Cancer‐Cell‐Specific Drug Delivery by a Tumor‐Homing CPP‐Gossypol Conjugate Employing a Tracelessly Cleavable Linker
Tumor‐targeted drug delivery is highly important for improving chemotherapy, as it reduces the dose of cytotoxic agents and minimizes the death of healthy tissues. Towards this goal, a conjugate was synthesized of gossypol and a MCF‐7 cancer cell specific CPP (cell penetrating peptide), thus providi...
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| Veröffentlicht in: | Chemistry : a European journal 2020-03, Vol.26 (14), p.3010-3015 |
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| creator | Maity, Suman Kumar Stahl, Paul Hensel, Astrid Knauer, Shirley Hirschhäuser, Christoph Schmuck, Carsten |
| description | Tumor‐targeted drug delivery is highly important for improving chemotherapy, as it reduces the dose of cytotoxic agents and minimizes the death of healthy tissues. Towards this goal, a conjugate was synthesized of gossypol and a MCF‐7 cancer cell specific CPP (cell penetrating peptide), thus providing a selective drug delivery system. Utilizing the aldehyde moiety of gossypol, the tumor homing CPP RLYMRYYSPTTRRYG was attached through a semi‐labile imine linker, which was cleaved in a traceless fashion under aqueous conditions and had a half‐life of approximately 10 hours. The conjugate killed MCF‐7 cells to a significantly greater extent than HeLa cells or healthy fibroblasts.
Selective drug delivery: A Cancer‐cell specific drug delivery system was developed by conjugating a tumor homing peptide and gossypol through a cleavable linker. The Schiff's base linked conjugate killed the targeted MCF‐7 cells selectively compared to HeLa cells used as a control (see figure). |
| doi_str_mv | 10.1002/chem.201905159 |
| format | Article |
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Selective drug delivery: A Cancer‐cell specific drug delivery system was developed by conjugating a tumor homing peptide and gossypol through a cleavable linker. The Schiff's base linked conjugate killed the targeted MCF‐7 cells selectively compared to HeLa cells used as a control (see figure).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201905159</identifier><identifier>PMID: 31840306</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aldehydes ; Aldehydes - chemistry ; Amino Acid Sequence ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Cancer ; Cell-Penetrating Peptides - chemistry ; Chemistry ; Chemotherapy ; cleavable linker ; Communication ; Communications ; Conjugates ; Cytotoxic agents ; Cytotoxicity ; Drug delivery ; Drug delivery systems ; Drug Delivery Systems - methods ; Drug Liberation ; Fibroblasts ; Fibroblasts - cytology ; Gossypol ; Gossypol - chemistry ; Gossypol - pharmacology ; HeLa Cells ; Homing ; Humans ; imine linkage ; Imines - chemistry ; MCF-7 Cells ; Thiazolidines - chemistry ; tumor-homing peptide ; Tumors</subject><ispartof>Chemistry : a European journal, 2020-03, Vol.26 (14), p.3010-3015</ispartof><rights>2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5059-480803e168e0b80859fdc1fccd7a6b72ed41f9af6112082c00d16a3e7c6c3cad3</citedby><cites>FETCH-LOGICAL-c5059-480803e168e0b80859fdc1fccd7a6b72ed41f9af6112082c00d16a3e7c6c3cad3</cites><orcidid>0000-0002-9409-1550 ; 0000-0001-6062-0357</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201905159$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201905159$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31840306$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Maity, Suman Kumar</creatorcontrib><creatorcontrib>Stahl, Paul</creatorcontrib><creatorcontrib>Hensel, Astrid</creatorcontrib><creatorcontrib>Knauer, Shirley</creatorcontrib><creatorcontrib>Hirschhäuser, Christoph</creatorcontrib><creatorcontrib>Schmuck, Carsten</creatorcontrib><title>Cancer‐Cell‐Specific Drug Delivery by a Tumor‐Homing CPP‐Gossypol Conjugate Employing a Tracelessly Cleavable Linker</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Tumor‐targeted drug delivery is highly important for improving chemotherapy, as it reduces the dose of cytotoxic agents and minimizes the death of healthy tissues. Towards this goal, a conjugate was synthesized of gossypol and a MCF‐7 cancer cell specific CPP (cell penetrating peptide), thus providing a selective drug delivery system. Utilizing the aldehyde moiety of gossypol, the tumor homing CPP RLYMRYYSPTTRRYG was attached through a semi‐labile imine linker, which was cleaved in a traceless fashion under aqueous conditions and had a half‐life of approximately 10 hours. The conjugate killed MCF‐7 cells to a significantly greater extent than HeLa cells or healthy fibroblasts.
Selective drug delivery: A Cancer‐cell specific drug delivery system was developed by conjugating a tumor homing peptide and gossypol through a cleavable linker. The Schiff's base linked conjugate killed the targeted MCF‐7 cells selectively compared to HeLa cells used as a control (see figure).</description><subject>Aldehydes</subject><subject>Aldehydes - chemistry</subject><subject>Amino Acid Sequence</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cancer</subject><subject>Cell-Penetrating Peptides - chemistry</subject><subject>Chemistry</subject><subject>Chemotherapy</subject><subject>cleavable linker</subject><subject>Communication</subject><subject>Communications</subject><subject>Conjugates</subject><subject>Cytotoxic agents</subject><subject>Cytotoxicity</subject><subject>Drug delivery</subject><subject>Drug delivery systems</subject><subject>Drug Delivery Systems - methods</subject><subject>Drug Liberation</subject><subject>Fibroblasts</subject><subject>Fibroblasts - cytology</subject><subject>Gossypol</subject><subject>Gossypol - chemistry</subject><subject>Gossypol - pharmacology</subject><subject>HeLa Cells</subject><subject>Homing</subject><subject>Humans</subject><subject>imine linkage</subject><subject>Imines - chemistry</subject><subject>MCF-7 Cells</subject><subject>Thiazolidines - chemistry</subject><subject>tumor-homing peptide</subject><subject>Tumors</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>EIF</sourceid><recordid>eNqFkcFu1DAQhi0EokvhyhFZ4pztOI6d-IKE0qVbaRGVKGfLcSbbLE4cnM2iSBx4BJ6RJyHRlqU9cRpb_uabkX9CXjNYMoD4wt5hs4yBKRBMqCdkwUTMIp5K8ZQsQCVpJAVXZ-RF3-8AQEnOn5MzzrIEOMgF-ZGb1mL4_fNXjs5N5XOHtq5qSy_DsKWX6OoDhpEWIzX0dmj8jK59U7dbmt_cTJcr3_dj5x3NfbsbtmaPdNV0zo8zMvUEY9Fh37uR5g7NwRQO6aZuv2J4SZ5VxvX46r6eky8fVrf5Otp8urrO328iK0CoKMkgA45MZgjFdBaqKi2rrC1TI4s0xjJhlTKVZCyGLLYAJZOGY2ql5daU_Jy8O3q7oWiwtNjug3G6C3Vjwqi9qfXjl7a-01t_0CmkKubZJHh7Lwj-24D9Xu_8ENppZx3zVAiWyGSmlkfKhulPAlanCQz0nJae09KntKaGNw_3OuF_45kAdQS-1w7H_-h0vl59_Cf_A_YMp3I</recordid><startdate>20200309</startdate><enddate>20200309</enddate><creator>Maity, Suman Kumar</creator><creator>Stahl, Paul</creator><creator>Hensel, Astrid</creator><creator>Knauer, Shirley</creator><creator>Hirschhäuser, Christoph</creator><creator>Schmuck, Carsten</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-9409-1550</orcidid><orcidid>https://orcid.org/0000-0001-6062-0357</orcidid></search><sort><creationdate>20200309</creationdate><title>Cancer‐Cell‐Specific Drug Delivery by a Tumor‐Homing CPP‐Gossypol Conjugate Employing a Tracelessly Cleavable Linker</title><author>Maity, Suman Kumar ; Stahl, Paul ; Hensel, Astrid ; Knauer, Shirley ; Hirschhäuser, Christoph ; Schmuck, Carsten</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5059-480803e168e0b80859fdc1fccd7a6b72ed41f9af6112082c00d16a3e7c6c3cad3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aldehydes</topic><topic>Aldehydes - chemistry</topic><topic>Amino Acid Sequence</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cancer</topic><topic>Cell-Penetrating Peptides - chemistry</topic><topic>Chemistry</topic><topic>Chemotherapy</topic><topic>cleavable linker</topic><topic>Communication</topic><topic>Communications</topic><topic>Conjugates</topic><topic>Cytotoxic agents</topic><topic>Cytotoxicity</topic><topic>Drug delivery</topic><topic>Drug delivery systems</topic><topic>Drug Delivery Systems - methods</topic><topic>Drug Liberation</topic><topic>Fibroblasts</topic><topic>Fibroblasts - cytology</topic><topic>Gossypol</topic><topic>Gossypol - chemistry</topic><topic>Gossypol - pharmacology</topic><topic>HeLa Cells</topic><topic>Homing</topic><topic>Humans</topic><topic>imine linkage</topic><topic>Imines - chemistry</topic><topic>MCF-7 Cells</topic><topic>Thiazolidines - chemistry</topic><topic>tumor-homing peptide</topic><topic>Tumors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Maity, Suman Kumar</creatorcontrib><creatorcontrib>Stahl, Paul</creatorcontrib><creatorcontrib>Hensel, Astrid</creatorcontrib><creatorcontrib>Knauer, Shirley</creatorcontrib><creatorcontrib>Hirschhäuser, Christoph</creatorcontrib><creatorcontrib>Schmuck, Carsten</creatorcontrib><collection>Wiley Online Library Open Access</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Maity, Suman Kumar</au><au>Stahl, Paul</au><au>Hensel, Astrid</au><au>Knauer, Shirley</au><au>Hirschhäuser, Christoph</au><au>Schmuck, Carsten</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cancer‐Cell‐Specific Drug Delivery by a Tumor‐Homing CPP‐Gossypol Conjugate Employing a Tracelessly Cleavable Linker</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2020-03-09</date><risdate>2020</risdate><volume>26</volume><issue>14</issue><spage>3010</spage><epage>3015</epage><pages>3010-3015</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Tumor‐targeted drug delivery is highly important for improving chemotherapy, as it reduces the dose of cytotoxic agents and minimizes the death of healthy tissues. Towards this goal, a conjugate was synthesized of gossypol and a MCF‐7 cancer cell specific CPP (cell penetrating peptide), thus providing a selective drug delivery system. Utilizing the aldehyde moiety of gossypol, the tumor homing CPP RLYMRYYSPTTRRYG was attached through a semi‐labile imine linker, which was cleaved in a traceless fashion under aqueous conditions and had a half‐life of approximately 10 hours. The conjugate killed MCF‐7 cells to a significantly greater extent than HeLa cells or healthy fibroblasts.
Selective drug delivery: A Cancer‐cell specific drug delivery system was developed by conjugating a tumor homing peptide and gossypol through a cleavable linker. The Schiff's base linked conjugate killed the targeted MCF‐7 cells selectively compared to HeLa cells used as a control (see figure).</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31840306</pmid><doi>10.1002/chem.201905159</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-9409-1550</orcidid><orcidid>https://orcid.org/0000-0001-6062-0357</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Aldehydes Aldehydes - chemistry Amino Acid Sequence Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cancer Cell-Penetrating Peptides - chemistry Chemistry Chemotherapy cleavable linker Communication Communications Conjugates Cytotoxic agents Cytotoxicity Drug delivery Drug delivery systems Drug Delivery Systems - methods Drug Liberation Fibroblasts Fibroblasts - cytology Gossypol Gossypol - chemistry Gossypol - pharmacology HeLa Cells Homing Humans imine linkage Imines - chemistry MCF-7 Cells Thiazolidines - chemistry tumor-homing peptide Tumors |
| title | Cancer‐Cell‐Specific Drug Delivery by a Tumor‐Homing CPP‐Gossypol Conjugate Employing a Tracelessly Cleavable Linker |
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