Detection of free radicals during the cellular metabolism of adriamycin
Experiments were conducted to determine which free radicals are generated during the metabolism of adriamycin (ADM) by canine tracheal epithelial (CTE) cells, guinea pig enterocytes, and rat hepatocytes. The technique employed in this study was spin trapping; the spin trap utilized was 5,5-dimethyl-...
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| Veröffentlicht in: | Free radical biology & medicine 1990, Vol.9 (5), p.415-421 |
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| creator | Turner, Marvin J. Everman, David B. Ellington, Sharon P. Fields, Charles E. |
| description | Experiments were conducted to determine which free radicals are generated during the metabolism of adriamycin (ADM) by canine tracheal epithelial (CTE) cells, guinea pig enterocytes, and rat hepatocytes. The technique employed in this study was spin trapping; the spin trap utilized was 5,5-dimethyl-1-pyrroline-1-oxide (DMPO). The spin adduct 2-hydroxy-5,5-dimethyl-1-pyrrolidinyloxyl (DMPO-OH) was observed during the metabolism of ADM by CTE cells. However, the addition of dimethyl sulfoxide to the in vitro system suggested that superoxide is initially spin trapped by nitrone, and that the adduct 2-hydroperoxy-5, 5-dimethyl-1-pyrrolidinyloxyl (DMPO-OOH) is rapidly bioreduced to afford DMPO-OH. The addition of superoxide dismutase to the system indicated that superoxide generation was primarily intracellular. The adriamycin semiquinone free radical (ADM-SQ) was produced during the metabolism by enterocytes and hepatocytes. The rate of the production of ADM-SQ was enhanced under anaerobic conditions, suggesting that molecular oxygen was responsible for the degradation of this carbon-centered free radical. However, spin trapping of oxygen radicals was not observed; this observation suggests that these reactive intermediates are not produced at concentrations sufficient for detection by spin-trapping experiments. |
| doi_str_mv | 10.1016/0891-5849(90)90018-E |
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The technique employed in this study was spin trapping; the spin trap utilized was 5,5-dimethyl-1-pyrroline-1-oxide (DMPO). The spin adduct 2-hydroxy-5,5-dimethyl-1-pyrrolidinyloxyl (DMPO-OH) was observed during the metabolism of ADM by CTE cells. However, the addition of dimethyl sulfoxide to the in vitro system suggested that superoxide is initially spin trapped by nitrone, and that the adduct 2-hydroperoxy-5, 5-dimethyl-1-pyrrolidinyloxyl (DMPO-OOH) is rapidly bioreduced to afford DMPO-OH. The addition of superoxide dismutase to the system indicated that superoxide generation was primarily intracellular. The adriamycin semiquinone free radical (ADM-SQ) was produced during the metabolism by enterocytes and hepatocytes. The rate of the production of ADM-SQ was enhanced under anaerobic conditions, suggesting that molecular oxygen was responsible for the degradation of this carbon-centered free radical. However, spin trapping of oxygen radicals was not observed; this observation suggests that these reactive intermediates are not produced at concentrations sufficient for detection by spin-trapping experiments.</description><identifier>ISSN: 0891-5849</identifier><identifier>EISSN: 1873-4596</identifier><identifier>DOI: 10.1016/0891-5849(90)90018-E</identifier><identifier>PMID: 1963415</identifier><identifier>CODEN: FRBMEH</identifier><language>eng</language><publisher>New York, NY: Elsevier Inc</publisher><subject>Adriamycin ; Adriamycin semiquinone free radical ; Animals ; Antineoplastic agents ; Biological and medical sciences ; Chemotherapy ; Dogs ; Doxorubicin - chemistry ; Doxorubicin - metabolism ; Drug metabolism ; Electron Spin Resonance Spectroscopy ; Free Radicals ; Guinea Pigs ; Hydroxides - metabolism ; Hydroxyl Radical ; In Vitro Techniques ; Intestinal Mucosa - metabolism ; Liver - metabolism ; Male ; Medical sciences ; Pharmacology. Drug treatments ; Rats ; Rats, Inbred F344 ; Spin trapping ; Superoxide ; Superoxides - metabolism ; Trachea - metabolism</subject><ispartof>Free radical biology & medicine, 1990, Vol.9 (5), p.415-421</ispartof><rights>1990</rights><rights>1991 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c418t-e1a79e52665bcf86c24271e4bcdfeb4791f75e5338524fe5c59e054aa0c46a693</citedby><cites>FETCH-LOGICAL-c418t-e1a79e52665bcf86c24271e4bcdfeb4791f75e5338524fe5c59e054aa0c46a693</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0891-5849(90)90018-E$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,782,786,3552,4026,27930,27931,27932,46002</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19640395$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1963415$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Turner, Marvin J.</creatorcontrib><creatorcontrib>Everman, David B.</creatorcontrib><creatorcontrib>Ellington, Sharon P.</creatorcontrib><creatorcontrib>Fields, Charles E.</creatorcontrib><title>Detection of free radicals during the cellular metabolism of adriamycin</title><title>Free radical biology & medicine</title><addtitle>Free Radic Biol Med</addtitle><description>Experiments were conducted to determine which free radicals are generated during the metabolism of adriamycin (ADM) by canine tracheal epithelial (CTE) cells, guinea pig enterocytes, and rat hepatocytes. The technique employed in this study was spin trapping; the spin trap utilized was 5,5-dimethyl-1-pyrroline-1-oxide (DMPO). The spin adduct 2-hydroxy-5,5-dimethyl-1-pyrrolidinyloxyl (DMPO-OH) was observed during the metabolism of ADM by CTE cells. However, the addition of dimethyl sulfoxide to the in vitro system suggested that superoxide is initially spin trapped by nitrone, and that the adduct 2-hydroperoxy-5, 5-dimethyl-1-pyrrolidinyloxyl (DMPO-OOH) is rapidly bioreduced to afford DMPO-OH. The addition of superoxide dismutase to the system indicated that superoxide generation was primarily intracellular. The adriamycin semiquinone free radical (ADM-SQ) was produced during the metabolism by enterocytes and hepatocytes. The rate of the production of ADM-SQ was enhanced under anaerobic conditions, suggesting that molecular oxygen was responsible for the degradation of this carbon-centered free radical. However, spin trapping of oxygen radicals was not observed; this observation suggests that these reactive intermediates are not produced at concentrations sufficient for detection by spin-trapping experiments.</description><subject>Adriamycin</subject><subject>Adriamycin semiquinone free radical</subject><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Biological and medical sciences</subject><subject>Chemotherapy</subject><subject>Dogs</subject><subject>Doxorubicin - chemistry</subject><subject>Doxorubicin - metabolism</subject><subject>Drug metabolism</subject><subject>Electron Spin Resonance Spectroscopy</subject><subject>Free Radicals</subject><subject>Guinea Pigs</subject><subject>Hydroxides - metabolism</subject><subject>Hydroxyl Radical</subject><subject>In Vitro Techniques</subject><subject>Intestinal Mucosa - metabolism</subject><subject>Liver - metabolism</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Rats, Inbred F344</subject><subject>Spin trapping</subject><subject>Superoxide</subject><subject>Superoxides - metabolism</subject><subject>Trachea - metabolism</subject><issn>0891-5849</issn><issn>1873-4596</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1990</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1LAzEQhoMotVb_gcJeFD2sJt0km1wEqbUKBS96DtnsRCP7UZNdof_erC3qSU9zmOd9GZ5B6JjgS4IJv8JCkpQJKs8lvpAYE5HOd9CYiDxLKZN8F42_kX10EMIbxpiyTIzQiEieUcLGaHELHZjOtU3S2sR6gMTr0hldhaTsvWteku4VEgNV1VfaJzV0umgrF-qB16V3ul4b1xyiPRszcLSdE_R8N3-a3afLx8XD7GaZGkpElwLRuQQ25ZwVxgpupnSaE6CFKS0UNJfE5gxYlgk2pRaYYRIwo1pjQ7nmMpugs03vyrfvPYRO1S4M1-kG2j4ogWO3IORfkDDBI5pFkG5A49sQPFi18q7Wfq0IVoNoNVhUg0UlsfoSreYxdrLt74sayp_Qxmzcn273OkSb1uvGuPAboziTA3e94SBa-3DgVTAOGgOl8_Exqmzd34d8AnwemU8</recordid><startdate>1990</startdate><enddate>1990</enddate><creator>Turner, Marvin J.</creator><creator>Everman, David B.</creator><creator>Ellington, Sharon P.</creator><creator>Fields, Charles E.</creator><general>Elsevier Inc</general><general>Elsevier Science</general><scope>IQODW</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>7U7</scope><scope>C1K</scope><scope>7X8</scope></search><sort><creationdate>1990</creationdate><title>Detection of free radicals during the cellular metabolism of adriamycin</title><author>Turner, Marvin J. ; Everman, David B. ; Ellington, Sharon P. ; Fields, Charles E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c418t-e1a79e52665bcf86c24271e4bcdfeb4791f75e5338524fe5c59e054aa0c46a693</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1990</creationdate><topic>Adriamycin</topic><topic>Adriamycin semiquinone free radical</topic><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Biological and medical sciences</topic><topic>Chemotherapy</topic><topic>Dogs</topic><topic>Doxorubicin - chemistry</topic><topic>Doxorubicin - metabolism</topic><topic>Drug metabolism</topic><topic>Electron Spin Resonance Spectroscopy</topic><topic>Free Radicals</topic><topic>Guinea Pigs</topic><topic>Hydroxides - metabolism</topic><topic>Hydroxyl Radical</topic><topic>In Vitro Techniques</topic><topic>Intestinal Mucosa - metabolism</topic><topic>Liver - metabolism</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Rats</topic><topic>Rats, Inbred F344</topic><topic>Spin trapping</topic><topic>Superoxide</topic><topic>Superoxides - metabolism</topic><topic>Trachea - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Turner, Marvin J.</creatorcontrib><creatorcontrib>Everman, David B.</creatorcontrib><creatorcontrib>Ellington, Sharon P.</creatorcontrib><creatorcontrib>Fields, Charles E.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>MEDLINE - Academic</collection><jtitle>Free radical biology & medicine</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Turner, Marvin J.</au><au>Everman, David B.</au><au>Ellington, Sharon P.</au><au>Fields, Charles E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Detection of free radicals during the cellular metabolism of adriamycin</atitle><jtitle>Free radical biology & medicine</jtitle><addtitle>Free Radic Biol Med</addtitle><date>1990</date><risdate>1990</risdate><volume>9</volume><issue>5</issue><spage>415</spage><epage>421</epage><pages>415-421</pages><issn>0891-5849</issn><eissn>1873-4596</eissn><coden>FRBMEH</coden><abstract>Experiments were conducted to determine which free radicals are generated during the metabolism of adriamycin (ADM) by canine tracheal epithelial (CTE) cells, guinea pig enterocytes, and rat hepatocytes. The technique employed in this study was spin trapping; the spin trap utilized was 5,5-dimethyl-1-pyrroline-1-oxide (DMPO). The spin adduct 2-hydroxy-5,5-dimethyl-1-pyrrolidinyloxyl (DMPO-OH) was observed during the metabolism of ADM by CTE cells. However, the addition of dimethyl sulfoxide to the in vitro system suggested that superoxide is initially spin trapped by nitrone, and that the adduct 2-hydroperoxy-5, 5-dimethyl-1-pyrrolidinyloxyl (DMPO-OOH) is rapidly bioreduced to afford DMPO-OH. The addition of superoxide dismutase to the system indicated that superoxide generation was primarily intracellular. The adriamycin semiquinone free radical (ADM-SQ) was produced during the metabolism by enterocytes and hepatocytes. The rate of the production of ADM-SQ was enhanced under anaerobic conditions, suggesting that molecular oxygen was responsible for the degradation of this carbon-centered free radical. However, spin trapping of oxygen radicals was not observed; this observation suggests that these reactive intermediates are not produced at concentrations sufficient for detection by spin-trapping experiments.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>1963415</pmid><doi>10.1016/0891-5849(90)90018-E</doi><tpages>7</tpages></addata></record> |
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| subjects | Adriamycin Adriamycin semiquinone free radical Animals Antineoplastic agents Biological and medical sciences Chemotherapy Dogs Doxorubicin - chemistry Doxorubicin - metabolism Drug metabolism Electron Spin Resonance Spectroscopy Free Radicals Guinea Pigs Hydroxides - metabolism Hydroxyl Radical In Vitro Techniques Intestinal Mucosa - metabolism Liver - metabolism Male Medical sciences Pharmacology. Drug treatments Rats Rats, Inbred F344 Spin trapping Superoxide Superoxides - metabolism Trachea - metabolism |
| title | Detection of free radicals during the cellular metabolism of adriamycin |
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