Dual modules-molecularly imprinted patch-enabled enantioselectively controlled release of racemic drugs for transdermal delivery
[Display omitted] •Dual modules-molecularly imprinted patch enantioselectively releases eutomers in racemates and inhibits distomers.•Molecularly imprinted patch shows excellent mechanical strength and skin adhesion.•Imprinted polymers show specific adsorption and chiral pressure sensitive shows sel...
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Veröffentlicht in: | International journal of pharmaceutics 2024-11, Vol.665, p.124707, Article 124707 |
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container_title | International journal of pharmaceutics |
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creator | Zhang, Yang Liu, Xiaowen Wu, Jiaxu Quan, Peng Liu, Chao Liu, Jie Liu, Mingzhe Fang, Liang |
description | [Display omitted]
•Dual modules-molecularly imprinted patch enantioselectively releases eutomers in racemates and inhibits distomers.•Molecularly imprinted patch shows excellent mechanical strength and skin adhesion.•Imprinted polymers show specific adsorption and chiral pressure sensitive shows selectively controlled release.•Synergistic effects of chiral interaction and molecular force achieve enantioselectively controlled release.
Over 90 % of chiral drugs applied in transdermal drug delivery system (TDDS) are racemates, significantly increasing risks of side effects. Herein, we designed a chiral molecularly imprinted patch (CMIP) that achieved enantioselectively controlled release of S-enantiomers (eutomers) and inhibited the release of R-enantiomers (distomers) for transdermal drug delivery. It is composed of chiral pressure sensitive adhesive (PSA) and molecularly imprinted polymers (MIP), showing better transdermal delivery of S-enantiomers than that of R-enantiomers in vitro (1.86-fold) and in vivo (3.74-fold), significantly decreasing the intake of distomers. Additionally, synthesized fluorescent probe enantiomers visualized enantioselective process of CMIP. Furthermore, investigations of molecular mechanism indicated that dependence on spatial conformation was dominant. On one hand, imprinted cavity of MIP with D-isomer and stronger chiral interaction with R-enantiomers led to more specific adsorption. On the other hand, L-isomer of PSA controlled the release of S-enantiomers by multiple interaction including chiral H-bond, π-π interaction and Van der Waals force. Tthus, the innovatively designed transdermal patch with enantioselective ability released eutomers of racemate and simultaneously inhibited release of distomers, significantly improving therapeutical efficiency and avoiding overdose. |
doi_str_mv | 10.1016/j.ijpharm.2024.124707 |
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•Dual modules-molecularly imprinted patch enantioselectively releases eutomers in racemates and inhibits distomers.•Molecularly imprinted patch shows excellent mechanical strength and skin adhesion.•Imprinted polymers show specific adsorption and chiral pressure sensitive shows selectively controlled release.•Synergistic effects of chiral interaction and molecular force achieve enantioselectively controlled release.
Over 90 % of chiral drugs applied in transdermal drug delivery system (TDDS) are racemates, significantly increasing risks of side effects. Herein, we designed a chiral molecularly imprinted patch (CMIP) that achieved enantioselectively controlled release of S-enantiomers (eutomers) and inhibited the release of R-enantiomers (distomers) for transdermal drug delivery. It is composed of chiral pressure sensitive adhesive (PSA) and molecularly imprinted polymers (MIP), showing better transdermal delivery of S-enantiomers than that of R-enantiomers in vitro (1.86-fold) and in vivo (3.74-fold), significantly decreasing the intake of distomers. Additionally, synthesized fluorescent probe enantiomers visualized enantioselective process of CMIP. Furthermore, investigations of molecular mechanism indicated that dependence on spatial conformation was dominant. On one hand, imprinted cavity of MIP with D-isomer and stronger chiral interaction with R-enantiomers led to more specific adsorption. On the other hand, L-isomer of PSA controlled the release of S-enantiomers by multiple interaction including chiral H-bond, π-π interaction and Van der Waals force. Tthus, the innovatively designed transdermal patch with enantioselective ability released eutomers of racemate and simultaneously inhibited release of distomers, significantly improving therapeutical efficiency and avoiding overdose.</description><identifier>ISSN: 0378-5173</identifier><identifier>ISSN: 1873-3476</identifier><identifier>EISSN: 1873-3476</identifier><identifier>DOI: 10.1016/j.ijpharm.2024.124707</identifier><identifier>PMID: 39284425</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>Chiral ; Enantioselective controlled release ; Imprinted polymer ; Pressure sensitive adhesive ; Transdermal drug delivery</subject><ispartof>International journal of pharmaceutics, 2024-11, Vol.665, p.124707, Article 124707</ispartof><rights>2024</rights><rights>Copyright © 2024. Published by Elsevier B.V.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c1585-4f6a1ed9a7ae8d677cf299f67807de80bb08d850fef5f31a5ff004eacb36c0983</cites><orcidid>0000-0001-9966-3880</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ijpharm.2024.124707$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39284425$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Yang</creatorcontrib><creatorcontrib>Liu, Xiaowen</creatorcontrib><creatorcontrib>Wu, Jiaxu</creatorcontrib><creatorcontrib>Quan, Peng</creatorcontrib><creatorcontrib>Liu, Chao</creatorcontrib><creatorcontrib>Liu, Jie</creatorcontrib><creatorcontrib>Liu, Mingzhe</creatorcontrib><creatorcontrib>Fang, Liang</creatorcontrib><title>Dual modules-molecularly imprinted patch-enabled enantioselectively controlled release of racemic drugs for transdermal delivery</title><title>International journal of pharmaceutics</title><addtitle>Int J Pharm</addtitle><description>[Display omitted]
•Dual modules-molecularly imprinted patch enantioselectively releases eutomers in racemates and inhibits distomers.•Molecularly imprinted patch shows excellent mechanical strength and skin adhesion.•Imprinted polymers show specific adsorption and chiral pressure sensitive shows selectively controlled release.•Synergistic effects of chiral interaction and molecular force achieve enantioselectively controlled release.
Over 90 % of chiral drugs applied in transdermal drug delivery system (TDDS) are racemates, significantly increasing risks of side effects. Herein, we designed a chiral molecularly imprinted patch (CMIP) that achieved enantioselectively controlled release of S-enantiomers (eutomers) and inhibited the release of R-enantiomers (distomers) for transdermal drug delivery. It is composed of chiral pressure sensitive adhesive (PSA) and molecularly imprinted polymers (MIP), showing better transdermal delivery of S-enantiomers than that of R-enantiomers in vitro (1.86-fold) and in vivo (3.74-fold), significantly decreasing the intake of distomers. Additionally, synthesized fluorescent probe enantiomers visualized enantioselective process of CMIP. Furthermore, investigations of molecular mechanism indicated that dependence on spatial conformation was dominant. On one hand, imprinted cavity of MIP with D-isomer and stronger chiral interaction with R-enantiomers led to more specific adsorption. On the other hand, L-isomer of PSA controlled the release of S-enantiomers by multiple interaction including chiral H-bond, π-π interaction and Van der Waals force. Tthus, the innovatively designed transdermal patch with enantioselective ability released eutomers of racemate and simultaneously inhibited release of distomers, significantly improving therapeutical efficiency and avoiding overdose.</description><subject>Chiral</subject><subject>Enantioselective controlled release</subject><subject>Imprinted polymer</subject><subject>Pressure sensitive adhesive</subject><subject>Transdermal drug delivery</subject><issn>0378-5173</issn><issn>1873-3476</issn><issn>1873-3476</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkEFvFCEYhomxsdvqT9DM0cusH8MMMCdj2lpNmnjRM2Hgw7KBYYWZJnvrTy-bXb16-gI8L2--h5D3FLYUKP-02_rd_lHnuO2g67e06wWIV2RDpWAt6wV_TTbAhGwHKtgluSplBwC8o-wNuWRjJ_u-Gzbk-XbVoYnJrgFLG1NAswadw6HxcZ_9vKBt9noxjy3Oegr1VOe8-FSwoot_woqaNC85heNrrte6YJNck7XB6E1j8_q7NC7lZsl6LhZzrJUWQw3nw1ty4XQo-O48r8mvr3c_b761Dz_uv998eWgNHeTQ9o5rinbUQqO0XAjjunF0XEgQFiVME0grB3DoBseoHpwD6FGbiXEDo2TX5OPp331Of1Ysi4q-GAxBz5jWohgFDv0ggFd0OKEmp1IyOlVNRJ0PioI6ylc7dZavjvLVSX7NfThXrFNE-y_113YFPp8ArIs-ecyqGI-zQetzlals8v-peAGqeJx3</recordid><startdate>20241115</startdate><enddate>20241115</enddate><creator>Zhang, Yang</creator><creator>Liu, Xiaowen</creator><creator>Wu, Jiaxu</creator><creator>Quan, Peng</creator><creator>Liu, Chao</creator><creator>Liu, Jie</creator><creator>Liu, Mingzhe</creator><creator>Fang, Liang</creator><general>Elsevier B.V</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-9966-3880</orcidid></search><sort><creationdate>20241115</creationdate><title>Dual modules-molecularly imprinted patch-enabled enantioselectively controlled release of racemic drugs for transdermal delivery</title><author>Zhang, Yang ; Liu, Xiaowen ; Wu, Jiaxu ; Quan, Peng ; Liu, Chao ; Liu, Jie ; Liu, Mingzhe ; Fang, Liang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1585-4f6a1ed9a7ae8d677cf299f67807de80bb08d850fef5f31a5ff004eacb36c0983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Chiral</topic><topic>Enantioselective controlled release</topic><topic>Imprinted polymer</topic><topic>Pressure sensitive adhesive</topic><topic>Transdermal drug delivery</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Yang</creatorcontrib><creatorcontrib>Liu, Xiaowen</creatorcontrib><creatorcontrib>Wu, Jiaxu</creatorcontrib><creatorcontrib>Quan, Peng</creatorcontrib><creatorcontrib>Liu, Chao</creatorcontrib><creatorcontrib>Liu, Jie</creatorcontrib><creatorcontrib>Liu, Mingzhe</creatorcontrib><creatorcontrib>Fang, Liang</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>International journal of pharmaceutics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Yang</au><au>Liu, Xiaowen</au><au>Wu, Jiaxu</au><au>Quan, Peng</au><au>Liu, Chao</au><au>Liu, Jie</au><au>Liu, Mingzhe</au><au>Fang, Liang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dual modules-molecularly imprinted patch-enabled enantioselectively controlled release of racemic drugs for transdermal delivery</atitle><jtitle>International journal of pharmaceutics</jtitle><addtitle>Int J Pharm</addtitle><date>2024-11-15</date><risdate>2024</risdate><volume>665</volume><spage>124707</spage><pages>124707-</pages><artnum>124707</artnum><issn>0378-5173</issn><issn>1873-3476</issn><eissn>1873-3476</eissn><abstract>[Display omitted]
•Dual modules-molecularly imprinted patch enantioselectively releases eutomers in racemates and inhibits distomers.•Molecularly imprinted patch shows excellent mechanical strength and skin adhesion.•Imprinted polymers show specific adsorption and chiral pressure sensitive shows selectively controlled release.•Synergistic effects of chiral interaction and molecular force achieve enantioselectively controlled release.
Over 90 % of chiral drugs applied in transdermal drug delivery system (TDDS) are racemates, significantly increasing risks of side effects. Herein, we designed a chiral molecularly imprinted patch (CMIP) that achieved enantioselectively controlled release of S-enantiomers (eutomers) and inhibited the release of R-enantiomers (distomers) for transdermal drug delivery. It is composed of chiral pressure sensitive adhesive (PSA) and molecularly imprinted polymers (MIP), showing better transdermal delivery of S-enantiomers than that of R-enantiomers in vitro (1.86-fold) and in vivo (3.74-fold), significantly decreasing the intake of distomers. Additionally, synthesized fluorescent probe enantiomers visualized enantioselective process of CMIP. Furthermore, investigations of molecular mechanism indicated that dependence on spatial conformation was dominant. On one hand, imprinted cavity of MIP with D-isomer and stronger chiral interaction with R-enantiomers led to more specific adsorption. On the other hand, L-isomer of PSA controlled the release of S-enantiomers by multiple interaction including chiral H-bond, π-π interaction and Van der Waals force. Tthus, the innovatively designed transdermal patch with enantioselective ability released eutomers of racemate and simultaneously inhibited release of distomers, significantly improving therapeutical efficiency and avoiding overdose.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>39284425</pmid><doi>10.1016/j.ijpharm.2024.124707</doi><orcidid>https://orcid.org/0000-0001-9966-3880</orcidid></addata></record> |
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subjects | Chiral Enantioselective controlled release Imprinted polymer Pressure sensitive adhesive Transdermal drug delivery |
title | Dual modules-molecularly imprinted patch-enabled enantioselectively controlled release of racemic drugs for transdermal delivery |
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