Controlled Molecular Arrangement of Cinnamic Acid in Layered Double Hydroxide through pi-pi Interaction for Controlled Release
Cinnamic acid (CA) was successfully incorporated into Zn-Al layered double hydroxide (LDH) through coprecipitation. The CA moiety was stabilized in the interlayer space through not only electrostatic interaction but also intermolecular π-π interaction. It was noteworthy that the CA arrangement was f...
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| Veröffentlicht in: | International journal of molecular sciences 2024-04, Vol.25 (8), p.4506 |
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| creator | Kim, Taeho Paek, Seung-Min Wang, Kang-Kyun Park, Jin Kuen Salles, Fabrice Oh, Jae-Min |
| description | Cinnamic acid (CA) was successfully incorporated into Zn-Al layered double hydroxide (LDH) through coprecipitation. The CA moiety was stabilized in the interlayer space through not only electrostatic interaction but also intermolecular π-π interaction. It was noteworthy that the CA arrangement was fairly independent of the charge density of LDH, showing the important role of the layer-CA and CA-CA interactions in molecular stabilization. Computer simulations using the Monte Carlo method as well as analytical approaches including infrared, UV-vis spectroscopy, and differential scanning calorimetry showed the existence of intermolecular interaction. In order to reinforce molecular stabilization, a neutral derivative of CA, cinnamaldehyde (CAD), was additionally incorporated into LDH. It was clearly shown that CAD played a role as a π-π interaction mediator to enhance the stabilization of CA. The time-dependent release of CA from LDH was first governed by the layer charge density of LDH; however, the existence of CAD provided additional stabilization to the CA arrangement to slow down the release kinetics. |
| doi_str_mv | 10.3390/ijms25084506 |
| format | Article |
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The CA moiety was stabilized in the interlayer space through not only electrostatic interaction but also intermolecular π-π interaction. It was noteworthy that the CA arrangement was fairly independent of the charge density of LDH, showing the important role of the layer-CA and CA-CA interactions in molecular stabilization. Computer simulations using the Monte Carlo method as well as analytical approaches including infrared, UV-vis spectroscopy, and differential scanning calorimetry showed the existence of intermolecular interaction. In order to reinforce molecular stabilization, a neutral derivative of CA, cinnamaldehyde (CAD), was additionally incorporated into LDH. It was clearly shown that CAD played a role as a π-π interaction mediator to enhance the stabilization of CA. The time-dependent release of CA from LDH was first governed by the layer charge density of LDH; however, the existence of CAD provided additional stabilization to the CA arrangement to slow down the release kinetics.</description><identifier>ISSN: 1422-0067</identifier><identifier>ISSN: 1661-6596</identifier><identifier>EISSN: 1422-0067</identifier><identifier>DOI: 10.3390/ijms25084506</identifier><identifier>PMID: 38674090</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Acids ; Acrolein - analogs & derivatives ; Acrolein - chemistry ; Calorimetry ; Calorimetry, Differential Scanning ; Cellulose ; Chemical Sciences ; Cinnamates - chemistry ; Cosmetics ; Delayed-Action Preparations - chemistry ; Drug delivery systems ; Functional foods & nutraceuticals ; Hydroxides ; Hydroxides - chemistry ; Kinetics ; Life Sciences ; Material chemistry ; Monte Carlo Method ; Pharmaceutical sciences ; Polymers ; Simulation methods ; Spectrum analysis ; Zinc compounds</subject><ispartof>International journal of molecular sciences, 2024-04, Vol.25 (8), p.4506</ispartof><rights>COPYRIGHT 2024 MDPI AG</rights><rights>2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c387t-c8dd379a133076377bf08bd216339d19ac7392a80f15865b437be104cd5589ae3</cites><orcidid>0000-0001-8069-533X ; 0000-0003-1638-9957 ; 0000-0003-4923-2809 ; 0009-0006-4240-4021 ; 0000-0002-0386-5160</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38674090$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-04554392$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, Taeho</creatorcontrib><creatorcontrib>Paek, Seung-Min</creatorcontrib><creatorcontrib>Wang, Kang-Kyun</creatorcontrib><creatorcontrib>Park, Jin Kuen</creatorcontrib><creatorcontrib>Salles, Fabrice</creatorcontrib><creatorcontrib>Oh, Jae-Min</creatorcontrib><title>Controlled Molecular Arrangement of Cinnamic Acid in Layered Double Hydroxide through pi-pi Interaction for Controlled Release</title><title>International journal of molecular sciences</title><addtitle>Int J Mol Sci</addtitle><description>Cinnamic acid (CA) was successfully incorporated into Zn-Al layered double hydroxide (LDH) through coprecipitation. The CA moiety was stabilized in the interlayer space through not only electrostatic interaction but also intermolecular π-π interaction. It was noteworthy that the CA arrangement was fairly independent of the charge density of LDH, showing the important role of the layer-CA and CA-CA interactions in molecular stabilization. Computer simulations using the Monte Carlo method as well as analytical approaches including infrared, UV-vis spectroscopy, and differential scanning calorimetry showed the existence of intermolecular interaction. In order to reinforce molecular stabilization, a neutral derivative of CA, cinnamaldehyde (CAD), was additionally incorporated into LDH. It was clearly shown that CAD played a role as a π-π interaction mediator to enhance the stabilization of CA. The time-dependent release of CA from LDH was first governed by the layer charge density of LDH; however, the existence of CAD provided additional stabilization to the CA arrangement to slow down the release kinetics.</description><subject>Acids</subject><subject>Acrolein - analogs & derivatives</subject><subject>Acrolein - chemistry</subject><subject>Calorimetry</subject><subject>Calorimetry, Differential Scanning</subject><subject>Cellulose</subject><subject>Chemical Sciences</subject><subject>Cinnamates - chemistry</subject><subject>Cosmetics</subject><subject>Delayed-Action Preparations - chemistry</subject><subject>Drug delivery systems</subject><subject>Functional foods & nutraceuticals</subject><subject>Hydroxides</subject><subject>Hydroxides - chemistry</subject><subject>Kinetics</subject><subject>Life Sciences</subject><subject>Material chemistry</subject><subject>Monte Carlo Method</subject><subject>Pharmaceutical sciences</subject><subject>Polymers</subject><subject>Simulation methods</subject><subject>Spectrum analysis</subject><subject>Zinc compounds</subject><issn>1422-0067</issn><issn>1661-6596</issn><issn>1422-0067</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>8G5</sourceid><sourceid>BENPR</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNpdkc-L1DAUx4so7rp68ywBLwp2fWmSpjmW8ccsjAii55ImrzMZ0mRMW3Eu_u1mmHUZJIeEx-f73sv3WxQvKdwypuC9249TJaDhAupHxTXlVVUC1PLxxfuqeDZNe4CKVUI9La5YU0sOCq6LP6sY5hS9R0u-RI9m8TqRNiUdtjhimEkcyMqFoEdnSGucJS6QjT5iyooPcek9kvXRpvjbWSTzLsVluyMHVx4cuQszJm1mFwMZYiIXs76hRz3h8-LJoP2EL-7vm-LHp4_fV-ty8_Xz3ardlIY1ci5NYy2TSlPGQNZMyn6AprcVrbMFliptJFOVbmCgoqlFz5nskQI3VohGaWQ3xdtz35323SG5UadjF7Xr1u2mO9WAC8Fzj180s2_O7CHFnwtOcze6yaD3OmBcpo4Bl4qrbHdGX_-H7uOSQv7JiaoVZaB4pm7P1FZ77FwY4pxdycdiNjUGHFyut1IxIYACy4J3Z4FJcZoSDg8rU-hOoXeXoWf81f0WSz-ifYD_pcz-Al-kpkM</recordid><startdate>20240419</startdate><enddate>20240419</enddate><creator>Kim, Taeho</creator><creator>Paek, Seung-Min</creator><creator>Wang, Kang-Kyun</creator><creator>Park, Jin Kuen</creator><creator>Salles, Fabrice</creator><creator>Oh, Jae-Min</creator><general>MDPI AG</general><general>MDPI</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>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>MBDVC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0001-8069-533X</orcidid><orcidid>https://orcid.org/0000-0003-1638-9957</orcidid><orcidid>https://orcid.org/0000-0003-4923-2809</orcidid><orcidid>https://orcid.org/0009-0006-4240-4021</orcidid><orcidid>https://orcid.org/0000-0002-0386-5160</orcidid></search><sort><creationdate>20240419</creationdate><title>Controlled Molecular Arrangement of Cinnamic Acid in Layered Double Hydroxide through pi-pi Interaction for Controlled Release</title><author>Kim, Taeho ; Paek, Seung-Min ; Wang, Kang-Kyun ; Park, Jin Kuen ; Salles, Fabrice ; Oh, Jae-Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c387t-c8dd379a133076377bf08bd216339d19ac7392a80f15865b437be104cd5589ae3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Acids</topic><topic>Acrolein - analogs & derivatives</topic><topic>Acrolein - chemistry</topic><topic>Calorimetry</topic><topic>Calorimetry, Differential Scanning</topic><topic>Cellulose</topic><topic>Chemical Sciences</topic><topic>Cinnamates - chemistry</topic><topic>Cosmetics</topic><topic>Delayed-Action Preparations - chemistry</topic><topic>Drug delivery systems</topic><topic>Functional foods & nutraceuticals</topic><topic>Hydroxides</topic><topic>Hydroxides - chemistry</topic><topic>Kinetics</topic><topic>Life Sciences</topic><topic>Material chemistry</topic><topic>Monte Carlo Method</topic><topic>Pharmaceutical sciences</topic><topic>Polymers</topic><topic>Simulation methods</topic><topic>Spectrum analysis</topic><topic>Zinc compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Taeho</creatorcontrib><creatorcontrib>Paek, Seung-Min</creatorcontrib><creatorcontrib>Wang, Kang-Kyun</creatorcontrib><creatorcontrib>Park, Jin Kuen</creatorcontrib><creatorcontrib>Salles, Fabrice</creatorcontrib><creatorcontrib>Oh, Jae-Min</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Research Library</collection><collection>Research Library (Corporate)</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>International journal of molecular sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Taeho</au><au>Paek, Seung-Min</au><au>Wang, Kang-Kyun</au><au>Park, Jin Kuen</au><au>Salles, Fabrice</au><au>Oh, Jae-Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Controlled Molecular Arrangement of Cinnamic Acid in Layered Double Hydroxide through pi-pi Interaction for Controlled Release</atitle><jtitle>International journal of molecular sciences</jtitle><addtitle>Int J Mol Sci</addtitle><date>2024-04-19</date><risdate>2024</risdate><volume>25</volume><issue>8</issue><spage>4506</spage><pages>4506-</pages><issn>1422-0067</issn><issn>1661-6596</issn><eissn>1422-0067</eissn><abstract>Cinnamic acid (CA) was successfully incorporated into Zn-Al layered double hydroxide (LDH) through coprecipitation. The CA moiety was stabilized in the interlayer space through not only electrostatic interaction but also intermolecular π-π interaction. It was noteworthy that the CA arrangement was fairly independent of the charge density of LDH, showing the important role of the layer-CA and CA-CA interactions in molecular stabilization. Computer simulations using the Monte Carlo method as well as analytical approaches including infrared, UV-vis spectroscopy, and differential scanning calorimetry showed the existence of intermolecular interaction. In order to reinforce molecular stabilization, a neutral derivative of CA, cinnamaldehyde (CAD), was additionally incorporated into LDH. It was clearly shown that CAD played a role as a π-π interaction mediator to enhance the stabilization of CA. 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| subjects | Acids Acrolein - analogs & derivatives Acrolein - chemistry Calorimetry Calorimetry, Differential Scanning Cellulose Chemical Sciences Cinnamates - chemistry Cosmetics Delayed-Action Preparations - chemistry Drug delivery systems Functional foods & nutraceuticals Hydroxides Hydroxides - chemistry Kinetics Life Sciences Material chemistry Monte Carlo Method Pharmaceutical sciences Polymers Simulation methods Spectrum analysis Zinc compounds |
| title | Controlled Molecular Arrangement of Cinnamic Acid in Layered Double Hydroxide through pi-pi Interaction for Controlled Release |
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