Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds
Само за регистроване кориснике
2016
Аутори
Radivojević, JelenaŠkaro, Sanja
Šenerović, Lidija
Vasiljević, Branka
Guzik, Maciej
Kenny, Shane T.
Maslak, Veselin
Nikodinović-Runić, Jasmina
O'Connor, Kevin E.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.8-7.0 mM and 0.1-6.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in ...the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.
Кључне речи:
Polyhydroxyalkanoate / (R)-3-Hydroxyalkanoic acids / Antimicrobial activity / Chemical derivatizationИзвор:
Applied Microbiology and Biotechnology, 2016, 100, 1, 161-172Издавач:
- Springer, New York
Финансирање / пројекти:
- Изучавање микробиолошког диверзитета и карактеризација корисних срединских микроорганизама (RS-173048)
- Bioplastech Ltd., Dublin, Ireland
Напомена:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3595
DOI: 10.1007/s00253-015-6984-4
ISSN: 0175-7598
PubMed: 26399414
WoS: 000367916200013
Scopus: 2-s2.0-84952987959
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Radivojević, Jelena AU - Škaro, Sanja AU - Šenerović, Lidija AU - Vasiljević, Branka AU - Guzik, Maciej AU - Kenny, Shane T. AU - Maslak, Veselin AU - Nikodinović-Runić, Jasmina AU - O'Connor, Kevin E. PY - 2016 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2025 AB - A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.8-7.0 mM and 0.1-6.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line. PB - Springer, New York T2 - Applied Microbiology and Biotechnology T1 - Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds VL - 100 IS - 1 SP - 161 EP - 172 DO - 10.1007/s00253-015-6984-4 ER -
@article{ author = "Radivojević, Jelena and Škaro, Sanja and Šenerović, Lidija and Vasiljević, Branka and Guzik, Maciej and Kenny, Shane T. and Maslak, Veselin and Nikodinović-Runić, Jasmina and O'Connor, Kevin E.", year = "2016", abstract = "A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.8-7.0 mM and 0.1-6.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.", publisher = "Springer, New York", journal = "Applied Microbiology and Biotechnology", title = "Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds", volume = "100", number = "1", pages = "161-172", doi = "10.1007/s00253-015-6984-4" }
Radivojević, J., Škaro, S., Šenerović, L., Vasiljević, B., Guzik, M., Kenny, S. T., Maslak, V., Nikodinović-Runić, J.,& O'Connor, K. E.. (2016). Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds. in Applied Microbiology and Biotechnology Springer, New York., 100(1), 161-172. https://doi.org/10.1007/s00253-015-6984-4
Radivojević J, Škaro S, Šenerović L, Vasiljević B, Guzik M, Kenny ST, Maslak V, Nikodinović-Runić J, O'Connor KE. Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds. in Applied Microbiology and Biotechnology. 2016;100(1):161-172. doi:10.1007/s00253-015-6984-4 .
Radivojević, Jelena, Škaro, Sanja, Šenerović, Lidija, Vasiljević, Branka, Guzik, Maciej, Kenny, Shane T., Maslak, Veselin, Nikodinović-Runić, Jasmina, O'Connor, Kevin E., "Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds" in Applied Microbiology and Biotechnology, 100, no. 1 (2016):161-172, https://doi.org/10.1007/s00253-015-6984-4 . .