Protocatechuic Acid and its Derivatives: Synthesis, Antioxidant Properties, and Potential In Vivo Wound Healing Applications

IF 3.4 4区 医学 Q2 CHEMISTRY, MEDICINAL
ChemMedChem Pub Date : 2025-08-18 DOI:10.1002/cmdc.202500280
Sumit Maurya, Sumit Manna, Mala Singh, Dharmendra Singh, Malay Nayak, Sudip Mukherjee, Arunava Manna
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引用次数: 0

Abstract

Treatment of chronic wounds is a potential healthcare problem, affecting people globally. Traditional methods of wound healing are prone to several limitations, like infections, oxidative stress, and development of secondary wounds. Management of oxidative stress is an interesting platform to deal with chronic wounds. For this study, novel derivatives of protocatechuic acid, a naturally occurring phenolic acid, were designed by modifying the carboxylic acid moiety while preserving the hydroxyl groups for radical scavenging. So, a series of amide conjugates were synthesized by incorporating various amine moieties. Glucose conjugates were obtained through both click chemistry and direct coupling strategies and a chlorinated derivative was also prepared. The antioxidant potential of the compounds was screened using DPPH assay, followed by in vitro DCFDA assay on HEK-293T cell line. Top 5 lead molecules were checked for biocompatibility through MTT assay, which provided us with top 2 leads, Compounds 12 and 17 which were examined for a wound healing study on Wistar rats along with the starting compound 1. It was observed that Compound 17 demonstrated excellent wound tissue regeneration on day 12, as compared to the control group, suggesting the promising role of triazole and glucose moieties conjugation for relieving oxidative stress and wound management.

Abstract Image

原儿茶酸及其衍生物:合成、抗氧化性能和潜在的体内伤口愈合应用。
慢性伤口的治疗是一个潜在的卫生保健问题,影响着全球人民。传统的伤口愈合方法容易受到一些限制,如感染、氧化应激和继发伤口的发展。氧化应激的管理是处理慢性伤口的一个有趣的平台。在这项研究中,原儿茶酸是一种天然存在的酚酸,通过修饰羧酸部分同时保留羟基来清除自由基,设计了新的衍生物。因此,一系列的酰胺缀合物是通过结合不同的胺基团合成的。通过点击化学和直接偶联两种方法得到了葡萄糖缀合物,并制备了氯化衍生物。采用DPPH法筛选化合物的抗氧化能力,然后在HEK-293T细胞系上进行体外DCFDA试验。通过MTT法检测前5个先导分子的生物相容性,为我们提供了前2个先导分子,化合物12和17,与起始化合物1一起用于Wistar大鼠伤口愈合研究。与对照组相比,化合物17在第12天表现出良好的伤口组织再生,这表明三唑和葡萄糖缀合物在缓解氧化应激和伤口管理方面具有良好的作用。
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来源期刊
ChemMedChem
ChemMedChem 医学-药学
CiteScore
6.70
自引率
2.90%
发文量
280
审稿时长
1 months
期刊介绍: Quality research. Outstanding publications. With an impact factor of 3.124 (2019), ChemMedChem is a top journal for research at the interface of chemistry, biology and medicine. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. ChemMedChem publishes primary as well as critical secondary and tertiary information from authors across and for the world. Its mission is to integrate the wide and flourishing field of medicinal and pharmaceutical sciences, ranging from drug design and discovery to drug development and delivery, from molecular modeling to combinatorial chemistry, from target validation to lead generation and ADMET studies. ChemMedChem typically covers topics on small molecules, therapeutic macromolecules, peptides, peptidomimetics, and aptamers, protein-drug conjugates, nucleic acid therapies, and beginning 2017, nanomedicine, particularly 1) targeted nanodelivery, 2) theranostic nanoparticles, and 3) nanodrugs. Contents ChemMedChem publishes an attractive mixture of: Full Papers and Communications Reviews and Minireviews Patent Reviews Highlights and Concepts Book and Multimedia Reviews.
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