Human metabolites and transformation products of cyclophosphamide and ifosfamide: analysis, occurrence and formation during abiotic treatments
This study describes a gas chromatography-mass spectrometry analytical method for the analysis of cytostatic cyclophosphamide (CP), ifosfamide (IF) and their selected metabolites/transformation products (TPs): carboxy-cyclophosphamide (carboxy-CP), keto-cyclophosphamide (keto-CP) and 3-dechloroethyl...
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| Veröffentlicht in: | Environmental science and pollution research international 2016-06, Vol.23 (11), p.11209-11223 |
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| creator | Česen, Marjeta Kosjek, Tina Busetti, Francesco Kompare, Boris Heath, Ester |
| description | This study describes a gas chromatography-mass spectrometry analytical method for the analysis of cytostatic cyclophosphamide (CP), ifosfamide (IF) and their selected metabolites/transformation products (TPs): carboxy-cyclophosphamide (carboxy-CP), keto-cyclophosphamide (keto-CP) and 3-dechloroethyl-ifosfamide/
N
-dechloroethyl-cyclophosphamide (
N
-decl-CP) in wastewater (WW). Keto-cyclophosphamide, CP and IF were extracted with Oasis HLB and
N
-decl-CP and carboxy-CP with Isolute ENV+ cartridges. Analyte derivatization was performed by silylation (metabolites/TPs) and acetylation (CP and IF). The recoveries and LOQs of the developed method were 58, 87 and 103 % and 77.7, 43.7 and 6.7 ng L
−1
for carboxy-CP, keto-CP and
N
-decl-CP, respectively. After validation, the analytical method was applied to hospital WW and influent and effluent samples of a receiving WW treatment plant. In hospital WW, levels up to 2690, 47.0, 13,200, 2100 and 178 ng L
−1
were detected for CP, IF, carboxy-CP,
N
-decl-CP and keto-CP, respectively, while in influent and effluent samples concentrations were below LOQs. The formation of TPs during abiotic treatments was also studied. Liquid chromatography-high-resolution mass spectrometry was used to identify CP and IF TPs in ultrapure water, treated with UV and UV/H
2
O
2
. UV treatment produced four CP TPs and four IF TPs, while UV/H
2
O
2
resulted in five CPs and four IF TPs. Besides already known TPs, three novel TPs (CP-TP138a, imino-ifosfamide and IF-TP138) have been tentatively identified. In hospital WW treated by UV/O
3
/H
2
O
2
, none of the target metabolites/TPs resulted above LOQs. |
| doi_str_mv | 10.1007/s11356-016-6321-1 |
| format | Article |
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N
-dechloroethyl-cyclophosphamide (
N
-decl-CP) in wastewater (WW). Keto-cyclophosphamide, CP and IF were extracted with Oasis HLB and
N
-decl-CP and carboxy-CP with Isolute ENV+ cartridges. Analyte derivatization was performed by silylation (metabolites/TPs) and acetylation (CP and IF). The recoveries and LOQs of the developed method were 58, 87 and 103 % and 77.7, 43.7 and 6.7 ng L
−1
for carboxy-CP, keto-CP and
N
-decl-CP, respectively. After validation, the analytical method was applied to hospital WW and influent and effluent samples of a receiving WW treatment plant. In hospital WW, levels up to 2690, 47.0, 13,200, 2100 and 178 ng L
−1
were detected for CP, IF, carboxy-CP,
N
-decl-CP and keto-CP, respectively, while in influent and effluent samples concentrations were below LOQs. The formation of TPs during abiotic treatments was also studied. Liquid chromatography-high-resolution mass spectrometry was used to identify CP and IF TPs in ultrapure water, treated with UV and UV/H
2
O
2
. UV treatment produced four CP TPs and four IF TPs, while UV/H
2
O
2
resulted in five CPs and four IF TPs. Besides already known TPs, three novel TPs (CP-TP138a, imino-ifosfamide and IF-TP138) have been tentatively identified. In hospital WW treated by UV/O
3
/H
2
O
2
, none of the target metabolites/TPs resulted above LOQs.</description><identifier>ISSN: 0944-1344</identifier><identifier>EISSN: 1614-7499</identifier><identifier>DOI: 10.1007/s11356-016-6321-1</identifier><identifier>PMID: 26920534</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Analytical methods ; Antineoplastic Agents, Alkylating - analysis ; Antineoplastic Agents, Alkylating - metabolism ; Aquatic Pollution ; Atmospheric Protection/Air Quality Control/Air Pollution ; Cell division ; Chemotherapy ; Chromatography ; Cyclophosphamide - analysis ; Cyclophosphamide - metabolism ; Cytotoxicity ; Earth and Environmental Science ; Ecotoxicology ; Effluents ; Environment ; Environmental Chemistry ; Environmental Health ; Environmental Monitoring - methods ; Environmental science ; Gas chromatography ; Gas Chromatography-Mass Spectrometry - methods ; Hospitals ; Humans ; Hydrogen peroxide ; Ifosfamide - analysis ; Ifosfamide - metabolism ; Liquid chromatography ; Mass spectrometry ; Metabolites ; Research Article ; Scientific imaging ; Studies ; Waste Water - analysis ; Waste Water Technology ; Water Management ; Water Pollutants, Chemical - analysis ; Water Pollutants, Chemical - metabolism ; Water Pollution Control ; Water treatment</subject><ispartof>Environmental science and pollution research international, 2016-06, Vol.23 (11), p.11209-11223</ispartof><rights>Springer-Verlag Berlin Heidelberg 2016</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c442t-7a4383962b8bd999e9f9551bdd88850704ea7ef9ffdcdbf94654999103b821273</citedby><cites>FETCH-LOGICAL-c442t-7a4383962b8bd999e9f9551bdd88850704ea7ef9ffdcdbf94654999103b821273</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11356-016-6321-1$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11356-016-6321-1$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26920534$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Česen, Marjeta</creatorcontrib><creatorcontrib>Kosjek, Tina</creatorcontrib><creatorcontrib>Busetti, Francesco</creatorcontrib><creatorcontrib>Kompare, Boris</creatorcontrib><creatorcontrib>Heath, Ester</creatorcontrib><title>Human metabolites and transformation products of cyclophosphamide and ifosfamide: analysis, occurrence and formation during abiotic treatments</title><title>Environmental science and pollution research international</title><addtitle>Environ Sci Pollut Res</addtitle><addtitle>Environ Sci Pollut Res Int</addtitle><description>This study describes a gas chromatography-mass spectrometry analytical method for the analysis of cytostatic cyclophosphamide (CP), ifosfamide (IF) and their selected metabolites/transformation products (TPs): carboxy-cyclophosphamide (carboxy-CP), keto-cyclophosphamide (keto-CP) and 3-dechloroethyl-ifosfamide/
N
-dechloroethyl-cyclophosphamide (
N
-decl-CP) in wastewater (WW). Keto-cyclophosphamide, CP and IF were extracted with Oasis HLB and
N
-decl-CP and carboxy-CP with Isolute ENV+ cartridges. Analyte derivatization was performed by silylation (metabolites/TPs) and acetylation (CP and IF). The recoveries and LOQs of the developed method were 58, 87 and 103 % and 77.7, 43.7 and 6.7 ng L
−1
for carboxy-CP, keto-CP and
N
-decl-CP, respectively. After validation, the analytical method was applied to hospital WW and influent and effluent samples of a receiving WW treatment plant. In hospital WW, levels up to 2690, 47.0, 13,200, 2100 and 178 ng L
−1
were detected for CP, IF, carboxy-CP,
N
-decl-CP and keto-CP, respectively, while in influent and effluent samples concentrations were below LOQs. The formation of TPs during abiotic treatments was also studied. Liquid chromatography-high-resolution mass spectrometry was used to identify CP and IF TPs in ultrapure water, treated with UV and UV/H
2
O
2
. UV treatment produced four CP TPs and four IF TPs, while UV/H
2
O
2
resulted in five CPs and four IF TPs. Besides already known TPs, three novel TPs (CP-TP138a, imino-ifosfamide and IF-TP138) have been tentatively identified. In hospital WW treated by UV/O
3
/H
2
O
2
, none of the target metabolites/TPs resulted above LOQs.</description><subject>Analytical methods</subject><subject>Antineoplastic Agents, Alkylating - analysis</subject><subject>Antineoplastic Agents, Alkylating - metabolism</subject><subject>Aquatic Pollution</subject><subject>Atmospheric Protection/Air Quality Control/Air Pollution</subject><subject>Cell division</subject><subject>Chemotherapy</subject><subject>Chromatography</subject><subject>Cyclophosphamide - analysis</subject><subject>Cyclophosphamide - metabolism</subject><subject>Cytotoxicity</subject><subject>Earth and Environmental Science</subject><subject>Ecotoxicology</subject><subject>Effluents</subject><subject>Environment</subject><subject>Environmental Chemistry</subject><subject>Environmental Health</subject><subject>Environmental Monitoring - methods</subject><subject>Environmental science</subject><subject>Gas chromatography</subject><subject>Gas Chromatography-Mass Spectrometry - methods</subject><subject>Hospitals</subject><subject>Humans</subject><subject>Hydrogen peroxide</subject><subject>Ifosfamide - analysis</subject><subject>Ifosfamide - metabolism</subject><subject>Liquid chromatography</subject><subject>Mass spectrometry</subject><subject>Metabolites</subject><subject>Research Article</subject><subject>Scientific imaging</subject><subject>Studies</subject><subject>Waste Water - analysis</subject><subject>Waste Water Technology</subject><subject>Water Management</subject><subject>Water Pollutants, Chemical - analysis</subject><subject>Water Pollutants, Chemical - metabolism</subject><subject>Water Pollution Control</subject><subject>Water treatment</subject><issn>0944-1344</issn><issn>1614-7499</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</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>eNqFkcuKFTEURYMo9rX1A5xIgRMHluYkqTycSaO20OBExyGVh52mqlImqcH9Cb_Z3K72gSCOwoF19iF7IfQU8CvAWLwuAHTgPQbec0qgh3voABxYL5hS99EBK8Z6oIydoUel3GBMsCLiITojXBE8UHZA3y-32Szd7KsZ0xSrL51ZXFezWUpIeTY1pqVbc3KbraVLobNHO6X1OpX12szR-Vs-hlTC7fimzWY6llhedsnaLWe_2B36nee2HJevnRljqtG2a97U2S-1PEYPgpmKf3L3nqMv7999vrjsrz59-Hjx9qq3jJHaC8OopIqTUY5OKeVVUMMAo3NSygELzLwRPqgQnHVjUIwPrREFmI6SABH0HL3Yc9vPvm2-VD3HYv00mcWnrWiQWApKBKj_o6J1KoggvKHP_0Jv0pZbHTtFOMESNwp2yuZUSvZBrznOJh81YH3yqnevunnVJ68a2s6zu-RtnL37tfFTZAPIDpT1VK3Pf5z-Z-oPdxGvqQ</recordid><startdate>20160601</startdate><enddate>20160601</enddate><creator>Česen, Marjeta</creator><creator>Kosjek, Tina</creator><creator>Busetti, Francesco</creator><creator>Kompare, Boris</creator><creator>Heath, Ester</creator><general>Springer Berlin Heidelberg</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>3V.</scope><scope>7QL</scope><scope>7SN</scope><scope>7T7</scope><scope>7TV</scope><scope>7U7</scope><scope>7WY</scope><scope>7WZ</scope><scope>7X7</scope><scope>7XB</scope><scope>87Z</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8FL</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BEZIV</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FRNLG</scope><scope>FYUFA</scope><scope>F~G</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K60</scope><scope>K6~</scope><scope>K9.</scope><scope>L.-</scope><scope>M0C</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7N</scope><scope>P64</scope><scope>PATMY</scope><scope>PQBIZ</scope><scope>PQBZA</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PYCSY</scope><scope>Q9U</scope><scope>7X8</scope><scope>7ST</scope><scope>SOI</scope></search><sort><creationdate>20160601</creationdate><title>Human metabolites and transformation products of cyclophosphamide and ifosfamide: analysis, occurrence and formation during abiotic treatments</title><author>Česen, Marjeta ; Kosjek, Tina ; Busetti, Francesco ; Kompare, Boris ; Heath, Ester</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c442t-7a4383962b8bd999e9f9551bdd88850704ea7ef9ffdcdbf94654999103b821273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Analytical methods</topic><topic>Antineoplastic Agents, Alkylating - 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Academic</collection><collection>Environment Abstracts</collection><collection>Environment Abstracts</collection><jtitle>Environmental science and pollution research international</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Česen, Marjeta</au><au>Kosjek, Tina</au><au>Busetti, Francesco</au><au>Kompare, Boris</au><au>Heath, Ester</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Human metabolites and transformation products of cyclophosphamide and ifosfamide: analysis, occurrence and formation during abiotic treatments</atitle><jtitle>Environmental science and pollution research international</jtitle><stitle>Environ Sci Pollut Res</stitle><addtitle>Environ Sci Pollut Res Int</addtitle><date>2016-06-01</date><risdate>2016</risdate><volume>23</volume><issue>11</issue><spage>11209</spage><epage>11223</epage><pages>11209-11223</pages><issn>0944-1344</issn><eissn>1614-7499</eissn><abstract>This study describes a gas chromatography-mass spectrometry analytical method for the analysis of cytostatic cyclophosphamide (CP), ifosfamide (IF) and their selected metabolites/transformation products (TPs): carboxy-cyclophosphamide (carboxy-CP), keto-cyclophosphamide (keto-CP) and 3-dechloroethyl-ifosfamide/
N
-dechloroethyl-cyclophosphamide (
N
-decl-CP) in wastewater (WW). Keto-cyclophosphamide, CP and IF were extracted with Oasis HLB and
N
-decl-CP and carboxy-CP with Isolute ENV+ cartridges. Analyte derivatization was performed by silylation (metabolites/TPs) and acetylation (CP and IF). The recoveries and LOQs of the developed method were 58, 87 and 103 % and 77.7, 43.7 and 6.7 ng L
−1
for carboxy-CP, keto-CP and
N
-decl-CP, respectively. After validation, the analytical method was applied to hospital WW and influent and effluent samples of a receiving WW treatment plant. In hospital WW, levels up to 2690, 47.0, 13,200, 2100 and 178 ng L
−1
were detected for CP, IF, carboxy-CP,
N
-decl-CP and keto-CP, respectively, while in influent and effluent samples concentrations were below LOQs. The formation of TPs during abiotic treatments was also studied. Liquid chromatography-high-resolution mass spectrometry was used to identify CP and IF TPs in ultrapure water, treated with UV and UV/H
2
O
2
. UV treatment produced four CP TPs and four IF TPs, while UV/H
2
O
2
resulted in five CPs and four IF TPs. Besides already known TPs, three novel TPs (CP-TP138a, imino-ifosfamide and IF-TP138) have been tentatively identified. In hospital WW treated by UV/O
3
/H
2
O
2
, none of the target metabolites/TPs resulted above LOQs.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><pmid>26920534</pmid><doi>10.1007/s11356-016-6321-1</doi><tpages>15</tpages></addata></record> |
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| ispartof | Environmental science and pollution research international, 2016-06, Vol.23 (11), p.11209-11223 |
| issn | 0944-1344 1614-7499 |
| language | eng |
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| source | MEDLINE; SpringerNature Journals |
| subjects | Analytical methods Antineoplastic Agents, Alkylating - analysis Antineoplastic Agents, Alkylating - metabolism Aquatic Pollution Atmospheric Protection/Air Quality Control/Air Pollution Cell division Chemotherapy Chromatography Cyclophosphamide - analysis Cyclophosphamide - metabolism Cytotoxicity Earth and Environmental Science Ecotoxicology Effluents Environment Environmental Chemistry Environmental Health Environmental Monitoring - methods Environmental science Gas chromatography Gas Chromatography-Mass Spectrometry - methods Hospitals Humans Hydrogen peroxide Ifosfamide - analysis Ifosfamide - metabolism Liquid chromatography Mass spectrometry Metabolites Research Article Scientific imaging Studies Waste Water - analysis Waste Water Technology Water Management Water Pollutants, Chemical - analysis Water Pollutants, Chemical - metabolism Water Pollution Control Water treatment |
| title | Human metabolites and transformation products of cyclophosphamide and ifosfamide: analysis, occurrence and formation during abiotic treatments |
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