Site-directed decapsulation of bolaamphiphilic vesicles with enzymatic cleavable surface groups
Stable nano-sized vesicles with a monolayer encapsulating membrane were prepared from novel bolaamphiphiles with choline ester head groups. The head groups were covalently bound to the alkyl chain of the bolaamphiphiles either via the nitrogen atom of the choline moiety, or via the choline ester...
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| Veröffentlicht in: | Journal of controlled release 2012-06, Vol.160 (2), p.306-314 |
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| creator | Popov, Mary Grinberg, Sarina Linder, Charles Waner, Tal Levi-Hevroni, Bosmat Deckelbaum, Richard J. Heldman, Eliahu |
| description | Stable nano-sized vesicles with a monolayer encapsulating membrane were prepared from novel bolaamphiphiles with choline ester head groups. The head groups were covalently bound to the alkyl chain of the bolaamphiphiles either via the nitrogen atom of the choline moiety, or via the choline ester's methyl group. Both types of bolaamphiphiles competed with acetylthiocholine for binding to acetylcholine esterase (AChE), yet, only the choline ester head groups bound to the alkyl chain via the nitrogen atom of the choline moiety were hydrolyzed by the enzyme. Likewise, only vesicles composed of bolaamphiphiles with head groups that were hydrolyzed by AChE released their encapsulated material upon exposure to the enzyme. Injection of carboxyfluorescein (CF)-loaded vesicles with cleavable choline ester head groups into mice resulted in the accumulation of CF in tissues that express high AChE activity, including the brain. By comparison, when vesicles with choline ester head groups that are not hydrolyzed by AChE were injected into mice, there was no accumulation of CF in tissues that highly express the enzyme. These results imply that bolaamphiphilic vesicles with surface groups that are substrates to enzymes which are highly expressed in target organs may potentially be used as a drug delivery system with controlled site-directed drug release.
Bolaamphiphilic vesicles (left) release encapsulated CF when exposed to ChE (middle). Encapsulated CF accumulates in the brain after the vesicles penetrate the BBB and are destabilized by brain ChE (right). [Display omitted] |
| doi_str_mv | 10.1016/j.jconrel.2011.12.022 |
| format | Article |
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Bolaamphiphilic vesicles (left) release encapsulated CF when exposed to ChE (middle). Encapsulated CF accumulates in the brain after the vesicles penetrate the BBB and are destabilized by brain ChE (right). [Display omitted]</description><identifier>ISSN: 0168-3659</identifier><identifier>EISSN: 1873-4995</identifier><identifier>DOI: 10.1016/j.jconrel.2011.12.022</identifier><identifier>PMID: 22226780</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>Acetylcholine ; Acetylcholine - chemical synthesis ; Acetylcholine - chemistry ; Acetylcholine - pharmacokinetics ; acetylcholinesterase ; Acetylcholinesterase - chemistry ; Acetylcholinesterase - metabolism ; Animals ; Bolaamphiphiles ; brain ; choline ; Choline esterase ; Cryoelectron Microscopy ; Drug Carriers - chemical synthesis ; Drug Carriers - chemistry ; Drug Carriers - pharmacokinetics ; Drug delivery ; drug delivery systems ; Drug Stability ; drugs ; encapsulation ; Fluoresceins - administration & dosage ; Fluoresceins - chemistry ; Fluoresceins - pharmacokinetics ; Fluorescent Dyes - administration & dosage ; Fluorescent Dyes - chemistry ; Fluorescent Dyes - pharmacokinetics ; Furans - chemical synthesis ; Furans - chemistry ; Furans - pharmacokinetics ; Hydrolysis ; Injections, Intravenous ; Light ; Male ; Mice ; Mice, Inbred ICR ; Microscopy, Electron, Transmission ; Molecular Structure ; nitrogen ; Pyridones - chemical synthesis ; Pyridones - chemistry ; Pyridones - pharmacokinetics ; Scattering, Radiation ; Tissue Distribution ; tissues ; Vesicles</subject><ispartof>Journal of controlled release, 2012-06, Vol.160 (2), p.306-314</ispartof><rights>2011 Elsevier B.V.</rights><rights>Copyright © 2011 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-8a064377561c438826ff1926c4cda25a0a52518003f4517e4289ce25c43b0e273</citedby><cites>FETCH-LOGICAL-c389t-8a064377561c438826ff1926c4cda25a0a52518003f4517e4289ce25c43b0e273</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0168365911011485$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22226780$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Popov, Mary</creatorcontrib><creatorcontrib>Grinberg, Sarina</creatorcontrib><creatorcontrib>Linder, Charles</creatorcontrib><creatorcontrib>Waner, Tal</creatorcontrib><creatorcontrib>Levi-Hevroni, Bosmat</creatorcontrib><creatorcontrib>Deckelbaum, Richard J.</creatorcontrib><creatorcontrib>Heldman, Eliahu</creatorcontrib><title>Site-directed decapsulation of bolaamphiphilic vesicles with enzymatic cleavable surface groups</title><title>Journal of controlled release</title><addtitle>J Control Release</addtitle><description>Stable nano-sized vesicles with a monolayer encapsulating membrane were prepared from novel bolaamphiphiles with choline ester head groups. The head groups were covalently bound to the alkyl chain of the bolaamphiphiles either via the nitrogen atom of the choline moiety, or via the choline ester's methyl group. Both types of bolaamphiphiles competed with acetylthiocholine for binding to acetylcholine esterase (AChE), yet, only the choline ester head groups bound to the alkyl chain via the nitrogen atom of the choline moiety were hydrolyzed by the enzyme. Likewise, only vesicles composed of bolaamphiphiles with head groups that were hydrolyzed by AChE released their encapsulated material upon exposure to the enzyme. Injection of carboxyfluorescein (CF)-loaded vesicles with cleavable choline ester head groups into mice resulted in the accumulation of CF in tissues that express high AChE activity, including the brain. By comparison, when vesicles with choline ester head groups that are not hydrolyzed by AChE were injected into mice, there was no accumulation of CF in tissues that highly express the enzyme. These results imply that bolaamphiphilic vesicles with surface groups that are substrates to enzymes which are highly expressed in target organs may potentially be used as a drug delivery system with controlled site-directed drug release.
Bolaamphiphilic vesicles (left) release encapsulated CF when exposed to ChE (middle). Encapsulated CF accumulates in the brain after the vesicles penetrate the BBB and are destabilized by brain ChE (right). [Display omitted]</description><subject>Acetylcholine</subject><subject>Acetylcholine - chemical synthesis</subject><subject>Acetylcholine - chemistry</subject><subject>Acetylcholine - pharmacokinetics</subject><subject>acetylcholinesterase</subject><subject>Acetylcholinesterase - chemistry</subject><subject>Acetylcholinesterase - metabolism</subject><subject>Animals</subject><subject>Bolaamphiphiles</subject><subject>brain</subject><subject>choline</subject><subject>Choline esterase</subject><subject>Cryoelectron Microscopy</subject><subject>Drug Carriers - chemical synthesis</subject><subject>Drug Carriers - chemistry</subject><subject>Drug Carriers - pharmacokinetics</subject><subject>Drug delivery</subject><subject>drug delivery systems</subject><subject>Drug Stability</subject><subject>drugs</subject><subject>encapsulation</subject><subject>Fluoresceins - administration & dosage</subject><subject>Fluoresceins - chemistry</subject><subject>Fluoresceins - pharmacokinetics</subject><subject>Fluorescent Dyes - administration & dosage</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Fluorescent Dyes - pharmacokinetics</subject><subject>Furans - chemical synthesis</subject><subject>Furans - chemistry</subject><subject>Furans - pharmacokinetics</subject><subject>Hydrolysis</subject><subject>Injections, Intravenous</subject><subject>Light</subject><subject>Male</subject><subject>Mice</subject><subject>Mice, Inbred ICR</subject><subject>Microscopy, Electron, Transmission</subject><subject>Molecular Structure</subject><subject>nitrogen</subject><subject>Pyridones - chemical synthesis</subject><subject>Pyridones - chemistry</subject><subject>Pyridones - pharmacokinetics</subject><subject>Scattering, Radiation</subject><subject>Tissue Distribution</subject><subject>tissues</subject><subject>Vesicles</subject><issn>0168-3659</issn><issn>1873-4995</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0U1v3CAQBmBUpWo2aX9CG4692OXDYHyKolWbRIrUwzZnxOJxwgobB-yNkl9ftt7kWoSEhJ6ZQS8IfaWkpITKH7tyZ8MQwZeMUFpSVhLGPqAVVTUvqqYRJ2iVnSq4FM0pOktpRwgRvKo_oVOWl6wVWSG9cRMUrYtgJ2hxC9aMafZmcmHAocPb4I3px0eXt3cW7yE56yHhZzc9YhheX_psLc53Zm-2HnCaY2cs4IcY5jF9Rh874xN8OZ7n6P7Xzz_rm-Lu9_Xt-uqusFw1U6EMkRWvayGprbhSTHYdbZi0lW0NE4YYwQRVhPCuErSGiqnGAhMZbwmwmp-j70vfMYanGdKke5cseG8GCHPSOTMlOVEVz1Qs1MaQUoROj9H1Jr5kdHBS7_QxW33IVlOmc7a57ttxxLztoX2vegszg4sFdCZo8xBd0veb3EEQQmsp_4nLRUCOYu8g6mQdDBaWD9BtcP95xF_VX5ba</recordid><startdate>20120610</startdate><enddate>20120610</enddate><creator>Popov, Mary</creator><creator>Grinberg, Sarina</creator><creator>Linder, Charles</creator><creator>Waner, Tal</creator><creator>Levi-Hevroni, Bosmat</creator><creator>Deckelbaum, Richard J.</creator><creator>Heldman, Eliahu</creator><general>Elsevier B.V</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></search><sort><creationdate>20120610</creationdate><title>Site-directed decapsulation of bolaamphiphilic vesicles with enzymatic cleavable surface groups</title><author>Popov, Mary ; Grinberg, Sarina ; Linder, Charles ; Waner, Tal ; Levi-Hevroni, Bosmat ; Deckelbaum, Richard J. ; Heldman, Eliahu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-8a064377561c438826ff1926c4cda25a0a52518003f4517e4289ce25c43b0e273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Acetylcholine</topic><topic>Acetylcholine - chemical synthesis</topic><topic>Acetylcholine - chemistry</topic><topic>Acetylcholine - pharmacokinetics</topic><topic>acetylcholinesterase</topic><topic>Acetylcholinesterase - chemistry</topic><topic>Acetylcholinesterase - metabolism</topic><topic>Animals</topic><topic>Bolaamphiphiles</topic><topic>brain</topic><topic>choline</topic><topic>Choline esterase</topic><topic>Cryoelectron Microscopy</topic><topic>Drug Carriers - chemical synthesis</topic><topic>Drug Carriers - chemistry</topic><topic>Drug Carriers - pharmacokinetics</topic><topic>Drug delivery</topic><topic>drug delivery systems</topic><topic>Drug Stability</topic><topic>drugs</topic><topic>encapsulation</topic><topic>Fluoresceins - administration & dosage</topic><topic>Fluoresceins - chemistry</topic><topic>Fluoresceins - pharmacokinetics</topic><topic>Fluorescent Dyes - administration & dosage</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Fluorescent Dyes - pharmacokinetics</topic><topic>Furans - chemical synthesis</topic><topic>Furans - chemistry</topic><topic>Furans - pharmacokinetics</topic><topic>Hydrolysis</topic><topic>Injections, Intravenous</topic><topic>Light</topic><topic>Male</topic><topic>Mice</topic><topic>Mice, Inbred ICR</topic><topic>Microscopy, Electron, Transmission</topic><topic>Molecular Structure</topic><topic>nitrogen</topic><topic>Pyridones - chemical synthesis</topic><topic>Pyridones - chemistry</topic><topic>Pyridones - pharmacokinetics</topic><topic>Scattering, Radiation</topic><topic>Tissue Distribution</topic><topic>tissues</topic><topic>Vesicles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Popov, Mary</creatorcontrib><creatorcontrib>Grinberg, Sarina</creatorcontrib><creatorcontrib>Linder, Charles</creatorcontrib><creatorcontrib>Waner, Tal</creatorcontrib><creatorcontrib>Levi-Hevroni, Bosmat</creatorcontrib><creatorcontrib>Deckelbaum, Richard J.</creatorcontrib><creatorcontrib>Heldman, Eliahu</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><jtitle>Journal of controlled release</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Popov, Mary</au><au>Grinberg, Sarina</au><au>Linder, Charles</au><au>Waner, Tal</au><au>Levi-Hevroni, Bosmat</au><au>Deckelbaum, Richard J.</au><au>Heldman, Eliahu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Site-directed decapsulation of bolaamphiphilic vesicles with enzymatic cleavable surface groups</atitle><jtitle>Journal of controlled release</jtitle><addtitle>J Control Release</addtitle><date>2012-06-10</date><risdate>2012</risdate><volume>160</volume><issue>2</issue><spage>306</spage><epage>314</epage><pages>306-314</pages><issn>0168-3659</issn><eissn>1873-4995</eissn><abstract>Stable nano-sized vesicles with a monolayer encapsulating membrane were prepared from novel bolaamphiphiles with choline ester head groups. The head groups were covalently bound to the alkyl chain of the bolaamphiphiles either via the nitrogen atom of the choline moiety, or via the choline ester's methyl group. Both types of bolaamphiphiles competed with acetylthiocholine for binding to acetylcholine esterase (AChE), yet, only the choline ester head groups bound to the alkyl chain via the nitrogen atom of the choline moiety were hydrolyzed by the enzyme. Likewise, only vesicles composed of bolaamphiphiles with head groups that were hydrolyzed by AChE released their encapsulated material upon exposure to the enzyme. Injection of carboxyfluorescein (CF)-loaded vesicles with cleavable choline ester head groups into mice resulted in the accumulation of CF in tissues that express high AChE activity, including the brain. By comparison, when vesicles with choline ester head groups that are not hydrolyzed by AChE were injected into mice, there was no accumulation of CF in tissues that highly express the enzyme. These results imply that bolaamphiphilic vesicles with surface groups that are substrates to enzymes which are highly expressed in target organs may potentially be used as a drug delivery system with controlled site-directed drug release.
Bolaamphiphilic vesicles (left) release encapsulated CF when exposed to ChE (middle). Encapsulated CF accumulates in the brain after the vesicles penetrate the BBB and are destabilized by brain ChE (right). [Display omitted]</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>22226780</pmid><doi>10.1016/j.jconrel.2011.12.022</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0168-3659 |
| ispartof | Journal of controlled release, 2012-06, Vol.160 (2), p.306-314 |
| issn | 0168-3659 1873-4995 |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Acetylcholine Acetylcholine - chemical synthesis Acetylcholine - chemistry Acetylcholine - pharmacokinetics acetylcholinesterase Acetylcholinesterase - chemistry Acetylcholinesterase - metabolism Animals Bolaamphiphiles brain choline Choline esterase Cryoelectron Microscopy Drug Carriers - chemical synthesis Drug Carriers - chemistry Drug Carriers - pharmacokinetics Drug delivery drug delivery systems Drug Stability drugs encapsulation Fluoresceins - administration & dosage Fluoresceins - chemistry Fluoresceins - pharmacokinetics Fluorescent Dyes - administration & dosage Fluorescent Dyes - chemistry Fluorescent Dyes - pharmacokinetics Furans - chemical synthesis Furans - chemistry Furans - pharmacokinetics Hydrolysis Injections, Intravenous Light Male Mice Mice, Inbred ICR Microscopy, Electron, Transmission Molecular Structure nitrogen Pyridones - chemical synthesis Pyridones - chemistry Pyridones - pharmacokinetics Scattering, Radiation Tissue Distribution tissues Vesicles |
| title | Site-directed decapsulation of bolaamphiphilic vesicles with enzymatic cleavable surface groups |
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