Inhibitory action of emulsified sulfoquinovosyl acylglycerol on mammalian DNA polymerases
We reported previously that sulfoquinovosyl diacylglycerol and sulfoquinovosyl monoacylglycerol (SQDG/SQMG) are potent inhibitors of mammalian DNA polymerases and DNA topoisomerase II, and can be potent immunosuppressive agents and anticancer chemotherapy agents [Matsumoto, Y., Sahara, H., Fujita T....
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| Veröffentlicht in: | Lipids 2003-10, Vol.38 (10), p.1065-1074 |
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| creator | Mizushina, Yoshiyuki Maeda, Naoki Kawasaki, Miho Ichikawa, Hideki Murakami, Chikako Takemura, Masaharu Xu, Xianai Sugawara, Fumio Fukumori, Yoshinobu Yoshida, Hiromi Sakaguchi, Kengo |
| description | We reported previously that sulfoquinovosyl diacylglycerol and sulfoquinovosyl monoacylglycerol (SQDG/SQMG) are potent inhibitors of mammalian DNA polymerases and DNA topoisomerase II, and can be potent immunosuppressive agents and anticancer chemotherapy agents [Matsumoto, Y., Sahara, H., Fujita T., Shimozawa, K., Takenouchi, M., Torigoe, T., Hanashima, S., Yamazaki, T., Takahashi, S., Sugawara, F., et al., An Immunosuppressive Effect by Synthetic Sulfonolipids Deduced from Sulfonoquinovosyl Diacylglycerols of Sea Urchin, Transplantation 74, 261–267 (2002); Sahara, H., Hanashima, S., Yamazaki, T., Takahashi, S., Sugawara, F., Ohtani, S., Ishikawa, M., Mizushina, Y., Ohta, K., Shimozawa, K., et al., Anti‐tumor Effect of Chemically Synthesized Sulfolipids Based on Sea Urchin's Natural Sulfonoquinovosylmonoacylglycerols, Jpn. J. Cancer Res. 93, 85–92 (2002)]. In those experiments, the in vivo effectiveness greatly depended on the degree of water solubility of SQDG/SQMG. In the present work, we studied the emulsification of SQDG/SQMG in terms of their use in in vivo experiments. Lipid emulsions containing SQDG/SQMG (oil‐in‐water emulsions) in which the particle size was smaller than 100 nm were designed and synthesized, and then the biochemical modes of emulsified SQDG/SQMG were studied in comparison with those of SQDG/SQMG solubilized by DMSO. Emulsified SQDG/SQMG are also selective mammalian DNA polymerase inhibitors and potent antineoplastic agents but do not inhibit the DNA topoisomerase II activity. The growth inhibition effect of emulsified SQMG to NUGC‐3 cancer cells was twofold stronger than DMSO‐soluble, SQMG (69 and 151 μM, respectively). From these results, the properties of lipid emulsions containing SQDG/SQMG and their possible use in in vivo experiments including clinical use are discussed. |
| doi_str_mv | 10.1007/s11745-006-1162-1 |
| format | Article |
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J. Cancer Res. 93, 85–92 (2002)]. In those experiments, the in vivo effectiveness greatly depended on the degree of water solubility of SQDG/SQMG. In the present work, we studied the emulsification of SQDG/SQMG in terms of their use in in vivo experiments. Lipid emulsions containing SQDG/SQMG (oil‐in‐water emulsions) in which the particle size was smaller than 100 nm were designed and synthesized, and then the biochemical modes of emulsified SQDG/SQMG were studied in comparison with those of SQDG/SQMG solubilized by DMSO. Emulsified SQDG/SQMG are also selective mammalian DNA polymerase inhibitors and potent antineoplastic agents but do not inhibit the DNA topoisomerase II activity. The growth inhibition effect of emulsified SQMG to NUGC‐3 cancer cells was twofold stronger than DMSO‐soluble, SQMG (69 and 151 μM, respectively). From these results, the properties of lipid emulsions containing SQDG/SQMG and their possible use in in vivo experiments including clinical use are discussed.</description><identifier>ISSN: 0024-4201</identifier><identifier>EISSN: 1558-9307</identifier><identifier>DOI: 10.1007/s11745-006-1162-1</identifier><identifier>PMID: 14669972</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer‐Verlag</publisher><subject>Animals ; Anti-HIV Agents - pharmacology ; Anticancer properties ; Antineoplastic drugs ; Cattle ; Cell Line, Tumor ; Cell Survival - drug effects ; Cell Survival - physiology ; Chemotherapy ; Deoxyribonucleic acid ; Diglycerides ; DNA ; DNA polymerase ; DNA topoisomerase ; DNA topoisomerase (ATP-hydrolysing) ; DNA-directed DNA polymerase ; DNA-Directed DNA Polymerase - metabolism ; Dose-Response Relationship, Drug ; Emulsification ; Emulsions ; Enzyme Inhibitors - pharmacology ; Experiments ; Gastric cancer ; Glycolipids - pharmacology ; Growth inhibition ; Humans ; Immunosuppression ; Immunosuppressive agents ; Lipids ; Mammals ; Nucleic Acid Synthesis Inhibitors ; Proteins ; Rats ; Sulfolipids ; Transplantation</subject><ispartof>Lipids, 2003-10, Vol.38 (10), p.1065-1074</ispartof><rights>2003 American Oil Chemists' Society (AOCS)</rights><rights>AOCS Press 2003.</rights><rights>AOCS Press 2003</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4685-61c760e3debddbb60c5eeb821f67b4e65ac012409ef36991d8abbfd3c20a3b7c3</citedby><cites>FETCH-LOGICAL-c4685-61c760e3debddbb60c5eeb821f67b4e65ac012409ef36991d8abbfd3c20a3b7c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1007%2Fs11745-006-1162-1$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1007%2Fs11745-006-1162-1$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14669972$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mizushina, Yoshiyuki</creatorcontrib><creatorcontrib>Maeda, Naoki</creatorcontrib><creatorcontrib>Kawasaki, Miho</creatorcontrib><creatorcontrib>Ichikawa, Hideki</creatorcontrib><creatorcontrib>Murakami, Chikako</creatorcontrib><creatorcontrib>Takemura, Masaharu</creatorcontrib><creatorcontrib>Xu, Xianai</creatorcontrib><creatorcontrib>Sugawara, Fumio</creatorcontrib><creatorcontrib>Fukumori, Yoshinobu</creatorcontrib><creatorcontrib>Yoshida, Hiromi</creatorcontrib><creatorcontrib>Sakaguchi, Kengo</creatorcontrib><title>Inhibitory action of emulsified sulfoquinovosyl acylglycerol on mammalian DNA polymerases</title><title>Lipids</title><addtitle>Lipids</addtitle><description>We reported previously that sulfoquinovosyl diacylglycerol and sulfoquinovosyl monoacylglycerol (SQDG/SQMG) are potent inhibitors of mammalian DNA polymerases and DNA topoisomerase II, and can be potent immunosuppressive agents and anticancer chemotherapy agents [Matsumoto, Y., Sahara, H., Fujita T., Shimozawa, K., Takenouchi, M., Torigoe, T., Hanashima, S., Yamazaki, T., Takahashi, S., Sugawara, F., et al., An Immunosuppressive Effect by Synthetic Sulfonolipids Deduced from Sulfonoquinovosyl Diacylglycerols of Sea Urchin, Transplantation 74, 261–267 (2002); Sahara, H., Hanashima, S., Yamazaki, T., Takahashi, S., Sugawara, F., Ohtani, S., Ishikawa, M., Mizushina, Y., Ohta, K., Shimozawa, K., et al., Anti‐tumor Effect of Chemically Synthesized Sulfolipids Based on Sea Urchin's Natural Sulfonoquinovosylmonoacylglycerols, Jpn. J. Cancer Res. 93, 85–92 (2002)]. In those experiments, the in vivo effectiveness greatly depended on the degree of water solubility of SQDG/SQMG. In the present work, we studied the emulsification of SQDG/SQMG in terms of their use in in vivo experiments. Lipid emulsions containing SQDG/SQMG (oil‐in‐water emulsions) in which the particle size was smaller than 100 nm were designed and synthesized, and then the biochemical modes of emulsified SQDG/SQMG were studied in comparison with those of SQDG/SQMG solubilized by DMSO. Emulsified SQDG/SQMG are also selective mammalian DNA polymerase inhibitors and potent antineoplastic agents but do not inhibit the DNA topoisomerase II activity. The growth inhibition effect of emulsified SQMG to NUGC‐3 cancer cells was twofold stronger than DMSO‐soluble, SQMG (69 and 151 μM, respectively). From these results, the properties of lipid emulsions containing SQDG/SQMG and their possible use in in vivo experiments including clinical use are discussed.</description><subject>Animals</subject><subject>Anti-HIV Agents - pharmacology</subject><subject>Anticancer properties</subject><subject>Antineoplastic drugs</subject><subject>Cattle</subject><subject>Cell Line, Tumor</subject><subject>Cell Survival - drug effects</subject><subject>Cell Survival - physiology</subject><subject>Chemotherapy</subject><subject>Deoxyribonucleic acid</subject><subject>Diglycerides</subject><subject>DNA</subject><subject>DNA polymerase</subject><subject>DNA topoisomerase</subject><subject>DNA topoisomerase (ATP-hydrolysing)</subject><subject>DNA-directed DNA polymerase</subject><subject>DNA-Directed DNA Polymerase - metabolism</subject><subject>Dose-Response Relationship, Drug</subject><subject>Emulsification</subject><subject>Emulsions</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Experiments</subject><subject>Gastric cancer</subject><subject>Glycolipids - pharmacology</subject><subject>Growth inhibition</subject><subject>Humans</subject><subject>Immunosuppression</subject><subject>Immunosuppressive agents</subject><subject>Lipids</subject><subject>Mammals</subject><subject>Nucleic Acid Synthesis Inhibitors</subject><subject>Proteins</subject><subject>Rats</subject><subject>Sulfolipids</subject><subject>Transplantation</subject><issn>0024-4201</issn><issn>1558-9307</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNqF0UuLFDEUBeAgDk47-gPcSKHgrvTePKuWwzy0oVEXunAVklRKM6QqbdLlUP_eDN0gCOIqBL57OHAIeYHwFgHUu4KouGgBZIsoaYuPyAaF6NqegXpMNgCUt5wCnpOnpdzVL_JePCHnyKXse0U35Nt2_hFsOKS8NsYdQpqbNDZ-WmIJY_BDU5Y4pp9LmNOvVNZY0Rq_x9X5nGJT9WSmycRg5ub642WzT3GdfDbFl2fkbDSx-Oen94J8vb35cvWh3X16v7263LWOy060Ep2S4Nng7TBYK8EJ721HcZTKci-FcYCUQ-9HVjvj0Blrx4E5CoZZ5dgFeXPM3efa05eDnkJxPkYz-7QUrVAgUJAVvvoL3qUlz7Wb7roOaS-RVfT6X4iqTlHec8arwqNyOZWS_aj3OUwmrxpBP0yjj9PoOo1-mEZjvXl5Sl7s5Ic_F6ctKlBHcB-iX_-fqHfbz9cIUrDffNGakg</recordid><startdate>200310</startdate><enddate>200310</enddate><creator>Mizushina, Yoshiyuki</creator><creator>Maeda, Naoki</creator><creator>Kawasaki, Miho</creator><creator>Ichikawa, Hideki</creator><creator>Murakami, Chikako</creator><creator>Takemura, Masaharu</creator><creator>Xu, Xianai</creator><creator>Sugawara, Fumio</creator><creator>Fukumori, Yoshinobu</creator><creator>Yoshida, Hiromi</creator><creator>Sakaguchi, Kengo</creator><general>Springer‐Verlag</general><general>Springer Nature B.V</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>7QL</scope><scope>7QP</scope><scope>7QR</scope><scope>7T7</scope><scope>7TK</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>8AO</scope><scope>8C1</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7P</scope><scope>PCBAR</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>7X8</scope></search><sort><creationdate>200310</creationdate><title>Inhibitory action of emulsified sulfoquinovosyl acylglycerol on mammalian DNA polymerases</title><author>Mizushina, Yoshiyuki ; Maeda, Naoki ; Kawasaki, Miho ; Ichikawa, Hideki ; Murakami, Chikako ; Takemura, Masaharu ; Xu, Xianai ; Sugawara, Fumio ; Fukumori, Yoshinobu ; Yoshida, Hiromi ; Sakaguchi, Kengo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4685-61c760e3debddbb60c5eeb821f67b4e65ac012409ef36991d8abbfd3c20a3b7c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Animals</topic><topic>Anti-HIV Agents - pharmacology</topic><topic>Anticancer properties</topic><topic>Antineoplastic drugs</topic><topic>Cattle</topic><topic>Cell Line, Tumor</topic><topic>Cell Survival - drug effects</topic><topic>Cell Survival - physiology</topic><topic>Chemotherapy</topic><topic>Deoxyribonucleic acid</topic><topic>Diglycerides</topic><topic>DNA</topic><topic>DNA polymerase</topic><topic>DNA topoisomerase</topic><topic>DNA topoisomerase (ATP-hydrolysing)</topic><topic>DNA-directed DNA polymerase</topic><topic>DNA-Directed DNA Polymerase - metabolism</topic><topic>Dose-Response Relationship, Drug</topic><topic>Emulsification</topic><topic>Emulsions</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Experiments</topic><topic>Gastric cancer</topic><topic>Glycolipids - pharmacology</topic><topic>Growth inhibition</topic><topic>Humans</topic><topic>Immunosuppression</topic><topic>Immunosuppressive agents</topic><topic>Lipids</topic><topic>Mammals</topic><topic>Nucleic Acid Synthesis Inhibitors</topic><topic>Proteins</topic><topic>Rats</topic><topic>Sulfolipids</topic><topic>Transplantation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mizushina, Yoshiyuki</creatorcontrib><creatorcontrib>Maeda, Naoki</creatorcontrib><creatorcontrib>Kawasaki, Miho</creatorcontrib><creatorcontrib>Ichikawa, Hideki</creatorcontrib><creatorcontrib>Murakami, Chikako</creatorcontrib><creatorcontrib>Takemura, Masaharu</creatorcontrib><creatorcontrib>Xu, Xianai</creatorcontrib><creatorcontrib>Sugawara, Fumio</creatorcontrib><creatorcontrib>Fukumori, Yoshinobu</creatorcontrib><creatorcontrib>Yoshida, Hiromi</creatorcontrib><creatorcontrib>Sakaguchi, Kengo</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>Public Health Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Biological Science Database</collection><collection>Earth, Atmospheric & Aquatic Science Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>MEDLINE - Academic</collection><jtitle>Lipids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mizushina, Yoshiyuki</au><au>Maeda, Naoki</au><au>Kawasaki, Miho</au><au>Ichikawa, Hideki</au><au>Murakami, Chikako</au><au>Takemura, Masaharu</au><au>Xu, Xianai</au><au>Sugawara, Fumio</au><au>Fukumori, Yoshinobu</au><au>Yoshida, Hiromi</au><au>Sakaguchi, Kengo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibitory action of emulsified sulfoquinovosyl acylglycerol on mammalian DNA polymerases</atitle><jtitle>Lipids</jtitle><addtitle>Lipids</addtitle><date>2003-10</date><risdate>2003</risdate><volume>38</volume><issue>10</issue><spage>1065</spage><epage>1074</epage><pages>1065-1074</pages><issn>0024-4201</issn><eissn>1558-9307</eissn><abstract>We reported previously that sulfoquinovosyl diacylglycerol and sulfoquinovosyl monoacylglycerol (SQDG/SQMG) are potent inhibitors of mammalian DNA polymerases and DNA topoisomerase II, and can be potent immunosuppressive agents and anticancer chemotherapy agents [Matsumoto, Y., Sahara, H., Fujita T., Shimozawa, K., Takenouchi, M., Torigoe, T., Hanashima, S., Yamazaki, T., Takahashi, S., Sugawara, F., et al., An Immunosuppressive Effect by Synthetic Sulfonolipids Deduced from Sulfonoquinovosyl Diacylglycerols of Sea Urchin, Transplantation 74, 261–267 (2002); Sahara, H., Hanashima, S., Yamazaki, T., Takahashi, S., Sugawara, F., Ohtani, S., Ishikawa, M., Mizushina, Y., Ohta, K., Shimozawa, K., et al., Anti‐tumor Effect of Chemically Synthesized Sulfolipids Based on Sea Urchin's Natural Sulfonoquinovosylmonoacylglycerols, Jpn. J. Cancer Res. 93, 85–92 (2002)]. In those experiments, the in vivo effectiveness greatly depended on the degree of water solubility of SQDG/SQMG. In the present work, we studied the emulsification of SQDG/SQMG in terms of their use in in vivo experiments. Lipid emulsions containing SQDG/SQMG (oil‐in‐water emulsions) in which the particle size was smaller than 100 nm were designed and synthesized, and then the biochemical modes of emulsified SQDG/SQMG were studied in comparison with those of SQDG/SQMG solubilized by DMSO. Emulsified SQDG/SQMG are also selective mammalian DNA polymerase inhibitors and potent antineoplastic agents but do not inhibit the DNA topoisomerase II activity. The growth inhibition effect of emulsified SQMG to NUGC‐3 cancer cells was twofold stronger than DMSO‐soluble, SQMG (69 and 151 μM, respectively). From these results, the properties of lipid emulsions containing SQDG/SQMG and their possible use in in vivo experiments including clinical use are discussed.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer‐Verlag</pub><pmid>14669972</pmid><doi>10.1007/s11745-006-1162-1</doi><tpages>10</tpages></addata></record> |
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| subjects | Animals Anti-HIV Agents - pharmacology Anticancer properties Antineoplastic drugs Cattle Cell Line, Tumor Cell Survival - drug effects Cell Survival - physiology Chemotherapy Deoxyribonucleic acid Diglycerides DNA DNA polymerase DNA topoisomerase DNA topoisomerase (ATP-hydrolysing) DNA-directed DNA polymerase DNA-Directed DNA Polymerase - metabolism Dose-Response Relationship, Drug Emulsification Emulsions Enzyme Inhibitors - pharmacology Experiments Gastric cancer Glycolipids - pharmacology Growth inhibition Humans Immunosuppression Immunosuppressive agents Lipids Mammals Nucleic Acid Synthesis Inhibitors Proteins Rats Sulfolipids Transplantation |
| title | Inhibitory action of emulsified sulfoquinovosyl acylglycerol on mammalian DNA polymerases |
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