Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives.
Аутори
Đorđević Aleksić, JelenaKolarević, Stoimir
Jovanović Marić, Jovana
Novaković, Irena
Sladić, Dušan
Vuković-Gačić, Branka
Конференцијски прилог (Објављена верзија)
,
Federation of European Microbiological Societies - FEMS
Метаподаци
Приказ свих података о документуАпстракт
Background: Biologically active compounds, originating from a variety of natural sources: plants, animals and microor- ganisms, have great potential for use as antimicrobial agents. Avarol, a compound originating from the Mediterranean sponge Disidea avara, exhibits a number of biological activities including antimicrobial activity. Considering that, avarol was taken as a model for the synthesis of 2-tert-butyl-1,4-benzoquinone (TBQ) derivatives.
Objectives: TBQ was chosen because of its similar chemical structure with avarol who showed strong biological activity but is more accessible and economical than avarol. By selecting the thiol group, we aimed at combining the action of two strong functional groups of natural origin, quinones and thiols, which both have antimicrobial activity.
Methods: In this work antimicrobial activity of TBQ and its derivatives: 2-tert-butyl-5-(isopropylthio)-1.4-benzoqui- none, 2-tert-butyl-5-(propylthio)-1.4-benzoquinone, 2-tert-butyl-5,6-(ethylendithio)...-1.4-benzoquinone, 2-tert-bu- tyl-5-(phenylthio)-1.4-benzoquinone and 2-tert-butyl-6-(phenylthio)-1.4-benzoquinone was evaluated by the MIC mi- crodilution method on 7 different ATCC bacterial strains.
Results: All compounds tested showed stronger antimicrobial activity against Gram positive bacterial strains (Entero- coccus faecalis, Staphylococcus aureus, Bacillus spp.). A strong antimicrobial effect (MIC value less than 100μM) was shown by 2-tert-butyl-5,6- (ethylendithio)-1,4-benzoquinone, 2-tert-butyl-5-(phenylthio)-1.4-benzoquinone deriva- tives and 2-tert-butyl-6-(phenylthio)-1,4-benzoquinone against S.aureus. TBQ, 2-tert-butyl-5-(isopropylthio)-1,4-ben- zoquinone, 2-tert-butyl-5, 6-(ethylendithio)-1,4-benzoquinone and 2-tert-butyl-5-(phenylthio)-1.4-benzoquinone showed strong antimicrobial effect against Bacillus spp. According to our results, chemical modifications of TBQ in- crease its antimicrobial activity while derivative 2-tert-butyl-5,6-(ethylendithio)-1.4-benzoquinone is the best candi- date for further testing.
Кључне речи:
2-tert-butyl-1,4-benzoquinone / antimicrobial activity / Biologically active / avarol / Gram positive bacterial strainsИзвор:
FEMS Online Conference on Microbiology 2020, 2020, 223-Издавач:
- Federation of European Microbiological Societies - FEMS
Институција/група
Institut za multidisciplinarna istraživanjaTY - CONF AU - Đorđević Aleksić, Jelena AU - Kolarević, Stoimir AU - Jovanović Marić, Jovana AU - Novaković, Irena AU - Sladić, Dušan AU - Vuković-Gačić, Branka PY - 2020 UR - http://rimsi.imsi.bg.ac.rs/handle/123456789/2155 AB - Background: Biologically active compounds, originating from a variety of natural sources: plants, animals and microor- ganisms, have great potential for use as antimicrobial agents. Avarol, a compound originating from the Mediterranean sponge Disidea avara, exhibits a number of biological activities including antimicrobial activity. Considering that, avarol was taken as a model for the synthesis of 2-tert-butyl-1,4-benzoquinone (TBQ) derivatives. Objectives: TBQ was chosen because of its similar chemical structure with avarol who showed strong biological activity but is more accessible and economical than avarol. By selecting the thiol group, we aimed at combining the action of two strong functional groups of natural origin, quinones and thiols, which both have antimicrobial activity. Methods: In this work antimicrobial activity of TBQ and its derivatives: 2-tert-butyl-5-(isopropylthio)-1.4-benzoqui- none, 2-tert-butyl-5-(propylthio)-1.4-benzoquinone, 2-tert-butyl-5,6-(ethylendithio)-1.4-benzoquinone, 2-tert-bu- tyl-5-(phenylthio)-1.4-benzoquinone and 2-tert-butyl-6-(phenylthio)-1.4-benzoquinone was evaluated by the MIC mi- crodilution method on 7 different ATCC bacterial strains. Results: All compounds tested showed stronger antimicrobial activity against Gram positive bacterial strains (Entero- coccus faecalis, Staphylococcus aureus, Bacillus spp.). A strong antimicrobial effect (MIC value less than 100μM) was shown by 2-tert-butyl-5,6- (ethylendithio)-1,4-benzoquinone, 2-tert-butyl-5-(phenylthio)-1.4-benzoquinone deriva- tives and 2-tert-butyl-6-(phenylthio)-1,4-benzoquinone against S.aureus. TBQ, 2-tert-butyl-5-(isopropylthio)-1,4-ben- zoquinone, 2-tert-butyl-5, 6-(ethylendithio)-1,4-benzoquinone and 2-tert-butyl-5-(phenylthio)-1.4-benzoquinone showed strong antimicrobial effect against Bacillus spp. According to our results, chemical modifications of TBQ in- crease its antimicrobial activity while derivative 2-tert-butyl-5,6-(ethylendithio)-1.4-benzoquinone is the best candi- date for further testing. PB - Federation of European Microbiological Societies - FEMS C3 - FEMS Online Conference on Microbiology 2020 T1 - Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives. SP - 223 UR - https://hdl.handle.net/21.15107/rcub_rimsi_2155 ER -
@conference{ author = "Đorđević Aleksić, Jelena and Kolarević, Stoimir and Jovanović Marić, Jovana and Novaković, Irena and Sladić, Dušan and Vuković-Gačić, Branka", year = "2020", abstract = "Background: Biologically active compounds, originating from a variety of natural sources: plants, animals and microor- ganisms, have great potential for use as antimicrobial agents. Avarol, a compound originating from the Mediterranean sponge Disidea avara, exhibits a number of biological activities including antimicrobial activity. Considering that, avarol was taken as a model for the synthesis of 2-tert-butyl-1,4-benzoquinone (TBQ) derivatives. Objectives: TBQ was chosen because of its similar chemical structure with avarol who showed strong biological activity but is more accessible and economical than avarol. By selecting the thiol group, we aimed at combining the action of two strong functional groups of natural origin, quinones and thiols, which both have antimicrobial activity. Methods: In this work antimicrobial activity of TBQ and its derivatives: 2-tert-butyl-5-(isopropylthio)-1.4-benzoqui- none, 2-tert-butyl-5-(propylthio)-1.4-benzoquinone, 2-tert-butyl-5,6-(ethylendithio)-1.4-benzoquinone, 2-tert-bu- tyl-5-(phenylthio)-1.4-benzoquinone and 2-tert-butyl-6-(phenylthio)-1.4-benzoquinone was evaluated by the MIC mi- crodilution method on 7 different ATCC bacterial strains. Results: All compounds tested showed stronger antimicrobial activity against Gram positive bacterial strains (Entero- coccus faecalis, Staphylococcus aureus, Bacillus spp.). A strong antimicrobial effect (MIC value less than 100μM) was shown by 2-tert-butyl-5,6- (ethylendithio)-1,4-benzoquinone, 2-tert-butyl-5-(phenylthio)-1.4-benzoquinone deriva- tives and 2-tert-butyl-6-(phenylthio)-1,4-benzoquinone against S.aureus. TBQ, 2-tert-butyl-5-(isopropylthio)-1,4-ben- zoquinone, 2-tert-butyl-5, 6-(ethylendithio)-1,4-benzoquinone and 2-tert-butyl-5-(phenylthio)-1.4-benzoquinone showed strong antimicrobial effect against Bacillus spp. According to our results, chemical modifications of TBQ in- crease its antimicrobial activity while derivative 2-tert-butyl-5,6-(ethylendithio)-1.4-benzoquinone is the best candi- date for further testing.", publisher = "Federation of European Microbiological Societies - FEMS", journal = "FEMS Online Conference on Microbiology 2020", title = "Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives.", pages = "223", url = "https://hdl.handle.net/21.15107/rcub_rimsi_2155" }
Đorđević Aleksić, J., Kolarević, S., Jovanović Marić, J., Novaković, I., Sladić, D.,& Vuković-Gačić, B.. (2020). Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives.. in FEMS Online Conference on Microbiology 2020 Federation of European Microbiological Societies - FEMS., 223. https://hdl.handle.net/21.15107/rcub_rimsi_2155
Đorđević Aleksić J, Kolarević S, Jovanović Marić J, Novaković I, Sladić D, Vuković-Gačić B. Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives.. in FEMS Online Conference on Microbiology 2020. 2020;:223. https://hdl.handle.net/21.15107/rcub_rimsi_2155 .
Đorđević Aleksić, Jelena, Kolarević, Stoimir, Jovanović Marić, Jovana, Novaković, Irena, Sladić, Dušan, Vuković-Gačić, Branka, "Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives." in FEMS Online Conference on Microbiology 2020 (2020):223, https://hdl.handle.net/21.15107/rcub_rimsi_2155 .