Role of boronic acid moieties in poly(amido amine)s for gene delivery
The effects of the presence of two different types of phenylboronic acids as side groups in disulfide-containing poly(amido amine)s (SS-PAA) were investigated in the application of these polymers as gene delivery vectors. To this purpose, a para-carboxyphenylboronic acid was grafted on a SS-PAA with...
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| Veröffentlicht in: | Journal of controlled release 2011-10, Vol.155 (2), p.331-340 |
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| creator | Piest, Martin Engbersen, Johan F.J. |
| description | The effects of the presence of two different types of phenylboronic acids as side groups in disulfide-containing poly(amido amine)s (SS-PAA) were investigated in the application of these polymers as gene delivery vectors. To this purpose, a
para-carboxyphenylboronic acid was grafted on a SS-PAA with pending aminobutyl side chains, resulting in p(DAB–4CPBA) and an
ortho-aminomethylphenylboronic acid was incorporated through copolymerization, resulting in p(DAB–2AMPBA). Both polymers have 30% of phenylboronic acid side chains and 70% of residual aminobutyl side chains and were compared with the non-boronated benzoylated analogue p(DAB–Bz) of similar M
w. It was found that the presence of phenylboronic acid moieties improved polyplex formation with plasmid DNA since smaller and more monodisperse polyplexes were formed as compared to their non-boronated counterparts. The transfection efficiency of polyplexes of p(DAB–4CPBA) was approximately similar to that of p(DAB–Bz) and commercial PEI (Exgen), both in the absence and the presence of serum, indicating that p(DAB–4CPBA) and p(DAB–Bz) are potent gene delivery vectors. However, the polymers with phenylboronic acid functionalities showed increased cytotoxicity, which is stronger for the
ortho-aminophenylboronic acid containing polyplexes of p(DAB–2AMPBA) than for the p(DAB–4CPBA) analog. The cytotoxic effect may be caused by increased membrane disruptive interaction as was indicated by the increased hemolytic activity observed for these polymers.
[Display omitted] |
| doi_str_mv | 10.1016/j.jconrel.2011.07.011 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_902351940</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0168365911004901</els_id><sourcerecordid>898840376</sourcerecordid><originalsourceid>FETCH-LOGICAL-c497t-7ff58b3896b34e4db63d1999ea597c22a51929ada4759942a219731cb188969d3</originalsourceid><addsrcrecordid>eNqF0MFu1DAQBmALgehSeATAFwQ9JNiOHXtOCFWFIlWqBPRsOfak8iqJF3u30r59vdoFjr14Lt_MeH5C3nLWcsb7z-t27dOScWoF47xluq3lGVlxo7tGAqjnZFWdabpewRl5VcqaMaY6qV-SM8G1EaaXK3L1M01I00iHlNMSPXU-BjqniNuIhcaFbtK0_-TmGBKt74IXhY4p03tckAac4gPm_WvyYnRTwTenek7uvl39vrxubm6__7j8etN4CXrb6HFUZugM9EMnUYah7wIHAHQKtBfCKQ4CXHBSKwApnOCgO-4HbmoPhO6cfDzO3eT0Z4dla-dYPE6TWzDtigUmujpDsielAWMq032V6ih9TqVkHO0mx9nlveXMHqK2a3uK2h6itkzbWmrfu9OG3TBj-Nf1N9sKPpyAK95NY3aLj-W_k1pq0avq3h_d6JJ197mau191k2KMG27gcMyXo8Ca7UPEbIuPuHgMMaPf2pDiE599BMAopik</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>898840376</pqid></control><display><type>article</type><title>Role of boronic acid moieties in poly(amido amine)s for gene delivery</title><source>MEDLINE</source><source>ScienceDirect Journals (5 years ago - present)</source><creator>Piest, Martin ; Engbersen, Johan F.J.</creator><creatorcontrib>Piest, Martin ; Engbersen, Johan F.J.</creatorcontrib><description>The effects of the presence of two different types of phenylboronic acids as side groups in disulfide-containing poly(amido amine)s (SS-PAA) were investigated in the application of these polymers as gene delivery vectors. To this purpose, a
para-carboxyphenylboronic acid was grafted on a SS-PAA with pending aminobutyl side chains, resulting in p(DAB–4CPBA) and an
ortho-aminomethylphenylboronic acid was incorporated through copolymerization, resulting in p(DAB–2AMPBA). Both polymers have 30% of phenylboronic acid side chains and 70% of residual aminobutyl side chains and were compared with the non-boronated benzoylated analogue p(DAB–Bz) of similar M
w. It was found that the presence of phenylboronic acid moieties improved polyplex formation with plasmid DNA since smaller and more monodisperse polyplexes were formed as compared to their non-boronated counterparts. The transfection efficiency of polyplexes of p(DAB–4CPBA) was approximately similar to that of p(DAB–Bz) and commercial PEI (Exgen), both in the absence and the presence of serum, indicating that p(DAB–4CPBA) and p(DAB–Bz) are potent gene delivery vectors. However, the polymers with phenylboronic acid functionalities showed increased cytotoxicity, which is stronger for the
ortho-aminophenylboronic acid containing polyplexes of p(DAB–2AMPBA) than for the p(DAB–4CPBA) analog. The cytotoxic effect may be caused by increased membrane disruptive interaction as was indicated by the increased hemolytic activity observed for these polymers.
[Display omitted]</description><identifier>ISSN: 0168-3659</identifier><identifier>EISSN: 1873-4995</identifier><identifier>DOI: 10.1016/j.jconrel.2011.07.011</identifier><identifier>PMID: 21782864</identifier><identifier>CODEN: JCREEC</identifier><language>eng</language><publisher>Kidlington: Elsevier B.V</publisher><subject>acids ; Animals ; Biological and medical sciences ; Bioreducible polymer ; blood serum ; Boronic Acids - chemical synthesis ; Boronic Acids - chemistry ; Boronic Acids - pharmacology ; Cell Survival ; Cercopithecus aethiops ; COS Cells ; Cricetinae ; cytotoxicity ; DNA - administration & dosage ; DNA - genetics ; Drug Carriers - chemical synthesis ; Drug Carriers - chemistry ; Erythrocytes - drug effects ; Gene delivery ; Gene Transfer Techniques ; General pharmacology ; genes ; hemolysis ; Hemolysis - drug effects ; Humans ; Medical sciences ; Molecular Structure ; Nylons - chemical synthesis ; Nylons - chemistry ; Nylons - pharmacology ; Pharmaceutical technology. Pharmaceutical industry ; Pharmacology. Drug treatments ; Phenylboronic acid ; plasmids ; Poly(amido amine) ; Polyamines - chemistry ; polymers ; Polyplex ; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization ; Transfection</subject><ispartof>Journal of controlled release, 2011-10, Vol.155 (2), p.331-340</ispartof><rights>2011 Elsevier B.V.</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c497t-7ff58b3896b34e4db63d1999ea597c22a51929ada4759942a219731cb188969d3</citedby><cites>FETCH-LOGICAL-c497t-7ff58b3896b34e4db63d1999ea597c22a51929ada4759942a219731cb188969d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.jconrel.2011.07.011$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>309,310,314,780,784,789,790,3550,23930,23931,25140,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24747265$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21782864$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Piest, Martin</creatorcontrib><creatorcontrib>Engbersen, Johan F.J.</creatorcontrib><title>Role of boronic acid moieties in poly(amido amine)s for gene delivery</title><title>Journal of controlled release</title><addtitle>J Control Release</addtitle><description>The effects of the presence of two different types of phenylboronic acids as side groups in disulfide-containing poly(amido amine)s (SS-PAA) were investigated in the application of these polymers as gene delivery vectors. To this purpose, a
para-carboxyphenylboronic acid was grafted on a SS-PAA with pending aminobutyl side chains, resulting in p(DAB–4CPBA) and an
ortho-aminomethylphenylboronic acid was incorporated through copolymerization, resulting in p(DAB–2AMPBA). Both polymers have 30% of phenylboronic acid side chains and 70% of residual aminobutyl side chains and were compared with the non-boronated benzoylated analogue p(DAB–Bz) of similar M
w. It was found that the presence of phenylboronic acid moieties improved polyplex formation with plasmid DNA since smaller and more monodisperse polyplexes were formed as compared to their non-boronated counterparts. The transfection efficiency of polyplexes of p(DAB–4CPBA) was approximately similar to that of p(DAB–Bz) and commercial PEI (Exgen), both in the absence and the presence of serum, indicating that p(DAB–4CPBA) and p(DAB–Bz) are potent gene delivery vectors. However, the polymers with phenylboronic acid functionalities showed increased cytotoxicity, which is stronger for the
ortho-aminophenylboronic acid containing polyplexes of p(DAB–2AMPBA) than for the p(DAB–4CPBA) analog. The cytotoxic effect may be caused by increased membrane disruptive interaction as was indicated by the increased hemolytic activity observed for these polymers.
[Display omitted]</description><subject>acids</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Bioreducible polymer</subject><subject>blood serum</subject><subject>Boronic Acids - chemical synthesis</subject><subject>Boronic Acids - chemistry</subject><subject>Boronic Acids - pharmacology</subject><subject>Cell Survival</subject><subject>Cercopithecus aethiops</subject><subject>COS Cells</subject><subject>Cricetinae</subject><subject>cytotoxicity</subject><subject>DNA - administration & dosage</subject><subject>DNA - genetics</subject><subject>Drug Carriers - chemical synthesis</subject><subject>Drug Carriers - chemistry</subject><subject>Erythrocytes - drug effects</subject><subject>Gene delivery</subject><subject>Gene Transfer Techniques</subject><subject>General pharmacology</subject><subject>genes</subject><subject>hemolysis</subject><subject>Hemolysis - drug effects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Nylons - chemical synthesis</subject><subject>Nylons - chemistry</subject><subject>Nylons - pharmacology</subject><subject>Pharmaceutical technology. Pharmaceutical industry</subject><subject>Pharmacology. Drug treatments</subject><subject>Phenylboronic acid</subject><subject>plasmids</subject><subject>Poly(amido amine)</subject><subject>Polyamines - chemistry</subject><subject>polymers</subject><subject>Polyplex</subject><subject>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</subject><subject>Transfection</subject><issn>0168-3659</issn><issn>1873-4995</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0MFu1DAQBmALgehSeATAFwQ9JNiOHXtOCFWFIlWqBPRsOfak8iqJF3u30r59vdoFjr14Lt_MeH5C3nLWcsb7z-t27dOScWoF47xluq3lGVlxo7tGAqjnZFWdabpewRl5VcqaMaY6qV-SM8G1EaaXK3L1M01I00iHlNMSPXU-BjqniNuIhcaFbtK0_-TmGBKt74IXhY4p03tckAac4gPm_WvyYnRTwTenek7uvl39vrxubm6__7j8etN4CXrb6HFUZugM9EMnUYah7wIHAHQKtBfCKQ4CXHBSKwApnOCgO-4HbmoPhO6cfDzO3eT0Z4dla-dYPE6TWzDtigUmujpDsielAWMq032V6ih9TqVkHO0mx9nlveXMHqK2a3uK2h6itkzbWmrfu9OG3TBj-Nf1N9sKPpyAK95NY3aLj-W_k1pq0avq3h_d6JJ197mau191k2KMG27gcMyXo8Ca7UPEbIuPuHgMMaPf2pDiE599BMAopik</recordid><startdate>20111030</startdate><enddate>20111030</enddate><creator>Piest, Martin</creator><creator>Engbersen, Johan F.J.</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>FBQ</scope><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>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>RC3</scope></search><sort><creationdate>20111030</creationdate><title>Role of boronic acid moieties in poly(amido amine)s for gene delivery</title><author>Piest, Martin ; Engbersen, Johan F.J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c497t-7ff58b3896b34e4db63d1999ea597c22a51929ada4759942a219731cb188969d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>acids</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Bioreducible polymer</topic><topic>blood serum</topic><topic>Boronic Acids - chemical synthesis</topic><topic>Boronic Acids - chemistry</topic><topic>Boronic Acids - pharmacology</topic><topic>Cell Survival</topic><topic>Cercopithecus aethiops</topic><topic>COS Cells</topic><topic>Cricetinae</topic><topic>cytotoxicity</topic><topic>DNA - administration & dosage</topic><topic>DNA - genetics</topic><topic>Drug Carriers - chemical synthesis</topic><topic>Drug Carriers - chemistry</topic><topic>Erythrocytes - drug effects</topic><topic>Gene delivery</topic><topic>Gene Transfer Techniques</topic><topic>General pharmacology</topic><topic>genes</topic><topic>hemolysis</topic><topic>Hemolysis - drug effects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Nylons - chemical synthesis</topic><topic>Nylons - chemistry</topic><topic>Nylons - pharmacology</topic><topic>Pharmaceutical technology. Pharmaceutical industry</topic><topic>Pharmacology. Drug treatments</topic><topic>Phenylboronic acid</topic><topic>plasmids</topic><topic>Poly(amido amine)</topic><topic>Polyamines - chemistry</topic><topic>polymers</topic><topic>Polyplex</topic><topic>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</topic><topic>Transfection</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Piest, Martin</creatorcontrib><creatorcontrib>Engbersen, Johan F.J.</creatorcontrib><collection>AGRIS</collection><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>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>Journal of controlled release</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Piest, Martin</au><au>Engbersen, Johan F.J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Role of boronic acid moieties in poly(amido amine)s for gene delivery</atitle><jtitle>Journal of controlled release</jtitle><addtitle>J Control Release</addtitle><date>2011-10-30</date><risdate>2011</risdate><volume>155</volume><issue>2</issue><spage>331</spage><epage>340</epage><pages>331-340</pages><issn>0168-3659</issn><eissn>1873-4995</eissn><coden>JCREEC</coden><abstract>The effects of the presence of two different types of phenylboronic acids as side groups in disulfide-containing poly(amido amine)s (SS-PAA) were investigated in the application of these polymers as gene delivery vectors. To this purpose, a
para-carboxyphenylboronic acid was grafted on a SS-PAA with pending aminobutyl side chains, resulting in p(DAB–4CPBA) and an
ortho-aminomethylphenylboronic acid was incorporated through copolymerization, resulting in p(DAB–2AMPBA). Both polymers have 30% of phenylboronic acid side chains and 70% of residual aminobutyl side chains and were compared with the non-boronated benzoylated analogue p(DAB–Bz) of similar M
w. It was found that the presence of phenylboronic acid moieties improved polyplex formation with plasmid DNA since smaller and more monodisperse polyplexes were formed as compared to their non-boronated counterparts. The transfection efficiency of polyplexes of p(DAB–4CPBA) was approximately similar to that of p(DAB–Bz) and commercial PEI (Exgen), both in the absence and the presence of serum, indicating that p(DAB–4CPBA) and p(DAB–Bz) are potent gene delivery vectors. However, the polymers with phenylboronic acid functionalities showed increased cytotoxicity, which is stronger for the
ortho-aminophenylboronic acid containing polyplexes of p(DAB–2AMPBA) than for the p(DAB–4CPBA) analog. The cytotoxic effect may be caused by increased membrane disruptive interaction as was indicated by the increased hemolytic activity observed for these polymers.
[Display omitted]</abstract><cop>Kidlington</cop><pub>Elsevier B.V</pub><pmid>21782864</pmid><doi>10.1016/j.jconrel.2011.07.011</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | acids Animals Biological and medical sciences Bioreducible polymer blood serum Boronic Acids - chemical synthesis Boronic Acids - chemistry Boronic Acids - pharmacology Cell Survival Cercopithecus aethiops COS Cells Cricetinae cytotoxicity DNA - administration & dosage DNA - genetics Drug Carriers - chemical synthesis Drug Carriers - chemistry Erythrocytes - drug effects Gene delivery Gene Transfer Techniques General pharmacology genes hemolysis Hemolysis - drug effects Humans Medical sciences Molecular Structure Nylons - chemical synthesis Nylons - chemistry Nylons - pharmacology Pharmaceutical technology. Pharmaceutical industry Pharmacology. Drug treatments Phenylboronic acid plasmids Poly(amido amine) Polyamines - chemistry polymers Polyplex Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Transfection |
| title | Role of boronic acid moieties in poly(amido amine)s for gene delivery |
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