Evaluation of antioxidant and cytotoxic properties of phenolic N-acylhydrazones: structure–activity relationship
Cancer is still a relentless public health issue. Particularly, colorectal cancer is the third most prevalent cancer in men and the second in women. Moreover, cancer development and growth are associated with various cell disorders, such as oxidative stress and inflammation. The quest for efficient...
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| Format: | Article |
| Language: | English |
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The Royal Society
2022-06-01
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| Series: | Royal Society Open Science |
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| Online Access: | https://royalsocietypublishing.org/doi/10.1098/rsos.211853 |
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| author | Jovica Branković Nevena Milivojević Vesna Milovanović Dušica Simijonović Zorica D. Petrović Zoran Marković Dragana S. Šeklić Marko N. Živanović Milena D. Vukić Vladimir P. Petrović |
| author_facet | Jovica Branković Nevena Milivojević Vesna Milovanović Dušica Simijonović Zorica D. Petrović Zoran Marković Dragana S. Šeklić Marko N. Živanović Milena D. Vukić Vladimir P. Petrović |
| author_sort | Jovica Branković |
| collection | DOAJ |
| description | Cancer is still a relentless public health issue. Particularly, colorectal cancer is the third most prevalent cancer in men and the second in women. Moreover, cancer development and growth are associated with various cell disorders, such as oxidative stress and inflammation. The quest for efficient therapeutics is a challenging task, especially when it comes to achieving both cytotoxicity and selectivity. Herein, five series of phenolic N-acylhydrazones were synthesized and evaluated for their antioxidant potency, as well as their influence on HCT-116 and MRC-5 cells viability. Among 40 examined analogues, 20 of them expressed antioxidant activity against the DPPH radical. Furthermore, density functional theory was employed to estimate the antioxidant potency of the selected analogues from the thermodynamical aspect, as well as the preferable free-radical scavenging pathway. Cytotoxicity assay exposed enhanced selectivity of a number of analogues toward cancer cells. The structure–activity analysis revealed the impact of the type and position of the functional groups on both cell viability and selectivity toward cancer cells. |
| first_indexed | 2024-04-09T15:28:14Z |
| format | Article |
| id | doaj.art-aabfbbf8f354413c9f0fa57ba0912ff4 |
| institution | Directory Open Access Journal |
| issn | 2054-5703 |
| language | English |
| last_indexed | 2024-04-09T15:28:14Z |
| publishDate | 2022-06-01 |
| publisher | The Royal Society |
| record_format | Article |
| series | Royal Society Open Science |
| spelling | doaj.art-aabfbbf8f354413c9f0fa57ba0912ff42023-04-28T10:52:23ZengThe Royal SocietyRoyal Society Open Science2054-57032022-06-019610.1098/rsos.211853Evaluation of antioxidant and cytotoxic properties of phenolic N-acylhydrazones: structure–activity relationshipJovica Branković0Nevena Milivojević1Vesna Milovanović2Dušica Simijonović3Zorica D. Petrović4Zoran Marković5Dragana S. Šeklić6Marko N. Živanović7Milena D. Vukić8Vladimir P. Petrović9University of Kragujevac, Faculty of Science, Department of Chemistry, R. Domanovića 12, 34000 Kragujevac, SerbiaUniversity of Kragujevac, Institute for Information Technologies, Kragujevac, Department of Science, Jovana Cvijića bb, 34000 Kragujevac, SerbiaUniversity of Kragujevac, Faculty of Agronomy in Čačak, Ljubićska 30, Čačak, SerbiaUniversity of Kragujevac, Institute for Information Technologies, Kragujevac, Department of Science, Jovana Cvijića bb, 34000 Kragujevac, SerbiaUniversity of Kragujevac, Faculty of Science, Department of Chemistry, R. Domanovića 12, 34000 Kragujevac, SerbiaUniversity of Kragujevac, Institute for Information Technologies, Kragujevac, Department of Science, Jovana Cvijića bb, 34000 Kragujevac, SerbiaUniversity of Kragujevac, Institute for Information Technologies, Kragujevac, Department of Science, Jovana Cvijića bb, 34000 Kragujevac, SerbiaUniversity of Kragujevac, Institute for Information Technologies, Kragujevac, Department of Science, Jovana Cvijića bb, 34000 Kragujevac, SerbiaUniversity of Kragujevac, Faculty of Science, Department of Chemistry, R. Domanovića 12, 34000 Kragujevac, SerbiaUniversity of Kragujevac, Faculty of Science, Department of Chemistry, R. Domanovića 12, 34000 Kragujevac, SerbiaCancer is still a relentless public health issue. Particularly, colorectal cancer is the third most prevalent cancer in men and the second in women. Moreover, cancer development and growth are associated with various cell disorders, such as oxidative stress and inflammation. The quest for efficient therapeutics is a challenging task, especially when it comes to achieving both cytotoxicity and selectivity. Herein, five series of phenolic N-acylhydrazones were synthesized and evaluated for their antioxidant potency, as well as their influence on HCT-116 and MRC-5 cells viability. Among 40 examined analogues, 20 of them expressed antioxidant activity against the DPPH radical. Furthermore, density functional theory was employed to estimate the antioxidant potency of the selected analogues from the thermodynamical aspect, as well as the preferable free-radical scavenging pathway. Cytotoxicity assay exposed enhanced selectivity of a number of analogues toward cancer cells. The structure–activity analysis revealed the impact of the type and position of the functional groups on both cell viability and selectivity toward cancer cells.https://royalsocietypublishing.org/doi/10.1098/rsos.211853phenolic N-acylhydrazonesantioxidant activitycytotoxic activitystructure–activity relationshipdensity functional theory |
| spellingShingle | Jovica Branković Nevena Milivojević Vesna Milovanović Dušica Simijonović Zorica D. Petrović Zoran Marković Dragana S. Šeklić Marko N. Živanović Milena D. Vukić Vladimir P. Petrović Evaluation of antioxidant and cytotoxic properties of phenolic N-acylhydrazones: structure–activity relationship Royal Society Open Science phenolic N-acylhydrazones antioxidant activity cytotoxic activity structure–activity relationship density functional theory |
| title | Evaluation of antioxidant and cytotoxic properties of phenolic N-acylhydrazones: structure–activity relationship |
| title_full | Evaluation of antioxidant and cytotoxic properties of phenolic N-acylhydrazones: structure–activity relationship |
| title_fullStr | Evaluation of antioxidant and cytotoxic properties of phenolic N-acylhydrazones: structure–activity relationship |
| title_full_unstemmed | Evaluation of antioxidant and cytotoxic properties of phenolic N-acylhydrazones: structure–activity relationship |
| title_short | Evaluation of antioxidant and cytotoxic properties of phenolic N-acylhydrazones: structure–activity relationship |
| title_sort | evaluation of antioxidant and cytotoxic properties of phenolic n acylhydrazones structure activity relationship |
| topic | phenolic N-acylhydrazones antioxidant activity cytotoxic activity structure–activity relationship density functional theory |
| url | https://royalsocietypublishing.org/doi/10.1098/rsos.211853 |
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