Antioxidant and Anticancer Activities of Synthesized Methylated and Acetylated Derivatives of Natural Bromophenols
Natural bromophenols are important secondary metabolites in marine algae. Derivatives of these bromophenol are potential candidates for the drug development due to their biological activities, such as antioxidant, anticancer, anti-diabetic and anti-inflammatory activity. In our present study, we hav...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-04-01
|
| Series: | Antioxidants |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2076-3921/11/4/786 |
| _version_ | 1797437067992498176 |
|---|---|
| author | Hui Dong Li Wang Meng Guo Dimitrios Stagos Antonis Giakountis Varvara Trachana Xiukun Lin Yankai Liu Ming Liu |
| author_facet | Hui Dong Li Wang Meng Guo Dimitrios Stagos Antonis Giakountis Varvara Trachana Xiukun Lin Yankai Liu Ming Liu |
| author_sort | Hui Dong |
| collection | DOAJ |
| description | Natural bromophenols are important secondary metabolites in marine algae. Derivatives of these bromophenol are potential candidates for the drug development due to their biological activities, such as antioxidant, anticancer, anti-diabetic and anti-inflammatory activity. In our present study, we have designed and synthesized a series of new methylated and acetylated bromophenol derivatives from easily available materials using simple operation procedures and evaluated their antioxidant and anticancer activities on the cellular level. The results showed that 2.,3-dibromo-1-(((2-bromo-4,5-dimethoxybenzyl)oxy)methyl)-4,5-dimethoxybenzene (<b>3b-9</b>) and (oxybis(methylene))bis(4-bromo-6-methoxy-3,1-phenylene) diacetate (<b>4b-3</b>) compounds ameliorated H<sub>2</sub>O<sub>2</sub>-induced oxidative damage and ROS generation in HaCaT keratinocytes. Compounds 2.,3-dibromo-1-(((2-bromo-4,5-dimethoxybenzyl)oxy)methyl)-4,5-dimethoxybenzene (<b>3b-9</b>) and (oxybis(methylene) )bis(4-bromo-6-methoxy-3,1-phenylene) diacetate (<b>4b-3</b>) also increased the TrxR1 and HO-1 expression while not affecting Nrf2 expression in HaCaT. In addition, compounds (oxybis(methylene)bis(2-bromo-6-methoxy-4,1-phenylene) diacetate (<b>4b</b><b>-4</b>) inhibited the viability and induced apoptosis of leukemia K562 cells while not affecting the cell cycle distribution. The present work indicated that some of these bromophenol derivatives possess significant antioxidant and anticancer potential, which merits further investigation. |
| first_indexed | 2024-03-09T11:13:39Z |
| format | Article |
| id | doaj.art-1527f6462ee4405796bf9ec1983d4f69 |
| institution | Directory Open Access Journal |
| issn | 2076-3921 |
| language | English |
| last_indexed | 2024-03-09T11:13:39Z |
| publishDate | 2022-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antioxidants |
| spelling | doaj.art-1527f6462ee4405796bf9ec1983d4f692023-12-01T00:36:53ZengMDPI AGAntioxidants2076-39212022-04-0111478610.3390/antiox11040786Antioxidant and Anticancer Activities of Synthesized Methylated and Acetylated Derivatives of Natural BromophenolsHui Dong0Li Wang1Meng Guo2Dimitrios Stagos3Antonis Giakountis4Varvara Trachana5Xiukun Lin6Yankai Liu7Ming Liu8Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaDepartment of Biochemistry and Biotechnology, University of Thessaly, Biopolis, 41500 Larissa, GreeceDepartment of Biochemistry and Biotechnology, University of Thessaly, Biopolis, 41500 Larissa, GreeceDepartment of Biology, Faculty of Medicine, School of Health Sciences, University of Thessaly, Biopolis, 41500 Larissa, GreeceDepartment of Pharmacology, School of Pharmacy, Southwest Medical University, 319 Zhongshan Road, Jiangyang, Luzhou 646000, ChinaKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaNatural bromophenols are important secondary metabolites in marine algae. Derivatives of these bromophenol are potential candidates for the drug development due to their biological activities, such as antioxidant, anticancer, anti-diabetic and anti-inflammatory activity. In our present study, we have designed and synthesized a series of new methylated and acetylated bromophenol derivatives from easily available materials using simple operation procedures and evaluated their antioxidant and anticancer activities on the cellular level. The results showed that 2.,3-dibromo-1-(((2-bromo-4,5-dimethoxybenzyl)oxy)methyl)-4,5-dimethoxybenzene (<b>3b-9</b>) and (oxybis(methylene))bis(4-bromo-6-methoxy-3,1-phenylene) diacetate (<b>4b-3</b>) compounds ameliorated H<sub>2</sub>O<sub>2</sub>-induced oxidative damage and ROS generation in HaCaT keratinocytes. Compounds 2.,3-dibromo-1-(((2-bromo-4,5-dimethoxybenzyl)oxy)methyl)-4,5-dimethoxybenzene (<b>3b-9</b>) and (oxybis(methylene) )bis(4-bromo-6-methoxy-3,1-phenylene) diacetate (<b>4b-3</b>) also increased the TrxR1 and HO-1 expression while not affecting Nrf2 expression in HaCaT. In addition, compounds (oxybis(methylene)bis(2-bromo-6-methoxy-4,1-phenylene) diacetate (<b>4b</b><b>-4</b>) inhibited the viability and induced apoptosis of leukemia K562 cells while not affecting the cell cycle distribution. The present work indicated that some of these bromophenol derivatives possess significant antioxidant and anticancer potential, which merits further investigation.https://www.mdpi.com/2076-3921/11/4/786bromophenol derivativesantioxidantanticancerK562HaCaT |
| spellingShingle | Hui Dong Li Wang Meng Guo Dimitrios Stagos Antonis Giakountis Varvara Trachana Xiukun Lin Yankai Liu Ming Liu Antioxidant and Anticancer Activities of Synthesized Methylated and Acetylated Derivatives of Natural Bromophenols Antioxidants bromophenol derivatives antioxidant anticancer K562 HaCaT |
| title | Antioxidant and Anticancer Activities of Synthesized Methylated and Acetylated Derivatives of Natural Bromophenols |
| title_full | Antioxidant and Anticancer Activities of Synthesized Methylated and Acetylated Derivatives of Natural Bromophenols |
| title_fullStr | Antioxidant and Anticancer Activities of Synthesized Methylated and Acetylated Derivatives of Natural Bromophenols |
| title_full_unstemmed | Antioxidant and Anticancer Activities of Synthesized Methylated and Acetylated Derivatives of Natural Bromophenols |
| title_short | Antioxidant and Anticancer Activities of Synthesized Methylated and Acetylated Derivatives of Natural Bromophenols |
| title_sort | antioxidant and anticancer activities of synthesized methylated and acetylated derivatives of natural bromophenols |
| topic | bromophenol derivatives antioxidant anticancer K562 HaCaT |
| url | https://www.mdpi.com/2076-3921/11/4/786 |
| work_keys_str_mv | AT huidong antioxidantandanticanceractivitiesofsynthesizedmethylatedandacetylatedderivativesofnaturalbromophenols AT liwang antioxidantandanticanceractivitiesofsynthesizedmethylatedandacetylatedderivativesofnaturalbromophenols AT mengguo antioxidantandanticanceractivitiesofsynthesizedmethylatedandacetylatedderivativesofnaturalbromophenols AT dimitriosstagos antioxidantandanticanceractivitiesofsynthesizedmethylatedandacetylatedderivativesofnaturalbromophenols AT antonisgiakountis antioxidantandanticanceractivitiesofsynthesizedmethylatedandacetylatedderivativesofnaturalbromophenols AT varvaratrachana antioxidantandanticanceractivitiesofsynthesizedmethylatedandacetylatedderivativesofnaturalbromophenols AT xiukunlin antioxidantandanticanceractivitiesofsynthesizedmethylatedandacetylatedderivativesofnaturalbromophenols AT yankailiu antioxidantandanticanceractivitiesofsynthesizedmethylatedandacetylatedderivativesofnaturalbromophenols AT mingliu antioxidantandanticanceractivitiesofsynthesizedmethylatedandacetylatedderivativesofnaturalbromophenols |