Triplet-sensitized photooxygenation of therapeutic retinoids
The triplet-sensitized photooxygenation of retinoic acid in hydroorganic buffer, methyl retinoate in a variety of solvents, and methyl 13-cis-retinoate and etretinate in ethanol has been investigated. By high-performance liquid chromatographic analysis, one major peroxide product was formed from eac...
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| Veröffentlicht in: | Pharmaceutical research 1991-07, Vol.8 (7), p.826-831 |
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| creator | HUMPHRIES, K. A CURLEY, R. W |
| description | The triplet-sensitized photooxygenation of retinoic acid in hydroorganic buffer, methyl retinoate in a variety of solvents, and methyl 13-cis-retinoate and etretinate in ethanol has been investigated. By high-performance liquid chromatographic analysis, one major peroxide product was formed from each retinoid substrate under all conditions investigated. The structures of these peroxides have been assigned relying on high-field nuclear magnetic resonance and mass and ultraviolet spectroscopy. While product structures were not influenced, the rate of product formation was found to vary with solvent, substrate, and perhaps the nature of the sensitizer. The retinoid peroxides isolated are stable toward nucleophiles and weakly acidic and basic conditions. Possible reasons for rate variations in the photooxygenations are discussed. |
| doi_str_mv | 10.1023/A:1015887025379 |
| format | Article |
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A ; CURLEY, R. W</creator><creatorcontrib>HUMPHRIES, K. A ; CURLEY, R. W</creatorcontrib><description>The triplet-sensitized photooxygenation of retinoic acid in hydroorganic buffer, methyl retinoate in a variety of solvents, and methyl 13-cis-retinoate and etretinate in ethanol has been investigated. By high-performance liquid chromatographic analysis, one major peroxide product was formed from each retinoid substrate under all conditions investigated. The structures of these peroxides have been assigned relying on high-field nuclear magnetic resonance and mass and ultraviolet spectroscopy. While product structures were not influenced, the rate of product formation was found to vary with solvent, substrate, and perhaps the nature of the sensitizer. The retinoid peroxides isolated are stable toward nucleophiles and weakly acidic and basic conditions. Possible reasons for rate variations in the photooxygenations are discussed.</description><identifier>ISSN: 0724-8741</identifier><identifier>EISSN: 1573-904X</identifier><identifier>DOI: 10.1023/A:1015887025379</identifier><identifier>PMID: 1924133</identifier><identifier>CODEN: PHREEB</identifier><language>eng</language><publisher>New York, NY: Springer</publisher><subject>Biological and medical sciences ; Chromatography, High Pressure Liquid ; General pharmacology ; Indicators and Reagents ; Magnetic Resonance Spectroscopy ; Medical sciences ; Oxygen - chemistry ; Peroxides ; Pharmaceutical technology. Pharmaceutical industry ; Pharmacology. 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W</creatorcontrib><title>Triplet-sensitized photooxygenation of therapeutic retinoids</title><title>Pharmaceutical research</title><addtitle>Pharm Res</addtitle><description>The triplet-sensitized photooxygenation of retinoic acid in hydroorganic buffer, methyl retinoate in a variety of solvents, and methyl 13-cis-retinoate and etretinate in ethanol has been investigated. By high-performance liquid chromatographic analysis, one major peroxide product was formed from each retinoid substrate under all conditions investigated. The structures of these peroxides have been assigned relying on high-field nuclear magnetic resonance and mass and ultraviolet spectroscopy. While product structures were not influenced, the rate of product formation was found to vary with solvent, substrate, and perhaps the nature of the sensitizer. The retinoid peroxides isolated are stable toward nucleophiles and weakly acidic and basic conditions. Possible reasons for rate variations in the photooxygenations are discussed.</description><subject>Biological and medical sciences</subject><subject>Chromatography, High Pressure Liquid</subject><subject>General pharmacology</subject><subject>Indicators and Reagents</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Oxygen - chemistry</subject><subject>Peroxides</subject><subject>Pharmaceutical technology. Pharmaceutical industry</subject><subject>Pharmacology. Drug treatments</subject><subject>Photochemistry</subject><subject>Retinoids - chemistry</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>0724-8741</issn><issn>1573-904X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpNj01LxDAURYMo4zi6diV0o7vqS5M0ibgZxC8YcDOCu5Kmr06k09QkBcdf74BduLqLc7jcS8g5hWsKBbtZ3lKgQikJhWBSH5A5FZLlGvj7IZmDLHiuJKfH5CTGTwBQVPMZmVFdcMrYnNytgxs6THnEPrrkfrDJho1P3n_vPrA3yfk-822WNhjMgGNyNguYXO9dE0_JUWu6iGdTLsjb48P6_jlfvT693C9X-VCwMuVS69qWqME0kjU14n4pWJCtVoZpzhorWsaMVCVSbimrmxZAWmEs1bLEgi3I1V_vEPzXiDFVWxctdp3p0Y-xkgUVXEC5Fy8mcay32FRDcFsTdtV0d88vJ26iNV0bTG9d_KcpQUFJ9gs_SWSq</recordid><startdate>19910701</startdate><enddate>19910701</enddate><creator>HUMPHRIES, K. A</creator><creator>CURLEY, R. 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Pharmaceutical industry</topic><topic>Pharmacology. Drug treatments</topic><topic>Photochemistry</topic><topic>Retinoids - chemistry</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>HUMPHRIES, K. A</creatorcontrib><creatorcontrib>CURLEY, R. W</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>MEDLINE - Academic</collection><jtitle>Pharmaceutical research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>HUMPHRIES, K. A</au><au>CURLEY, R. W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Triplet-sensitized photooxygenation of therapeutic retinoids</atitle><jtitle>Pharmaceutical research</jtitle><addtitle>Pharm Res</addtitle><date>1991-07-01</date><risdate>1991</risdate><volume>8</volume><issue>7</issue><spage>826</spage><epage>831</epage><pages>826-831</pages><issn>0724-8741</issn><eissn>1573-904X</eissn><coden>PHREEB</coden><abstract>The triplet-sensitized photooxygenation of retinoic acid in hydroorganic buffer, methyl retinoate in a variety of solvents, and methyl 13-cis-retinoate and etretinate in ethanol has been investigated. By high-performance liquid chromatographic analysis, one major peroxide product was formed from each retinoid substrate under all conditions investigated. The structures of these peroxides have been assigned relying on high-field nuclear magnetic resonance and mass and ultraviolet spectroscopy. While product structures were not influenced, the rate of product formation was found to vary with solvent, substrate, and perhaps the nature of the sensitizer. The retinoid peroxides isolated are stable toward nucleophiles and weakly acidic and basic conditions. Possible reasons for rate variations in the photooxygenations are discussed.</abstract><cop>New York, NY</cop><pub>Springer</pub><pmid>1924133</pmid><doi>10.1023/A:1015887025379</doi><tpages>6</tpages></addata></record> |
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| ispartof | Pharmaceutical research, 1991-07, Vol.8 (7), p.826-831 |
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| language | eng |
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| source | MEDLINE; Springer Online Journals - JUSTICE |
| subjects | Biological and medical sciences Chromatography, High Pressure Liquid General pharmacology Indicators and Reagents Magnetic Resonance Spectroscopy Medical sciences Oxygen - chemistry Peroxides Pharmaceutical technology. Pharmaceutical industry Pharmacology. Drug treatments Photochemistry Retinoids - chemistry Spectrometry, Mass, Fast Atom Bombardment Spectrophotometry, Ultraviolet |
| title | Triplet-sensitized photooxygenation of therapeutic retinoids |
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