Magnetic Norbornene Polymer as Multiresponsive Nanocarrier for Site Specific Cancer Therapy
A site-specific, stimuli-responsive nanocarrier has been synthesized by conjugating folate, magnetic particles and doxorubicin to the backbone of norbornene polymer. Monomers, namely, cis-5-norbornene-6-(diethoxyphosphoryl)hexanote (mono 1), norbornene grafted poly(ethyleneglycol)-folate (mono 2),...
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| Veröffentlicht in: | Bioconjugate chemistry 2014-02, Vol.25 (2), p.276-285 |
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| creator | Rao N, Vijayakameswara Ganivada, Mutyala Naidu Sarkar, Santu Dinda, Himadri Chatterjee, Koushik Dalui, Tanmoy Das Sarma, Jayasri Shunmugam, Raja |
| description | A site-specific, stimuli-responsive nanocarrier has been synthesized by conjugating folate, magnetic particles and doxorubicin to the backbone of norbornene polymer. Monomers, namely, cis-5-norbornene-6-(diethoxyphosphoryl)hexanote (mono 1), norbornene grafted poly(ethyleneglycol)-folate (mono 2), and norbornene derived doxorubicin (mono 3) are carefully designed to demonstrate the smart nanorcarrier capabilities. The synthesis and complete characterization of all three monomers are elaborately discussed. Their copolymerization is done by controlled/living ring-opening metathesis polymerization (ROMP) to get the triblock copolymer PHOS-FOL-DOX. NMR spectroscopy and gel permeation chromatography confirm the formation of the triblock copolymer, while FT-IR spectroscopy, thermogravimetric analysis, along with transmission electron microscope confirm the anchoring of iron particle (Fe 3 O 4 ) to the PHOS-FOL-DOX. Drug release profile shows the importance of having the hydrazone linker that helps to release the drug exactly at the mild acidic conditions resembling the pH of the cancerous cells. The newly designed nanocarrier shows greater internalization (about 8 times) due to magnetic field. Also, increased intracellular DOX release is observed due to the folate receptor. From these results, it is clear that PHOS-FOL-DOX has the potential to act as a smart nanoreservoir with the magnetic field guidance, folate receptor targeting, and finally pH stimulation. |
| doi_str_mv | 10.1021/bc400409n |
| format | Article |
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Monomers, namely, cis-5-norbornene-6-(diethoxyphosphoryl)hexanote (mono 1), norbornene grafted poly(ethyleneglycol)-folate (mono 2), and norbornene derived doxorubicin (mono 3) are carefully designed to demonstrate the smart nanorcarrier capabilities. The synthesis and complete characterization of all three monomers are elaborately discussed. Their copolymerization is done by controlled/living ring-opening metathesis polymerization (ROMP) to get the triblock copolymer PHOS-FOL-DOX. NMR spectroscopy and gel permeation chromatography confirm the formation of the triblock copolymer, while FT-IR spectroscopy, thermogravimetric analysis, along with transmission electron microscope confirm the anchoring of iron particle (Fe 3 O 4 ) to the PHOS-FOL-DOX. Drug release profile shows the importance of having the hydrazone linker that helps to release the drug exactly at the mild acidic conditions resembling the pH of the cancerous cells. The newly designed nanocarrier shows greater internalization (about 8 times) due to magnetic field. Also, increased intracellular DOX release is observed due to the folate receptor. From these results, it is clear that PHOS-FOL-DOX has the potential to act as a smart nanoreservoir with the magnetic field guidance, folate receptor targeting, and finally pH stimulation.</description><identifier>ISSN: 1043-1802</identifier><identifier>EISSN: 1520-4812</identifier><identifier>DOI: 10.1021/bc400409n</identifier><identifier>PMID: 24364417</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Boron Compounds - chemistry ; Cancer therapies ; Cells ; Chemical compounds ; Chromatography ; Drug Carriers ; Magnetics ; Microscopy, Electron, Transmission ; Nanotechnology ; Polymers ; Polymers - chemistry ; Spectroscopy, Fourier Transform Infrared ; Thermogravimetric analysis ; Thermogravimetry ; Transmission electron microscopy</subject><ispartof>Bioconjugate chemistry, 2014-02, Vol.25 (2), p.276-285</ispartof><rights>Copyright © 2013 American Chemical Society</rights><rights>Copyright American Chemical Society Feb 19, 2014</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a343t-21d29acc0ce15d0b9ecdfd79ff13652009dc39eb0911dfb2fd1652ff8dd9536d3</citedby><cites>FETCH-LOGICAL-a343t-21d29acc0ce15d0b9ecdfd79ff13652009dc39eb0911dfb2fd1652ff8dd9536d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bc400409n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bc400409n$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24364417$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rao N, Vijayakameswara</creatorcontrib><creatorcontrib>Ganivada, Mutyala Naidu</creatorcontrib><creatorcontrib>Sarkar, Santu</creatorcontrib><creatorcontrib>Dinda, Himadri</creatorcontrib><creatorcontrib>Chatterjee, Koushik</creatorcontrib><creatorcontrib>Dalui, Tanmoy</creatorcontrib><creatorcontrib>Das Sarma, Jayasri</creatorcontrib><creatorcontrib>Shunmugam, Raja</creatorcontrib><title>Magnetic Norbornene Polymer as Multiresponsive Nanocarrier for Site Specific Cancer Therapy</title><title>Bioconjugate chemistry</title><addtitle>Bioconjugate Chem</addtitle><description>A site-specific, stimuli-responsive nanocarrier has been synthesized by conjugating folate, magnetic particles and doxorubicin to the backbone of norbornene polymer. Monomers, namely, cis-5-norbornene-6-(diethoxyphosphoryl)hexanote (mono 1), norbornene grafted poly(ethyleneglycol)-folate (mono 2), and norbornene derived doxorubicin (mono 3) are carefully designed to demonstrate the smart nanorcarrier capabilities. The synthesis and complete characterization of all three monomers are elaborately discussed. Their copolymerization is done by controlled/living ring-opening metathesis polymerization (ROMP) to get the triblock copolymer PHOS-FOL-DOX. NMR spectroscopy and gel permeation chromatography confirm the formation of the triblock copolymer, while FT-IR spectroscopy, thermogravimetric analysis, along with transmission electron microscope confirm the anchoring of iron particle (Fe 3 O 4 ) to the PHOS-FOL-DOX. Drug release profile shows the importance of having the hydrazone linker that helps to release the drug exactly at the mild acidic conditions resembling the pH of the cancerous cells. The newly designed nanocarrier shows greater internalization (about 8 times) due to magnetic field. Also, increased intracellular DOX release is observed due to the folate receptor. From these results, it is clear that PHOS-FOL-DOX has the potential to act as a smart nanoreservoir with the magnetic field guidance, folate receptor targeting, and finally pH stimulation.</description><subject>Boron Compounds - chemistry</subject><subject>Cancer therapies</subject><subject>Cells</subject><subject>Chemical compounds</subject><subject>Chromatography</subject><subject>Drug Carriers</subject><subject>Magnetics</subject><subject>Microscopy, Electron, Transmission</subject><subject>Nanotechnology</subject><subject>Polymers</subject><subject>Polymers - chemistry</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><subject>Thermogravimetric analysis</subject><subject>Thermogravimetry</subject><subject>Transmission electron microscopy</subject><issn>1043-1802</issn><issn>1520-4812</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNplkE1LxDAQhoMorq4e_ANSEEEP1Uma1uYoi1-wfsDqyUNJk4lWuklNWmH_vVlWRfQ0w8zDO--8hOxROKHA6GmtOAAHYdfIFs0ZpLykbD32wLOUlsBGZDuENwAQtGSbZMR4VnBOz7bI8618sdg3KrlzvnbeosXkwbWLOfpEhuR2aPvGY-icDc0HJnfSOiW9b-LaOJ_Mmh6TWYeqMVFjIq2Ki8dX9LJb7JANI9uAu191TJ4uLx4n1-n0_upmcj5NZcazPmVUMyGVAoU011ALVNroM2EMzYr4DQitMoF1NE-1qZnRNI6NKbUWeVbobEyOVrqdd-8Dhr6aN0Fh20qLbggVzQEKQXkOET34g765wdvobkkxyEsoykgdryjlXQgeTdX5Zi79oqJQLROvfhKP7P6X4lDPUf-Q3xFH4HAFSBV-Xfsn9AkMmod5</recordid><startdate>20140219</startdate><enddate>20140219</enddate><creator>Rao N, Vijayakameswara</creator><creator>Ganivada, Mutyala Naidu</creator><creator>Sarkar, Santu</creator><creator>Dinda, Himadri</creator><creator>Chatterjee, Koushik</creator><creator>Dalui, Tanmoy</creator><creator>Das Sarma, Jayasri</creator><creator>Shunmugam, Raja</creator><general>American Chemical Society</general><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>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20140219</creationdate><title>Magnetic Norbornene Polymer as Multiresponsive Nanocarrier for Site Specific Cancer Therapy</title><author>Rao N, Vijayakameswara ; Ganivada, Mutyala Naidu ; Sarkar, Santu ; Dinda, Himadri ; Chatterjee, Koushik ; Dalui, Tanmoy ; Das Sarma, Jayasri ; Shunmugam, Raja</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a343t-21d29acc0ce15d0b9ecdfd79ff13652009dc39eb0911dfb2fd1652ff8dd9536d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Boron Compounds - chemistry</topic><topic>Cancer therapies</topic><topic>Cells</topic><topic>Chemical compounds</topic><topic>Chromatography</topic><topic>Drug Carriers</topic><topic>Magnetics</topic><topic>Microscopy, Electron, Transmission</topic><topic>Nanotechnology</topic><topic>Polymers</topic><topic>Polymers - chemistry</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><topic>Thermogravimetric analysis</topic><topic>Thermogravimetry</topic><topic>Transmission electron microscopy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rao N, Vijayakameswara</creatorcontrib><creatorcontrib>Ganivada, Mutyala Naidu</creatorcontrib><creatorcontrib>Sarkar, Santu</creatorcontrib><creatorcontrib>Dinda, Himadri</creatorcontrib><creatorcontrib>Chatterjee, Koushik</creatorcontrib><creatorcontrib>Dalui, Tanmoy</creatorcontrib><creatorcontrib>Das Sarma, Jayasri</creatorcontrib><creatorcontrib>Shunmugam, Raja</creatorcontrib><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>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioconjugate chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rao N, Vijayakameswara</au><au>Ganivada, Mutyala Naidu</au><au>Sarkar, Santu</au><au>Dinda, Himadri</au><au>Chatterjee, Koushik</au><au>Dalui, Tanmoy</au><au>Das Sarma, Jayasri</au><au>Shunmugam, Raja</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Magnetic Norbornene Polymer as Multiresponsive Nanocarrier for Site Specific Cancer Therapy</atitle><jtitle>Bioconjugate chemistry</jtitle><addtitle>Bioconjugate Chem</addtitle><date>2014-02-19</date><risdate>2014</risdate><volume>25</volume><issue>2</issue><spage>276</spage><epage>285</epage><pages>276-285</pages><issn>1043-1802</issn><eissn>1520-4812</eissn><abstract>A site-specific, stimuli-responsive nanocarrier has been synthesized by conjugating folate, magnetic particles and doxorubicin to the backbone of norbornene polymer. Monomers, namely, cis-5-norbornene-6-(diethoxyphosphoryl)hexanote (mono 1), norbornene grafted poly(ethyleneglycol)-folate (mono 2), and norbornene derived doxorubicin (mono 3) are carefully designed to demonstrate the smart nanorcarrier capabilities. The synthesis and complete characterization of all three monomers are elaborately discussed. Their copolymerization is done by controlled/living ring-opening metathesis polymerization (ROMP) to get the triblock copolymer PHOS-FOL-DOX. NMR spectroscopy and gel permeation chromatography confirm the formation of the triblock copolymer, while FT-IR spectroscopy, thermogravimetric analysis, along with transmission electron microscope confirm the anchoring of iron particle (Fe 3 O 4 ) to the PHOS-FOL-DOX. Drug release profile shows the importance of having the hydrazone linker that helps to release the drug exactly at the mild acidic conditions resembling the pH of the cancerous cells. The newly designed nanocarrier shows greater internalization (about 8 times) due to magnetic field. Also, increased intracellular DOX release is observed due to the folate receptor. From these results, it is clear that PHOS-FOL-DOX has the potential to act as a smart nanoreservoir with the magnetic field guidance, folate receptor targeting, and finally pH stimulation.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24364417</pmid><doi>10.1021/bc400409n</doi><tpages>10</tpages></addata></record> |
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| subjects | Boron Compounds - chemistry Cancer therapies Cells Chemical compounds Chromatography Drug Carriers Magnetics Microscopy, Electron, Transmission Nanotechnology Polymers Polymers - chemistry Spectroscopy, Fourier Transform Infrared Thermogravimetric analysis Thermogravimetry Transmission electron microscopy |
| title | Magnetic Norbornene Polymer as Multiresponsive Nanocarrier for Site Specific Cancer Therapy |
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