Preparation of Cyclic-1,N2-propano-2′-deoxyguanosine-d7 as an Internal Standard for ESI-MS/MS Determination of DNA Damage from Acetaldehyde
Cyclic-1,N2-propano-2′-deoxyguanosine-d7 (CPr-dG-d7) was prepared as an isotopic internal standard (IS) for electrospray ionization tandem mass spectrometry (ESI-MS/MS) quantification of CPr-dG in DNA as a candidate cancer risk marker of acetaldehyde intake, mainly from drinking. The deuterated comp...
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| Veröffentlicht in: | Analytical Sciences 2019/12/10, Vol.35(12), pp.1393-1397 |
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| creator | ESAKA, Yukihiro KUNISHIMA, Saki ARUGA, Hiromitsu YAMAMOTO, Takuhei MURAKAMI, Hiroya TESHIMA, Norio UNO, Bunji |
| description | Cyclic-1,N2-propano-2′-deoxyguanosine-d7 (CPr-dG-d7) was prepared as an isotopic internal standard (IS) for electrospray ionization tandem mass spectrometry (ESI-MS/MS) quantification of CPr-dG in DNA as a candidate cancer risk marker of acetaldehyde intake, mainly from drinking. The deuterated compound was reasonably synthesized from acetaldehyde-d4 and 2′-deoxyguanosine in deuterium oxide (D2O), preventing the deuterium atoms of acetaldehyde-d4 from being substituted by hydrogen atoms, which occurred seriously in aqueous synthesis media via keto–enol tautomerism. Furthermore, another deuterium atom was added from D2O to form CPr-dG-d7. After four weeks of storage in H2O at 10°C, CPr-dG-d7 was found to be sufficiently stable for practical use. The calibration curve of CPr-dG by using a hydrophilic interaction chromatography–ESI-MS/MS system with CPr-dG-d7 as the IS showed sufficient linearity from 1.0 × 10−10 to 4.0 × 10−9 M with r2 = 0.998. |
| doi_str_mv | 10.2116/analsci.19N023 |
| format | Article |
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The deuterated compound was reasonably synthesized from acetaldehyde-d4 and 2′-deoxyguanosine in deuterium oxide (D2O), preventing the deuterium atoms of acetaldehyde-d4 from being substituted by hydrogen atoms, which occurred seriously in aqueous synthesis media via keto–enol tautomerism. Furthermore, another deuterium atom was added from D2O to form CPr-dG-d7. After four weeks of storage in H2O at 10°C, CPr-dG-d7 was found to be sufficiently stable for practical use. The calibration curve of CPr-dG by using a hydrophilic interaction chromatography–ESI-MS/MS system with CPr-dG-d7 as the IS showed sufficient linearity from 1.0 × 10−10 to 4.0 × 10−9 M with r2 = 0.998.</description><identifier>ISSN: 0910-6340</identifier><identifier>EISSN: 1348-2246</identifier><identifier>DOI: 10.2116/analsci.19N023</identifier><language>eng</language><publisher>Singapore: The Japan Society for Analytical Chemistry</publisher><subject>Acetaldehyde ; acetaldehyde-d4 ; Analytical Chemistry ; Calibration ; cancer risk marker ; Chemistry ; Cyclic-1,N2-propano-2′-deoxyguanosine-d7 ; D2O ; Deoxyguanosine ; Deoxyribonucleic acid ; Deuteration ; Deuterium ; DNA ; DNA damage ; ESI-MS/MS ; Health risks ; Heavy water ; Hydrogen atoms ; Ionization ; Ions ; isotopic internal standard ; Linearity ; Mass spectrometry ; Mass spectroscopy ; Tautomerism</subject><ispartof>Analytical Sciences, 2019/12/10, Vol.35(12), pp.1393-1397</ispartof><rights>2019 by The Japan Society for Analytical Chemistry</rights><rights>The Japan Society for Analytical Chemistry 2019</rights><rights>Copyright Japan Science and Technology Agency 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c566t-abff90e4d72d0c2ceda17f6a3c7614bd85dd17126f9141adb99d218f8c28cb003</citedby><cites>FETCH-LOGICAL-c566t-abff90e4d72d0c2ceda17f6a3c7614bd85dd17126f9141adb99d218f8c28cb003</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.2116/analsci.19N023$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.2116/analsci.19N023$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,1877,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>ESAKA, Yukihiro</creatorcontrib><creatorcontrib>KUNISHIMA, Saki</creatorcontrib><creatorcontrib>ARUGA, Hiromitsu</creatorcontrib><creatorcontrib>YAMAMOTO, Takuhei</creatorcontrib><creatorcontrib>MURAKAMI, Hiroya</creatorcontrib><creatorcontrib>TESHIMA, Norio</creatorcontrib><creatorcontrib>UNO, Bunji</creatorcontrib><title>Preparation of Cyclic-1,N2-propano-2′-deoxyguanosine-d7 as an Internal Standard for ESI-MS/MS Determination of DNA Damage from Acetaldehyde</title><title>Analytical Sciences</title><addtitle>ANAL. SCI</addtitle><description>Cyclic-1,N2-propano-2′-deoxyguanosine-d7 (CPr-dG-d7) was prepared as an isotopic internal standard (IS) for electrospray ionization tandem mass spectrometry (ESI-MS/MS) quantification of CPr-dG in DNA as a candidate cancer risk marker of acetaldehyde intake, mainly from drinking. The deuterated compound was reasonably synthesized from acetaldehyde-d4 and 2′-deoxyguanosine in deuterium oxide (D2O), preventing the deuterium atoms of acetaldehyde-d4 from being substituted by hydrogen atoms, which occurred seriously in aqueous synthesis media via keto–enol tautomerism. Furthermore, another deuterium atom was added from D2O to form CPr-dG-d7. After four weeks of storage in H2O at 10°C, CPr-dG-d7 was found to be sufficiently stable for practical use. The calibration curve of CPr-dG by using a hydrophilic interaction chromatography–ESI-MS/MS system with CPr-dG-d7 as the IS showed sufficient linearity from 1.0 × 10−10 to 4.0 × 10−9 M with r2 = 0.998.</description><subject>Acetaldehyde</subject><subject>acetaldehyde-d4</subject><subject>Analytical Chemistry</subject><subject>Calibration</subject><subject>cancer risk marker</subject><subject>Chemistry</subject><subject>Cyclic-1,N2-propano-2′-deoxyguanosine-d7</subject><subject>D2O</subject><subject>Deoxyguanosine</subject><subject>Deoxyribonucleic acid</subject><subject>Deuteration</subject><subject>Deuterium</subject><subject>DNA</subject><subject>DNA damage</subject><subject>ESI-MS/MS</subject><subject>Health risks</subject><subject>Heavy water</subject><subject>Hydrogen atoms</subject><subject>Ionization</subject><subject>Ions</subject><subject>isotopic internal standard</subject><subject>Linearity</subject><subject>Mass spectrometry</subject><subject>Mass spectroscopy</subject><subject>Tautomerism</subject><issn>0910-6340</issn><issn>1348-2246</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1Uc2qEzEUHkTBenXrOuDGhWmTk-n8LEtbtXBvFarr4TQ56Z0yTWoyBbvzBXwZH8knMb1zqSC4ySGc74fvfFn2WooxSFlM0GEXdTuW9VqAepKNpMorDpAXT7ORqKXghcrF8-xFjHshJFQAo-zn50BHDNi33jFv2fysu1Zz-W4N_Bj8EZ3n8PvHL27Ifz_vTukfW0fclAwjQ8dWrqeQnNmmR2cwGGZ9YMvNit9tJncbtqC0P7Tu6rBYz9gCD7gjZoM_sJmmHjtD92dDL7NnNoWgV4_zJvv6fvll_pHffvqwms9uuZ4WRc9xa20tKDclGKFBk0FZ2gKVLguZb001NUaWEgpby1yi2da1AVnZSkOlt0Kom-ztoJsifjtR7JtDGzV1HTryp9gAVErJalpDgr75B7r3p0vghFJQ5unU6iI4HlA6-BgD2eYY2gOGcyNFc2mneWynGdpJhMlAiAnodhT-yv6XsRwY-9in410NMPSt7ugKV9NGwsP7wLvu9T2Ghpz6A6LErcg</recordid><startdate>20191210</startdate><enddate>20191210</enddate><creator>ESAKA, Yukihiro</creator><creator>KUNISHIMA, Saki</creator><creator>ARUGA, Hiromitsu</creator><creator>YAMAMOTO, Takuhei</creator><creator>MURAKAMI, Hiroya</creator><creator>TESHIMA, Norio</creator><creator>UNO, Bunji</creator><general>The Japan Society for Analytical Chemistry</general><general>Springer Nature Singapore</general><general>Japan Science and Technology Agency</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QQ</scope><scope>7SE</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>H8G</scope><scope>JG9</scope><scope>L7M</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20191210</creationdate><title>Preparation of Cyclic-1,N2-propano-2′-deoxyguanosine-d7 as an Internal Standard for ESI-MS/MS Determination of DNA Damage from Acetaldehyde</title><author>ESAKA, Yukihiro ; KUNISHIMA, Saki ; ARUGA, Hiromitsu ; YAMAMOTO, Takuhei ; MURAKAMI, Hiroya ; TESHIMA, Norio ; UNO, Bunji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c566t-abff90e4d72d0c2ceda17f6a3c7614bd85dd17126f9141adb99d218f8c28cb003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Acetaldehyde</topic><topic>acetaldehyde-d4</topic><topic>Analytical Chemistry</topic><topic>Calibration</topic><topic>cancer risk marker</topic><topic>Chemistry</topic><topic>Cyclic-1,N2-propano-2′-deoxyguanosine-d7</topic><topic>D2O</topic><topic>Deoxyguanosine</topic><topic>Deoxyribonucleic acid</topic><topic>Deuteration</topic><topic>Deuterium</topic><topic>DNA</topic><topic>DNA damage</topic><topic>ESI-MS/MS</topic><topic>Health risks</topic><topic>Heavy water</topic><topic>Hydrogen atoms</topic><topic>Ionization</topic><topic>Ions</topic><topic>isotopic internal standard</topic><topic>Linearity</topic><topic>Mass spectrometry</topic><topic>Mass spectroscopy</topic><topic>Tautomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>ESAKA, Yukihiro</creatorcontrib><creatorcontrib>KUNISHIMA, Saki</creatorcontrib><creatorcontrib>ARUGA, Hiromitsu</creatorcontrib><creatorcontrib>YAMAMOTO, Takuhei</creatorcontrib><creatorcontrib>MURAKAMI, Hiroya</creatorcontrib><creatorcontrib>TESHIMA, Norio</creatorcontrib><creatorcontrib>UNO, Bunji</creatorcontrib><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Copper Technical Reference Library</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Analytical Sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>ESAKA, Yukihiro</au><au>KUNISHIMA, Saki</au><au>ARUGA, Hiromitsu</au><au>YAMAMOTO, Takuhei</au><au>MURAKAMI, Hiroya</au><au>TESHIMA, Norio</au><au>UNO, Bunji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation of Cyclic-1,N2-propano-2′-deoxyguanosine-d7 as an Internal Standard for ESI-MS/MS Determination of DNA Damage from Acetaldehyde</atitle><jtitle>Analytical Sciences</jtitle><stitle>ANAL. SCI</stitle><date>2019-12-10</date><risdate>2019</risdate><volume>35</volume><issue>12</issue><spage>1393</spage><epage>1397</epage><pages>1393-1397</pages><issn>0910-6340</issn><eissn>1348-2246</eissn><abstract>Cyclic-1,N2-propano-2′-deoxyguanosine-d7 (CPr-dG-d7) was prepared as an isotopic internal standard (IS) for electrospray ionization tandem mass spectrometry (ESI-MS/MS) quantification of CPr-dG in DNA as a candidate cancer risk marker of acetaldehyde intake, mainly from drinking. The deuterated compound was reasonably synthesized from acetaldehyde-d4 and 2′-deoxyguanosine in deuterium oxide (D2O), preventing the deuterium atoms of acetaldehyde-d4 from being substituted by hydrogen atoms, which occurred seriously in aqueous synthesis media via keto–enol tautomerism. Furthermore, another deuterium atom was added from D2O to form CPr-dG-d7. After four weeks of storage in H2O at 10°C, CPr-dG-d7 was found to be sufficiently stable for practical use. The calibration curve of CPr-dG by using a hydrophilic interaction chromatography–ESI-MS/MS system with CPr-dG-d7 as the IS showed sufficient linearity from 1.0 × 10−10 to 4.0 × 10−9 M with r2 = 0.998.</abstract><cop>Singapore</cop><pub>The Japan Society for Analytical Chemistry</pub><doi>10.2116/analsci.19N023</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Acetaldehyde acetaldehyde-d4 Analytical Chemistry Calibration cancer risk marker Chemistry Cyclic-1,N2-propano-2′-deoxyguanosine-d7 D2O Deoxyguanosine Deoxyribonucleic acid Deuteration Deuterium DNA DNA damage ESI-MS/MS Health risks Heavy water Hydrogen atoms Ionization Ions isotopic internal standard Linearity Mass spectrometry Mass spectroscopy Tautomerism |
| title | Preparation of Cyclic-1,N2-propano-2′-deoxyguanosine-d7 as an Internal Standard for ESI-MS/MS Determination of DNA Damage from Acetaldehyde |
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