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Current OA management requires a combination of pharmaceutical and non-pharmacological strategies, including intraarticular injections of hyaluronic acid (HA). However, several lines of evidence reported that HA oxidation by reactive oxygen species (ROS) is linked with HA cleavage and fragmentation, resulting in reduced HA viscosity. Resolvin D1 (RvD1) is a lipid mediator that is biosynthesized from omega-3 polyunsaturated fatty acids and is a good candidate with the potential to regulate a panoply of biological processes, including tissue repair, inflammation, oxidative stress, and cell death in OA. Herein, newly designed and synthesized imidazole-derived RvD1 analogues were introduced to compare their potential antioxidant properties with commercially available RvD1. Their antioxidant capacities were investigated by several in vitro chemical assays including oxygen radical absorbance capacity, 2,2-diphenyl-1-picrylhydrazyl radical scavenging, ferric ion reducing antioxidant power, hydroxyl radical scavenging, and HA fragmentation assay. All results proved that imidazole-derived RvD1 analogues showed excellent antioxidant performance compared to RvD1 due to their structural modifications. Interestingly, they scavenged the formed reactive oxygen species (ROS) and protected HA from degradation, as verified by agarose gel electrophoresis and gel permission chromatography. A computational study using Gaussian 09 with DFT calculations and a B3LYP\/6-31 G (d, p) basis set was also employed to study the relationship between the antioxidant properties and chemical structures as well as calculation of the molecular structures, frontier orbital energy, molecular electrostatic potential, and bond length. The results showed that the antioxidant activity of our analogues was higher than that of RvD1. In conclusion, the findings suggest that imidazole-derived RvD1 analogues can be good candidates as antioxidant molecules for the treatment of oxidative stress-related diseases like OA. Therefore, they can prolong the longevity of HA in the knee and thus may improve the mobility of the articulation.<\/jats:p>","DOI":"10.3390\/antiox13040386","type":"journal-article","created":{"date-parts":[[2024,3,22]],"date-time":"2024-03-22T10:03:59Z","timestamp":1711101839000},"page":"386","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Development of New Resolvin D1 Analogues for Osteoarthritis Therapy: Acellular and Computational Approaches to Study Their Antioxidant Activities"],"prefix":"10.3390","volume":"13","author":[{"ORCID":"https:\/\/orcid.org\/0009-0006-1070-9453","authenticated-orcid":false,"given":"Zahra","family":"Kariminezhad","sequence":"first","affiliation":[{"name":"Orthopedic Research Laboratory, H\u00f4pital du Sacr\u00e9-C\u0153ur de Montr\u00e9al, Universit\u00e9 de Montr\u00e9al, Montr\u00e9al, QC H4J 1C5, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3589-6463","authenticated-orcid":false,"given":"Mahdi","family":"Rahimi","sequence":"additional","affiliation":[{"name":"Orthopedic Research Laboratory, H\u00f4pital du Sacr\u00e9-C\u0153ur de Montr\u00e9al, Universit\u00e9 de Montr\u00e9al, Montr\u00e9al, QC H4J 1C5, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Julio","family":"Fernandes","sequence":"additional","affiliation":[{"name":"Orthopedic Research Laboratory, H\u00f4pital du Sacr\u00e9-C\u0153ur de Montr\u00e9al, Universit\u00e9 de Montr\u00e9al, Montr\u00e9al, QC H4J 1C5, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0394-1653","authenticated-orcid":false,"given":"Ren\u00e9","family":"Maltais","sequence":"additional","affiliation":[{"name":"Department of Molecular Medicine, Faculty of Medicine, Universit\u00e9 Laval, Qu\u00e9bec, QC G1V 0A6, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4340-7284","authenticated-orcid":false,"given":"Jean-Yves","family":"Sanc\u00e9au","sequence":"additional","affiliation":[{"name":"Department of Molecular Medicine, Faculty of Medicine, Universit\u00e9 Laval, Qu\u00e9bec, QC G1V 0A6, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Donald","family":"Poirier","sequence":"additional","affiliation":[{"name":"Department of Molecular Medicine, Faculty of Medicine, Universit\u00e9 Laval, Qu\u00e9bec, QC G1V 0A6, Canada"},{"name":"Organic Synthesis Service, Medicinal Chemistry Platform, CHU de Qu\u00e9bec Research Center, Universit\u00e9 Laval, Qu\u00e9bec, QC G1V 4G2, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hassan","family":"Fahmi","sequence":"additional","affiliation":[{"name":"Osteoarthritis Research Unit, University of Montreal Hospital Research Center (CRCHUM), Montr\u00e9al, QC H2X 0A9, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohamed","family":"Benderdour","sequence":"additional","affiliation":[{"name":"Orthopedic Research Laboratory, H\u00f4pital du Sacr\u00e9-C\u0153ur de Montr\u00e9al, Universit\u00e9 de Montr\u00e9al, Montr\u00e9al, QC H4J 1C5, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,3,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/j.reth.2020.07.007","article-title":"Degenerative osteoarthritis a reversible chronic disease","volume":"15","year":"2020","journal-title":"Regen. 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