A facile Friedel–Crafts acylation for the synthesis of polyethylenimine-grafted multi-walled carbon nanotubes as efficient gene delivery vectors
[Display omitted] Low chemical reactivity of carbon nanotubes is one of the major obstacles in their functionalization via chemical reactions. As a non-destructive method, Friedel-Crafts acylation was suggested among the explored reactions for which only a few methods have been reported under harsh...
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| Veröffentlicht in: | International journal of pharmaceutics 2016-04, Vol.502 (1-2), p.125-137 |
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| container_title | International journal of pharmaceutics |
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| creator | Nia, Azadeh Hashem Amini, Abbas Taghavi, Sahar Eshghi, Hossein Abnous, Khalil Ramezani, Mohammad |
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Low chemical reactivity of carbon nanotubes is one of the major obstacles in their functionalization via chemical reactions. As a non-destructive method, Friedel-Crafts acylation was suggested among the explored reactions for which only a few methods have been reported under harsh reaction conditions, e.g., high temperature all leading to low yields. In this study, we propose a novel method for the acylation of multi-walled carbon nanotubes (MWCNTs) at a low temperature (i.e., 42°C), using SiO2-Al2O3 as a catalyst and 6-bromohexanoic acid as the acylating agent to produce high yield functionalized MWCNTs. After acylation, MWCNTs are conjugated with polyethylenimines (PEIs) with three molecular weights (1.8, 10 and 25kDa). Three different MWCNT-PEI conjugates are synthesized and evaluated for their condensation ability, viability, size and zeta potential properties. The transfection efficiency of the functionalized MWCNTs is evaluated using luciferase assay and flow cytometry in a Neuroblastoma cell line. MWCNT-PEI (10kDa) conjugate shows the highest transfection efficacy compared to others. For this carrier transfection efficacy exceeds the amount of PEI 25kDa at similar carrier to plasmid weight ratio (C/P) and is around 3 times higher compared to PEI 25kDa at C/P=0.8 as positive control regarding its high transfection efficiency and low cytotoxicity. |
| doi_str_mv | 10.1016/j.ijpharm.2016.02.034 |
| format | Article |
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Low chemical reactivity of carbon nanotubes is one of the major obstacles in their functionalization via chemical reactions. As a non-destructive method, Friedel-Crafts acylation was suggested among the explored reactions for which only a few methods have been reported under harsh reaction conditions, e.g., high temperature all leading to low yields. In this study, we propose a novel method for the acylation of multi-walled carbon nanotubes (MWCNTs) at a low temperature (i.e., 42°C), using SiO2-Al2O3 as a catalyst and 6-bromohexanoic acid as the acylating agent to produce high yield functionalized MWCNTs. After acylation, MWCNTs are conjugated with polyethylenimines (PEIs) with three molecular weights (1.8, 10 and 25kDa). Three different MWCNT-PEI conjugates are synthesized and evaluated for their condensation ability, viability, size and zeta potential properties. The transfection efficiency of the functionalized MWCNTs is evaluated using luciferase assay and flow cytometry in a Neuroblastoma cell line. MWCNT-PEI (10kDa) conjugate shows the highest transfection efficacy compared to others. For this carrier transfection efficacy exceeds the amount of PEI 25kDa at similar carrier to plasmid weight ratio (C/P) and is around 3 times higher compared to PEI 25kDa at C/P=0.8 as positive control regarding its high transfection efficiency and low cytotoxicity.</description><identifier>ISSN: 0378-5173</identifier><identifier>EISSN: 1873-3476</identifier><identifier>DOI: 10.1016/j.ijpharm.2016.02.034</identifier><identifier>PMID: 26906459</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>Acylation ; Aluminum Compounds - chemistry ; Animals ; Caproates - chemistry ; Cell Line, Tumor ; Chlorides - chemistry ; Friedel-Crafts acylation ; Functionalization ; Gene delivery ; Gene Transfer Techniques ; Green Fluorescent Proteins - genetics ; Mice ; Multi-walled carbon nanotube ; Nanotubes, Carbon - chemistry ; Polyethyleneimine - administration & dosage ; Polyethyleneimine - chemistry ; Polyethylenimine ; Silicon Dioxide - chemistry</subject><ispartof>International journal of pharmaceutics, 2016-04, Vol.502 (1-2), p.125-137</ispartof><rights>2016 Elsevier B.V.</rights><rights>Copyright © 2016 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c398t-6b1f1abcef585fbaf946cd4ffc6604a0490cf51b856e775469c392888e08e82d3</citedby><cites>FETCH-LOGICAL-c398t-6b1f1abcef585fbaf946cd4ffc6604a0490cf51b856e775469c392888e08e82d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0378517316301272$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26906459$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nia, Azadeh Hashem</creatorcontrib><creatorcontrib>Amini, Abbas</creatorcontrib><creatorcontrib>Taghavi, Sahar</creatorcontrib><creatorcontrib>Eshghi, Hossein</creatorcontrib><creatorcontrib>Abnous, Khalil</creatorcontrib><creatorcontrib>Ramezani, Mohammad</creatorcontrib><title>A facile Friedel–Crafts acylation for the synthesis of polyethylenimine-grafted multi-walled carbon nanotubes as efficient gene delivery vectors</title><title>International journal of pharmaceutics</title><addtitle>Int J Pharm</addtitle><description>[Display omitted]
Low chemical reactivity of carbon nanotubes is one of the major obstacles in their functionalization via chemical reactions. As a non-destructive method, Friedel-Crafts acylation was suggested among the explored reactions for which only a few methods have been reported under harsh reaction conditions, e.g., high temperature all leading to low yields. In this study, we propose a novel method for the acylation of multi-walled carbon nanotubes (MWCNTs) at a low temperature (i.e., 42°C), using SiO2-Al2O3 as a catalyst and 6-bromohexanoic acid as the acylating agent to produce high yield functionalized MWCNTs. After acylation, MWCNTs are conjugated with polyethylenimines (PEIs) with three molecular weights (1.8, 10 and 25kDa). Three different MWCNT-PEI conjugates are synthesized and evaluated for their condensation ability, viability, size and zeta potential properties. The transfection efficiency of the functionalized MWCNTs is evaluated using luciferase assay and flow cytometry in a Neuroblastoma cell line. MWCNT-PEI (10kDa) conjugate shows the highest transfection efficacy compared to others. For this carrier transfection efficacy exceeds the amount of PEI 25kDa at similar carrier to plasmid weight ratio (C/P) and is around 3 times higher compared to PEI 25kDa at C/P=0.8 as positive control regarding its high transfection efficiency and low cytotoxicity.</description><subject>Acylation</subject><subject>Aluminum Compounds - chemistry</subject><subject>Animals</subject><subject>Caproates - chemistry</subject><subject>Cell Line, Tumor</subject><subject>Chlorides - chemistry</subject><subject>Friedel-Crafts acylation</subject><subject>Functionalization</subject><subject>Gene delivery</subject><subject>Gene Transfer Techniques</subject><subject>Green Fluorescent Proteins - genetics</subject><subject>Mice</subject><subject>Multi-walled carbon nanotube</subject><subject>Nanotubes, Carbon - chemistry</subject><subject>Polyethyleneimine - administration & dosage</subject><subject>Polyethyleneimine - chemistry</subject><subject>Polyethylenimine</subject><subject>Silicon Dioxide - chemistry</subject><issn>0378-5173</issn><issn>1873-3476</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU2O1DAUhCMEYnoGjgDykk2CHcc_WaFRi4GRRmIDa8txnqfdcuLGdhplxxnghpwEt7phO6unJ31VJVVV1RuCG4IJf79v3P6w03Fq2vI2uG0w7Z5VGyIFrWkn-PNqg6mQNSOCXlXXKe0xxrwl9GV11fIe8471m-rXLbLaOA_oLjoYwf_5-Xsbtc0JabN6nV2YkQ0R5R2gtM7lJJdQsOgQ_Ap5t3qY3eRmqB9PMhjRtPjs6h_a-_IYHYfiMOs55GWA4poQWOuMgzmjR5gBlVB3hLiiI5gcYnpVvbDaJ3h9uTfVt7uPX7ef64cvn-63tw-1ob3MNR-IJXowYJlkdtC277gZO2sN57jTuOuxsYwMknEQgnW8L7pWSglYgmxHelO9O_seYvi-QMpqcsmA93qGsCRFJGYMY4rF06gQHaNUUFJQdkZNDClFsOoQ3aTjqghWp-XUXl2WU6flFG5VWa7o3l4ilmGC8b_q31QF-HAGoHRydBBVOpVoYHSxFKfG4J6I-As9PbEP</recordid><startdate>20160411</startdate><enddate>20160411</enddate><creator>Nia, Azadeh Hashem</creator><creator>Amini, Abbas</creator><creator>Taghavi, Sahar</creator><creator>Eshghi, Hossein</creator><creator>Abnous, Khalil</creator><creator>Ramezani, Mohammad</creator><general>Elsevier B.V</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>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>RC3</scope></search><sort><creationdate>20160411</creationdate><title>A facile Friedel–Crafts acylation for the synthesis of polyethylenimine-grafted multi-walled carbon nanotubes as efficient gene delivery vectors</title><author>Nia, Azadeh Hashem ; Amini, Abbas ; Taghavi, Sahar ; Eshghi, Hossein ; Abnous, Khalil ; Ramezani, Mohammad</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c398t-6b1f1abcef585fbaf946cd4ffc6604a0490cf51b856e775469c392888e08e82d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Acylation</topic><topic>Aluminum Compounds - chemistry</topic><topic>Animals</topic><topic>Caproates - chemistry</topic><topic>Cell Line, Tumor</topic><topic>Chlorides - chemistry</topic><topic>Friedel-Crafts acylation</topic><topic>Functionalization</topic><topic>Gene delivery</topic><topic>Gene Transfer Techniques</topic><topic>Green Fluorescent Proteins - genetics</topic><topic>Mice</topic><topic>Multi-walled carbon nanotube</topic><topic>Nanotubes, Carbon - chemistry</topic><topic>Polyethyleneimine - administration & dosage</topic><topic>Polyethyleneimine - chemistry</topic><topic>Polyethylenimine</topic><topic>Silicon Dioxide - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nia, Azadeh Hashem</creatorcontrib><creatorcontrib>Amini, Abbas</creatorcontrib><creatorcontrib>Taghavi, Sahar</creatorcontrib><creatorcontrib>Eshghi, Hossein</creatorcontrib><creatorcontrib>Abnous, Khalil</creatorcontrib><creatorcontrib>Ramezani, Mohammad</creatorcontrib><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><collection>Genetics Abstracts</collection><jtitle>International journal of pharmaceutics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nia, Azadeh Hashem</au><au>Amini, Abbas</au><au>Taghavi, Sahar</au><au>Eshghi, Hossein</au><au>Abnous, Khalil</au><au>Ramezani, Mohammad</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A facile Friedel–Crafts acylation for the synthesis of polyethylenimine-grafted multi-walled carbon nanotubes as efficient gene delivery vectors</atitle><jtitle>International journal of pharmaceutics</jtitle><addtitle>Int J Pharm</addtitle><date>2016-04-11</date><risdate>2016</risdate><volume>502</volume><issue>1-2</issue><spage>125</spage><epage>137</epage><pages>125-137</pages><issn>0378-5173</issn><eissn>1873-3476</eissn><abstract>[Display omitted]
Low chemical reactivity of carbon nanotubes is one of the major obstacles in their functionalization via chemical reactions. As a non-destructive method, Friedel-Crafts acylation was suggested among the explored reactions for which only a few methods have been reported under harsh reaction conditions, e.g., high temperature all leading to low yields. In this study, we propose a novel method for the acylation of multi-walled carbon nanotubes (MWCNTs) at a low temperature (i.e., 42°C), using SiO2-Al2O3 as a catalyst and 6-bromohexanoic acid as the acylating agent to produce high yield functionalized MWCNTs. After acylation, MWCNTs are conjugated with polyethylenimines (PEIs) with three molecular weights (1.8, 10 and 25kDa). Three different MWCNT-PEI conjugates are synthesized and evaluated for their condensation ability, viability, size and zeta potential properties. The transfection efficiency of the functionalized MWCNTs is evaluated using luciferase assay and flow cytometry in a Neuroblastoma cell line. MWCNT-PEI (10kDa) conjugate shows the highest transfection efficacy compared to others. For this carrier transfection efficacy exceeds the amount of PEI 25kDa at similar carrier to plasmid weight ratio (C/P) and is around 3 times higher compared to PEI 25kDa at C/P=0.8 as positive control regarding its high transfection efficiency and low cytotoxicity.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>26906459</pmid><doi>10.1016/j.ijpharm.2016.02.034</doi><tpages>13</tpages></addata></record> |
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| subjects | Acylation Aluminum Compounds - chemistry Animals Caproates - chemistry Cell Line, Tumor Chlorides - chemistry Friedel-Crafts acylation Functionalization Gene delivery Gene Transfer Techniques Green Fluorescent Proteins - genetics Mice Multi-walled carbon nanotube Nanotubes, Carbon - chemistry Polyethyleneimine - administration & dosage Polyethyleneimine - chemistry Polyethylenimine Silicon Dioxide - chemistry |
| title | A facile Friedel–Crafts acylation for the synthesis of polyethylenimine-grafted multi-walled carbon nanotubes as efficient gene delivery vectors |
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