Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives
[Display omitted] •Thirteen novel quartenary ammonium spinosyn derivatives were synthesized.•Greatly enhanced antiproliferative activities.•Lipophicility has a great influence on the antiproliferative effects of these derivatives.•Compound 11d exhibited remarkably enhanced OXPHS inhibition and apopt...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2018-11, Vol.28 (20), p.3346-3349 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Ma, Da-You Wang, Long-Long Lai, Qin Peng, Kun-Jian Li, Xuan Li, Zeng-Xia Liu, Li-Jun Luo, Zhi-Yong Liu, Su-You |
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•Thirteen novel quartenary ammonium spinosyn derivatives were synthesized.•Greatly enhanced antiproliferative activities.•Lipophicility has a great influence on the antiproliferative effects of these derivatives.•Compound 11d exhibited remarkably enhanced OXPHS inhibition and apoptosis inducing ability.
In order to enhance the mitochondria-targeting ability of spinosad. A series of quartenary ammonium spinosyn derivatives was designed and synthesized. Some of the derivatives displayed greatly enhanced antiproliferative ability towards tested human cancer cell lines. The structure activity relationship study indicated that lipophilicity has a great influence on the antiproliferative effects of these derivatives. The most active compound 11d exhibited remarkably enhanced OXPHS inhibition and apoptosis inducing ability than spinosyn A. |
| doi_str_mv | 10.1016/j.bmcl.2018.09.005 |
| format | Article |
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•Thirteen novel quartenary ammonium spinosyn derivatives were synthesized.•Greatly enhanced antiproliferative activities.•Lipophicility has a great influence on the antiproliferative effects of these derivatives.•Compound 11d exhibited remarkably enhanced OXPHS inhibition and apoptosis inducing ability.
In order to enhance the mitochondria-targeting ability of spinosad. A series of quartenary ammonium spinosyn derivatives was designed and synthesized. Some of the derivatives displayed greatly enhanced antiproliferative ability towards tested human cancer cell lines. The structure activity relationship study indicated that lipophilicity has a great influence on the antiproliferative effects of these derivatives. The most active compound 11d exhibited remarkably enhanced OXPHS inhibition and apoptosis inducing ability than spinosyn A.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2018.09.005</identifier><identifier>PMID: 30201293</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antiproliferative activity ; Apoptosis - drug effects ; Cell Line, Tumor ; Derivatives ; Drug Screening Assays, Antitumor ; Humans ; Hydrophobic and Hydrophilic Interactions ; Macrolides - chemical synthesis ; Macrolides - chemistry ; Macrolides - pharmacology ; Mitochondria ; Mitochondria - metabolism ; Molecular Structure ; Oxidative Phosphorylation - drug effects ; Quaternary Ammonium Compounds - chemical synthesis ; Quaternary Ammonium Compounds - chemistry ; Quaternary Ammonium Compounds - pharmacology ; Respiration ; Spinosad ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2018-11, Vol.28 (20), p.3346-3349</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright © 2018 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-58ee452ba8d082b8c0fda41ecc7b07e10b6cac94f8ee6dd1f6bb48903e2bd3833</citedby><cites>FETCH-LOGICAL-c356t-58ee452ba8d082b8c0fda41ecc7b07e10b6cac94f8ee6dd1f6bb48903e2bd3833</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2018.09.005$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30201293$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ma, Da-You</creatorcontrib><creatorcontrib>Wang, Long-Long</creatorcontrib><creatorcontrib>Lai, Qin</creatorcontrib><creatorcontrib>Peng, Kun-Jian</creatorcontrib><creatorcontrib>Li, Xuan</creatorcontrib><creatorcontrib>Li, Zeng-Xia</creatorcontrib><creatorcontrib>Liu, Li-Jun</creatorcontrib><creatorcontrib>Luo, Zhi-Yong</creatorcontrib><creatorcontrib>Liu, Su-You</creatorcontrib><title>Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
•Thirteen novel quartenary ammonium spinosyn derivatives were synthesized.•Greatly enhanced antiproliferative activities.•Lipophicility has a great influence on the antiproliferative effects of these derivatives.•Compound 11d exhibited remarkably enhanced OXPHS inhibition and apoptosis inducing ability.
In order to enhance the mitochondria-targeting ability of spinosad. A series of quartenary ammonium spinosyn derivatives was designed and synthesized. Some of the derivatives displayed greatly enhanced antiproliferative ability towards tested human cancer cell lines. The structure activity relationship study indicated that lipophilicity has a great influence on the antiproliferative effects of these derivatives. The most active compound 11d exhibited remarkably enhanced OXPHS inhibition and apoptosis inducing ability than spinosyn A.</description><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antiproliferative activity</subject><subject>Apoptosis - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Derivatives</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Hydrophobic and Hydrophilic Interactions</subject><subject>Macrolides - chemical synthesis</subject><subject>Macrolides - chemistry</subject><subject>Macrolides - pharmacology</subject><subject>Mitochondria</subject><subject>Mitochondria - metabolism</subject><subject>Molecular Structure</subject><subject>Oxidative Phosphorylation - drug effects</subject><subject>Quaternary Ammonium Compounds - chemical synthesis</subject><subject>Quaternary Ammonium Compounds - chemistry</subject><subject>Quaternary Ammonium Compounds - pharmacology</subject><subject>Respiration</subject><subject>Spinosad</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1LxDAQhoMoun78AQ_So5fWSZN2U_Ai4hcIHlTwIIR8TDFLm65Ju7D_3qyrHj0Mc3nel5mHkFMKBQVaXywK3ZuuKIGKApoCoNohM8prnjMO1S6ZQVNDLhr-dkAOY1wAUA6c75MDBilUNmxG3p_XfvzA6GKmvE0zumUYOtdiUKNbYaZMWm50GLOhzfywwi77nFQY0auwzlTfD95NfRaXzg9x7TOLwa2-s_GY7LWqi3jys4_I6-3Ny_V9_vh093B99ZgbVtVjXglEXpVaCQui1MJAaxWnaMxcwxwp6Noo0_A2cbW1tK215qIBhqW2TDB2RM63ven0zwnjKHsXDXad8jhMUZYUSsbmVNQJLbeoCUOMAVu5DK5Pn0gKcmNVLuTGqtxYldDIZDWFzn76J92j_Yv8akzA5RbA9OXKYZDROPQGrQtoRmkH91__F21tjBA</recordid><startdate>20181101</startdate><enddate>20181101</enddate><creator>Ma, Da-You</creator><creator>Wang, Long-Long</creator><creator>Lai, Qin</creator><creator>Peng, Kun-Jian</creator><creator>Li, Xuan</creator><creator>Li, Zeng-Xia</creator><creator>Liu, Li-Jun</creator><creator>Luo, Zhi-Yong</creator><creator>Liu, Su-You</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20181101</creationdate><title>Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives</title><author>Ma, Da-You ; Wang, Long-Long ; Lai, Qin ; Peng, Kun-Jian ; Li, Xuan ; Li, Zeng-Xia ; Liu, Li-Jun ; Luo, Zhi-Yong ; Liu, Su-You</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-58ee452ba8d082b8c0fda41ecc7b07e10b6cac94f8ee6dd1f6bb48903e2bd3833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antiproliferative activity</topic><topic>Apoptosis - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Derivatives</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Hydrophobic and Hydrophilic Interactions</topic><topic>Macrolides - chemical synthesis</topic><topic>Macrolides - chemistry</topic><topic>Macrolides - pharmacology</topic><topic>Mitochondria</topic><topic>Mitochondria - metabolism</topic><topic>Molecular Structure</topic><topic>Oxidative Phosphorylation - drug effects</topic><topic>Quaternary Ammonium Compounds - chemical synthesis</topic><topic>Quaternary Ammonium Compounds - chemistry</topic><topic>Quaternary Ammonium Compounds - pharmacology</topic><topic>Respiration</topic><topic>Spinosad</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ma, Da-You</creatorcontrib><creatorcontrib>Wang, Long-Long</creatorcontrib><creatorcontrib>Lai, Qin</creatorcontrib><creatorcontrib>Peng, Kun-Jian</creatorcontrib><creatorcontrib>Li, Xuan</creatorcontrib><creatorcontrib>Li, Zeng-Xia</creatorcontrib><creatorcontrib>Liu, Li-Jun</creatorcontrib><creatorcontrib>Luo, Zhi-Yong</creatorcontrib><creatorcontrib>Liu, Su-You</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ma, Da-You</au><au>Wang, Long-Long</au><au>Lai, Qin</au><au>Peng, Kun-Jian</au><au>Li, Xuan</au><au>Li, Zeng-Xia</au><au>Liu, Li-Jun</au><au>Luo, Zhi-Yong</au><au>Liu, Su-You</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2018-11-01</date><risdate>2018</risdate><volume>28</volume><issue>20</issue><spage>3346</spage><epage>3349</epage><pages>3346-3349</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
•Thirteen novel quartenary ammonium spinosyn derivatives were synthesized.•Greatly enhanced antiproliferative activities.•Lipophicility has a great influence on the antiproliferative effects of these derivatives.•Compound 11d exhibited remarkably enhanced OXPHS inhibition and apoptosis inducing ability.
In order to enhance the mitochondria-targeting ability of spinosad. A series of quartenary ammonium spinosyn derivatives was designed and synthesized. Some of the derivatives displayed greatly enhanced antiproliferative ability towards tested human cancer cell lines. The structure activity relationship study indicated that lipophilicity has a great influence on the antiproliferative effects of these derivatives. The most active compound 11d exhibited remarkably enhanced OXPHS inhibition and apoptosis inducing ability than spinosyn A.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>30201293</pmid><doi>10.1016/j.bmcl.2018.09.005</doi><tpages>4</tpages></addata></record> |
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| subjects | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antiproliferative activity Apoptosis - drug effects Cell Line, Tumor Derivatives Drug Screening Assays, Antitumor Humans Hydrophobic and Hydrophilic Interactions Macrolides - chemical synthesis Macrolides - chemistry Macrolides - pharmacology Mitochondria Mitochondria - metabolism Molecular Structure Oxidative Phosphorylation - drug effects Quaternary Ammonium Compounds - chemical synthesis Quaternary Ammonium Compounds - chemistry Quaternary Ammonium Compounds - pharmacology Respiration Spinosad Structure-Activity Relationship |
| title | Synthesis and antiproliferative activities of novel quartenary ammonium spinosyn derivatives |
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