Synthesis and activity of a folate targeted monodisperse PEG camptothecin conjugate
[Display omitted] A folate targeted camptothecin small molecule drug conjugate (SMDC) was synthesized using a monodisperse PEG spacer linked to folate via a releasable disulfide carbonate linker. Cell cytotoxicity in human KB cells exhibited an IC50 of 6nM. Importantly, activity of the prodrug was b...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2013-11, Vol.23 (21), p.5810-5813 |
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| container_end_page | 5813 |
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| container_issue | 21 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 23 |
| creator | Henne, Walter A. Kularatne, Sumith A. Hakenjos, John Carron, Joshua D. Henne, Kristene L. |
| description | [Display omitted]
A folate targeted camptothecin small molecule drug conjugate (SMDC) was synthesized using a monodisperse PEG spacer linked to folate via a releasable disulfide carbonate linker. Cell cytotoxicity in human KB cells exhibited an IC50 of 6nM. Importantly, activity of the prodrug was blocked by excess folate, demonstrating receptor-mediated celluar uptake of the PEG conjugate. |
| doi_str_mv | 10.1016/j.bmcl.2013.08.113 |
| format | Article |
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A folate targeted camptothecin small molecule drug conjugate (SMDC) was synthesized using a monodisperse PEG spacer linked to folate via a releasable disulfide carbonate linker. Cell cytotoxicity in human KB cells exhibited an IC50 of 6nM. Importantly, activity of the prodrug was blocked by excess folate, demonstrating receptor-mediated celluar uptake of the PEG conjugate.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2013.08.113</identifier><identifier>PMID: 24064501</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antineoplastic Agents, Phytogenic - administration & dosage ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - pharmacokinetics ; Antineoplastic Agents, Phytogenic - pharmacology ; Camptothecin ; Camptothecin - administration & dosage ; Camptothecin - analogs & derivatives ; Camptothecin - pharmacokinetics ; Camptothecin - pharmacology ; chemistry ; cytotoxicity ; Drug Delivery Systems ; drugs ; Folate conjugate ; Folate Receptors, GPI-Anchored - metabolism ; folic acid ; Folic Acid - chemistry ; Humans ; inhibitory concentration 50 ; KB Cells ; Monodisperse PEG ; Neoplasms - drug therapy ; Neoplasms - metabolism ; PEG ; Polyethylene Glycols - chemistry ; Prodrugs - administration & dosage ; Prodrugs - chemistry ; Prodrugs - pharmacokinetics ; Prodrugs - pharmacology ; Small molecule drug conjugate ; SMDC</subject><ispartof>Bioorganic & medicinal chemistry letters, 2013-11, Vol.23 (21), p.5810-5813</ispartof><rights>2013 Elsevier Ltd</rights><rights>Copyright © 2013 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c479t-95911f3fedcd4a7a53d73d7ec7d8c5507ab330d73ee8811e00cc9930b6a0f713</citedby><cites>FETCH-LOGICAL-c479t-95911f3fedcd4a7a53d73d7ec7d8c5507ab330d73ee8811e00cc9930b6a0f713</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2013.08.113$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,45974</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24064501$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Henne, Walter A.</creatorcontrib><creatorcontrib>Kularatne, Sumith A.</creatorcontrib><creatorcontrib>Hakenjos, John</creatorcontrib><creatorcontrib>Carron, Joshua D.</creatorcontrib><creatorcontrib>Henne, Kristene L.</creatorcontrib><title>Synthesis and activity of a folate targeted monodisperse PEG camptothecin conjugate</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
A folate targeted camptothecin small molecule drug conjugate (SMDC) was synthesized using a monodisperse PEG spacer linked to folate via a releasable disulfide carbonate linker. Cell cytotoxicity in human KB cells exhibited an IC50 of 6nM. Importantly, activity of the prodrug was blocked by excess folate, demonstrating receptor-mediated celluar uptake of the PEG conjugate.</description><subject>Antineoplastic Agents, Phytogenic - administration & dosage</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - pharmacokinetics</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Camptothecin</subject><subject>Camptothecin - administration & dosage</subject><subject>Camptothecin - analogs & derivatives</subject><subject>Camptothecin - pharmacokinetics</subject><subject>Camptothecin - pharmacology</subject><subject>chemistry</subject><subject>cytotoxicity</subject><subject>Drug Delivery Systems</subject><subject>drugs</subject><subject>Folate conjugate</subject><subject>Folate Receptors, GPI-Anchored - metabolism</subject><subject>folic acid</subject><subject>Folic Acid - chemistry</subject><subject>Humans</subject><subject>inhibitory concentration 50</subject><subject>KB Cells</subject><subject>Monodisperse PEG</subject><subject>Neoplasms - drug therapy</subject><subject>Neoplasms - metabolism</subject><subject>PEG</subject><subject>Polyethylene Glycols - chemistry</subject><subject>Prodrugs - administration & dosage</subject><subject>Prodrugs - chemistry</subject><subject>Prodrugs - pharmacokinetics</subject><subject>Prodrugs - pharmacology</subject><subject>Small molecule drug conjugate</subject><subject>SMDC</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1rGzEQhkVpadykf6CHVsdedjNjSfsBvZSQJoVACk6gNyFLs67M7sqV5ID_fWWc9pjCwMDwvC_Dw9gHhBoBm8ttvZ7sWC8BRQ1djShesQXKRlZCgnrNFtA3UHW9_HnG3qW0BUAJUr5lZ0sJjVSAC7ZaHeb8i5JP3MyOG5v9k88HHgZu-BBGk4lnEzeUyfEpzMH5tKOYiP-4vuHWTLscSt76mdswb_ebErhgbwYzJnr_vM_Zw7frh6vb6u7-5vvV17vKyrbPVa96xEEM5KyTpjVKuLYM2dZ1VilozVoIKDeirkMkAGv7XsC6MTC0KM7Z51PtLobfe0pZTz5ZGkczU9gnjQqgVZ2U8H9USiERmv7YujyhNoaUIg16F_1k4kEj6KN2vdVH7fqoXUOni_YS-vjcv19P5P5F_nouwKcTMJigzSb6pB9XpaG8iGKpuq4QX04EFWNPnqJO1tNsyflINmsX_Esf_AEkMZyu</recordid><startdate>20131101</startdate><enddate>20131101</enddate><creator>Henne, Walter A.</creator><creator>Kularatne, Sumith A.</creator><creator>Hakenjos, John</creator><creator>Carron, Joshua D.</creator><creator>Henne, Kristene L.</creator><general>Elsevier Ltd</general><scope>FBQ</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>20131101</creationdate><title>Synthesis and activity of a folate targeted monodisperse PEG camptothecin conjugate</title><author>Henne, Walter A. ; Kularatne, Sumith A. ; Hakenjos, John ; Carron, Joshua D. ; Henne, Kristene L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c479t-95911f3fedcd4a7a53d73d7ec7d8c5507ab330d73ee8811e00cc9930b6a0f713</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Antineoplastic Agents, Phytogenic - administration & dosage</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - pharmacokinetics</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Camptothecin</topic><topic>Camptothecin - administration & dosage</topic><topic>Camptothecin - analogs & derivatives</topic><topic>Camptothecin - pharmacokinetics</topic><topic>Camptothecin - pharmacology</topic><topic>chemistry</topic><topic>cytotoxicity</topic><topic>Drug Delivery Systems</topic><topic>drugs</topic><topic>Folate conjugate</topic><topic>Folate Receptors, GPI-Anchored - metabolism</topic><topic>folic acid</topic><topic>Folic Acid - chemistry</topic><topic>Humans</topic><topic>inhibitory concentration 50</topic><topic>KB Cells</topic><topic>Monodisperse PEG</topic><topic>Neoplasms - drug therapy</topic><topic>Neoplasms - metabolism</topic><topic>PEG</topic><topic>Polyethylene Glycols - chemistry</topic><topic>Prodrugs - administration & dosage</topic><topic>Prodrugs - chemistry</topic><topic>Prodrugs - pharmacokinetics</topic><topic>Prodrugs - pharmacology</topic><topic>Small molecule drug conjugate</topic><topic>SMDC</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Henne, Walter A.</creatorcontrib><creatorcontrib>Kularatne, Sumith A.</creatorcontrib><creatorcontrib>Hakenjos, John</creatorcontrib><creatorcontrib>Carron, Joshua D.</creatorcontrib><creatorcontrib>Henne, Kristene L.</creatorcontrib><collection>AGRIS</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>Henne, Walter A.</au><au>Kularatne, Sumith A.</au><au>Hakenjos, John</au><au>Carron, Joshua D.</au><au>Henne, Kristene L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and activity of a folate targeted monodisperse PEG camptothecin conjugate</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2013-11-01</date><risdate>2013</risdate><volume>23</volume><issue>21</issue><spage>5810</spage><epage>5813</epage><pages>5810-5813</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
A folate targeted camptothecin small molecule drug conjugate (SMDC) was synthesized using a monodisperse PEG spacer linked to folate via a releasable disulfide carbonate linker. Cell cytotoxicity in human KB cells exhibited an IC50 of 6nM. Importantly, activity of the prodrug was blocked by excess folate, demonstrating receptor-mediated celluar uptake of the PEG conjugate.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>24064501</pmid><doi>10.1016/j.bmcl.2013.08.113</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2013-11, Vol.23 (21), p.5810-5813 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Antineoplastic Agents, Phytogenic - administration & dosage Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - pharmacokinetics Antineoplastic Agents, Phytogenic - pharmacology Camptothecin Camptothecin - administration & dosage Camptothecin - analogs & derivatives Camptothecin - pharmacokinetics Camptothecin - pharmacology chemistry cytotoxicity Drug Delivery Systems drugs Folate conjugate Folate Receptors, GPI-Anchored - metabolism folic acid Folic Acid - chemistry Humans inhibitory concentration 50 KB Cells Monodisperse PEG Neoplasms - drug therapy Neoplasms - metabolism PEG Polyethylene Glycols - chemistry Prodrugs - administration & dosage Prodrugs - chemistry Prodrugs - pharmacokinetics Prodrugs - pharmacology Small molecule drug conjugate SMDC |
| title | Synthesis and activity of a folate targeted monodisperse PEG camptothecin conjugate |
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