Bioreducible poly(amido amine)s with oligoamine side chains: Synthesis, characterization, and structural effects on gene delivery
A group of bioreducible poly(amido amine)s containing multiple disulfide linkages in main chain and oligoamines in side chain ( SS–PAOAs) were prepared by Michael-type polyaddition of N-tert-butyloxycarbonyl ( N-Boc) protected oligoamine to the disulfide-containing cystaminebisacrylamide, followed b...
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| Veröffentlicht in: | Journal of controlled release 2008-03, Vol.126 (2), p.166-174 |
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| creator | Lin, Chao Blaauboer, Cees-Jan Timoneda, Miguel Mateos Lok, Martin C. van Steenbergen, Mies Hennink, Wim E. Zhong, Zhiyuan Feijen, Jan Engbersen, Johan F.J. |
| description | A group of bioreducible poly(amido amine)s containing multiple disulfide linkages in main chain and oligoamines in side chain (
SS–PAOAs) were prepared by Michael-type polyaddition of
N-tert-butyloxycarbonyl (
N-Boc) protected oligoamine to the disulfide-containing cystaminebisacrylamide, followed by deprotection of the Boc-protective groups. These linear polymers show strong DNA condensation capability at low N/P ratios. The chemical structure of oligoamine side chains (
i.e. amine type and amino spacer length) in the
SS–PAOAs has a distinct effect on their buffer capacity, transfection efficiency and toxicity profile. The
SS–PAOAs containing secondary amino functions in the side chain show high buffer capacities and are able to transfect COS-7 cells
in vitro at low N/P ratios, with transfection efficiencies similar or even higher than those of 25 kDa branched pEI, along with very low cytotoxicity as determined by XTT assay. Increase of the alkyl spacer from ethylene to propylene between the amino units in side chains results in significant lower transfection and increased toxicity. This study presents detailed factors influencing the relationship between structure and gene delivery properties and may provide helpful insights for the further development of safe and efficient non-viral vectors. |
| doi_str_mv | 10.1016/j.jconrel.2007.11.012 |
| format | Article |
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SS–PAOAs) were prepared by Michael-type polyaddition of
N-tert-butyloxycarbonyl (
N-Boc) protected oligoamine to the disulfide-containing cystaminebisacrylamide, followed by deprotection of the Boc-protective groups. These linear polymers show strong DNA condensation capability at low N/P ratios. The chemical structure of oligoamine side chains (
i.e. amine type and amino spacer length) in the
SS–PAOAs has a distinct effect on their buffer capacity, transfection efficiency and toxicity profile. The
SS–PAOAs containing secondary amino functions in the side chain show high buffer capacities and are able to transfect COS-7 cells
in vitro at low N/P ratios, with transfection efficiencies similar or even higher than those of 25 kDa branched pEI, along with very low cytotoxicity as determined by XTT assay. Increase of the alkyl spacer from ethylene to propylene between the amino units in side chains results in significant lower transfection and increased toxicity. This study presents detailed factors influencing the relationship between structure and gene delivery properties and may provide helpful insights for the further development of safe and efficient non-viral vectors.</description><identifier>ISSN: 0168-3659</identifier><identifier>EISSN: 1873-4995</identifier><identifier>DOI: 10.1016/j.jconrel.2007.11.012</identifier><identifier>PMID: 18162194</identifier><identifier>CODEN: JCREEC</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Animals ; Biological and medical sciences ; Cell Survival - drug effects ; Cell Survival - physiology ; Cercopithecus aethiops ; COS Cells ; Disulfide reduction ; Gene delivery ; Gene Transfer Techniques ; General pharmacology ; Medical sciences ; Nylons - chemistry ; Nylons - pharmacology ; Oligoamine ; Pharmaceutical technology. Pharmaceutical industry ; Pharmacology. Drug treatments ; Poly(amido amine) ; Polyamines - administration & dosage ; Polyamines - chemistry ; Polyplex</subject><ispartof>Journal of controlled release, 2008-03, Vol.126 (2), p.166-174</ispartof><rights>2007 Elsevier B.V.</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c424t-57d9b35c9e8c8c053a542ecde37ff7a4ab3e91b99b3b6786aca2f6286b74bbca3</citedby><cites>FETCH-LOGICAL-c424t-57d9b35c9e8c8c053a542ecde37ff7a4ab3e91b99b3b6786aca2f6286b74bbca3</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.2007.11.012$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20086030$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18162194$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lin, Chao</creatorcontrib><creatorcontrib>Blaauboer, Cees-Jan</creatorcontrib><creatorcontrib>Timoneda, Miguel Mateos</creatorcontrib><creatorcontrib>Lok, Martin C.</creatorcontrib><creatorcontrib>van Steenbergen, Mies</creatorcontrib><creatorcontrib>Hennink, Wim E.</creatorcontrib><creatorcontrib>Zhong, Zhiyuan</creatorcontrib><creatorcontrib>Feijen, Jan</creatorcontrib><creatorcontrib>Engbersen, Johan F.J.</creatorcontrib><title>Bioreducible poly(amido amine)s with oligoamine side chains: Synthesis, characterization, and structural effects on gene delivery</title><title>Journal of controlled release</title><addtitle>J Control Release</addtitle><description>A group of bioreducible poly(amido amine)s containing multiple disulfide linkages in main chain and oligoamines in side chain (
SS–PAOAs) were prepared by Michael-type polyaddition of
N-tert-butyloxycarbonyl (
N-Boc) protected oligoamine to the disulfide-containing cystaminebisacrylamide, followed by deprotection of the Boc-protective groups. These linear polymers show strong DNA condensation capability at low N/P ratios. The chemical structure of oligoamine side chains (
i.e. amine type and amino spacer length) in the
SS–PAOAs has a distinct effect on their buffer capacity, transfection efficiency and toxicity profile. The
SS–PAOAs containing secondary amino functions in the side chain show high buffer capacities and are able to transfect COS-7 cells
in vitro at low N/P ratios, with transfection efficiencies similar or even higher than those of 25 kDa branched pEI, along with very low cytotoxicity as determined by XTT assay. Increase of the alkyl spacer from ethylene to propylene between the amino units in side chains results in significant lower transfection and increased toxicity. This study presents detailed factors influencing the relationship between structure and gene delivery properties and may provide helpful insights for the further development of safe and efficient non-viral vectors.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cell Survival - drug effects</subject><subject>Cell Survival - physiology</subject><subject>Cercopithecus aethiops</subject><subject>COS Cells</subject><subject>Disulfide reduction</subject><subject>Gene delivery</subject><subject>Gene Transfer Techniques</subject><subject>General pharmacology</subject><subject>Medical sciences</subject><subject>Nylons - chemistry</subject><subject>Nylons - pharmacology</subject><subject>Oligoamine</subject><subject>Pharmaceutical technology. Pharmaceutical industry</subject><subject>Pharmacology. Drug treatments</subject><subject>Poly(amido amine)</subject><subject>Polyamines - administration & dosage</subject><subject>Polyamines - chemistry</subject><subject>Polyplex</subject><issn>0168-3659</issn><issn>1873-4995</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAQhi0EotvCTwD5AgKpCXbifHFBtIIWqRIH4Gw540nXK6-92E7Rcus_x8tGcOxlLI2eeWf8EPKCs5Iz3r7blBvwLqAtK8a6kvOS8eoRWfG-qwsxDM1jsspcX9RtM5yQ0xg3jLGmFt1TcsJ73lZ8ECtyf2F8QD2DGS3Snbf7N2prtKe5Onwb6S-T1tRbc-v_dmg0GimslXHxPf22d2mN0cTzQysoSBjMb5WMd-dUOU1jCjOkOShLcZoQUqTe0VvMQRqtucOwf0aeTMpGfL68Z-TH50_fL6-Lm69XXy4_3hQgKpGKptPDWDcwYA895I-oRlQIGutumjol1FjjwMchQ2Pb9a0CVU1t1bdjJ8YRVH1GXh9zd8H_nDEmuTUR0Frl0M9R8qERLRd9BpsjCMHHGHCSu2C2KuwlZ_LgXm7k4l4e3EvOZXaf514uC-Zxi_r_1CI7A68WQEVQdgrKgYn_uJzVt6xmmftw5DDruDMYZASDDlCbkBVK7c0Dp_wB7lioag</recordid><startdate>20080303</startdate><enddate>20080303</enddate><creator>Lin, Chao</creator><creator>Blaauboer, Cees-Jan</creator><creator>Timoneda, Miguel Mateos</creator><creator>Lok, Martin C.</creator><creator>van Steenbergen, Mies</creator><creator>Hennink, Wim E.</creator><creator>Zhong, Zhiyuan</creator><creator>Feijen, Jan</creator><creator>Engbersen, Johan F.J.</creator><general>Elsevier B.V</general><general>Elsevier</general><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>7QO</scope><scope>7U9</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>RC3</scope></search><sort><creationdate>20080303</creationdate><title>Bioreducible poly(amido amine)s with oligoamine side chains: Synthesis, characterization, and structural effects on gene delivery</title><author>Lin, Chao ; Blaauboer, Cees-Jan ; Timoneda, Miguel Mateos ; Lok, Martin C. ; van Steenbergen, Mies ; Hennink, Wim E. ; Zhong, Zhiyuan ; Feijen, Jan ; Engbersen, Johan F.J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c424t-57d9b35c9e8c8c053a542ecde37ff7a4ab3e91b99b3b6786aca2f6286b74bbca3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cell Survival - drug effects</topic><topic>Cell Survival - physiology</topic><topic>Cercopithecus aethiops</topic><topic>COS Cells</topic><topic>Disulfide reduction</topic><topic>Gene delivery</topic><topic>Gene Transfer Techniques</topic><topic>General pharmacology</topic><topic>Medical sciences</topic><topic>Nylons - chemistry</topic><topic>Nylons - pharmacology</topic><topic>Oligoamine</topic><topic>Pharmaceutical technology. Pharmaceutical industry</topic><topic>Pharmacology. Drug treatments</topic><topic>Poly(amido amine)</topic><topic>Polyamines - administration & dosage</topic><topic>Polyamines - chemistry</topic><topic>Polyplex</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lin, Chao</creatorcontrib><creatorcontrib>Blaauboer, Cees-Jan</creatorcontrib><creatorcontrib>Timoneda, Miguel Mateos</creatorcontrib><creatorcontrib>Lok, Martin C.</creatorcontrib><creatorcontrib>van Steenbergen, Mies</creatorcontrib><creatorcontrib>Hennink, Wim E.</creatorcontrib><creatorcontrib>Zhong, Zhiyuan</creatorcontrib><creatorcontrib>Feijen, Jan</creatorcontrib><creatorcontrib>Engbersen, Johan F.J.</creatorcontrib><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>Biotechnology Research Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</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>Lin, Chao</au><au>Blaauboer, Cees-Jan</au><au>Timoneda, Miguel Mateos</au><au>Lok, Martin C.</au><au>van Steenbergen, Mies</au><au>Hennink, Wim E.</au><au>Zhong, Zhiyuan</au><au>Feijen, Jan</au><au>Engbersen, Johan F.J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bioreducible poly(amido amine)s with oligoamine side chains: Synthesis, characterization, and structural effects on gene delivery</atitle><jtitle>Journal of controlled release</jtitle><addtitle>J Control Release</addtitle><date>2008-03-03</date><risdate>2008</risdate><volume>126</volume><issue>2</issue><spage>166</spage><epage>174</epage><pages>166-174</pages><issn>0168-3659</issn><eissn>1873-4995</eissn><coden>JCREEC</coden><abstract>A group of bioreducible poly(amido amine)s containing multiple disulfide linkages in main chain and oligoamines in side chain (
SS–PAOAs) were prepared by Michael-type polyaddition of
N-tert-butyloxycarbonyl (
N-Boc) protected oligoamine to the disulfide-containing cystaminebisacrylamide, followed by deprotection of the Boc-protective groups. These linear polymers show strong DNA condensation capability at low N/P ratios. The chemical structure of oligoamine side chains (
i.e. amine type and amino spacer length) in the
SS–PAOAs has a distinct effect on their buffer capacity, transfection efficiency and toxicity profile. The
SS–PAOAs containing secondary amino functions in the side chain show high buffer capacities and are able to transfect COS-7 cells
in vitro at low N/P ratios, with transfection efficiencies similar or even higher than those of 25 kDa branched pEI, along with very low cytotoxicity as determined by XTT assay. Increase of the alkyl spacer from ethylene to propylene between the amino units in side chains results in significant lower transfection and increased toxicity. This study presents detailed factors influencing the relationship between structure and gene delivery properties and may provide helpful insights for the further development of safe and efficient non-viral vectors.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>18162194</pmid><doi>10.1016/j.jconrel.2007.11.012</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0168-3659 |
| ispartof | Journal of controlled release, 2008-03, Vol.126 (2), p.166-174 |
| issn | 0168-3659 1873-4995 |
| language | eng |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Animals Biological and medical sciences Cell Survival - drug effects Cell Survival - physiology Cercopithecus aethiops COS Cells Disulfide reduction Gene delivery Gene Transfer Techniques General pharmacology Medical sciences Nylons - chemistry Nylons - pharmacology Oligoamine Pharmaceutical technology. Pharmaceutical industry Pharmacology. Drug treatments Poly(amido amine) Polyamines - administration & dosage Polyamines - chemistry Polyplex |
| title | Bioreducible poly(amido amine)s with oligoamine side chains: Synthesis, characterization, and structural effects on gene delivery |
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