Design, synthesis of novel lipids as chemical permeation enhancers and development of nanoparticle system for transdermal drug delivery
In the present study, we designed and developed novel lipids that include (Z)-1-(Octadec-9-en-1-yl)-pyrrolidine (Cy5T), 1, 1-Di-((Z)-octadec-9-en-1-yl)pyrrolidin-1-ium iodide (Cy5), (Z)-1-(Octadec-9-en-1-yl)-piperidine (Cy6T), and 1, 1-Di-((Z)-octadec-9-en-1-yl) piperidin-1-ium iodide (Cy6) to enhan...
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| creator | Marepally, Srujan Boakye, Cedar H A Shah, Punit P Etukala, Jagan Reddy Vemuri, Adithi Singh, Mandip |
| description | In the present study, we designed and developed novel lipids that include (Z)-1-(Octadec-9-en-1-yl)-pyrrolidine (Cy5T), 1, 1-Di-((Z)-octadec-9-en-1-yl)pyrrolidin-1-ium iodide (Cy5), (Z)-1-(Octadec-9-en-1-yl)-piperidine (Cy6T), and 1, 1-Di-((Z)-octadec-9-en-1-yl) piperidin-1-ium iodide (Cy6) to enhance the transdermal permeation of some selected drugs. Firstly, we evaluated the transdermal permeation efficacies of these lipids as chemical permeation enhancers in vehicle formulations for melatonin, ß-estradiol, caffeine, α-MSH, and spantide using franz diffusion cells. Among them Cy5 lipid was determined to be the most efficient by increasing the transdermal permeation of melatonin, ß-estradiol, caffeine, α-MSH, and spantide by 1.5 to 3.26-fold more at the epidermal layer and 1.3 to 2.5-fold more at the dermal layer, in comparison to either NMP or OA. Hence we developed a nanoparticle system (cy5 lipid ethanol drug nanoparticles) to evaluate any further improvement in the drug penetration. Cy5 lipid formed uniformly sized nanoparticles ranging from 150-200 nm depending on the type of drug. Further, Cy5 based nanoparticle system significantly (p |
| doi_str_mv | 10.1371/journal.pone.0082581 |
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Firstly, we evaluated the transdermal permeation efficacies of these lipids as chemical permeation enhancers in vehicle formulations for melatonin, ß-estradiol, caffeine, α-MSH, and spantide using franz diffusion cells. Among them Cy5 lipid was determined to be the most efficient by increasing the transdermal permeation of melatonin, ß-estradiol, caffeine, α-MSH, and spantide by 1.5 to 3.26-fold more at the epidermal layer and 1.3 to 2.5-fold more at the dermal layer, in comparison to either NMP or OA. Hence we developed a nanoparticle system (cy5 lipid ethanol drug nanoparticles) to evaluate any further improvement in the drug penetration. Cy5 lipid formed uniformly sized nanoparticles ranging from 150-200 nm depending on the type of drug. Further, Cy5 based nanoparticle system significantly (p<0.05) increased the permeation of all the drugs in comparison to the lipid solution and standard permeation enhancers. There were about 1.54 to 22-fold more of drug retained in the dermis for the Cy5 based nanoparticles compared to OA/NMP standard enhancers and 3.87 to 66.67-fold more than lipid solution. In addition, epifluorescent microscopic analysis in rhodamine-PE permeation studies confirmed the superior permeation enhancement of LEDs (detection of fluorescence up to skin depth of 340 μm) more than lipid solution, which revealed fluorescence up to skin depth of only 260 μm. In summary the present findings demonstrate that i) cationic lipid with 5 membered amine heterocyclic ring has higher permeating efficacy than the 6 membered amine hertocyclic ring. ii) The nanoparticle system prepared with Cy5 showed significant (p<0.05) increase in the permeation of the drugs than the control penetration enhancers, oleic acid and NMP.</description><identifier>ISSN: 1932-6203</identifier><identifier>EISSN: 1932-6203</identifier><identifier>DOI: 10.1371/journal.pone.0082581</identifier><identifier>PMID: 24349315</identifier><language>eng</language><publisher>United States: Public Library of Science</publisher><subject>17β-Estradiol ; alpha-MSH - metabolism ; Animals ; Caffeine ; Caffeine - metabolism ; Chemical synthesis ; Chemistry, Pharmaceutical ; Chromatography, High Pressure Liquid ; Dermis ; Diffusion cells ; Drug abuse ; Drug delivery ; Drug Delivery Systems ; Drug development ; Drugs ; Estradiol ; Estradiol - metabolism ; Estrogens ; Ethanol ; Ethanol - chemistry ; Fatty acids ; Fluorescence ; Formulations ; Humans ; Iodides ; LEDs ; Lipids ; Lipids - chemistry ; Melanocyte stimulating hormone ; Melatonin ; Melatonin - metabolism ; Microscopic analysis ; Monounsaturated fatty acids ; Nanoparticles ; Nanoparticles - chemistry ; Oleic acid ; Penetration ; Permeability ; Pharmaceutical sciences ; Pharmacy ; Piperidine ; Pyrrolidine ; Rats ; Rhodamine ; Sex hormones ; Skin ; Skin - metabolism ; Spectrum analysis ; Substance P - analogs & derivatives ; Substance P - metabolism ; Transdermal drug delivery systems ; Transdermal medication ; Vehicles</subject><ispartof>PloS one, 2013-12, Vol.8 (12), p.e82581</ispartof><rights>COPYRIGHT 2013 Public Library of Science</rights><rights>2013 Marepally et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License: http://creativecommons.org/licenses/by/4.0/ (the “License”), which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2013 Marepally et al 2013 Marepally et al</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c692t-d8c809f2f904b1201039ebd232c3c6273d8f222aae99b4654ada84cbc2ba72d73</citedby><cites>FETCH-LOGICAL-c692t-d8c809f2f904b1201039ebd232c3c6273d8f222aae99b4654ada84cbc2ba72d73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC3861410/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC3861410/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,2095,2914,23846,27903,27904,53770,53772,79347,79348</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24349315$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><contributor>Koul, Hari K</contributor><creatorcontrib>Marepally, Srujan</creatorcontrib><creatorcontrib>Boakye, Cedar H A</creatorcontrib><creatorcontrib>Shah, Punit P</creatorcontrib><creatorcontrib>Etukala, Jagan Reddy</creatorcontrib><creatorcontrib>Vemuri, Adithi</creatorcontrib><creatorcontrib>Singh, Mandip</creatorcontrib><title>Design, synthesis of novel lipids as chemical permeation enhancers and development of nanoparticle system for transdermal drug delivery</title><title>PloS one</title><addtitle>PLoS One</addtitle><description>In the present study, we designed and developed novel lipids that include (Z)-1-(Octadec-9-en-1-yl)-pyrrolidine (Cy5T), 1, 1-Di-((Z)-octadec-9-en-1-yl)pyrrolidin-1-ium iodide (Cy5), (Z)-1-(Octadec-9-en-1-yl)-piperidine (Cy6T), and 1, 1-Di-((Z)-octadec-9-en-1-yl) piperidin-1-ium iodide (Cy6) to enhance the transdermal permeation of some selected drugs. Firstly, we evaluated the transdermal permeation efficacies of these lipids as chemical permeation enhancers in vehicle formulations for melatonin, ß-estradiol, caffeine, α-MSH, and spantide using franz diffusion cells. Among them Cy5 lipid was determined to be the most efficient by increasing the transdermal permeation of melatonin, ß-estradiol, caffeine, α-MSH, and spantide by 1.5 to 3.26-fold more at the epidermal layer and 1.3 to 2.5-fold more at the dermal layer, in comparison to either NMP or OA. Hence we developed a nanoparticle system (cy5 lipid ethanol drug nanoparticles) to evaluate any further improvement in the drug penetration. Cy5 lipid formed uniformly sized nanoparticles ranging from 150-200 nm depending on the type of drug. Further, Cy5 based nanoparticle system significantly (p<0.05) increased the permeation of all the drugs in comparison to the lipid solution and standard permeation enhancers. There were about 1.54 to 22-fold more of drug retained in the dermis for the Cy5 based nanoparticles compared to OA/NMP standard enhancers and 3.87 to 66.67-fold more than lipid solution. In addition, epifluorescent microscopic analysis in rhodamine-PE permeation studies confirmed the superior permeation enhancement of LEDs (detection of fluorescence up to skin depth of 340 μm) more than lipid solution, which revealed fluorescence up to skin depth of only 260 μm. In summary the present findings demonstrate that i) cationic lipid with 5 membered amine heterocyclic ring has higher permeating efficacy than the 6 membered amine hertocyclic ring. ii) The nanoparticle system prepared with Cy5 showed significant (p<0.05) increase in the permeation of the drugs than the control penetration enhancers, oleic acid and NMP.</description><subject>17β-Estradiol</subject><subject>alpha-MSH - metabolism</subject><subject>Animals</subject><subject>Caffeine</subject><subject>Caffeine - metabolism</subject><subject>Chemical synthesis</subject><subject>Chemistry, Pharmaceutical</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Dermis</subject><subject>Diffusion cells</subject><subject>Drug abuse</subject><subject>Drug delivery</subject><subject>Drug Delivery Systems</subject><subject>Drug development</subject><subject>Drugs</subject><subject>Estradiol</subject><subject>Estradiol - metabolism</subject><subject>Estrogens</subject><subject>Ethanol</subject><subject>Ethanol - chemistry</subject><subject>Fatty acids</subject><subject>Fluorescence</subject><subject>Formulations</subject><subject>Humans</subject><subject>Iodides</subject><subject>LEDs</subject><subject>Lipids</subject><subject>Lipids - chemistry</subject><subject>Melanocyte stimulating hormone</subject><subject>Melatonin</subject><subject>Melatonin - metabolism</subject><subject>Microscopic analysis</subject><subject>Monounsaturated fatty acids</subject><subject>Nanoparticles</subject><subject>Nanoparticles - chemistry</subject><subject>Oleic acid</subject><subject>Penetration</subject><subject>Permeability</subject><subject>Pharmaceutical sciences</subject><subject>Pharmacy</subject><subject>Piperidine</subject><subject>Pyrrolidine</subject><subject>Rats</subject><subject>Rhodamine</subject><subject>Sex hormones</subject><subject>Skin</subject><subject>Skin - metabolism</subject><subject>Spectrum analysis</subject><subject>Substance P - analogs & derivatives</subject><subject>Substance P - metabolism</subject><subject>Transdermal drug delivery systems</subject><subject>Transdermal medication</subject><subject>Vehicles</subject><issn>1932-6203</issn><issn>1932-6203</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>DOA</sourceid><recordid>eNqNk92K1DAYhoso7jp6B6IFQRCcMT9t2pwIy_o3sLDg32n4mqRthjbpJp3BuQJv28xOd5mCguQgIX3et8mb70uS5xitMC3wu43begvdanBWrxAqSV7iB8k55pQsGUH04cn6LHkSwgahnJaMPU7OSEYzTnF-nvz-oINp7Ns07O3YxnVIXZ1at9Nd2pnBqJBCSGWreyOhSwftew2jcTbVtgUrtY-AVanSUeGGXtvx1gCsG8CPRnY6WodR92ntfDp6sEFFk-il_LaJus7stN8_TR7V0AX9bJoXyY9PH79fflleXX9eX15cLSXjZFyqUpaI16TmKKswQRhRritFKJFUMlJQVdaEEADNeZWxPAMFZSYrSSooiCroInl59B06F8SUYRA4YwUrSkLLSKyPhHKwEYM3Pfi9cGDE7YbzjZguJgpAkmQ5RYrX0YBwRgtOy5oBQYjnefR6P_1tW_VayZiOh25mOv9iTSsatxPxnXAWL7dIXk0G3t1sdRj_ceSJaiCeytjaRTPZmyDFRVaUFKOC0Uit_kLFoQ6PG6uoNnF_JngzE0Rm1L_GBrYhiPW3r__PXv-cs69P2FZDN7bBddtDWYU5mB1B6V0IXtf3yWEkDk1wl4Y4NIGYmiDKXpymfi-6q3r6B7kLA9Y</recordid><startdate>20131212</startdate><enddate>20131212</enddate><creator>Marepally, Srujan</creator><creator>Boakye, Cedar H A</creator><creator>Shah, Punit P</creator><creator>Etukala, Jagan Reddy</creator><creator>Vemuri, Adithi</creator><creator>Singh, Mandip</creator><general>Public Library of Science</general><general>Public Library of Science (PLoS)</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>IOV</scope><scope>ISR</scope><scope>3V.</scope><scope>7QG</scope><scope>7QL</scope><scope>7QO</scope><scope>7RV</scope><scope>7SN</scope><scope>7SS</scope><scope>7T5</scope><scope>7TG</scope><scope>7TM</scope><scope>7U9</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>ARAPS</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>KB0</scope><scope>KL.</scope><scope>L6V</scope><scope>LK8</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M7N</scope><scope>M7P</scope><scope>M7S</scope><scope>NAPCQ</scope><scope>P5Z</scope><scope>P62</scope><scope>P64</scope><scope>PATMY</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope><scope>PYCSY</scope><scope>RC3</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20131212</creationdate><title>Design, synthesis of novel lipids as chemical permeation enhancers and development of nanoparticle system for transdermal drug delivery</title><author>Marepally, Srujan ; Boakye, Cedar H A ; Shah, Punit P ; Etukala, Jagan Reddy ; Vemuri, Adithi ; Singh, Mandip</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c692t-d8c809f2f904b1201039ebd232c3c6273d8f222aae99b4654ada84cbc2ba72d73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>17β-Estradiol</topic><topic>alpha-MSH - 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Firstly, we evaluated the transdermal permeation efficacies of these lipids as chemical permeation enhancers in vehicle formulations for melatonin, ß-estradiol, caffeine, α-MSH, and spantide using franz diffusion cells. Among them Cy5 lipid was determined to be the most efficient by increasing the transdermal permeation of melatonin, ß-estradiol, caffeine, α-MSH, and spantide by 1.5 to 3.26-fold more at the epidermal layer and 1.3 to 2.5-fold more at the dermal layer, in comparison to either NMP or OA. Hence we developed a nanoparticle system (cy5 lipid ethanol drug nanoparticles) to evaluate any further improvement in the drug penetration. Cy5 lipid formed uniformly sized nanoparticles ranging from 150-200 nm depending on the type of drug. Further, Cy5 based nanoparticle system significantly (p<0.05) increased the permeation of all the drugs in comparison to the lipid solution and standard permeation enhancers. There were about 1.54 to 22-fold more of drug retained in the dermis for the Cy5 based nanoparticles compared to OA/NMP standard enhancers and 3.87 to 66.67-fold more than lipid solution. In addition, epifluorescent microscopic analysis in rhodamine-PE permeation studies confirmed the superior permeation enhancement of LEDs (detection of fluorescence up to skin depth of 340 μm) more than lipid solution, which revealed fluorescence up to skin depth of only 260 μm. In summary the present findings demonstrate that i) cationic lipid with 5 membered amine heterocyclic ring has higher permeating efficacy than the 6 membered amine hertocyclic ring. ii) The nanoparticle system prepared with Cy5 showed significant (p<0.05) increase in the permeation of the drugs than the control penetration enhancers, oleic acid and NMP.</abstract><cop>United States</cop><pub>Public Library of Science</pub><pmid>24349315</pmid><doi>10.1371/journal.pone.0082581</doi><tpages>e82581</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1932-6203 |
| ispartof | PloS one, 2013-12, Vol.8 (12), p.e82581 |
| issn | 1932-6203 1932-6203 |
| language | eng |
| recordid | cdi_plos_journals_1467678238 |
| source | MEDLINE; DOAJ Directory of Open Access Journals; Public Library of Science (PLoS) Journals Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | 17β-Estradiol alpha-MSH - metabolism Animals Caffeine Caffeine - metabolism Chemical synthesis Chemistry, Pharmaceutical Chromatography, High Pressure Liquid Dermis Diffusion cells Drug abuse Drug delivery Drug Delivery Systems Drug development Drugs Estradiol Estradiol - metabolism Estrogens Ethanol Ethanol - chemistry Fatty acids Fluorescence Formulations Humans Iodides LEDs Lipids Lipids - chemistry Melanocyte stimulating hormone Melatonin Melatonin - metabolism Microscopic analysis Monounsaturated fatty acids Nanoparticles Nanoparticles - chemistry Oleic acid Penetration Permeability Pharmaceutical sciences Pharmacy Piperidine Pyrrolidine Rats Rhodamine Sex hormones Skin Skin - metabolism Spectrum analysis Substance P - analogs & derivatives Substance P - metabolism Transdermal drug delivery systems Transdermal medication Vehicles |
| title | Design, synthesis of novel lipids as chemical permeation enhancers and development of nanoparticle system for transdermal drug delivery |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T12%3A37%3A34IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-gale_plos_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Design,%20synthesis%20of%20novel%20lipids%20as%20chemical%20permeation%20enhancers%20and%20development%20of%20nanoparticle%20system%20for%20transdermal%20drug%20delivery&rft.jtitle=PloS%20one&rft.au=Marepally,%20Srujan&rft.date=2013-12-12&rft.volume=8&rft.issue=12&rft.spage=e82581&rft.pages=e82581-&rft.issn=1932-6203&rft.eissn=1932-6203&rft_id=info:doi/10.1371/journal.pone.0082581&rft_dat=%3Cgale_plos_%3EA478310763%3C/gale_plos_%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1467678238&rft_id=info:pmid/24349315&rft_galeid=A478310763&rft_doaj_id=oai_doaj_org_article_7a0c24530d9f46729637938f6a200955&rfr_iscdi=true |