Oxidation of phenothiazine and phenoxazine by Cunninghamella elegans
1. To determine the ability of fungi to metabolize sulphur- and oxygen-containing azaarenes, Cunninghamella elegans ATCC 9245 was grown in 125-ml flasks containing fluid Sabouraud medium. The cultures and controls were incubated at 28°C with shaking and dosed with 16.7 mM phenothiazine or phenoxazin...
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| Veröffentlicht in: | Xenobiotica 2001-11, Vol.31 (11), p.799-809 |
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| container_title | Xenobiotica |
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| creator | Sutherland, J. B. Freeman, J. P. Heinze, T. M. Moody, J. D. Parshikov, I. A. Williams, A. J. Zhang, D. |
| description | 1. To determine the ability of fungi to metabolize sulphur- and oxygen-containing azaarenes, Cunninghamella elegans ATCC 9245 was grown in 125-ml flasks containing fluid Sabouraud medium. The cultures and controls were incubated at 28°C with shaking and dosed with 16.7 mM phenothiazine or phenoxazine. After incubation for 72h, the mycelia and filtrates were extracted with ethyl acetate and the combined residues analysed by high-performance liquid chromatography. Residual phenothiazine and phenoxazine were 21 and 22%, respectively, of the total UV absorbance at 254 nm. 2. The metabolites were identified by mass spectrometry and proton nuclear magnetic resonance spectroscopy. The fungus oxidized phenothiazine to phenothiazine sulphoxide, 3-hydroxyphenothiazine sulphoxide, phenothiazin-3-one, and 3-hydroxyphenothiazine and oxidized phenoxazine to phenoxazin-3-one. 3. Three of the four compounds produced by C. elegans from phenothiazine were identical to those produced by mammals, supporting the use of the fungus as a microbial model for drug metabolism. |
| doi_str_mv | 10.1080/00498250110069140 |
| format | Article |
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B. ; Freeman, J. P. ; Heinze, T. M. ; Moody, J. D. ; Parshikov, I. A. ; Williams, A. J. ; Zhang, D.</creator><creatorcontrib>Sutherland, J. B. ; Freeman, J. P. ; Heinze, T. M. ; Moody, J. D. ; Parshikov, I. A. ; Williams, A. J. ; Zhang, D.</creatorcontrib><description>1. To determine the ability of fungi to metabolize sulphur- and oxygen-containing azaarenes, Cunninghamella elegans ATCC 9245 was grown in 125-ml flasks containing fluid Sabouraud medium. The cultures and controls were incubated at 28°C with shaking and dosed with 16.7 mM phenothiazine or phenoxazine. After incubation for 72h, the mycelia and filtrates were extracted with ethyl acetate and the combined residues analysed by high-performance liquid chromatography. Residual phenothiazine and phenoxazine were 21 and 22%, respectively, of the total UV absorbance at 254 nm. 2. The metabolites were identified by mass spectrometry and proton nuclear magnetic resonance spectroscopy. The fungus oxidized phenothiazine to phenothiazine sulphoxide, 3-hydroxyphenothiazine sulphoxide, phenothiazin-3-one, and 3-hydroxyphenothiazine and oxidized phenoxazine to phenoxazin-3-one. 3. Three of the four compounds produced by C. elegans from phenothiazine were identical to those produced by mammals, supporting the use of the fungus as a microbial model for drug metabolism.</description><identifier>ISSN: 0049-8254</identifier><identifier>EISSN: 1366-5928</identifier><identifier>DOI: 10.1080/00498250110069140</identifier><identifier>PMID: 11765142</identifier><identifier>CODEN: XENOBH</identifier><language>eng</language><publisher>London: Informa UK Ltd</publisher><subject>Biological and medical sciences ; Chromatography, High Pressure Liquid ; Cunninghamella - metabolism ; Cunninghamella elegans ; General pharmacology ; Medical sciences ; Oxazines - metabolism ; Oxidation-Reduction ; Pharmacokinetics. Pharmacogenetics. Drug-receptor interactions ; Pharmacology. Drug treatments ; phenothiazine ; phenothiazines ; Phenothiazines - metabolism ; phenoxazine ; Spectrophotometry, Ultraviolet ; Sulfoxides - metabolism</subject><ispartof>Xenobiotica, 2001-11, Vol.31 (11), p.799-809</ispartof><rights>2001 Informa UK Ltd All rights reserved: reproduction in whole or part not permitted 2001</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c463t-b5d1e51b2ac6c93b6ba2694b460ea524f678ba6b2c2217c334cd01946511ec83</citedby><cites>FETCH-LOGICAL-c463t-b5d1e51b2ac6c93b6ba2694b460ea524f678ba6b2c2217c334cd01946511ec83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/00498250110069140$$EPDF$$P50$$Ginformahealthcare$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/00498250110069140$$EHTML$$P50$$Ginformahealthcare$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,59647,59753,60436,60542,61221,61256,61402,61437</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14099511$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11765142$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sutherland, J. B.</creatorcontrib><creatorcontrib>Freeman, J. P.</creatorcontrib><creatorcontrib>Heinze, T. M.</creatorcontrib><creatorcontrib>Moody, J. D.</creatorcontrib><creatorcontrib>Parshikov, I. A.</creatorcontrib><creatorcontrib>Williams, A. J.</creatorcontrib><creatorcontrib>Zhang, D.</creatorcontrib><title>Oxidation of phenothiazine and phenoxazine by Cunninghamella elegans</title><title>Xenobiotica</title><addtitle>Xenobiotica</addtitle><description>1. To determine the ability of fungi to metabolize sulphur- and oxygen-containing azaarenes, Cunninghamella elegans ATCC 9245 was grown in 125-ml flasks containing fluid Sabouraud medium. The cultures and controls were incubated at 28°C with shaking and dosed with 16.7 mM phenothiazine or phenoxazine. After incubation for 72h, the mycelia and filtrates were extracted with ethyl acetate and the combined residues analysed by high-performance liquid chromatography. Residual phenothiazine and phenoxazine were 21 and 22%, respectively, of the total UV absorbance at 254 nm. 2. The metabolites were identified by mass spectrometry and proton nuclear magnetic resonance spectroscopy. The fungus oxidized phenothiazine to phenothiazine sulphoxide, 3-hydroxyphenothiazine sulphoxide, phenothiazin-3-one, and 3-hydroxyphenothiazine and oxidized phenoxazine to phenoxazin-3-one. 3. Three of the four compounds produced by C. elegans from phenothiazine were identical to those produced by mammals, supporting the use of the fungus as a microbial model for drug metabolism.</description><subject>Biological and medical sciences</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Cunninghamella - metabolism</subject><subject>Cunninghamella elegans</subject><subject>General pharmacology</subject><subject>Medical sciences</subject><subject>Oxazines - metabolism</subject><subject>Oxidation-Reduction</subject><subject>Pharmacokinetics. Pharmacogenetics. Drug-receptor interactions</subject><subject>Pharmacology. Drug treatments</subject><subject>phenothiazine</subject><subject>phenothiazines</subject><subject>Phenothiazines - metabolism</subject><subject>phenoxazine</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Sulfoxides - metabolism</subject><issn>0049-8254</issn><issn>1366-5928</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU9P3DAQxa2qFSy0H6AXlEu5hXoc25sILmj5VwmJC_do7DjEKLG3diJYPj1eZRFClejJGs_vjd68IeQn0BOgJf1NKa9KJigApbICTr-QBRRS5qJi5Vey2PbzBPB9chDjI00UMLZH9gGWUgBnC3Jx92wbHK13mW-zdWecHzuLL9aZDF0z_zzPtdpkq8k56x46HEzfY2Z684AufiffWuyj-bF7D8n91eX96ia_vbv-szq_zTWXxZgr0YARoBhqqatCSYVMVlxxSQ0Kxlu5LBVKxTRjsNRFwXVDoeLJKhhdFofkeB67Dv7vZOJYDzbqrRFn_BTrJSuEZEz8F4SSSVFKnkCYQR18jMG09TrYAcOmBlpvI67_iThpjnbDJzWY5l2xyzQBv3YARo19G9BpG985TqsqbZS4s5mzrvVhwCcf-qYecdP78CYqPvNx-kHeGezHTmMw9aOfgkuH-GSLVwzEp78</recordid><startdate>20011101</startdate><enddate>20011101</enddate><creator>Sutherland, J. B.</creator><creator>Freeman, J. P.</creator><creator>Heinze, T. M.</creator><creator>Moody, J. D.</creator><creator>Parshikov, I. A.</creator><creator>Williams, A. J.</creator><creator>Zhang, D.</creator><general>Informa UK Ltd</general><general>Taylor & Francis</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>M7N</scope><scope>7X8</scope></search><sort><creationdate>20011101</creationdate><title>Oxidation of phenothiazine and phenoxazine by Cunninghamella elegans</title><author>Sutherland, J. B. ; Freeman, J. P. ; Heinze, T. M. ; Moody, J. D. ; Parshikov, I. A. ; Williams, A. J. ; Zhang, D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c463t-b5d1e51b2ac6c93b6ba2694b460ea524f678ba6b2c2217c334cd01946511ec83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Biological and medical sciences</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Cunninghamella - metabolism</topic><topic>Cunninghamella elegans</topic><topic>General pharmacology</topic><topic>Medical sciences</topic><topic>Oxazines - metabolism</topic><topic>Oxidation-Reduction</topic><topic>Pharmacokinetics. Pharmacogenetics. Drug-receptor interactions</topic><topic>Pharmacology. Drug treatments</topic><topic>phenothiazine</topic><topic>phenothiazines</topic><topic>Phenothiazines - metabolism</topic><topic>phenoxazine</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Sulfoxides - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sutherland, J. B.</creatorcontrib><creatorcontrib>Freeman, J. P.</creatorcontrib><creatorcontrib>Heinze, T. M.</creatorcontrib><creatorcontrib>Moody, J. D.</creatorcontrib><creatorcontrib>Parshikov, I. A.</creatorcontrib><creatorcontrib>Williams, A. 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Residual phenothiazine and phenoxazine were 21 and 22%, respectively, of the total UV absorbance at 254 nm. 2. The metabolites were identified by mass spectrometry and proton nuclear magnetic resonance spectroscopy. The fungus oxidized phenothiazine to phenothiazine sulphoxide, 3-hydroxyphenothiazine sulphoxide, phenothiazin-3-one, and 3-hydroxyphenothiazine and oxidized phenoxazine to phenoxazin-3-one. 3. Three of the four compounds produced by C. elegans from phenothiazine were identical to those produced by mammals, supporting the use of the fungus as a microbial model for drug metabolism.</abstract><cop>London</cop><pub>Informa UK Ltd</pub><pmid>11765142</pmid><doi>10.1080/00498250110069140</doi><tpages>11</tpages></addata></record> |
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| source | MEDLINE; Taylor & Francis:Master (3349 titles); Taylor & Francis Medical Library - CRKN |
| subjects | Biological and medical sciences Chromatography, High Pressure Liquid Cunninghamella - metabolism Cunninghamella elegans General pharmacology Medical sciences Oxazines - metabolism Oxidation-Reduction Pharmacokinetics. Pharmacogenetics. Drug-receptor interactions Pharmacology. Drug treatments phenothiazine phenothiazines Phenothiazines - metabolism phenoxazine Spectrophotometry, Ultraviolet Sulfoxides - metabolism |
| title | Oxidation of phenothiazine and phenoxazine by Cunninghamella elegans |
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