Trajectory of the spectral/structural rearrangements for photo-oxidative reaction of neat ketoprofen and its cyclodextrin complex

Ketoprofen is a nonsteroidal anti-inflammatory drug used as mohrus tape which causes unwanted photosensitivity due to UV irradiation. In addition, photodegradation of ketoprofen induces its decarboxylation. Here, we aim to determine the effect of cyclodextrin on the photolysis of ketoprofen. Separat...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of inclusion phenomena and macrocyclic chemistry 2022-10, Vol.102 (9-10), p.791-800
Hauptverfasser: Hiroshige, Ryosuke, Goto, Satoru, Tsunoda, Chihiro, Ichii, Risa, Shimizu, Shota, Otsuka, Yuta, Makino, Kosho, Takahashi, Hideyo, Yokoyama, Hideshi
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 800
container_issue 9-10
container_start_page 791
container_title Journal of inclusion phenomena and macrocyclic chemistry
container_volume 102
creator Hiroshige, Ryosuke
Goto, Satoru
Tsunoda, Chihiro
Ichii, Risa
Shimizu, Shota
Otsuka, Yuta
Makino, Kosho
Takahashi, Hideyo
Yokoyama, Hideshi
description Ketoprofen is a nonsteroidal anti-inflammatory drug used as mohrus tape which causes unwanted photosensitivity due to UV irradiation. In addition, photodegradation of ketoprofen induces its decarboxylation. Here, we aim to determine the effect of cyclodextrin on the photolysis of ketoprofen. Separation technique using HPLC confirmed that UV irradiation of ketoprofen produced multiple products. A unique reaction proceeded in the presence of β-cyclodextrin. Furthermore, characterization by UV spectroscopy was performed, and the obtained spectra were analyzed using singular value decomposition. By analyzing the trajectory of the singular vector space, we were able to reflect the difference in the reaction pathway of ketoprofen with and without cyclodextrin. This study uses a singular value decomposition analysis, which is useful as a novel approach for solutions of radical reactions and a promising technique for analysis of radical reactions in the future. Graphical abstract
doi_str_mv 10.1007/s10847-022-01160-3
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2723515299</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2723515299</sourcerecordid><originalsourceid>FETCH-LOGICAL-c249t-62c7ac6668ccb882186ad841e1e5366dec9ea76726254b630cea5db668c5268a3</originalsourceid><addsrcrecordid>eNp9kM1PwyAchhujiXP6D3gi8YzjowV6NItfyRIv80wY_dV1dqUCNdvR_1xqTbzJhR_J877Ak2XXlNxSQuQiUKJyiQljmFAqCOYn2YwWkmOa1mmauVKYUybPs4sQdoQwwXI-y77W3uzARuePyNUobgGFPp29aRch-sHGIY3Ig_HedG-why4GVDuP-q2LDrtDU5nYfMKI2Ni4bqzpwET0DtH13tXQIdNVqEk5e7Stq-AQfdMh6_Z9C4fL7Kw2bYCr332evT7cr5dPePXy-Ly8W2HL8jJiwaw0VgihrN0oxagSplI5BQoFF6ICW4KRQqZ_FflGcGLBFNVm5AsmlOHz7GbqTW_6GCBEvXOD79KVmknGC1qwskwUmyjrXQgeat37Zm_8UVOiR9V6Uq2Tav2jWvMU4lMoJDhJ8n_V_6S-Aao1hKw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2723515299</pqid></control><display><type>article</type><title>Trajectory of the spectral/structural rearrangements for photo-oxidative reaction of neat ketoprofen and its cyclodextrin complex</title><source>SpringerNature Journals</source><creator>Hiroshige, Ryosuke ; Goto, Satoru ; Tsunoda, Chihiro ; Ichii, Risa ; Shimizu, Shota ; Otsuka, Yuta ; Makino, Kosho ; Takahashi, Hideyo ; Yokoyama, Hideshi</creator><creatorcontrib>Hiroshige, Ryosuke ; Goto, Satoru ; Tsunoda, Chihiro ; Ichii, Risa ; Shimizu, Shota ; Otsuka, Yuta ; Makino, Kosho ; Takahashi, Hideyo ; Yokoyama, Hideshi</creatorcontrib><description>Ketoprofen is a nonsteroidal anti-inflammatory drug used as mohrus tape which causes unwanted photosensitivity due to UV irradiation. In addition, photodegradation of ketoprofen induces its decarboxylation. Here, we aim to determine the effect of cyclodextrin on the photolysis of ketoprofen. Separation technique using HPLC confirmed that UV irradiation of ketoprofen produced multiple products. A unique reaction proceeded in the presence of β-cyclodextrin. Furthermore, characterization by UV spectroscopy was performed, and the obtained spectra were analyzed using singular value decomposition. By analyzing the trajectory of the singular vector space, we were able to reflect the difference in the reaction pathway of ketoprofen with and without cyclodextrin. This study uses a singular value decomposition analysis, which is useful as a novel approach for solutions of radical reactions and a promising technique for analysis of radical reactions in the future. Graphical abstract</description><identifier>ISSN: 1388-3127</identifier><identifier>EISSN: 1573-1111</identifier><identifier>DOI: 10.1007/s10847-022-01160-3</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Chemistry ; Chemistry and Materials Science ; Crystallography and Scattering Methods ; Cyclodextrins ; Decarboxylation ; Food Science ; Irradiation ; Ketoprofen ; Organic Chemistry ; Original Article ; Photodegradation ; Photolysis ; Photosensitivity ; Singular value decomposition ; Trajectory analysis ; Ultraviolet radiation ; Vector spaces</subject><ispartof>Journal of inclusion phenomena and macrocyclic chemistry, 2022-10, Vol.102 (9-10), p.791-800</ispartof><rights>The Author(s), under exclusive licence to Springer Nature B.V. 2022. Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c249t-62c7ac6668ccb882186ad841e1e5366dec9ea76726254b630cea5db668c5268a3</citedby><cites>FETCH-LOGICAL-c249t-62c7ac6668ccb882186ad841e1e5366dec9ea76726254b630cea5db668c5268a3</cites><orcidid>0000-0001-8088-9070</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10847-022-01160-3$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10847-022-01160-3$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>315,781,785,27928,27929,41492,42561,51323</link.rule.ids></links><search><creatorcontrib>Hiroshige, Ryosuke</creatorcontrib><creatorcontrib>Goto, Satoru</creatorcontrib><creatorcontrib>Tsunoda, Chihiro</creatorcontrib><creatorcontrib>Ichii, Risa</creatorcontrib><creatorcontrib>Shimizu, Shota</creatorcontrib><creatorcontrib>Otsuka, Yuta</creatorcontrib><creatorcontrib>Makino, Kosho</creatorcontrib><creatorcontrib>Takahashi, Hideyo</creatorcontrib><creatorcontrib>Yokoyama, Hideshi</creatorcontrib><title>Trajectory of the spectral/structural rearrangements for photo-oxidative reaction of neat ketoprofen and its cyclodextrin complex</title><title>Journal of inclusion phenomena and macrocyclic chemistry</title><addtitle>J Incl Phenom Macrocycl Chem</addtitle><description>Ketoprofen is a nonsteroidal anti-inflammatory drug used as mohrus tape which causes unwanted photosensitivity due to UV irradiation. In addition, photodegradation of ketoprofen induces its decarboxylation. Here, we aim to determine the effect of cyclodextrin on the photolysis of ketoprofen. Separation technique using HPLC confirmed that UV irradiation of ketoprofen produced multiple products. A unique reaction proceeded in the presence of β-cyclodextrin. Furthermore, characterization by UV spectroscopy was performed, and the obtained spectra were analyzed using singular value decomposition. By analyzing the trajectory of the singular vector space, we were able to reflect the difference in the reaction pathway of ketoprofen with and without cyclodextrin. This study uses a singular value decomposition analysis, which is useful as a novel approach for solutions of radical reactions and a promising technique for analysis of radical reactions in the future. Graphical abstract</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Crystallography and Scattering Methods</subject><subject>Cyclodextrins</subject><subject>Decarboxylation</subject><subject>Food Science</subject><subject>Irradiation</subject><subject>Ketoprofen</subject><subject>Organic Chemistry</subject><subject>Original Article</subject><subject>Photodegradation</subject><subject>Photolysis</subject><subject>Photosensitivity</subject><subject>Singular value decomposition</subject><subject>Trajectory analysis</subject><subject>Ultraviolet radiation</subject><subject>Vector spaces</subject><issn>1388-3127</issn><issn>1573-1111</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kM1PwyAchhujiXP6D3gi8YzjowV6NItfyRIv80wY_dV1dqUCNdvR_1xqTbzJhR_J877Ak2XXlNxSQuQiUKJyiQljmFAqCOYn2YwWkmOa1mmauVKYUybPs4sQdoQwwXI-y77W3uzARuePyNUobgGFPp29aRch-sHGIY3Ig_HedG-why4GVDuP-q2LDrtDU5nYfMKI2Ni4bqzpwET0DtH13tXQIdNVqEk5e7Stq-AQfdMh6_Z9C4fL7Kw2bYCr332evT7cr5dPePXy-Ly8W2HL8jJiwaw0VgihrN0oxagSplI5BQoFF6ICW4KRQqZ_FflGcGLBFNVm5AsmlOHz7GbqTW_6GCBEvXOD79KVmknGC1qwskwUmyjrXQgeat37Zm_8UVOiR9V6Uq2Tav2jWvMU4lMoJDhJ8n_V_6S-Aao1hKw</recordid><startdate>20221001</startdate><enddate>20221001</enddate><creator>Hiroshige, Ryosuke</creator><creator>Goto, Satoru</creator><creator>Tsunoda, Chihiro</creator><creator>Ichii, Risa</creator><creator>Shimizu, Shota</creator><creator>Otsuka, Yuta</creator><creator>Makino, Kosho</creator><creator>Takahashi, Hideyo</creator><creator>Yokoyama, Hideshi</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-8088-9070</orcidid></search><sort><creationdate>20221001</creationdate><title>Trajectory of the spectral/structural rearrangements for photo-oxidative reaction of neat ketoprofen and its cyclodextrin complex</title><author>Hiroshige, Ryosuke ; Goto, Satoru ; Tsunoda, Chihiro ; Ichii, Risa ; Shimizu, Shota ; Otsuka, Yuta ; Makino, Kosho ; Takahashi, Hideyo ; Yokoyama, Hideshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c249t-62c7ac6668ccb882186ad841e1e5366dec9ea76726254b630cea5db668c5268a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Crystallography and Scattering Methods</topic><topic>Cyclodextrins</topic><topic>Decarboxylation</topic><topic>Food Science</topic><topic>Irradiation</topic><topic>Ketoprofen</topic><topic>Organic Chemistry</topic><topic>Original Article</topic><topic>Photodegradation</topic><topic>Photolysis</topic><topic>Photosensitivity</topic><topic>Singular value decomposition</topic><topic>Trajectory analysis</topic><topic>Ultraviolet radiation</topic><topic>Vector spaces</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hiroshige, Ryosuke</creatorcontrib><creatorcontrib>Goto, Satoru</creatorcontrib><creatorcontrib>Tsunoda, Chihiro</creatorcontrib><creatorcontrib>Ichii, Risa</creatorcontrib><creatorcontrib>Shimizu, Shota</creatorcontrib><creatorcontrib>Otsuka, Yuta</creatorcontrib><creatorcontrib>Makino, Kosho</creatorcontrib><creatorcontrib>Takahashi, Hideyo</creatorcontrib><creatorcontrib>Yokoyama, Hideshi</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of inclusion phenomena and macrocyclic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hiroshige, Ryosuke</au><au>Goto, Satoru</au><au>Tsunoda, Chihiro</au><au>Ichii, Risa</au><au>Shimizu, Shota</au><au>Otsuka, Yuta</au><au>Makino, Kosho</au><au>Takahashi, Hideyo</au><au>Yokoyama, Hideshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Trajectory of the spectral/structural rearrangements for photo-oxidative reaction of neat ketoprofen and its cyclodextrin complex</atitle><jtitle>Journal of inclusion phenomena and macrocyclic chemistry</jtitle><stitle>J Incl Phenom Macrocycl Chem</stitle><date>2022-10-01</date><risdate>2022</risdate><volume>102</volume><issue>9-10</issue><spage>791</spage><epage>800</epage><pages>791-800</pages><issn>1388-3127</issn><eissn>1573-1111</eissn><abstract>Ketoprofen is a nonsteroidal anti-inflammatory drug used as mohrus tape which causes unwanted photosensitivity due to UV irradiation. In addition, photodegradation of ketoprofen induces its decarboxylation. Here, we aim to determine the effect of cyclodextrin on the photolysis of ketoprofen. Separation technique using HPLC confirmed that UV irradiation of ketoprofen produced multiple products. A unique reaction proceeded in the presence of β-cyclodextrin. Furthermore, characterization by UV spectroscopy was performed, and the obtained spectra were analyzed using singular value decomposition. By analyzing the trajectory of the singular vector space, we were able to reflect the difference in the reaction pathway of ketoprofen with and without cyclodextrin. This study uses a singular value decomposition analysis, which is useful as a novel approach for solutions of radical reactions and a promising technique for analysis of radical reactions in the future. Graphical abstract</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><doi>10.1007/s10847-022-01160-3</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-8088-9070</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1388-3127
ispartof Journal of inclusion phenomena and macrocyclic chemistry, 2022-10, Vol.102 (9-10), p.791-800
issn 1388-3127
1573-1111
language eng
recordid cdi_proquest_journals_2723515299
source SpringerNature Journals
subjects Chemistry
Chemistry and Materials Science
Crystallography and Scattering Methods
Cyclodextrins
Decarboxylation
Food Science
Irradiation
Ketoprofen
Organic Chemistry
Original Article
Photodegradation
Photolysis
Photosensitivity
Singular value decomposition
Trajectory analysis
Ultraviolet radiation
Vector spaces
title Trajectory of the spectral/structural rearrangements for photo-oxidative reaction of neat ketoprofen and its cyclodextrin complex
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-16T16%3A39%3A53IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Trajectory%20of%20the%20spectral/structural%20rearrangements%20for%20photo-oxidative%20reaction%20of%20neat%20ketoprofen%20and%20its%20cyclodextrin%20complex&rft.jtitle=Journal%20of%20inclusion%20phenomena%20and%20macrocyclic%20chemistry&rft.au=Hiroshige,%20Ryosuke&rft.date=2022-10-01&rft.volume=102&rft.issue=9-10&rft.spage=791&rft.epage=800&rft.pages=791-800&rft.issn=1388-3127&rft.eissn=1573-1111&rft_id=info:doi/10.1007/s10847-022-01160-3&rft_dat=%3Cproquest_cross%3E2723515299%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2723515299&rft_id=info:pmid/&rfr_iscdi=true