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具有抗感染、抗炎和伤口愈合特性的基于缩水甘油基-d-色氨酸醚的软膏。

-Glycidyl d-tryptophan ether-based ointment with anti-infective, anti-inflammatory, and wound-healing properties.

作者信息

Mahata Denial, Jana Malabendu, Mondal Suresh K, Manna Sounik, Jana Arundhuti, Chakraborty Anirban, Ghosh Ananta K, Chakraborty Ranadhir, Hazra Tapas K, Mandal Santi M

机构信息

Department of Bioscience and Biotechnology, Indian Institute of Technology Kharagpur Kharagpur 721302 WB India

Department of Neurological Sciences, Rush University Medical Centre Chicago IL USA.

出版信息

RSC Med Chem. 2025 Jan 20. doi: 10.1039/d4md00878b.


DOI:10.1039/d4md00878b
PMID:39935521
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11808565/
Abstract

Anti-infective hydrogel is an emerging and innovative material used as an antibacterial ointment or to coat medical devices. Here, we synthesized a novel derivative of -glycidyl d-tryptophan ether using the d-isoform of tryptophan through a ring-opening polymerization reaction. The compound was characterized using gel permeation chromatography (GPC), HPLC, H NMR, C NMR, MALDI-TOF-MS, and FTIR spectroscopy. The results demonstrated its antibacterial activity by inhibiting quorum sensing and subsequent biofilm formation. studies revealed the ability of the compound to promote wound healing by reducing inflammatory cytokine levels, such as tumor necrosis factor alpha, interleukin-1β, and IL-6. Moreover, the compound showed antioxidant activity by scavenging the DPPH radical due to the presence of polymeric hydroxyl acidic protons near the nitrogen. Since inflammation prompted ROS-initiated DNA strand breaks, it was also confirmed that the compound could reduce DNA strand break accumulation, as demonstrated through testing against bleomycin-induced DNA strand break accumulation. Therefore, the synthesized compound, which could be used as a base material for ointments, was found to be effective for antibacterial and wound healing actions by (a) inhibiting biofilm formation by bacteria, (b) reducing the expression of inflammatory cytokines, and (c) preventing the accumulation of DNA strand breaks through free-radical scavenging activity.

摘要

抗感染水凝胶是一种新兴的创新材料,可作为抗菌软膏或用于包覆医疗设备。在此,我们通过开环聚合反应,使用色氨酸的d-异构体合成了一种新型的-缩水甘油基-d-色氨酸醚衍生物。该化合物通过凝胶渗透色谱法(GPC)、高效液相色谱法(HPLC)、核磁共振氢谱(1H NMR)、核磁共振碳谱(13C NMR)、基质辅助激光解吸电离飞行时间质谱(MALDI-TOF-MS)和傅里叶变换红外光谱(FTIR)进行表征。结果表明,它通过抑制群体感应和随后的生物膜形成展现出抗菌活性。研究揭示了该化合物通过降低炎症细胞因子水平(如肿瘤坏死因子-α、白细胞介素-1β和白细胞介素-6)来促进伤口愈合的能力。此外,由于氮附近存在聚合羟基酸性质子,该化合物通过清除二苯基苦味酰基自由基显示出抗氧化活性。由于炎症会促使活性氧引发DNA链断裂,通过针对博来霉素诱导的DNA链断裂积累进行测试也证实,该化合物可以减少DNA链断裂的积累。因此,发现这种可作为软膏基础材料的合成化合物通过(a)抑制细菌生物膜形成、(b)降低炎症细胞因子的表达以及(c)通过自由基清除活性防止DNA链断裂的积累,在抗菌和伤口愈合方面具有效果。

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本文引用的文献

[1]
-Tryptophan suppresses enteric pathogen and pathobionts and prevents colitis by modulating microbial tryptophan metabolism.

iScience. 2022-8-3

[2]
Antibacterial Properties of D-Amino Acid Oxidase: Impact on the Food Industry.

Front Microbiol. 2019-12-3

[3]
Fluoroquinolone antibiotics show genotoxic effect through DNA-binding and oxidative damage.

Spectrochim Acta A Mol Biomol Spectrosc. 2020-2-15

[4]
Surface treatment strategies to combat implant-related infection from the beginning.

J Orthop Translat. 2018-9-28

[5]
Curd-Peptide Based Novel Hydrogel Inhibits Biofilm Formation, Quorum Sensing, Swimming Mortility of Multi-Antibiotic Resistant Clinical Isolates and Accelerates Wound Healing Activity.

Front Microbiol. 2019-5-14

[6]
Molecular self-assembly of copolymer from renewable phenols: new class of antimicrobial ointment base.

J Biomater Sci Polym Ed. 2018-11-13

[7]
Synthesis and Characterization of Lignin Hydrogels for Potential Applications as Drug Eluting Antimicrobial Coatings for Medical Materials.

ACS Sustain Chem Eng. 2018-7-2

[8]
Self-Assembled Tea Tannin Graft Copolymer as Nanocarriers for Antimicrobial Drug Delivery and Wound Healing Activity.

J Nanosci Nanotechnol. 2018-4-1

[9]
Bacterial secretion of D-arginine controls environmental microbial biodiversity.

ISME J. 2017-10-13

[10]
Lignin-graft-Polyoxazoline Conjugated Triazole a Novel Anti-Infective Ointment to Control Persistent Inflammation.

Sci Rep. 2017-4-12

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