Inhibitory effect of novel 5- O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response
We previously found that vitamin K 3 (menadione, 2-methyl-1,4-naphthoquinone) inhibits the activity of human mitochondrial DNA polymerase γ (pol γ). In this study, we focused on juglone (5-hydroxy-1,4-naphthoquinone), which is a 1,4-naphthoquinone derivative, and chemically synthesized novel juglone...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2011-10, Vol.19 (19), p.5803-5812 |
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| creator | Maruo, Sayako Kuriyama, Isoko Kuramochi, Kouji Tsubaki, Kazunori Yoshida, Hiromi Mizushina, Yoshiyuki |
| description | We previously found that vitamin K
3 (menadione, 2-methyl-1,4-naphthoquinone) inhibits the activity of human mitochondrial DNA polymerase γ (pol γ). In this study, we focused on juglone (5-hydroxy-1,4-naphthoquinone), which is a 1,4-naphthoquinone derivative, and chemically synthesized novel juglones conjugated with C2:0 to C22:6 fatty acid (5-
O-acyl juglones). The chemically modified juglones enhanced mammalian pol inhibition and their cytotoxic and anti-inflammatory activities. The juglone conjugated with oleic acid (C18:1-acyl juglone) showed the strongest inhibition of DNA replicative pol α activity and human colon carcinoma (HCT116) cell growth in 10 synthesized 5-
O-acyl juglones. C12:0-Acyl juglone was the strongest inhibitor of DNA repair-related pol λ, as well as the strongest suppression of the production of tumor necrosis factor (TNF)-α production induced by lipopolysaccharide (LPS) in the compounds tested. Moreover, this compound caused the greatest reduction in 12-
O-tetradecanoylphorbol-13-acetate (TPA)-induced acute inflammation in mouse ears. C12:0- and C18:1-Acyl juglones selectively inhibited the activities of mammalian pol species, but did not influence the activities of other pols and DNA metabolic enzymes tested. These data indicate that the novel 5-
O-acyl juglones target anti-cancer and/or anti-inflammatory agents based on mammalian pol inhibition. Moreover, the results suggest that acylation of juglone is an effective chemical modification to improve the anti-cancer and anti-inflammation of vitamin K
3 derivatives, such as juglone. |
| doi_str_mv | 10.1016/j.bmc.2011.08.023 |
| format | Article |
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3 (menadione, 2-methyl-1,4-naphthoquinone) inhibits the activity of human mitochondrial DNA polymerase γ (pol γ). In this study, we focused on juglone (5-hydroxy-1,4-naphthoquinone), which is a 1,4-naphthoquinone derivative, and chemically synthesized novel juglones conjugated with C2:0 to C22:6 fatty acid (5-
O-acyl juglones). The chemically modified juglones enhanced mammalian pol inhibition and their cytotoxic and anti-inflammatory activities. The juglone conjugated with oleic acid (C18:1-acyl juglone) showed the strongest inhibition of DNA replicative pol α activity and human colon carcinoma (HCT116) cell growth in 10 synthesized 5-
O-acyl juglones. C12:0-Acyl juglone was the strongest inhibitor of DNA repair-related pol λ, as well as the strongest suppression of the production of tumor necrosis factor (TNF)-α production induced by lipopolysaccharide (LPS) in the compounds tested. Moreover, this compound caused the greatest reduction in 12-
O-tetradecanoylphorbol-13-acetate (TPA)-induced acute inflammation in mouse ears. C12:0- and C18:1-Acyl juglones selectively inhibited the activities of mammalian pol species, but did not influence the activities of other pols and DNA metabolic enzymes tested. These data indicate that the novel 5-
O-acyl juglones target anti-cancer and/or anti-inflammatory agents based on mammalian pol inhibition. Moreover, the results suggest that acylation of juglone is an effective chemical modification to improve the anti-cancer and anti-inflammation of vitamin K
3 derivatives, such as juglone.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2011.08.023</identifier><identifier>PMID: 21903399</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>5- O-Acyl juglone ; acylation ; Animals ; Anti-cancer ; Anti-inflammation ; anti-inflammatory activity ; anti-inflammatory agents ; Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - therapeutic use ; Anti-Inflammatory Agents - toxicity ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - toxicity ; cell growth ; Cell Line, Tumor ; colorectal neoplasms ; cytotoxicity ; DNA polymerase ; DNA Polymerase beta - antagonists & inhibitors ; DNA Polymerase beta - metabolism ; DNA-directed DNA polymerase ; ears ; Enzyme inhibitor ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - therapeutic use ; Enzyme Inhibitors - toxicity ; Humans ; inflammation ; Inflammation - chemically induced ; Inflammation - drug therapy ; juglone ; lipopolysaccharides ; Lipopolysaccharides - toxicity ; menadione ; Mice ; mitochondrial DNA ; Naphthoquinones - chemistry ; Naphthoquinones - therapeutic use ; Naphthoquinones - toxicity ; oleic acid ; Tetradecanoylphorbol Acetate - toxicity ; Tumor Necrosis Factor-alpha - metabolism ; tumor necrosis factors</subject><ispartof>Bioorganic & medicinal chemistry, 2011-10, Vol.19 (19), p.5803-5812</ispartof><rights>2011 Elsevier Ltd</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c474t-e4ead14765d48ff03a98a20e35337653d19a61ed81963ea28ccc843c31a400383</citedby><cites>FETCH-LOGICAL-c474t-e4ead14765d48ff03a98a20e35337653d19a61ed81963ea28ccc843c31a400383</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089611006572$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21903399$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Maruo, Sayako</creatorcontrib><creatorcontrib>Kuriyama, Isoko</creatorcontrib><creatorcontrib>Kuramochi, Kouji</creatorcontrib><creatorcontrib>Tsubaki, Kazunori</creatorcontrib><creatorcontrib>Yoshida, Hiromi</creatorcontrib><creatorcontrib>Mizushina, Yoshiyuki</creatorcontrib><title>Inhibitory effect of novel 5- O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>We previously found that vitamin K
3 (menadione, 2-methyl-1,4-naphthoquinone) inhibits the activity of human mitochondrial DNA polymerase γ (pol γ). In this study, we focused on juglone (5-hydroxy-1,4-naphthoquinone), which is a 1,4-naphthoquinone derivative, and chemically synthesized novel juglones conjugated with C2:0 to C22:6 fatty acid (5-
O-acyl juglones). The chemically modified juglones enhanced mammalian pol inhibition and their cytotoxic and anti-inflammatory activities. The juglone conjugated with oleic acid (C18:1-acyl juglone) showed the strongest inhibition of DNA replicative pol α activity and human colon carcinoma (HCT116) cell growth in 10 synthesized 5-
O-acyl juglones. C12:0-Acyl juglone was the strongest inhibitor of DNA repair-related pol λ, as well as the strongest suppression of the production of tumor necrosis factor (TNF)-α production induced by lipopolysaccharide (LPS) in the compounds tested. Moreover, this compound caused the greatest reduction in 12-
O-tetradecanoylphorbol-13-acetate (TPA)-induced acute inflammation in mouse ears. C12:0- and C18:1-Acyl juglones selectively inhibited the activities of mammalian pol species, but did not influence the activities of other pols and DNA metabolic enzymes tested. These data indicate that the novel 5-
O-acyl juglones target anti-cancer and/or anti-inflammatory agents based on mammalian pol inhibition. Moreover, the results suggest that acylation of juglone is an effective chemical modification to improve the anti-cancer and anti-inflammation of vitamin K
3 derivatives, such as juglone.</description><subject>5- O-Acyl juglone</subject><subject>acylation</subject><subject>Animals</subject><subject>Anti-cancer</subject><subject>Anti-inflammation</subject><subject>anti-inflammatory activity</subject><subject>anti-inflammatory agents</subject><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - therapeutic use</subject><subject>Anti-Inflammatory Agents - toxicity</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - toxicity</subject><subject>cell growth</subject><subject>Cell Line, Tumor</subject><subject>colorectal neoplasms</subject><subject>cytotoxicity</subject><subject>DNA polymerase</subject><subject>DNA Polymerase beta - antagonists & inhibitors</subject><subject>DNA Polymerase beta - metabolism</subject><subject>DNA-directed DNA polymerase</subject><subject>ears</subject><subject>Enzyme inhibitor</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - therapeutic use</subject><subject>Enzyme Inhibitors - toxicity</subject><subject>Humans</subject><subject>inflammation</subject><subject>Inflammation - chemically induced</subject><subject>Inflammation - drug therapy</subject><subject>juglone</subject><subject>lipopolysaccharides</subject><subject>Lipopolysaccharides - toxicity</subject><subject>menadione</subject><subject>Mice</subject><subject>mitochondrial DNA</subject><subject>Naphthoquinones - chemistry</subject><subject>Naphthoquinones - therapeutic use</subject><subject>Naphthoquinones - toxicity</subject><subject>oleic acid</subject><subject>Tetradecanoylphorbol Acetate - toxicity</subject><subject>Tumor Necrosis Factor-alpha - metabolism</subject><subject>tumor necrosis factors</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkU1v1DAQhi0EokvhB3AB33ohYRw7iS1OVfmqVNED9Gx5ncnWK8de7Oyi3PjpeNnCEXGyNHre16N5CHnJoGbAurfbej3ZugHGapA1NPwRWTHRiYpzxR6TFahOViBVd0ae5bwFgEYo9pScNUxBYdSK_LwO927t5pgWiuOIdqZxpCEe0NO2oreVsYun2_3Gx4CZxkAnM03GOxPo-y-XdBf9MmEyGamxszu4eXlDrQkWE7XoPd2k-GO-pyYM1IXRH8O_P0uYdzFkfE6ejMZnfPHwnpO7jx--XX2ubm4_XV9d3lRW9GKuUKAZmOi7dhByHIEbJU0DyFvOy5APTJmO4SCZ6jiaRlprpeCWMyMAuOTn5OLUu0vx-x7zrCeXjxuagHGftVSKtS2I5j_IRomey66Q7ETaFHNOOOpdcpNJi2agj4b0VhdD-mhIg9TFUMm8emjfrycc_ib-KCnA6xMwmqjNJrms776WhhaAgep7KMS7E4HlXgeHSWfrsJx8cKkI1EN0_1jgF7CTqoQ</recordid><startdate>20111001</startdate><enddate>20111001</enddate><creator>Maruo, Sayako</creator><creator>Kuriyama, Isoko</creator><creator>Kuramochi, Kouji</creator><creator>Tsubaki, Kazunori</creator><creator>Yoshida, Hiromi</creator><creator>Mizushina, Yoshiyuki</creator><general>Elsevier Ltd</general><scope>FBQ</scope><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><scope>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20111001</creationdate><title>Inhibitory effect of novel 5- O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response</title><author>Maruo, Sayako ; Kuriyama, Isoko ; Kuramochi, Kouji ; Tsubaki, Kazunori ; Yoshida, Hiromi ; Mizushina, Yoshiyuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c474t-e4ead14765d48ff03a98a20e35337653d19a61ed81963ea28ccc843c31a400383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>5- O-Acyl juglone</topic><topic>acylation</topic><topic>Animals</topic><topic>Anti-cancer</topic><topic>Anti-inflammation</topic><topic>anti-inflammatory activity</topic><topic>anti-inflammatory agents</topic><topic>Anti-Inflammatory Agents - chemistry</topic><topic>Anti-Inflammatory Agents - therapeutic use</topic><topic>Anti-Inflammatory Agents - toxicity</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - toxicity</topic><topic>cell growth</topic><topic>Cell Line, Tumor</topic><topic>colorectal neoplasms</topic><topic>cytotoxicity</topic><topic>DNA polymerase</topic><topic>DNA Polymerase beta - antagonists & inhibitors</topic><topic>DNA Polymerase beta - metabolism</topic><topic>DNA-directed DNA polymerase</topic><topic>ears</topic><topic>Enzyme inhibitor</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - therapeutic use</topic><topic>Enzyme Inhibitors - toxicity</topic><topic>Humans</topic><topic>inflammation</topic><topic>Inflammation - chemically induced</topic><topic>Inflammation - drug therapy</topic><topic>juglone</topic><topic>lipopolysaccharides</topic><topic>Lipopolysaccharides - toxicity</topic><topic>menadione</topic><topic>Mice</topic><topic>mitochondrial DNA</topic><topic>Naphthoquinones - chemistry</topic><topic>Naphthoquinones - therapeutic use</topic><topic>Naphthoquinones - toxicity</topic><topic>oleic acid</topic><topic>Tetradecanoylphorbol Acetate - toxicity</topic><topic>Tumor Necrosis Factor-alpha - metabolism</topic><topic>tumor necrosis factors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Maruo, Sayako</creatorcontrib><creatorcontrib>Kuriyama, Isoko</creatorcontrib><creatorcontrib>Kuramochi, Kouji</creatorcontrib><creatorcontrib>Tsubaki, Kazunori</creatorcontrib><creatorcontrib>Yoshida, Hiromi</creatorcontrib><creatorcontrib>Mizushina, Yoshiyuki</creatorcontrib><collection>AGRIS</collection><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><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Maruo, Sayako</au><au>Kuriyama, Isoko</au><au>Kuramochi, Kouji</au><au>Tsubaki, Kazunori</au><au>Yoshida, Hiromi</au><au>Mizushina, Yoshiyuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibitory effect of novel 5- O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2011-10-01</date><risdate>2011</risdate><volume>19</volume><issue>19</issue><spage>5803</spage><epage>5812</epage><pages>5803-5812</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>We previously found that vitamin K
3 (menadione, 2-methyl-1,4-naphthoquinone) inhibits the activity of human mitochondrial DNA polymerase γ (pol γ). In this study, we focused on juglone (5-hydroxy-1,4-naphthoquinone), which is a 1,4-naphthoquinone derivative, and chemically synthesized novel juglones conjugated with C2:0 to C22:6 fatty acid (5-
O-acyl juglones). The chemically modified juglones enhanced mammalian pol inhibition and their cytotoxic and anti-inflammatory activities. The juglone conjugated with oleic acid (C18:1-acyl juglone) showed the strongest inhibition of DNA replicative pol α activity and human colon carcinoma (HCT116) cell growth in 10 synthesized 5-
O-acyl juglones. C12:0-Acyl juglone was the strongest inhibitor of DNA repair-related pol λ, as well as the strongest suppression of the production of tumor necrosis factor (TNF)-α production induced by lipopolysaccharide (LPS) in the compounds tested. Moreover, this compound caused the greatest reduction in 12-
O-tetradecanoylphorbol-13-acetate (TPA)-induced acute inflammation in mouse ears. C12:0- and C18:1-Acyl juglones selectively inhibited the activities of mammalian pol species, but did not influence the activities of other pols and DNA metabolic enzymes tested. These data indicate that the novel 5-
O-acyl juglones target anti-cancer and/or anti-inflammatory agents based on mammalian pol inhibition. Moreover, the results suggest that acylation of juglone is an effective chemical modification to improve the anti-cancer and anti-inflammation of vitamin K
3 derivatives, such as juglone.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>21903399</pmid><doi>10.1016/j.bmc.2011.08.023</doi><tpages>10</tpages></addata></record> |
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| subjects | 5- O-Acyl juglone acylation Animals Anti-cancer Anti-inflammation anti-inflammatory activity anti-inflammatory agents Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - therapeutic use Anti-Inflammatory Agents - toxicity Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - toxicity cell growth Cell Line, Tumor colorectal neoplasms cytotoxicity DNA polymerase DNA Polymerase beta - antagonists & inhibitors DNA Polymerase beta - metabolism DNA-directed DNA polymerase ears Enzyme inhibitor Enzyme Inhibitors - chemistry Enzyme Inhibitors - therapeutic use Enzyme Inhibitors - toxicity Humans inflammation Inflammation - chemically induced Inflammation - drug therapy juglone lipopolysaccharides Lipopolysaccharides - toxicity menadione Mice mitochondrial DNA Naphthoquinones - chemistry Naphthoquinones - therapeutic use Naphthoquinones - toxicity oleic acid Tetradecanoylphorbol Acetate - toxicity Tumor Necrosis Factor-alpha - metabolism tumor necrosis factors |
| title | Inhibitory effect of novel 5- O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response |
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