Liposome-encapsulated EF24-HPβCD inclusion complex: a preformulation study and biodistribution in a rat model
3,5-Bis(2-fluorobenzylidene)-4-piperidone (EF24) is an anti-proliferative diphenyldifluoroketone analog of curcumin with more potent activity. The authors describe a liposome preparation of EF24 using a “drug-in-CD-in liposome” approach. An aqueous solution of EF24 and hydroxypropyl-β-cyclodextrin (...
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Veröffentlicht in: | Journal of nanoparticle research : an interdisciplinary forum for nanoscale science and technology 2011-06, Vol.13 (6), p.2609-2623 |
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description | 3,5-Bis(2-fluorobenzylidene)-4-piperidone (EF24) is an anti-proliferative diphenyldifluoroketone analog of curcumin with more potent activity. The authors describe a liposome preparation of EF24 using a “drug-in-CD-in liposome” approach. An aqueous solution of EF24 and hydroxypropyl-β-cyclodextrin (HPβCD) inclusion complex (IC) was used to prepare EF24 liposomes. The liposome size was reduced by a combination of multiple freeze–thaw cycles. Co-encapsulation of glutathione inside the liposomes conferred them with the capability of labeling with imageable radionuclide Tc-99m. Phase solubility analysis of EF24-HPβCD mixture provided
k
1:1
value of 9.9 M
−1
. The enhanced aqueous solubility of EF24 (from 1.64 to 13.8 mg/mL) due to the presence of HPβCD helped in the liposome preparation. About 19% of the EF24 IC was encapsulated inside the liposomes (320.5 ± 2.6 nm) by dehydration–rehydration technique. With extrusion technique, the size of 177 ± 6.5 nm was obtained without any effect on encapsulation efficiency. The EF24-liposomes were evaluated for anti-proliferative activity in lung adenocarcinoma H441 and prostate cancer PC-3 cells. The EF24-liposomes demonstrated anti-proliferative activity superior to that of plain EF24 at 10 μM dose. When injected in rats, the Tc-99m-labeled EF24-liposomes cleared from blood with an α-
t
1/2
of 21.4 min and β-
t
1/2
of 397 min. Tissue radioactivity counting upon necropsy showed that the majority of clearance was due to the uptake in liver and spleen. The results suggest that using “drug-in-CD-in liposome” approach is a feasible strategy to formulate an effective parenteral preparation of EF24. In vitro studies show that the liposomal EF24 remains anti-proliferative, while presenting an opportunity to image its biodistribution. |
doi_str_mv | 10.1007/s11051-010-0154-5 |
format | Article |
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k
1:1
value of 9.9 M
−1
. The enhanced aqueous solubility of EF24 (from 1.64 to 13.8 mg/mL) due to the presence of HPβCD helped in the liposome preparation. About 19% of the EF24 IC was encapsulated inside the liposomes (320.5 ± 2.6 nm) by dehydration–rehydration technique. With extrusion technique, the size of 177 ± 6.5 nm was obtained without any effect on encapsulation efficiency. The EF24-liposomes were evaluated for anti-proliferative activity in lung adenocarcinoma H441 and prostate cancer PC-3 cells. The EF24-liposomes demonstrated anti-proliferative activity superior to that of plain EF24 at 10 μM dose. When injected in rats, the Tc-99m-labeled EF24-liposomes cleared from blood with an α-
t
1/2
of 21.4 min and β-
t
1/2
of 397 min. Tissue radioactivity counting upon necropsy showed that the majority of clearance was due to the uptake in liver and spleen. The results suggest that using “drug-in-CD-in liposome” approach is a feasible strategy to formulate an effective parenteral preparation of EF24. In vitro studies show that the liposomal EF24 remains anti-proliferative, while presenting an opportunity to image its biodistribution.</description><identifier>ISSN: 1388-0764</identifier><identifier>EISSN: 1572-896X</identifier><identifier>DOI: 10.1007/s11051-010-0154-5</identifier><identifier>PMID: 21779150</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Characterization and Evaluation of Materials ; Chemistry and Materials Science ; Inorganic Chemistry ; Lasers ; Materials Science ; Nanotechnology ; Optical Devices ; Optics ; Photonics ; Physical Chemistry ; Research Paper</subject><ispartof>Journal of nanoparticle research : an interdisciplinary forum for nanoscale science and technology, 2011-06, Vol.13 (6), p.2609-2623</ispartof><rights>Springer Science+Business Media B.V. 2010</rights><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c475t-3e98275932505d74d95f4423d91596f6bc2567682671e42ab1ab1b11e94b522a3</citedby><cites>FETCH-LOGICAL-c475t-3e98275932505d74d95f4423d91596f6bc2567682671e42ab1ab1b11e94b522a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11051-010-0154-5$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11051-010-0154-5$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>230,314,780,784,885,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21779150$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Agashe, H.</creatorcontrib><creatorcontrib>Lagisetty, P.</creatorcontrib><creatorcontrib>Sahoo, K.</creatorcontrib><creatorcontrib>Bourne, D.</creatorcontrib><creatorcontrib>Grady, B.</creatorcontrib><creatorcontrib>Awasthi, V.</creatorcontrib><title>Liposome-encapsulated EF24-HPβCD inclusion complex: a preformulation study and biodistribution in a rat model</title><title>Journal of nanoparticle research : an interdisciplinary forum for nanoscale science and technology</title><addtitle>J Nanopart Res</addtitle><addtitle>J Nanopart Res</addtitle><description>3,5-Bis(2-fluorobenzylidene)-4-piperidone (EF24) is an anti-proliferative diphenyldifluoroketone analog of curcumin with more potent activity. The authors describe a liposome preparation of EF24 using a “drug-in-CD-in liposome” approach. An aqueous solution of EF24 and hydroxypropyl-β-cyclodextrin (HPβCD) inclusion complex (IC) was used to prepare EF24 liposomes. The liposome size was reduced by a combination of multiple freeze–thaw cycles. Co-encapsulation of glutathione inside the liposomes conferred them with the capability of labeling with imageable radionuclide Tc-99m. Phase solubility analysis of EF24-HPβCD mixture provided
k
1:1
value of 9.9 M
−1
. The enhanced aqueous solubility of EF24 (from 1.64 to 13.8 mg/mL) due to the presence of HPβCD helped in the liposome preparation. About 19% of the EF24 IC was encapsulated inside the liposomes (320.5 ± 2.6 nm) by dehydration–rehydration technique. With extrusion technique, the size of 177 ± 6.5 nm was obtained without any effect on encapsulation efficiency. The EF24-liposomes were evaluated for anti-proliferative activity in lung adenocarcinoma H441 and prostate cancer PC-3 cells. The EF24-liposomes demonstrated anti-proliferative activity superior to that of plain EF24 at 10 μM dose. When injected in rats, the Tc-99m-labeled EF24-liposomes cleared from blood with an α-
t
1/2
of 21.4 min and β-
t
1/2
of 397 min. Tissue radioactivity counting upon necropsy showed that the majority of clearance was due to the uptake in liver and spleen. The results suggest that using “drug-in-CD-in liposome” approach is a feasible strategy to formulate an effective parenteral preparation of EF24. In vitro studies show that the liposomal EF24 remains anti-proliferative, while presenting an opportunity to image its biodistribution.</description><subject>Characterization and Evaluation of Materials</subject><subject>Chemistry and Materials Science</subject><subject>Inorganic Chemistry</subject><subject>Lasers</subject><subject>Materials Science</subject><subject>Nanotechnology</subject><subject>Optical Devices</subject><subject>Optics</subject><subject>Photonics</subject><subject>Physical Chemistry</subject><subject>Research Paper</subject><issn>1388-0764</issn><issn>1572-896X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkc1q3DAUhUVoaH7aB8gmeNmNEl1ZsqwsCmXyM4GBZNFCd0K2NImCLTmSXTqvlQfpM0WTSYd004CELpzvHq7uQegIyAkQIk4TAOGACZB8OcN8B-0DFxTXsvr5IddlXWMiKraHDlJ6IAQqKulHtEdBCAmc7CO_cENIobfY-lYPaer0aE1xcUkZnt_-eZqdF8633ZRc8EUb-qGzv88KXQzRLkPs1_haSeNkVoX2pmhcMC6N0TXTi-J8pqMeiz4Y231Cu0vdJfv59T1EPy4vvs_meHFzdT37tsAtE3zEpZU1FVyWlBNuBDOSLxmjpclDy2pZNS3llahqWgmwjOoG8mkArGQNp1SXh-jrxneYmt6a1vox6k4N0fU6rlTQTv2reHev7sIvVeadgYRs8OXVIIbHyaZR9S61tuu0t2FKCuqScy6IFO-jrJSC1YKSjMIGbWNIKa9wOxEQtY5UbSJVOVK1jlTx3HP89ivbjr8ZZoBugJQlf2ejeghT9Hm9_3F9BlMWrSg</recordid><startdate>20110601</startdate><enddate>20110601</enddate><creator>Agashe, H.</creator><creator>Lagisetty, P.</creator><creator>Sahoo, K.</creator><creator>Bourne, D.</creator><creator>Grady, B.</creator><creator>Awasthi, V.</creator><general>Springer Netherlands</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20110601</creationdate><title>Liposome-encapsulated EF24-HPβCD inclusion complex: a preformulation study and biodistribution in a rat model</title><author>Agashe, H. ; Lagisetty, P. ; Sahoo, K. ; Bourne, D. ; Grady, B. ; Awasthi, V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c475t-3e98275932505d74d95f4423d91596f6bc2567682671e42ab1ab1b11e94b522a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Characterization and Evaluation of Materials</topic><topic>Chemistry and Materials Science</topic><topic>Inorganic Chemistry</topic><topic>Lasers</topic><topic>Materials Science</topic><topic>Nanotechnology</topic><topic>Optical Devices</topic><topic>Optics</topic><topic>Photonics</topic><topic>Physical Chemistry</topic><topic>Research Paper</topic><toplevel>online_resources</toplevel><creatorcontrib>Agashe, H.</creatorcontrib><creatorcontrib>Lagisetty, P.</creatorcontrib><creatorcontrib>Sahoo, K.</creatorcontrib><creatorcontrib>Bourne, D.</creatorcontrib><creatorcontrib>Grady, B.</creatorcontrib><creatorcontrib>Awasthi, V.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of nanoparticle research : an interdisciplinary forum for nanoscale science and technology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Agashe, H.</au><au>Lagisetty, P.</au><au>Sahoo, K.</au><au>Bourne, D.</au><au>Grady, B.</au><au>Awasthi, V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Liposome-encapsulated EF24-HPβCD inclusion complex: a preformulation study and biodistribution in a rat model</atitle><jtitle>Journal of nanoparticle research : an interdisciplinary forum for nanoscale science and technology</jtitle><stitle>J Nanopart Res</stitle><addtitle>J Nanopart Res</addtitle><date>2011-06-01</date><risdate>2011</risdate><volume>13</volume><issue>6</issue><spage>2609</spage><epage>2623</epage><pages>2609-2623</pages><issn>1388-0764</issn><eissn>1572-896X</eissn><abstract>3,5-Bis(2-fluorobenzylidene)-4-piperidone (EF24) is an anti-proliferative diphenyldifluoroketone analog of curcumin with more potent activity. The authors describe a liposome preparation of EF24 using a “drug-in-CD-in liposome” approach. An aqueous solution of EF24 and hydroxypropyl-β-cyclodextrin (HPβCD) inclusion complex (IC) was used to prepare EF24 liposomes. The liposome size was reduced by a combination of multiple freeze–thaw cycles. Co-encapsulation of glutathione inside the liposomes conferred them with the capability of labeling with imageable radionuclide Tc-99m. Phase solubility analysis of EF24-HPβCD mixture provided
k
1:1
value of 9.9 M
−1
. The enhanced aqueous solubility of EF24 (from 1.64 to 13.8 mg/mL) due to the presence of HPβCD helped in the liposome preparation. About 19% of the EF24 IC was encapsulated inside the liposomes (320.5 ± 2.6 nm) by dehydration–rehydration technique. With extrusion technique, the size of 177 ± 6.5 nm was obtained without any effect on encapsulation efficiency. The EF24-liposomes were evaluated for anti-proliferative activity in lung adenocarcinoma H441 and prostate cancer PC-3 cells. The EF24-liposomes demonstrated anti-proliferative activity superior to that of plain EF24 at 10 μM dose. When injected in rats, the Tc-99m-labeled EF24-liposomes cleared from blood with an α-
t
1/2
of 21.4 min and β-
t
1/2
of 397 min. Tissue radioactivity counting upon necropsy showed that the majority of clearance was due to the uptake in liver and spleen. The results suggest that using “drug-in-CD-in liposome” approach is a feasible strategy to formulate an effective parenteral preparation of EF24. In vitro studies show that the liposomal EF24 remains anti-proliferative, while presenting an opportunity to image its biodistribution.</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><pmid>21779150</pmid><doi>10.1007/s11051-010-0154-5</doi><tpages>15</tpages><oa>free_for_read</oa></addata></record> |
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subjects | Characterization and Evaluation of Materials Chemistry and Materials Science Inorganic Chemistry Lasers Materials Science Nanotechnology Optical Devices Optics Photonics Physical Chemistry Research Paper |
title | Liposome-encapsulated EF24-HPβCD inclusion complex: a preformulation study and biodistribution in a rat model |
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