Trolox derivatives: Synthesis, structure-activity relationship and promote wound healing by regulating oxidative stress and inflammation.

IF 4.5 2区医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Bioorganic Chemistry Pub Date : 2024-12-07 DOI:10.1016/j.bioorg.2024.108045

Jie Zhao, Shan Gao, Long Zhou, Kuanrong Rong, Fangfang Zuo, Wenjian Tang, Lili Zhu

{"title":"Trolox derivatives: Synthesis, structure-activity relationship and promote wound healing by regulating oxidative stress and inflammation.","authors":"Jie Zhao, Shan Gao, Long Zhou, Kuanrong Rong, Fangfang Zuo, Wenjian Tang, Lili Zhu","doi":"10.1016/j.bioorg.2024.108045","DOIUrl":null,"url":null,"abstract":"To find new antioxidants, 13 Trolox amides (2a-2m) and 7 Trolox esters (3a-3g) were synthesized and evaluated for their anti-inflammatory and antioxidant activity. Compounds 2e, 2i, 3b and 3d showed potent anti-inflammatory and antioxidant activity, amongst them, 3d demonstrated the most photoprotective effects on UVB-irradiated human skin keratinocyte (HaCaT) cells (IC50 = 5.13 µM) through efficiently scavenging free radicals and dose-dependently reducing reactive oxygen species (ROS) and apoptosis generation, as well as effectively promoting wound healing. 3d protected HaCaT cells against oxidative stress, inflammation and cellular damage by the activation of Nrf2/HO-1 signaling and inhibition of NF-κB pathway, further significantly improving wound healing. In acute UVB-induced skin injury mouse model, 3d significantly reduced the level of pro-inflammatory factors, improved the effect of UVB radiation on the activity of antioxidant enzymes, and maintained normal metabolic capacity. In conclusion, 3d may be a potential candidate for developing cosmetics with UVB protective effect.","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"154 ","pages":"108045"},"PeriodicalIF":4.5000,"publicationDate":"2024-12-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bioorganic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1016/j.bioorg.2024.108045","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}

引用次数: 0

Abstract

To find new antioxidants, 13 Trolox amides (2a-2m) and 7 Trolox esters (3a-3g) were synthesized and evaluated for their anti-inflammatory and antioxidant activity. Compounds 2e, 2i, 3b and 3d showed potent anti-inflammatory and antioxidant activity, amongst them, 3d demonstrated the most photoprotective effects on UVB-irradiated human skin keratinocyte (HaCaT) cells (IC₅₀ = 5.13 µM) through efficiently scavenging free radicals and dose-dependently reducing reactive oxygen species (ROS) and apoptosis generation, as well as effectively promoting wound healing. 3d protected HaCaT cells against oxidative stress, inflammation and cellular damage by the activation of Nrf2/HO-1 signaling and inhibition of NF-κB pathway, further significantly improving wound healing. In acute UVB-induced skin injury mouse model, 3d significantly reduced the level of pro-inflammatory factors, improved the effect of UVB radiation on the activity of antioxidant enzymes, and maintained normal metabolic capacity. In conclusion, 3d may be a potential candidate for developing cosmetics with UVB protective effect.

查看原文本刊更多论文

求助全文

约1分钟内获得全文求助全文

来源期刊

Bioorganic Chemistry 生物-生化与分子生物学

CiteScore

9.70

自引率

3.90%

发文量

679

审稿时长

31 days

期刊介绍： Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry. For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature. The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.