Synthesis and biological evaluation of diarylheptanoids as potential antioxidant and anti-inflammatory agents
Reactive oxygen species (ROS) are key signaling molecules and their overproduction plays an important role in the inflammation process, the secretion of inflammatory cytokines such as IL-1β and IL-6 and the progression of inflammatory disorders. Decreasing oxidative stress represents a promising cha...
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| Veröffentlicht in: | European journal of medicinal chemistry 2018-01, Vol.144 (7), p.289-299 |
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| container_title | European journal of medicinal chemistry |
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| creator | Maurent, Kelly Vanucci-Bacqué, Corinne Baltas, Michel Nègre-Salvayre, Anne Augé, Nathalie Bedos-Belval, Florence |
| description | Reactive oxygen species (ROS) are key signaling molecules and their overproduction plays an important role in the inflammation process, the secretion of inflammatory cytokines such as IL-1β and IL-6 and the progression of inflammatory disorders. Decreasing oxidative stress represents a promising challenge in the design of antioxidant and anti-inflammatory agents. In the present study, a series of new diarylheptanoids containing allylic alcohol, amide, hydantoin or triazole fragments were synthesized and fully characterized. We evaluated the ability of these agents to block the production of intracellular ROS and the subsequent inflammatory events exerted by lipopolysaccharide (LPS) on murine macrophage RAW 264.7. Five diarylheptanoids were found to exhibit the dual required properties.
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•A series of macrocyclic and acyclic diaryl heptanoids were synthesized.•Antioxidant and anti-inflammatory effects of synthesized agents were investigated.•Five diaryl heptanoid exhibit promising dual required properties. |
| doi_str_mv | 10.1016/j.ejmech.2017.12.033 |
| format | Article |
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•A series of macrocyclic and acyclic diaryl heptanoids were synthesized.•Antioxidant and anti-inflammatory effects of synthesized agents were investigated.•Five diaryl heptanoid exhibit promising dual required properties.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2017.12.033</identifier><identifier>PMID: 29275229</identifier><language>eng</language><publisher>France: Elsevier Masson SAS</publisher><subject>Anti-inflammatory activity ; Antioxidant ; Chemical Sciences ; Diarylheptanoid ; Life Sciences ; Macrocycle ; Pharmaceutical sciences</subject><ispartof>European journal of medicinal chemistry, 2018-01, Vol.144 (7), p.289-299</ispartof><rights>2017 Elsevier Masson SAS</rights><rights>Copyright © 2017 Elsevier Masson SAS. All rights reserved.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c442t-2490131bce3b490cdd161b7fc8bf675e844be08e5d6ccc1278b26c8d976a6bee3</citedby><cites>FETCH-LOGICAL-c442t-2490131bce3b490cdd161b7fc8bf675e844be08e5d6ccc1278b26c8d976a6bee3</cites><orcidid>0000-0002-7232-6267 ; 0000-0002-6792-6815 ; 0000-0002-8785-7095</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2017.12.033$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,315,781,785,886,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29275229$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-03118254$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Maurent, Kelly</creatorcontrib><creatorcontrib>Vanucci-Bacqué, Corinne</creatorcontrib><creatorcontrib>Baltas, Michel</creatorcontrib><creatorcontrib>Nègre-Salvayre, Anne</creatorcontrib><creatorcontrib>Augé, Nathalie</creatorcontrib><creatorcontrib>Bedos-Belval, Florence</creatorcontrib><title>Synthesis and biological evaluation of diarylheptanoids as potential antioxidant and anti-inflammatory agents</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Reactive oxygen species (ROS) are key signaling molecules and their overproduction plays an important role in the inflammation process, the secretion of inflammatory cytokines such as IL-1β and IL-6 and the progression of inflammatory disorders. Decreasing oxidative stress represents a promising challenge in the design of antioxidant and anti-inflammatory agents. In the present study, a series of new diarylheptanoids containing allylic alcohol, amide, hydantoin or triazole fragments were synthesized and fully characterized. We evaluated the ability of these agents to block the production of intracellular ROS and the subsequent inflammatory events exerted by lipopolysaccharide (LPS) on murine macrophage RAW 264.7. Five diarylheptanoids were found to exhibit the dual required properties.
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•A series of macrocyclic and acyclic diaryl heptanoids were synthesized.•Antioxidant and anti-inflammatory effects of synthesized agents were investigated.•Five diaryl heptanoid exhibit promising dual required properties.</description><subject>Anti-inflammatory activity</subject><subject>Antioxidant</subject><subject>Chemical Sciences</subject><subject>Diarylheptanoid</subject><subject>Life Sciences</subject><subject>Macrocycle</subject><subject>Pharmaceutical sciences</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9kUtv1DAUhS0EotPCP0AoS7pI8LUTJ9lUqqo-kEZiAawtP246HjnxNPaMOv8eT1O6ZHVs67vnWPcQ8gVoBRTE922F2xHNpmIU2gpYRTl_R1bQiq7krKnfkxVljJcN4_UZOY9xSyltBKUfyRnrWdsw1q_I-Os4pQ1GFws12UK74MOjM8oXeFB-r5ILUxGGwjo1H_0Gd0lNwdlMx2IXEk7JZVZlCc_OZn2xOd1LNw1ejaNKYT4W6jGj8RP5MCgf8fOrXpA_d7e_bx7K9c_7HzfX69LUNUslq3sKHLRBrvPRWAsCdDuYTg-ibbCra420w8YKYwywttNMmM72rVBCI_ILcrn4bpSXu9mN-fMyKCcfrtfy9EY5QJeXdIDMflvY3Rye9hiTHF006L2aMOyjhL6jQHnftBmtF9TMIcYZhzdvoPJUitzKpRR5KkUCy0E8j319TdjrEe3b0L8WMnC1AJh3cnA4y2gcTgatm9EkaYP7f8JfQJqhWg</recordid><startdate>20180120</startdate><enddate>20180120</enddate><creator>Maurent, Kelly</creator><creator>Vanucci-Bacqué, Corinne</creator><creator>Baltas, Michel</creator><creator>Nègre-Salvayre, Anne</creator><creator>Augé, Nathalie</creator><creator>Bedos-Belval, Florence</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-7232-6267</orcidid><orcidid>https://orcid.org/0000-0002-6792-6815</orcidid><orcidid>https://orcid.org/0000-0002-8785-7095</orcidid></search><sort><creationdate>20180120</creationdate><title>Synthesis and biological evaluation of diarylheptanoids as potential antioxidant and anti-inflammatory agents</title><author>Maurent, Kelly ; Vanucci-Bacqué, Corinne ; Baltas, Michel ; Nègre-Salvayre, Anne ; Augé, Nathalie ; Bedos-Belval, Florence</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c442t-2490131bce3b490cdd161b7fc8bf675e844be08e5d6ccc1278b26c8d976a6bee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Anti-inflammatory activity</topic><topic>Antioxidant</topic><topic>Chemical Sciences</topic><topic>Diarylheptanoid</topic><topic>Life Sciences</topic><topic>Macrocycle</topic><topic>Pharmaceutical sciences</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Maurent, Kelly</creatorcontrib><creatorcontrib>Vanucci-Bacqué, Corinne</creatorcontrib><creatorcontrib>Baltas, Michel</creatorcontrib><creatorcontrib>Nègre-Salvayre, Anne</creatorcontrib><creatorcontrib>Augé, Nathalie</creatorcontrib><creatorcontrib>Bedos-Belval, Florence</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Maurent, Kelly</au><au>Vanucci-Bacqué, Corinne</au><au>Baltas, Michel</au><au>Nègre-Salvayre, Anne</au><au>Augé, Nathalie</au><au>Bedos-Belval, Florence</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological evaluation of diarylheptanoids as potential antioxidant and anti-inflammatory agents</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2018-01-20</date><risdate>2018</risdate><volume>144</volume><issue>7</issue><spage>289</spage><epage>299</epage><pages>289-299</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><abstract>Reactive oxygen species (ROS) are key signaling molecules and their overproduction plays an important role in the inflammation process, the secretion of inflammatory cytokines such as IL-1β and IL-6 and the progression of inflammatory disorders. Decreasing oxidative stress represents a promising challenge in the design of antioxidant and anti-inflammatory agents. In the present study, a series of new diarylheptanoids containing allylic alcohol, amide, hydantoin or triazole fragments were synthesized and fully characterized. We evaluated the ability of these agents to block the production of intracellular ROS and the subsequent inflammatory events exerted by lipopolysaccharide (LPS) on murine macrophage RAW 264.7. Five diarylheptanoids were found to exhibit the dual required properties.
[Display omitted]
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| source | Access via ScienceDirect (Elsevier) |
| subjects | Anti-inflammatory activity Antioxidant Chemical Sciences Diarylheptanoid Life Sciences Macrocycle Pharmaceutical sciences |
| title | Synthesis and biological evaluation of diarylheptanoids as potential antioxidant and anti-inflammatory agents |
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