloš K. and Medaković, Vesna and Milovanović, Jelena and Nikodinović-Runić, Jasmina and Maslak, V", year = "2024", abstract = "Poly(ethylene terephthalate) (PET) is widely used material in the healthcare due to its mechanical properties including resistance to chemicals and abrasion. However, it is susceptible to bacterial attachment and contamination. This study addresses some newly designed model compounds of PET with antimicrobial properties that could potentially be incorporated into PET materials. All compounds were synthesized for the first time by labeling an integral part of PET with chromophores in the form of esters of cinnamic and ferulic acids. After complete structural characterization, the effect of new compounds on microbial growth and communication (quorum sensing, QS) was analyzed and further investigated using molecular docking. The obtained results indicate that the introduction of chromophores that have one part of cinnamic acid enriched with a methoxy functional group in them acts as QS modulators. Moreover, compounds exhibited dose-dependent selectivity toward QS signaling pathways and the highest tested concentration of compounds showed Pseudomonas Quinolone Signal (PQS) inhibitory activity suggesting that these compounds have a potential effect on pyocyanin production. Docking studies demonstrated that compounds hold binding power to all four QS protein targets (LuxP, periplasmatic protein that binds AI-2 inducer and forms a complex able to transduce the autoinducer signal, RhIR protein that is a key QS transcriptional regulator that activates the genes involved in the synthesis of rhamnolipids and pyocyanin, AbaI protein that has a role in QS signal transduction, and LasR protein which is a key QS transcriptional regulator that activates transcription of genes coding for some virulence-associated traits) while the highest binding strength is observed with compounds 2 and 6 containing single cinnamic acid fragment, suggesting their further biomedical application.", publisher = "Elsevier", journal = "Journal of Molecular Structure", title = "Novel cinnamic acid-based PET derivatives as quorum sensing modulators", volume = "1300", pages = "137291", doi = "10.1016/j.molstruc.2023.137291" }
Škaro Bogojević, S., Perminova, D., Jakšić, J., Milčić, M. K., Medaković, V., Milovanović, J., Nikodinović-Runić, J.,& Maslak, V.. (2024). Novel cinnamic acid-based PET derivatives as quorum sensing modulators. in Journal of Molecular Structure Elsevier., 1300, 137291. https://doi.org/10.1016/j.molstruc.2023.137291
Škaro Bogojević S, Perminova D, Jakšić J, Milčić MK, Medaković V, Milovanović J, Nikodinović-Runić J, Maslak V. Novel cinnamic acid-based PET derivatives as quorum sensing modulators. in Journal of Molecular Structure. 2024;1300:137291. doi:10.1016/j.molstruc.2023.137291 .
Škaro Bogojević, Sanja, Perminova, D, Jakšić, Jovana, Milčić, Miloš K., Medaković, Vesna, Milovanović, Jelena, Nikodinović-Runić, Jasmina, Maslak, V, "Novel cinnamic acid-based PET derivatives as quorum sensing modulators" in Journal of Molecular Structure, 1300 (2024):137291, https://doi.org/10.1016/j.molstruc.2023.137291 . .