Synthesis and photodynamic properties of adamantylethoxy Zn(II) phthalocyanine derivatives in different media and in human red blood cells
Novel unsymmetrically substituted Zn(II) phthalocyanine bearing an adamantylethoxy group (AZnPc) was synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride with an appropriated phthalonitrile derivative (APc). Also, APc was used to obtain a new Zn(II) phthalocyanine bear...
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| Veröffentlicht in: | European journal of medicinal chemistry 2012-04, Vol.50, p.280-287 |
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| creator | Ochoa, A. Laura Tempesti, Tomas C. Spesia, Mariana B. Milanesio, M. Elisa Durantini, Edgardo N. |
| description | Novel unsymmetrically substituted Zn(II) phthalocyanine bearing an adamantylethoxy group (AZnPc) was synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride with an appropriated phthalonitrile derivative (APc). Also, APc was used to obtain a new Zn(II) phthalocyanine bearing four adamantylethoxy groups (A4ZnPc) by cyclotetramerization reaction. The spectroscopic and photodynamic properties of these photosensitizers were compared with those of a Zn(II) phthalocyanine substituted by four methoxy groups (M4ZnPc) in different media. Similar results were obtained in N,N-dimethylformamide. However, a higher photodynamic activity was found for AZnPc in a biomimetic system formed by reverse micelles. This behavior was also observed in the presence of human red blood (HRB) cells, which were used as an in vitro cellular model. Thus, AZnPc was the most effective photosensitizer to produce HRB cells hemolysis. The photodynamic effect produced a decrease in the HRB cells osmotic stability leading to the release of hemoglobin. Studies of photodynamic action mechanism showed that photohemolysis of HRB cells was protected in the presence of azide ion, while the addition of mannitol produced a negligible effect on the cellular photodamage, indicating the intermediacy of O2(1Δg). Therefore, the presence of an adamantyl unit in the phthalocyanine macrocycle represents an interesting molecular architecture for potential phototherapeutic agents.
The paper reports the synthesis and photodynamic activity of novel adamantylethoxy Zn(II)phthalocyanine derivatives in different media and in human red blood cells. [Display omitted]
► New adamantylethoxy Zn(II)phthalocyanine derivatives were synthesized. ► Spectroscopic and photodynamic properties were examined in different media and in human red blood cells. ► A higher photohemolytic activity was found for the phthalocyanine bearing an adamantyl unit. ► Photohemolysis was mainly produced by the intermediacy of singlet molecular oxygen. |
| doi_str_mv | 10.1016/j.ejmech.2012.02.005 |
| format | Article |
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The paper reports the synthesis and photodynamic activity of novel adamantylethoxy Zn(II)phthalocyanine derivatives in different media and in human red blood cells. [Display omitted]
► New adamantylethoxy Zn(II)phthalocyanine derivatives were synthesized. ► Spectroscopic and photodynamic properties were examined in different media and in human red blood cells. ► A higher photohemolytic activity was found for the phthalocyanine bearing an adamantyl unit. ► Photohemolysis was mainly produced by the intermediacy of singlet molecular oxygen.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2012.02.005</identifier><identifier>PMID: 22365412</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>Adamantane ; Biological and medical sciences ; Coordination Complexes - chemical synthesis ; Coordination Complexes - pharmacology ; Erythrocytes - drug effects ; Hemolysis - drug effects ; Human red blood ; Humans ; Indoles - chemical synthesis ; Indoles - pharmacology ; Light ; Mannitol - chemistry ; Medical sciences ; Micelles ; Molecular Structure ; Photodynamic properties ; Photoradiation therapy and photosensitizing agent ; Photosensitizing Agents - chemical synthesis ; Photosensitizing Agents - pharmacology ; Structure-Activity Relationship ; Synthesis ; Treatment with physical agents ; Treatment. General aspects ; Tumors ; Zinc(II) phthalocyanine</subject><ispartof>European journal of medicinal chemistry, 2012-04, Vol.50, p.280-287</ispartof><rights>2012 Elsevier Masson SAS</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-1e23225e77c723bc68fb33be2657acd1eceb906eaeb46ea024c223f7e238e7393</citedby><cites>FETCH-LOGICAL-c391t-1e23225e77c723bc68fb33be2657acd1eceb906eaeb46ea024c223f7e238e7393</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2012.02.005$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25755354$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22365412$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ochoa, A. Laura</creatorcontrib><creatorcontrib>Tempesti, Tomas C.</creatorcontrib><creatorcontrib>Spesia, Mariana B.</creatorcontrib><creatorcontrib>Milanesio, M. Elisa</creatorcontrib><creatorcontrib>Durantini, Edgardo N.</creatorcontrib><title>Synthesis and photodynamic properties of adamantylethoxy Zn(II) phthalocyanine derivatives in different media and in human red blood cells</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Novel unsymmetrically substituted Zn(II) phthalocyanine bearing an adamantylethoxy group (AZnPc) was synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride with an appropriated phthalonitrile derivative (APc). Also, APc was used to obtain a new Zn(II) phthalocyanine bearing four adamantylethoxy groups (A4ZnPc) by cyclotetramerization reaction. The spectroscopic and photodynamic properties of these photosensitizers were compared with those of a Zn(II) phthalocyanine substituted by four methoxy groups (M4ZnPc) in different media. Similar results were obtained in N,N-dimethylformamide. However, a higher photodynamic activity was found for AZnPc in a biomimetic system formed by reverse micelles. This behavior was also observed in the presence of human red blood (HRB) cells, which were used as an in vitro cellular model. Thus, AZnPc was the most effective photosensitizer to produce HRB cells hemolysis. The photodynamic effect produced a decrease in the HRB cells osmotic stability leading to the release of hemoglobin. Studies of photodynamic action mechanism showed that photohemolysis of HRB cells was protected in the presence of azide ion, while the addition of mannitol produced a negligible effect on the cellular photodamage, indicating the intermediacy of O2(1Δg). Therefore, the presence of an adamantyl unit in the phthalocyanine macrocycle represents an interesting molecular architecture for potential phototherapeutic agents.
The paper reports the synthesis and photodynamic activity of novel adamantylethoxy Zn(II)phthalocyanine derivatives in different media and in human red blood cells. [Display omitted]
► New adamantylethoxy Zn(II)phthalocyanine derivatives were synthesized. ► Spectroscopic and photodynamic properties were examined in different media and in human red blood cells. ► A higher photohemolytic activity was found for the phthalocyanine bearing an adamantyl unit. ► Photohemolysis was mainly produced by the intermediacy of singlet molecular oxygen.</description><subject>Adamantane</subject><subject>Biological and medical sciences</subject><subject>Coordination Complexes - chemical synthesis</subject><subject>Coordination Complexes - pharmacology</subject><subject>Erythrocytes - drug effects</subject><subject>Hemolysis - drug effects</subject><subject>Human red blood</subject><subject>Humans</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - pharmacology</subject><subject>Light</subject><subject>Mannitol - chemistry</subject><subject>Medical sciences</subject><subject>Micelles</subject><subject>Molecular Structure</subject><subject>Photodynamic properties</subject><subject>Photoradiation therapy and photosensitizing agent</subject><subject>Photosensitizing Agents - chemical synthesis</subject><subject>Photosensitizing Agents - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Synthesis</subject><subject>Treatment with physical agents</subject><subject>Treatment. General aspects</subject><subject>Tumors</subject><subject>Zinc(II) phthalocyanine</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc-KFDEQxoMo7uzqG4jkIuqhx_zpdE9fBFlcHVjwoF68hHRSTWfoTsYkM9iv4FNb44x6E4oEit9XVV8VIc84W3PGmze7NexmsONaMC7WDIOpB2TF22ZTSaHqh2TFhJCVErK-Itc57xgSDWOPyRXmG1VzsSI_Py-hjJB9piY4uh9jiW4JZvaW7lPcQyoeMo0DNc7MJpRlgjLGHwv9Fl5tt69RUUYzRbuY4ANQB8kfTfFHFPlAnR8GSBAKncF587sHpscDlqIJHO2nGB21ME35CXk0mCnD08t_Q77evf9y-7G6__Rhe_vuvrKy46XiIKQQCtrWtkL2ttkMvZQ9iEa1xjoOFvqONWCgr_FlorZod2hRtoFWdvKGvDzXRX_fD5CLnn0-TWACxEPWneg475pGIFmfSZtizgkGvU9-NmnRnOnTEfROn4-gT0fQDIMplD2_NDj0aPuv6M_WEXhxAUy2ZhqSCdbnf5xqlZKqRu7tmQNcx9FD0tl6CBZXmcAW7aL__yS_ADZTqck</recordid><startdate>20120401</startdate><enddate>20120401</enddate><creator>Ochoa, A. Laura</creator><creator>Tempesti, Tomas C.</creator><creator>Spesia, Mariana B.</creator><creator>Milanesio, M. Elisa</creator><creator>Durantini, Edgardo N.</creator><general>Elsevier Masson SAS</general><general>Elsevier</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>7X8</scope></search><sort><creationdate>20120401</creationdate><title>Synthesis and photodynamic properties of adamantylethoxy Zn(II) phthalocyanine derivatives in different media and in human red blood cells</title><author>Ochoa, A. Laura ; Tempesti, Tomas C. ; Spesia, Mariana B. ; Milanesio, M. Elisa ; Durantini, Edgardo N.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-1e23225e77c723bc68fb33be2657acd1eceb906eaeb46ea024c223f7e238e7393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Adamantane</topic><topic>Biological and medical sciences</topic><topic>Coordination Complexes - chemical synthesis</topic><topic>Coordination Complexes - pharmacology</topic><topic>Erythrocytes - drug effects</topic><topic>Hemolysis - drug effects</topic><topic>Human red blood</topic><topic>Humans</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - pharmacology</topic><topic>Light</topic><topic>Mannitol - chemistry</topic><topic>Medical sciences</topic><topic>Micelles</topic><topic>Molecular Structure</topic><topic>Photodynamic properties</topic><topic>Photoradiation therapy and photosensitizing agent</topic><topic>Photosensitizing Agents - chemical synthesis</topic><topic>Photosensitizing Agents - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Synthesis</topic><topic>Treatment with physical agents</topic><topic>Treatment. General aspects</topic><topic>Tumors</topic><topic>Zinc(II) phthalocyanine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ochoa, A. Laura</creatorcontrib><creatorcontrib>Tempesti, Tomas C.</creatorcontrib><creatorcontrib>Spesia, Mariana B.</creatorcontrib><creatorcontrib>Milanesio, M. Elisa</creatorcontrib><creatorcontrib>Durantini, Edgardo N.</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>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ochoa, A. Laura</au><au>Tempesti, Tomas C.</au><au>Spesia, Mariana B.</au><au>Milanesio, M. Elisa</au><au>Durantini, Edgardo N.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and photodynamic properties of adamantylethoxy Zn(II) phthalocyanine derivatives in different media and in human red blood cells</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2012-04-01</date><risdate>2012</risdate><volume>50</volume><spage>280</spage><epage>287</epage><pages>280-287</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Novel unsymmetrically substituted Zn(II) phthalocyanine bearing an adamantylethoxy group (AZnPc) was synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride with an appropriated phthalonitrile derivative (APc). Also, APc was used to obtain a new Zn(II) phthalocyanine bearing four adamantylethoxy groups (A4ZnPc) by cyclotetramerization reaction. The spectroscopic and photodynamic properties of these photosensitizers were compared with those of a Zn(II) phthalocyanine substituted by four methoxy groups (M4ZnPc) in different media. Similar results were obtained in N,N-dimethylformamide. However, a higher photodynamic activity was found for AZnPc in a biomimetic system formed by reverse micelles. This behavior was also observed in the presence of human red blood (HRB) cells, which were used as an in vitro cellular model. Thus, AZnPc was the most effective photosensitizer to produce HRB cells hemolysis. The photodynamic effect produced a decrease in the HRB cells osmotic stability leading to the release of hemoglobin. Studies of photodynamic action mechanism showed that photohemolysis of HRB cells was protected in the presence of azide ion, while the addition of mannitol produced a negligible effect on the cellular photodamage, indicating the intermediacy of O2(1Δg). Therefore, the presence of an adamantyl unit in the phthalocyanine macrocycle represents an interesting molecular architecture for potential phototherapeutic agents.
The paper reports the synthesis and photodynamic activity of novel adamantylethoxy Zn(II)phthalocyanine derivatives in different media and in human red blood cells. [Display omitted]
► New adamantylethoxy Zn(II)phthalocyanine derivatives were synthesized. ► Spectroscopic and photodynamic properties were examined in different media and in human red blood cells. ► A higher photohemolytic activity was found for the phthalocyanine bearing an adamantyl unit. ► Photohemolysis was mainly produced by the intermediacy of singlet molecular oxygen.</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>22365412</pmid><doi>10.1016/j.ejmech.2012.02.005</doi><tpages>8</tpages></addata></record> |
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| ispartof | European journal of medicinal chemistry, 2012-04, Vol.50, p.280-287 |
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| subjects | Adamantane Biological and medical sciences Coordination Complexes - chemical synthesis Coordination Complexes - pharmacology Erythrocytes - drug effects Hemolysis - drug effects Human red blood Humans Indoles - chemical synthesis Indoles - pharmacology Light Mannitol - chemistry Medical sciences Micelles Molecular Structure Photodynamic properties Photoradiation therapy and photosensitizing agent Photosensitizing Agents - chemical synthesis Photosensitizing Agents - pharmacology Structure-Activity Relationship Synthesis Treatment with physical agents Treatment. General aspects Tumors Zinc(II) phthalocyanine |
| title | Synthesis and photodynamic properties of adamantylethoxy Zn(II) phthalocyanine derivatives in different media and in human red blood cells |
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