PET imaging using 64Cu-labeled sulfophthalocyanines: Synthesis and biodistribution
Sulfonated metallo phthalocyanines (MPcS n ) are second generation photosensitizers advanced for photodynamic therapy of various medical applications. A series of ZnPcS n was demetallated and subsequently converted to the corresponding [ 64Cu]CuPcS n in 40–50% isolated yields and >98% radiochemic...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2011-12, Vol.21 (24), p.7470-7473 |
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| creator | Ranyuk, Elena R. Cauchon, Nicole Ali, Hasrat Lecomte, Roger Guérin, Brigitte van Lier, Johan E. |
| description | Sulfonated metallo phthalocyanines (MPcS
n
) are second generation photosensitizers advanced for photodynamic therapy of various medical applications. A series of ZnPcS
n
was demetallated and subsequently converted to the corresponding [
64Cu]CuPcS
n
in 40–50% isolated yields and >98% radiochemical purities. Tumor-bearing mice were injected with the
64Cu-labeled products and subjected to 3-h dynamic PET imaging studies. Biodistribution patterns showed characteristic differences between the various derivatives. Tumor uptake was detected only for the amphiphilic derivatives [
64Cu]CuPcS
2 and [
64Cu]CuPcS
3C
6 (1–1.5%ID/g). The biological data suggest that PET imaging with [
64Cu]CuPc can be used to establish structure–PDT efficacy relationships for Pc-based photosensitizers. |
| doi_str_mv | 10.1016/j.bmcl.2011.09.121 |
| format | Article |
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n
) are second generation photosensitizers advanced for photodynamic therapy of various medical applications. A series of ZnPcS
n
was demetallated and subsequently converted to the corresponding [
64Cu]CuPcS
n
in 40–50% isolated yields and >98% radiochemical purities. Tumor-bearing mice were injected with the
64Cu-labeled products and subjected to 3-h dynamic PET imaging studies. Biodistribution patterns showed characteristic differences between the various derivatives. Tumor uptake was detected only for the amphiphilic derivatives [
64Cu]CuPcS
2 and [
64Cu]CuPcS
3C
6 (1–1.5%ID/g). The biological data suggest that PET imaging with [
64Cu]CuPc can be used to establish structure–PDT efficacy relationships for Pc-based photosensitizers.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2011.09.121</identifier><identifier>PMID: 22050887</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Animals ; Biological and medical sciences ; chemistry ; Contrast media. Radiopharmaceuticals ; Copper Radioisotopes - chemistry ; Cu-64 ; image analysis ; Indoles - chemistry ; Indoles - pharmacokinetics ; Isotope Labeling ; Medical sciences ; Mice ; Neoplasms - diagnostic imaging ; Organometallic Compounds - chemistry ; PDT ; PET-imaging ; Pharmacology. Drug treatments ; photosensitizing agents ; Photosensitizing Agents - chemical synthesis ; Photosensitizing Agents - pharmacokinetics ; Phthalocyanine ; Positron-Emission Tomography ; Radiopharmaceuticals - chemical synthesis ; Radiopharmaceuticals - pharmacokinetics ; therapeutics ; Tissue Distribution</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-12, Vol.21 (24), p.7470-7473</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2867-bb4c126f1709c4303c393ba42a53e19d8cb37e38b8bdb8b0b5b137851f1dc1b03</citedby><cites>FETCH-LOGICAL-c2867-bb4c126f1709c4303c393ba42a53e19d8cb37e38b8bdb8b0b5b137851f1dc1b03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X1101376X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25272859$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22050887$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ranyuk, Elena R.</creatorcontrib><creatorcontrib>Cauchon, Nicole</creatorcontrib><creatorcontrib>Ali, Hasrat</creatorcontrib><creatorcontrib>Lecomte, Roger</creatorcontrib><creatorcontrib>Guérin, Brigitte</creatorcontrib><creatorcontrib>van Lier, Johan E.</creatorcontrib><title>PET imaging using 64Cu-labeled sulfophthalocyanines: Synthesis and biodistribution</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Sulfonated metallo phthalocyanines (MPcS
n
) are second generation photosensitizers advanced for photodynamic therapy of various medical applications. A series of ZnPcS
n
was demetallated and subsequently converted to the corresponding [
64Cu]CuPcS
n
in 40–50% isolated yields and >98% radiochemical purities. Tumor-bearing mice were injected with the
64Cu-labeled products and subjected to 3-h dynamic PET imaging studies. Biodistribution patterns showed characteristic differences between the various derivatives. Tumor uptake was detected only for the amphiphilic derivatives [
64Cu]CuPcS
2 and [
64Cu]CuPcS
3C
6 (1–1.5%ID/g). The biological data suggest that PET imaging with [
64Cu]CuPc can be used to establish structure–PDT efficacy relationships for Pc-based photosensitizers.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>chemistry</subject><subject>Contrast media. Radiopharmaceuticals</subject><subject>Copper Radioisotopes - chemistry</subject><subject>Cu-64</subject><subject>image analysis</subject><subject>Indoles - chemistry</subject><subject>Indoles - pharmacokinetics</subject><subject>Isotope Labeling</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Neoplasms - diagnostic imaging</subject><subject>Organometallic Compounds - chemistry</subject><subject>PDT</subject><subject>PET-imaging</subject><subject>Pharmacology. Drug treatments</subject><subject>photosensitizing agents</subject><subject>Photosensitizing Agents - chemical synthesis</subject><subject>Photosensitizing Agents - pharmacokinetics</subject><subject>Phthalocyanine</subject><subject>Positron-Emission Tomography</subject><subject>Radiopharmaceuticals - chemical synthesis</subject><subject>Radiopharmaceuticals - pharmacokinetics</subject><subject>therapeutics</subject><subject>Tissue Distribution</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkcuKFDEUQIMoTs_oD7jQ2sisqrx5VkrcSDM-YEBxZsBdyKu601Sn2qRK6L83Rbe6E-HmZnPuIycIvcDQYMDiza4xezs0BDBuoGswwY_QCjPBasqAP0Yr6ATUsmPfL9BlzjsAzICxp-iCEOAgZbtC377e3Fdhrzchbqo5L1mw9VwP2vjBuyrPQz8ettNWD6M96hiiz2-ru2Octj6HXOnoKhNGF_KUgpmnMMZn6Emvh-yfn-8r9PDh5n79qb798vHz-v1tbYkUbW0Ms5iIHrfQWUaBWtpRoxnRnHrcOWkNbT2VRhpXDhhuMG0lxz12FhugV-j61PeQxh-zz5Pah2z9MOjoxzmrDlosS4j_ILmQpBWkkORE2jTmnHyvDqnYSUeFQS3S1U4t0tUiXUGnivRS9PLcfjZ77_6U_LZcgNdnQGerhz7paEP-y3HSEsm7wr06cb0eld6kwjzclUm8_Bzlol3e_O5E-CL2Z_BJZRt8tN6F5O2k3Bj-tekvyI6oig</recordid><startdate>20111215</startdate><enddate>20111215</enddate><creator>Ranyuk, Elena R.</creator><creator>Cauchon, Nicole</creator><creator>Ali, Hasrat</creator><creator>Lecomte, Roger</creator><creator>Guérin, Brigitte</creator><creator>van Lier, Johan E.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20111215</creationdate><title>PET imaging using 64Cu-labeled sulfophthalocyanines: Synthesis and biodistribution</title><author>Ranyuk, Elena R. ; Cauchon, Nicole ; Ali, Hasrat ; Lecomte, Roger ; Guérin, Brigitte ; van Lier, Johan E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2867-bb4c126f1709c4303c393ba42a53e19d8cb37e38b8bdb8b0b5b137851f1dc1b03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>chemistry</topic><topic>Contrast media. Radiopharmaceuticals</topic><topic>Copper Radioisotopes - chemistry</topic><topic>Cu-64</topic><topic>image analysis</topic><topic>Indoles - chemistry</topic><topic>Indoles - pharmacokinetics</topic><topic>Isotope Labeling</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Neoplasms - diagnostic imaging</topic><topic>Organometallic Compounds - chemistry</topic><topic>PDT</topic><topic>PET-imaging</topic><topic>Pharmacology. Drug treatments</topic><topic>photosensitizing agents</topic><topic>Photosensitizing Agents - chemical synthesis</topic><topic>Photosensitizing Agents - pharmacokinetics</topic><topic>Phthalocyanine</topic><topic>Positron-Emission Tomography</topic><topic>Radiopharmaceuticals - chemical synthesis</topic><topic>Radiopharmaceuticals - pharmacokinetics</topic><topic>therapeutics</topic><topic>Tissue Distribution</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ranyuk, Elena R.</creatorcontrib><creatorcontrib>Cauchon, Nicole</creatorcontrib><creatorcontrib>Ali, Hasrat</creatorcontrib><creatorcontrib>Lecomte, Roger</creatorcontrib><creatorcontrib>Guérin, Brigitte</creatorcontrib><creatorcontrib>van Lier, Johan E.</creatorcontrib><collection>AGRIS</collection><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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ranyuk, Elena R.</au><au>Cauchon, Nicole</au><au>Ali, Hasrat</au><au>Lecomte, Roger</au><au>Guérin, Brigitte</au><au>van Lier, Johan E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>PET imaging using 64Cu-labeled sulfophthalocyanines: Synthesis and biodistribution</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2011-12-15</date><risdate>2011</risdate><volume>21</volume><issue>24</issue><spage>7470</spage><epage>7473</epage><pages>7470-7473</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Sulfonated metallo phthalocyanines (MPcS
n
) are second generation photosensitizers advanced for photodynamic therapy of various medical applications. A series of ZnPcS
n
was demetallated and subsequently converted to the corresponding [
64Cu]CuPcS
n
in 40–50% isolated yields and >98% radiochemical purities. Tumor-bearing mice were injected with the
64Cu-labeled products and subjected to 3-h dynamic PET imaging studies. Biodistribution patterns showed characteristic differences between the various derivatives. Tumor uptake was detected only for the amphiphilic derivatives [
64Cu]CuPcS
2 and [
64Cu]CuPcS
3C
6 (1–1.5%ID/g). The biological data suggest that PET imaging with [
64Cu]CuPc can be used to establish structure–PDT efficacy relationships for Pc-based photosensitizers.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>22050887</pmid><doi>10.1016/j.bmcl.2011.09.121</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2011-12, Vol.21 (24), p.7470-7473 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Animals Biological and medical sciences chemistry Contrast media. Radiopharmaceuticals Copper Radioisotopes - chemistry Cu-64 image analysis Indoles - chemistry Indoles - pharmacokinetics Isotope Labeling Medical sciences Mice Neoplasms - diagnostic imaging Organometallic Compounds - chemistry PDT PET-imaging Pharmacology. Drug treatments photosensitizing agents Photosensitizing Agents - chemical synthesis Photosensitizing Agents - pharmacokinetics Phthalocyanine Positron-Emission Tomography Radiopharmaceuticals - chemical synthesis Radiopharmaceuticals - pharmacokinetics therapeutics Tissue Distribution |
| title | PET imaging using 64Cu-labeled sulfophthalocyanines: Synthesis and biodistribution |
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