Photodynamic Action of Merocyanine 540 on Artificial and Natural Cell Membranes: Involvement of Singlet Molecular Oxygen
The photochemistry of merocyanine 540 (MC 540), a sensitizing dye that binds preferentially to leukemia and electrically excitable cells, has been investigated. MC 540-mediated photooxidation of histidine, arachidonate, and unsaturated phospholipid vesicles was assessed by spin label oximetry and sh...
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| Veröffentlicht in: | Proc. Natl. Acad. Sci. U.S.A.; (United States) 1987-05, Vol.84 (9), p.2999-3003 |
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| container_title | Proc. Natl. Acad. Sci. U.S.A.; (United States) |
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| creator | Kalyanaraman, B. Feix, J. B. Sieber, F. Thomas, J. P. Girotti, A. W. |
| description | The photochemistry of merocyanine 540 (MC 540), a sensitizing dye that binds preferentially to leukemia and electrically excitable cells, has been investigated. MC 540-mediated photooxidation of histidine, arachidonate, and unsaturated phospholipid vesicles was assessed by spin label oximetry and shown to involve type II (singlet oxygen) chemistry. The dye was also shown to be a potent sensitizer of lipid peroxidation in a natural cell membrane, the erythrocyte ghost. Inhibition by azide, stimulation by2H2O, and identification of the cholesterol product 5α -cholest-6-ene-3β ,5-diol in this system, all were consistent with singlet oxygen intermediacy. Finally, MC 540 was found to be considerably more phototoxic to K-562 leukemia cells in2H2O than in H2O. We conclude that singlet oxygen plays a major role in the phototherapeutic effects of this dye. |
| doi_str_mv | 10.1073/pnas.84.9.2999 |
| format | Article |
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B. ; Sieber, F. ; Thomas, J. P. ; Girotti, A. W.</creator><creatorcontrib>Kalyanaraman, B. ; Feix, J. B. ; Sieber, F. ; Thomas, J. P. ; Girotti, A. W. ; Medical College of Wisconsin, Milwaukee</creatorcontrib><description>The photochemistry of merocyanine 540 (MC 540), a sensitizing dye that binds preferentially to leukemia and electrically excitable cells, has been investigated. MC 540-mediated photooxidation of histidine, arachidonate, and unsaturated phospholipid vesicles was assessed by spin label oximetry and shown to involve type II (singlet oxygen) chemistry. The dye was also shown to be a potent sensitizer of lipid peroxidation in a natural cell membrane, the erythrocyte ghost. Inhibition by azide, stimulation by2H2O, and identification of the cholesterol product 5α -cholest-6-ene-3β ,5-diol in this system, all were consistent with singlet oxygen intermediacy. Finally, MC 540 was found to be considerably more phototoxic to K-562 leukemia cells in2H2O than in H2O. We conclude that singlet oxygen plays a major role in the phototherapeutic effects of this dye.</description><identifier>ISSN: 0027-8424</identifier><identifier>EISSN: 1091-6490</identifier><identifier>DOI: 10.1073/pnas.84.9.2999</identifier><identifier>PMID: 3033673</identifier><identifier>CODEN: PNASA6</identifier><language>eng</language><publisher>Washington, DC: National Academy of Sciences of the United States of America</publisher><subject>550601 - Medicine- Unsealed Radionuclides in Diagnostics ; 560120 - Radiation Effects on Biochemicals, Cells, & Tissue Culture ; ANIMAL CELLS ; Biological and medical sciences ; BIOLOGICAL EFFECTS ; BIOLOGICAL RADIATION EFFECTS ; CELL CONSTITUENTS ; CELL KILLING ; Cell Line ; Cell Membrane - drug effects ; Cell Membrane - metabolism ; CELL MEMBRANES ; Cell physiology ; CHEMICAL REACTIONS ; CHEMISTRY ; CHOLESTEROL ; Cholesterols ; CYANINE DYES ; Dimyristoylphosphatidylcholine ; DISEASES ; DOSE-RESPONSE RELATIONSHIPS ; DYES ; Effects of physical and chemical agents ; ELECTROMAGNETIC RADIATION ; ELECTRON SPIN RESONANCE ; Electron Spin Resonance Spectroscopy ; ELEMENTS ; Erythrocyte Membrane - drug effects ; Erythrocyte Membrane - metabolism ; erythrocytes ; Fluorescent Dyes ; fluorescent probes ; Fundamental and applied biological sciences. Psychology ; HEAVY WATER ; HEMIC DISEASES ; Humans ; HYDROGEN COMPOUNDS ; HYDROXY COMPOUNDS ; Irradiation ; LEUKEMIA ; Leukemia, Myeloid ; Lipid peroxides ; LIPIDS ; Liposomes ; MAGNETIC RESONANCE ; MEMBRANES ; merocyanine 540 ; Molecular and cellular biology ; NEAR ULTRAVIOLET RADIATION ; NEOPLASMS ; NONMETALS ; ORGANIC COMPOUNDS ; OXIDATION ; OXYGEN ; OXYGEN COMPOUNDS ; Oxygen consumption ; Phosphatidylcholines ; PHOTOCHEMISTRY ; Photooxidation ; Pyrimidinones - pharmacology ; RADIATION EFFECTS ; RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT ; RADIATIONS ; RADIOLOGY AND NUCLEAR MEDICINE ; RESONANCE ; Singlet Oxygen ; STEROIDS ; STEROLS ; TUMOR CELLS ; ULTRAVIOLET RADIATION ; vesicles ; WATER</subject><ispartof>Proc. Natl. Acad. Sci. U.S.A.; (United States), 1987-05, Vol.84 (9), p.2999-3003</ispartof><rights>1987 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c609t-a1a023a13998c8386234e4338ee6d27eccfe1c4538580b2a6a380542c04fc8d83</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Uhttp://www.pnas.org/content/84/9.cover.gif</thumbnail><linktopdf>$$Uhttps://www.jstor.org/stable/pdf/29313$$EPDF$$P50$$Gjstor$$H</linktopdf><linktohtml>$$Uhttps://www.jstor.org/stable/29313$$EHTML$$P50$$Gjstor$$H</linktohtml><link.rule.ids>230,314,723,776,780,799,881,27901,27902,53766,53768,57992,58225</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=8312096$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3033673$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/5934603$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Kalyanaraman, B.</creatorcontrib><creatorcontrib>Feix, J. B.</creatorcontrib><creatorcontrib>Sieber, F.</creatorcontrib><creatorcontrib>Thomas, J. P.</creatorcontrib><creatorcontrib>Girotti, A. W.</creatorcontrib><creatorcontrib>Medical College of Wisconsin, Milwaukee</creatorcontrib><title>Photodynamic Action of Merocyanine 540 on Artificial and Natural Cell Membranes: Involvement of Singlet Molecular Oxygen</title><title>Proc. Natl. Acad. Sci. U.S.A.; (United States)</title><addtitle>Proc Natl Acad Sci U S A</addtitle><description>The photochemistry of merocyanine 540 (MC 540), a sensitizing dye that binds preferentially to leukemia and electrically excitable cells, has been investigated. MC 540-mediated photooxidation of histidine, arachidonate, and unsaturated phospholipid vesicles was assessed by spin label oximetry and shown to involve type II (singlet oxygen) chemistry. The dye was also shown to be a potent sensitizer of lipid peroxidation in a natural cell membrane, the erythrocyte ghost. Inhibition by azide, stimulation by2H2O, and identification of the cholesterol product 5α -cholest-6-ene-3β ,5-diol in this system, all were consistent with singlet oxygen intermediacy. Finally, MC 540 was found to be considerably more phototoxic to K-562 leukemia cells in2H2O than in H2O. We conclude that singlet oxygen plays a major role in the phototherapeutic effects of this dye.</description><subject>550601 - Medicine- Unsealed Radionuclides in Diagnostics</subject><subject>560120 - Radiation Effects on Biochemicals, Cells, & Tissue Culture</subject><subject>ANIMAL CELLS</subject><subject>Biological and medical sciences</subject><subject>BIOLOGICAL EFFECTS</subject><subject>BIOLOGICAL RADIATION EFFECTS</subject><subject>CELL CONSTITUENTS</subject><subject>CELL KILLING</subject><subject>Cell Line</subject><subject>Cell Membrane - drug effects</subject><subject>Cell Membrane - metabolism</subject><subject>CELL MEMBRANES</subject><subject>Cell physiology</subject><subject>CHEMICAL REACTIONS</subject><subject>CHEMISTRY</subject><subject>CHOLESTEROL</subject><subject>Cholesterols</subject><subject>CYANINE DYES</subject><subject>Dimyristoylphosphatidylcholine</subject><subject>DISEASES</subject><subject>DOSE-RESPONSE RELATIONSHIPS</subject><subject>DYES</subject><subject>Effects of physical and chemical agents</subject><subject>ELECTROMAGNETIC RADIATION</subject><subject>ELECTRON SPIN RESONANCE</subject><subject>Electron Spin Resonance Spectroscopy</subject><subject>ELEMENTS</subject><subject>Erythrocyte Membrane - drug effects</subject><subject>Erythrocyte Membrane - metabolism</subject><subject>erythrocytes</subject><subject>Fluorescent Dyes</subject><subject>fluorescent probes</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>HEAVY WATER</subject><subject>HEMIC DISEASES</subject><subject>Humans</subject><subject>HYDROGEN COMPOUNDS</subject><subject>HYDROXY COMPOUNDS</subject><subject>Irradiation</subject><subject>LEUKEMIA</subject><subject>Leukemia, Myeloid</subject><subject>Lipid peroxides</subject><subject>LIPIDS</subject><subject>Liposomes</subject><subject>MAGNETIC RESONANCE</subject><subject>MEMBRANES</subject><subject>merocyanine 540</subject><subject>Molecular and cellular biology</subject><subject>NEAR ULTRAVIOLET RADIATION</subject><subject>NEOPLASMS</subject><subject>NONMETALS</subject><subject>ORGANIC COMPOUNDS</subject><subject>OXIDATION</subject><subject>OXYGEN</subject><subject>OXYGEN COMPOUNDS</subject><subject>Oxygen consumption</subject><subject>Phosphatidylcholines</subject><subject>PHOTOCHEMISTRY</subject><subject>Photooxidation</subject><subject>Pyrimidinones - pharmacology</subject><subject>RADIATION EFFECTS</subject><subject>RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT</subject><subject>RADIATIONS</subject><subject>RADIOLOGY AND NUCLEAR MEDICINE</subject><subject>RESONANCE</subject><subject>Singlet Oxygen</subject><subject>STEROIDS</subject><subject>STEROLS</subject><subject>TUMOR CELLS</subject><subject>ULTRAVIOLET RADIATION</subject><subject>vesicles</subject><subject>WATER</subject><issn>0027-8424</issn><issn>1091-6490</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc-LEzEUx4Moa61ePQjCILK3qS-TzEwieCjFHwu7rqCeQ5pm2iyZpJtkSvvfm6Gl1IueEvL9vG_ee1-EXmOYYWjJh62TccbojM8qzvkTNMHAcdlQDk_RBKBqS0Yr-hy9iPEBAHjN4ApdESCkackE7X9sfPKrg5O9UcVcJeNd4bviTgevDtIZp4uaQpFf5yGZzigjbSHdqvgu0xDyfaGtzXi_DNLp-LG4cTtvd7rXLo1GP41bW52KO2-1GqwMxf3-sNbuJXrWSRv1q9M5Rb-_fP61-Fbe3n-9WcxvS9UAT6XEEioiMeGcKUZYUxGqKSFM62ZVtVqpTmNFa8LyYMtKNpIwqGmlgHaKrRiZok9H3-2w7PVK5bZy12IbTC_DQXhpxN-KMxux9jtBgLZsrH93rPcxGRGVSVptlHdOqyRqTmiTVzlF16dPgn8cdEyiN1HlxeSV-CGKtq2hJsD_C2LaQlXniadodgRV8DEG3Z07xiDG4MUYvGBUcDEGnwveXs55xk9JZ_39SZdRSdvltJSJZ4wRXAFvLmxG-7N68c31v3TRDdYmvU8ZfHMEH2Ly4UxWnGBC_gBG5deK</recordid><startdate>19870501</startdate><enddate>19870501</enddate><creator>Kalyanaraman, B.</creator><creator>Feix, J. B.</creator><creator>Sieber, F.</creator><creator>Thomas, J. P.</creator><creator>Girotti, A. W.</creator><general>National Academy of Sciences of the United States of America</general><general>National Acad Sciences</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>8FD</scope><scope>FR3</scope><scope>M7Z</scope><scope>P64</scope><scope>7X8</scope><scope>OTOTI</scope><scope>5PM</scope></search><sort><creationdate>19870501</creationdate><title>Photodynamic Action of Merocyanine 540 on Artificial and Natural Cell Membranes: Involvement of Singlet Molecular Oxygen</title><author>Kalyanaraman, B. ; Feix, J. B. ; Sieber, F. ; Thomas, J. P. ; Girotti, A. W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c609t-a1a023a13998c8386234e4338ee6d27eccfe1c4538580b2a6a380542c04fc8d83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>550601 - Medicine- Unsealed Radionuclides in Diagnostics</topic><topic>560120 - Radiation Effects on Biochemicals, Cells, & Tissue Culture</topic><topic>ANIMAL CELLS</topic><topic>Biological and medical sciences</topic><topic>BIOLOGICAL EFFECTS</topic><topic>BIOLOGICAL RADIATION EFFECTS</topic><topic>CELL CONSTITUENTS</topic><topic>CELL KILLING</topic><topic>Cell Line</topic><topic>Cell Membrane - drug effects</topic><topic>Cell Membrane - metabolism</topic><topic>CELL MEMBRANES</topic><topic>Cell physiology</topic><topic>CHEMICAL REACTIONS</topic><topic>CHEMISTRY</topic><topic>CHOLESTEROL</topic><topic>Cholesterols</topic><topic>CYANINE DYES</topic><topic>Dimyristoylphosphatidylcholine</topic><topic>DISEASES</topic><topic>DOSE-RESPONSE RELATIONSHIPS</topic><topic>DYES</topic><topic>Effects of physical and chemical agents</topic><topic>ELECTROMAGNETIC RADIATION</topic><topic>ELECTRON SPIN RESONANCE</topic><topic>Electron Spin Resonance Spectroscopy</topic><topic>ELEMENTS</topic><topic>Erythrocyte Membrane - drug effects</topic><topic>Erythrocyte Membrane - metabolism</topic><topic>erythrocytes</topic><topic>Fluorescent Dyes</topic><topic>fluorescent probes</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>HEAVY WATER</topic><topic>HEMIC DISEASES</topic><topic>Humans</topic><topic>HYDROGEN COMPOUNDS</topic><topic>HYDROXY COMPOUNDS</topic><topic>Irradiation</topic><topic>LEUKEMIA</topic><topic>Leukemia, Myeloid</topic><topic>Lipid peroxides</topic><topic>LIPIDS</topic><topic>Liposomes</topic><topic>MAGNETIC RESONANCE</topic><topic>MEMBRANES</topic><topic>merocyanine 540</topic><topic>Molecular and cellular biology</topic><topic>NEAR ULTRAVIOLET RADIATION</topic><topic>NEOPLASMS</topic><topic>NONMETALS</topic><topic>ORGANIC COMPOUNDS</topic><topic>OXIDATION</topic><topic>OXYGEN</topic><topic>OXYGEN COMPOUNDS</topic><topic>Oxygen consumption</topic><topic>Phosphatidylcholines</topic><topic>PHOTOCHEMISTRY</topic><topic>Photooxidation</topic><topic>Pyrimidinones - pharmacology</topic><topic>RADIATION EFFECTS</topic><topic>RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT</topic><topic>RADIATIONS</topic><topic>RADIOLOGY AND NUCLEAR MEDICINE</topic><topic>RESONANCE</topic><topic>Singlet Oxygen</topic><topic>STEROIDS</topic><topic>STEROLS</topic><topic>TUMOR CELLS</topic><topic>ULTRAVIOLET RADIATION</topic><topic>vesicles</topic><topic>WATER</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kalyanaraman, B.</creatorcontrib><creatorcontrib>Feix, J. B.</creatorcontrib><creatorcontrib>Sieber, F.</creatorcontrib><creatorcontrib>Thomas, J. P.</creatorcontrib><creatorcontrib>Girotti, A. W.</creatorcontrib><creatorcontrib>Medical College of Wisconsin, Milwaukee</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>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 1</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>OSTI.GOV</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Proc. Natl. Acad. Sci. U.S.A.; (United States)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kalyanaraman, B.</au><au>Feix, J. B.</au><au>Sieber, F.</au><au>Thomas, J. P.</au><au>Girotti, A. W.</au><aucorp>Medical College of Wisconsin, Milwaukee</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photodynamic Action of Merocyanine 540 on Artificial and Natural Cell Membranes: Involvement of Singlet Molecular Oxygen</atitle><jtitle>Proc. Natl. Acad. Sci. U.S.A.; (United States)</jtitle><addtitle>Proc Natl Acad Sci U S A</addtitle><date>1987-05-01</date><risdate>1987</risdate><volume>84</volume><issue>9</issue><spage>2999</spage><epage>3003</epage><pages>2999-3003</pages><issn>0027-8424</issn><eissn>1091-6490</eissn><coden>PNASA6</coden><abstract>The photochemistry of merocyanine 540 (MC 540), a sensitizing dye that binds preferentially to leukemia and electrically excitable cells, has been investigated. MC 540-mediated photooxidation of histidine, arachidonate, and unsaturated phospholipid vesicles was assessed by spin label oximetry and shown to involve type II (singlet oxygen) chemistry. The dye was also shown to be a potent sensitizer of lipid peroxidation in a natural cell membrane, the erythrocyte ghost. Inhibition by azide, stimulation by2H2O, and identification of the cholesterol product 5α -cholest-6-ene-3β ,5-diol in this system, all were consistent with singlet oxygen intermediacy. Finally, MC 540 was found to be considerably more phototoxic to K-562 leukemia cells in2H2O than in H2O. We conclude that singlet oxygen plays a major role in the phototherapeutic effects of this dye.</abstract><cop>Washington, DC</cop><pub>National Academy of Sciences of the United States of America</pub><pmid>3033673</pmid><doi>10.1073/pnas.84.9.2999</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Proc. Natl. Acad. Sci. U.S.A.; (United States), 1987-05, Vol.84 (9), p.2999-3003 |
| issn | 0027-8424 1091-6490 |
| language | eng |
| recordid | cdi_pubmed_primary_3033673 |
| source | Jstor Complete Legacy; MEDLINE; PubMed Central; Alma/SFX Local Collection; Free Full-Text Journals in Chemistry |
| subjects | 550601 - Medicine- Unsealed Radionuclides in Diagnostics 560120 - Radiation Effects on Biochemicals, Cells, & Tissue Culture ANIMAL CELLS Biological and medical sciences BIOLOGICAL EFFECTS BIOLOGICAL RADIATION EFFECTS CELL CONSTITUENTS CELL KILLING Cell Line Cell Membrane - drug effects Cell Membrane - metabolism CELL MEMBRANES Cell physiology CHEMICAL REACTIONS CHEMISTRY CHOLESTEROL Cholesterols CYANINE DYES Dimyristoylphosphatidylcholine DISEASES DOSE-RESPONSE RELATIONSHIPS DYES Effects of physical and chemical agents ELECTROMAGNETIC RADIATION ELECTRON SPIN RESONANCE Electron Spin Resonance Spectroscopy ELEMENTS Erythrocyte Membrane - drug effects Erythrocyte Membrane - metabolism erythrocytes Fluorescent Dyes fluorescent probes Fundamental and applied biological sciences. Psychology HEAVY WATER HEMIC DISEASES Humans HYDROGEN COMPOUNDS HYDROXY COMPOUNDS Irradiation LEUKEMIA Leukemia, Myeloid Lipid peroxides LIPIDS Liposomes MAGNETIC RESONANCE MEMBRANES merocyanine 540 Molecular and cellular biology NEAR ULTRAVIOLET RADIATION NEOPLASMS NONMETALS ORGANIC COMPOUNDS OXIDATION OXYGEN OXYGEN COMPOUNDS Oxygen consumption Phosphatidylcholines PHOTOCHEMISTRY Photooxidation Pyrimidinones - pharmacology RADIATION EFFECTS RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT RADIATIONS RADIOLOGY AND NUCLEAR MEDICINE RESONANCE Singlet Oxygen STEROIDS STEROLS TUMOR CELLS ULTRAVIOLET RADIATION vesicles WATER |
| title | Photodynamic Action of Merocyanine 540 on Artificial and Natural Cell Membranes: Involvement of Singlet Molecular Oxygen |
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