Targeting gastrin-releasing peptide receptors of prostate cancer cells for photodynamic therapy with a phthalocyanine–bombesin conjugate
Sulfonated aluminum phthalocyanines (AlPcS) are potent photosensitizers for the photodynamic therapy (PDT) of cancer. In this study we evaluate the possibility to improve the efficacy of AlPcS-PDT for prostate cancer by targeting tetrasulfonated aluminum phthalocyanines (AlPcS 4) to the gastrin-rele...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2008-04, Vol.18 (7), p.2424-2427 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Dubuc, Céléna Langlois, Réjean Bénard, François Cauchon, Nicole Klarskov, Klaus Tone, Paul van Lier, Johan E. |
| description | Sulfonated aluminum phthalocyanines (AlPcS) are potent photosensitizers for the photodynamic therapy (PDT) of cancer. In this study we evaluate the possibility to improve the efficacy of AlPcS-PDT for prostate cancer by targeting tetrasulfonated aluminum phthalocyanines (AlPcS
4) to the gastrin-releasing peptide receptor (GRPR) through coupling to bombesin. A mono-carbohexyl derivative of AlPcS
4 is attached to 8-Aoc-bombesin(7–14)NH
2 via an amide bridge to yield a bombesin–AlPcS
4 conjugate linked by a C-14 spacer chain. The conjugate is characterized by mass spectroscopy and shown to bind to the GRPR with a relative binding affinity (RBA) of 2.3, taking bombesin (RBA
=
100) as unity. The in vitro photodynamic efficacy of the conjugate against PC-3 human prostate cancer cells is improved by a factor 2.5 over the non-conjugated mono-carbohexyl derivative of AlPcS
4. |
| doi_str_mv | 10.1016/j.bmcl.2008.02.051 |
| format | Article |
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4) to the gastrin-releasing peptide receptor (GRPR) through coupling to bombesin. A mono-carbohexyl derivative of AlPcS
4 is attached to 8-Aoc-bombesin(7–14)NH
2 via an amide bridge to yield a bombesin–AlPcS
4 conjugate linked by a C-14 spacer chain. The conjugate is characterized by mass spectroscopy and shown to bind to the GRPR with a relative binding affinity (RBA) of 2.3, taking bombesin (RBA
=
100) as unity. The in vitro photodynamic efficacy of the conjugate against PC-3 human prostate cancer cells is improved by a factor 2.5 over the non-conjugated mono-carbohexyl derivative of AlPcS
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4) to the gastrin-releasing peptide receptor (GRPR) through coupling to bombesin. A mono-carbohexyl derivative of AlPcS
4 is attached to 8-Aoc-bombesin(7–14)NH
2 via an amide bridge to yield a bombesin–AlPcS
4 conjugate linked by a C-14 spacer chain. The conjugate is characterized by mass spectroscopy and shown to bind to the GRPR with a relative binding affinity (RBA) of 2.3, taking bombesin (RBA
=
100) as unity. The in vitro photodynamic efficacy of the conjugate against PC-3 human prostate cancer cells is improved by a factor 2.5 over the non-conjugated mono-carbohexyl derivative of AlPcS
4.</description><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>Bombesin - chemistry</subject><subject>Bombesin - pharmacology</subject><subject>Bombesin conjugate</subject><subject>Cell Line, Tumor</subject><subject>Drug Delivery Systems - methods</subject><subject>Humans</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - pharmacology</subject><subject>Indoles - therapeutic use</subject><subject>Male</subject><subject>Mass Spectrometry</subject><subject>Medical sciences</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Organometallic Compounds - chemical synthesis</subject><subject>Organometallic Compounds - pharmacology</subject><subject>Organometallic Compounds - therapeutic use</subject><subject>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</subject><subject>Pharmacology. Drug treatments</subject><subject>Photochemotherapy</subject><subject>Photodynamic therapy</subject><subject>Photosensitizing Agents - chemical synthesis</subject><subject>Photosensitizing Agents - pharmacology</subject><subject>Photosensitizing Agents - therapeutic use</subject><subject>Prostatic Neoplasms - drug therapy</subject><subject>Prostatic Neoplasms - pathology</subject><subject>Receptors, Bombesin - metabolism</subject><subject>Sulfonated phthalocyanines</subject><issn>0960-894X</issn><issn>0968-0896</issn><issn>1464-3405</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkbuO1DAUhi0EYoeFF6BAbqBL8DUXiQatWEBaiWaR6CzHPp7xKImD7Vk0HTUtb8iTrMOMoIPKR_bnY5__Q-g5JTUltHm9r4fJjDUjpKsJq4mkD9CGikZUXBD5EG1I35Cq68WXC_QkpT0hVBAhHqML2nHWs6bboB-3Om4h-3mLtzrl6Ocqwgg6rTsLLNlbwBFMqUJMODi8xJCyzoCNng1EbGAcE3Yh4mUXcrDHWU_e4LyDqJcj_ubzDutylnd6DOaoZz_Dr-8_hzANUF7BJsz7w7Y0fIoeOT0meHZeL9Hn63e3Vx-qm0_vP169vamMoDJXQ8eN4dYOWnJoWguWMt0NtOlo0zpJreNtL1pJNLXUOEeGrtTCWO4aR2TLL9GrU98yydcDpKwmn9Yp9AzhkFRLRCNlz_4L0r6k2HNaQHYCTckmRXBqiX7S8agoUasqtVerKrWqUoSpoqpcenHufhgmsH-vnN0U4OUZ0Mno0cWSt09_OEaY5PL3PG9OHJTQ7jxElYyH4sb6Ii4rG_y__nEPmhu3MQ</recordid><startdate>20080401</startdate><enddate>20080401</enddate><creator>Dubuc, Céléna</creator><creator>Langlois, Réjean</creator><creator>Bénard, François</creator><creator>Cauchon, Nicole</creator><creator>Klarskov, Klaus</creator><creator>Tone, Paul</creator><creator>van Lier, Johan E.</creator><general>Elsevier Ltd</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20080401</creationdate><title>Targeting gastrin-releasing peptide receptors of prostate cancer cells for photodynamic therapy with a phthalocyanine–bombesin conjugate</title><author>Dubuc, Céléna ; Langlois, Réjean ; Bénard, François ; Cauchon, Nicole ; Klarskov, Klaus ; Tone, Paul ; van Lier, Johan E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-b83cc3ddba53e67ded12a8b168167f51df3794750a1d1cff0b850a4cd3f6f0573</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>Bombesin - chemistry</topic><topic>Bombesin - pharmacology</topic><topic>Bombesin conjugate</topic><topic>Cell Line, Tumor</topic><topic>Drug Delivery Systems - methods</topic><topic>Humans</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - pharmacology</topic><topic>Indoles - therapeutic use</topic><topic>Male</topic><topic>Mass Spectrometry</topic><topic>Medical sciences</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Organometallic Compounds - chemical synthesis</topic><topic>Organometallic Compounds - pharmacology</topic><topic>Organometallic Compounds - therapeutic use</topic><topic>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</topic><topic>Pharmacology. Drug treatments</topic><topic>Photochemotherapy</topic><topic>Photodynamic therapy</topic><topic>Photosensitizing Agents - chemical synthesis</topic><topic>Photosensitizing Agents - pharmacology</topic><topic>Photosensitizing Agents - therapeutic use</topic><topic>Prostatic Neoplasms - drug therapy</topic><topic>Prostatic Neoplasms - pathology</topic><topic>Receptors, Bombesin - metabolism</topic><topic>Sulfonated phthalocyanines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dubuc, Céléna</creatorcontrib><creatorcontrib>Langlois, Réjean</creatorcontrib><creatorcontrib>Bénard, François</creatorcontrib><creatorcontrib>Cauchon, Nicole</creatorcontrib><creatorcontrib>Klarskov, Klaus</creatorcontrib><creatorcontrib>Tone, Paul</creatorcontrib><creatorcontrib>van Lier, Johan E.</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dubuc, Céléna</au><au>Langlois, Réjean</au><au>Bénard, François</au><au>Cauchon, Nicole</au><au>Klarskov, Klaus</au><au>Tone, Paul</au><au>van Lier, Johan E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Targeting gastrin-releasing peptide receptors of prostate cancer cells for photodynamic therapy with a phthalocyanine–bombesin conjugate</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2008-04-01</date><risdate>2008</risdate><volume>18</volume><issue>7</issue><spage>2424</spage><epage>2427</epage><pages>2424-2427</pages><issn>0960-894X</issn><issn>0968-0896</issn><eissn>1464-3405</eissn><eissn>1464-3391</eissn><abstract>Sulfonated aluminum phthalocyanines (AlPcS) are potent photosensitizers for the photodynamic therapy (PDT) of cancer. In this study we evaluate the possibility to improve the efficacy of AlPcS-PDT for prostate cancer by targeting tetrasulfonated aluminum phthalocyanines (AlPcS
4) to the gastrin-releasing peptide receptor (GRPR) through coupling to bombesin. A mono-carbohexyl derivative of AlPcS
4 is attached to 8-Aoc-bombesin(7–14)NH
2 via an amide bridge to yield a bombesin–AlPcS
4 conjugate linked by a C-14 spacer chain. The conjugate is characterized by mass spectroscopy and shown to bind to the GRPR with a relative binding affinity (RBA) of 2.3, taking bombesin (RBA
=
100) as unity. The in vitro photodynamic efficacy of the conjugate against PC-3 human prostate cancer cells is improved by a factor 2.5 over the non-conjugated mono-carbohexyl derivative of AlPcS
4.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>18329268</pmid><doi>10.1016/j.bmcl.2008.02.051</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry, 2008-04, Vol.18 (7), p.2424-2427 |
| issn | 0960-894X 0968-0896 1464-3405 1464-3391 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Binding Sites Biological and medical sciences Bombesin - chemistry Bombesin - pharmacology Bombesin conjugate Cell Line, Tumor Drug Delivery Systems - methods Humans Indoles - chemical synthesis Indoles - pharmacology Indoles - therapeutic use Male Mass Spectrometry Medical sciences Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Organometallic Compounds - chemical synthesis Organometallic Compounds - pharmacology Organometallic Compounds - therapeutic use Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Photochemotherapy Photodynamic therapy Photosensitizing Agents - chemical synthesis Photosensitizing Agents - pharmacology Photosensitizing Agents - therapeutic use Prostatic Neoplasms - drug therapy Prostatic Neoplasms - pathology Receptors, Bombesin - metabolism Sulfonated phthalocyanines |
| title | Targeting gastrin-releasing peptide receptors of prostate cancer cells for photodynamic therapy with a phthalocyanine–bombesin conjugate |
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