Copolymer Involving 2-Hydroxyethyl Methacrylate and 2-Chloroquinyl Methacrylate: Synthesis, Characterization and In Vitro 2-Hydroxychloroquine Delivery Application
The Poly(2-chloroquinyl methacrylate- -2-hydroxyethyl methacrylate) (CQMA- -HEMA) drug carrier system was prepared with different compositions through a free-radical copolymerization route involving 2-chloroquinyl methacrylate (CQMA) and 2-hydroxyethyl methacrylate) (HEMA) using azobisisobutyronitri...
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| Veröffentlicht in: | Polymers 2021-11, Vol.13 (23), p.4072 |
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| creator | Aljubailah, Abeer Alharbi, Wafa Nazzal Odis Haidyrah, Ahmed S Al-Garni, Tahani Saad Saeed, Waseem Sharaf Semlali, Abdelhabib Alqahtani, Saad M S Al-Owais, Ahmad Abdulaziz Karami, Abdulnasser Mahmoud Aouak, Taieb |
| description | The Poly(2-chloroquinyl methacrylate-
-2-hydroxyethyl methacrylate) (CQMA-
-HEMA) drug carrier system was prepared with different compositions through a free-radical copolymerization route involving 2-chloroquinyl methacrylate (CQMA) and 2-hydroxyethyl methacrylate) (HEMA) using azobisisobutyronitrile as the initiator. 2-Chloroquinyl methacrylate monomer (CQMA) was synthesized from 2-hydroxychloroquine (HCQ) and methacryloyl chloride by an esterification reaction using triethylenetetramine as the catalyst. The structure of the CQMA and CQMA-
-HEMA copolymers was confirmed by a CHN elementary analysis, Fourier transform infra-red (FTIR) and nuclear magnetic resonance (NMR) analysis. The absence of residual aggregates of HCQ or HCQMA particles in the copolymers prepared was confirmed by a differential scanning calorimeter (DSC) and XR-diffraction (XRD) analyses. The gingival epithelial cancer cell line (Ca9-22) toxicity examined by a lactate dehydrogenase (LDH) assay revealed that the grafting of HCQ onto PHEMA slightly affected (4.2-9.5%) the viability of the polymer carrier. The cell adhesion and growth on the CQMA-
-HEMA drug carrier specimens carried out by the (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) (MTT) assay revealed the best performance with the specimen containing 3.96 wt% HCQ. The diffusion of HCQ through the polymer matrix obeyed the Fickian model. The solubility of HCQ in different media was improved, in which more than 5.22 times of the solubility of HCQ powder in water was obtained. According to Belzer, the in vitro HCQ dynamic release revealed the best performance with the drug carrier system containing 4.70 wt% CQMA. |
| doi_str_mv | 10.3390/polym13234072 |
| format | Article |
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-2-hydroxyethyl methacrylate) (CQMA-
-HEMA) drug carrier system was prepared with different compositions through a free-radical copolymerization route involving 2-chloroquinyl methacrylate (CQMA) and 2-hydroxyethyl methacrylate) (HEMA) using azobisisobutyronitrile as the initiator. 2-Chloroquinyl methacrylate monomer (CQMA) was synthesized from 2-hydroxychloroquine (HCQ) and methacryloyl chloride by an esterification reaction using triethylenetetramine as the catalyst. The structure of the CQMA and CQMA-
-HEMA copolymers was confirmed by a CHN elementary analysis, Fourier transform infra-red (FTIR) and nuclear magnetic resonance (NMR) analysis. The absence of residual aggregates of HCQ or HCQMA particles in the copolymers prepared was confirmed by a differential scanning calorimeter (DSC) and XR-diffraction (XRD) analyses. The gingival epithelial cancer cell line (Ca9-22) toxicity examined by a lactate dehydrogenase (LDH) assay revealed that the grafting of HCQ onto PHEMA slightly affected (4.2-9.5%) the viability of the polymer carrier. The cell adhesion and growth on the CQMA-
-HEMA drug carrier specimens carried out by the (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) (MTT) assay revealed the best performance with the specimen containing 3.96 wt% HCQ. The diffusion of HCQ through the polymer matrix obeyed the Fickian model. The solubility of HCQ in different media was improved, in which more than 5.22 times of the solubility of HCQ powder in water was obtained. According to Belzer, the in vitro HCQ dynamic release revealed the best performance with the drug carrier system containing 4.70 wt% CQMA.</description><identifier>ISSN: 2073-4360</identifier><identifier>EISSN: 2073-4360</identifier><identifier>DOI: 10.3390/polym13234072</identifier><identifier>PMID: 34883576</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Aqueous solutions ; Azobisisobutyronitrile ; Cell adhesion ; Chloride ; Copolymerization ; Copolymers ; Coronaviruses ; COVID-19 ; Drug carriers ; Drug dosages ; Esterification ; Fourier transforms ; Free radical polymerization ; Free radicals ; Lactate dehydrogenase ; Malaria ; Nitrogen ; NMR ; Nuclear magnetic resonance ; Polyhydroxyethyl methacrylate ; Polymerization ; Polymers ; Small intestine ; Solubility ; Stomach ; Toxicity</subject><ispartof>Polymers, 2021-11, Vol.13 (23), p.4072</ispartof><rights>2021 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>2021 by the authors. 2021</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-195354f58c25240806271d1d4e8bdebeccc384b1a69377977a555bd4d2411fa33</citedby><cites>FETCH-LOGICAL-c415t-195354f58c25240806271d1d4e8bdebeccc384b1a69377977a555bd4d2411fa33</cites><orcidid>0000-0002-5254-5665 ; 0000-0002-1643-0377</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8659029/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8659029/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34883576$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Aljubailah, Abeer</creatorcontrib><creatorcontrib>Alharbi, Wafa Nazzal Odis</creatorcontrib><creatorcontrib>Haidyrah, Ahmed S</creatorcontrib><creatorcontrib>Al-Garni, Tahani Saad</creatorcontrib><creatorcontrib>Saeed, Waseem Sharaf</creatorcontrib><creatorcontrib>Semlali, Abdelhabib</creatorcontrib><creatorcontrib>Alqahtani, Saad M S</creatorcontrib><creatorcontrib>Al-Owais, Ahmad Abdulaziz</creatorcontrib><creatorcontrib>Karami, Abdulnasser Mahmoud</creatorcontrib><creatorcontrib>Aouak, Taieb</creatorcontrib><title>Copolymer Involving 2-Hydroxyethyl Methacrylate and 2-Chloroquinyl Methacrylate: Synthesis, Characterization and In Vitro 2-Hydroxychloroquine Delivery Application</title><title>Polymers</title><addtitle>Polymers (Basel)</addtitle><description>The Poly(2-chloroquinyl methacrylate-
-2-hydroxyethyl methacrylate) (CQMA-
-HEMA) drug carrier system was prepared with different compositions through a free-radical copolymerization route involving 2-chloroquinyl methacrylate (CQMA) and 2-hydroxyethyl methacrylate) (HEMA) using azobisisobutyronitrile as the initiator. 2-Chloroquinyl methacrylate monomer (CQMA) was synthesized from 2-hydroxychloroquine (HCQ) and methacryloyl chloride by an esterification reaction using triethylenetetramine as the catalyst. The structure of the CQMA and CQMA-
-HEMA copolymers was confirmed by a CHN elementary analysis, Fourier transform infra-red (FTIR) and nuclear magnetic resonance (NMR) analysis. The absence of residual aggregates of HCQ or HCQMA particles in the copolymers prepared was confirmed by a differential scanning calorimeter (DSC) and XR-diffraction (XRD) analyses. The gingival epithelial cancer cell line (Ca9-22) toxicity examined by a lactate dehydrogenase (LDH) assay revealed that the grafting of HCQ onto PHEMA slightly affected (4.2-9.5%) the viability of the polymer carrier. The cell adhesion and growth on the CQMA-
-HEMA drug carrier specimens carried out by the (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) (MTT) assay revealed the best performance with the specimen containing 3.96 wt% HCQ. The diffusion of HCQ through the polymer matrix obeyed the Fickian model. The solubility of HCQ in different media was improved, in which more than 5.22 times of the solubility of HCQ powder in water was obtained. According to Belzer, the in vitro HCQ dynamic release revealed the best performance with the drug carrier system containing 4.70 wt% CQMA.</description><subject>Aqueous solutions</subject><subject>Azobisisobutyronitrile</subject><subject>Cell adhesion</subject><subject>Chloride</subject><subject>Copolymerization</subject><subject>Copolymers</subject><subject>Coronaviruses</subject><subject>COVID-19</subject><subject>Drug carriers</subject><subject>Drug dosages</subject><subject>Esterification</subject><subject>Fourier transforms</subject><subject>Free radical polymerization</subject><subject>Free radicals</subject><subject>Lactate dehydrogenase</subject><subject>Malaria</subject><subject>Nitrogen</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Polyhydroxyethyl methacrylate</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Small intestine</subject><subject>Solubility</subject><subject>Stomach</subject><subject>Toxicity</subject><issn>2073-4360</issn><issn>2073-4360</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNpdkUtP3DAUha2KqoOmLLtFltiS4mecsEBCgXZGAnXRx9ZyHM_EyGMHxzMi_Tv9o80MMDy8uZbOud-9VweALxh9pbREZ11wwwpTQhkS5AM4JEjQjNEcHbz6T8BR39-h8TGe51h8AhPKioJykR-Cf1XYQUyEc78JbmP9EpJsNjQxPAwmtYODt2NROg5OJQOVb0a9al2I4X5t_Tv9HP4cfGpNb_tTWLUqKp1MtH9VssHvmuce_rEphpcpeg8z8Mo4uzFxgJdd56zetX0GHxfK9eboqU7B72_Xv6pZdvPj-7y6vMk0wzxluOSUswUvNOGEoQLlROAGN8wUdWNqo7WmBauxyksqRCmE4pzXDWsIw3ihKJ2Ci0dut65XptHGp6ic7KJdqTjIoKx8q3jbymXYyCLnJSLlCDh5AmzPMX2Sd2Ed_bizJDkq8C6m0ZU9unQMfR_NYj8BI7mNVb6JdfQfv15r734Okf4Hts2jNg</recordid><startdate>20211123</startdate><enddate>20211123</enddate><creator>Aljubailah, Abeer</creator><creator>Alharbi, Wafa Nazzal Odis</creator><creator>Haidyrah, Ahmed S</creator><creator>Al-Garni, Tahani Saad</creator><creator>Saeed, Waseem Sharaf</creator><creator>Semlali, Abdelhabib</creator><creator>Alqahtani, Saad M S</creator><creator>Al-Owais, Ahmad Abdulaziz</creator><creator>Karami, Abdulnasser Mahmoud</creator><creator>Aouak, Taieb</creator><general>MDPI AG</general><general>MDPI</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>COVID</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-5254-5665</orcidid><orcidid>https://orcid.org/0000-0002-1643-0377</orcidid></search><sort><creationdate>20211123</creationdate><title>Copolymer Involving 2-Hydroxyethyl Methacrylate and 2-Chloroquinyl Methacrylate: Synthesis, Characterization and In Vitro 2-Hydroxychloroquine Delivery Application</title><author>Aljubailah, Abeer ; Alharbi, Wafa Nazzal Odis ; Haidyrah, Ahmed S ; Al-Garni, Tahani Saad ; Saeed, Waseem Sharaf ; Semlali, Abdelhabib ; Alqahtani, Saad M S ; Al-Owais, Ahmad Abdulaziz ; Karami, Abdulnasser Mahmoud ; Aouak, Taieb</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-195354f58c25240806271d1d4e8bdebeccc384b1a69377977a555bd4d2411fa33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aqueous solutions</topic><topic>Azobisisobutyronitrile</topic><topic>Cell adhesion</topic><topic>Chloride</topic><topic>Copolymerization</topic><topic>Copolymers</topic><topic>Coronaviruses</topic><topic>COVID-19</topic><topic>Drug carriers</topic><topic>Drug dosages</topic><topic>Esterification</topic><topic>Fourier transforms</topic><topic>Free radical polymerization</topic><topic>Free radicals</topic><topic>Lactate dehydrogenase</topic><topic>Malaria</topic><topic>Nitrogen</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Polyhydroxyethyl methacrylate</topic><topic>Polymerization</topic><topic>Polymers</topic><topic>Small intestine</topic><topic>Solubility</topic><topic>Stomach</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Aljubailah, Abeer</creatorcontrib><creatorcontrib>Alharbi, Wafa Nazzal Odis</creatorcontrib><creatorcontrib>Haidyrah, Ahmed S</creatorcontrib><creatorcontrib>Al-Garni, Tahani Saad</creatorcontrib><creatorcontrib>Saeed, Waseem Sharaf</creatorcontrib><creatorcontrib>Semlali, Abdelhabib</creatorcontrib><creatorcontrib>Alqahtani, Saad M S</creatorcontrib><creatorcontrib>Al-Owais, Ahmad Abdulaziz</creatorcontrib><creatorcontrib>Karami, Abdulnasser Mahmoud</creatorcontrib><creatorcontrib>Aouak, Taieb</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>Coronavirus Research Database</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>Access via ProQuest (Open Access)</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>PubMed Central (Full Participant titles)</collection><jtitle>Polymers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Aljubailah, Abeer</au><au>Alharbi, Wafa Nazzal Odis</au><au>Haidyrah, Ahmed S</au><au>Al-Garni, Tahani Saad</au><au>Saeed, Waseem Sharaf</au><au>Semlali, Abdelhabib</au><au>Alqahtani, Saad M S</au><au>Al-Owais, Ahmad Abdulaziz</au><au>Karami, Abdulnasser Mahmoud</au><au>Aouak, Taieb</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copolymer Involving 2-Hydroxyethyl Methacrylate and 2-Chloroquinyl Methacrylate: Synthesis, Characterization and In Vitro 2-Hydroxychloroquine Delivery Application</atitle><jtitle>Polymers</jtitle><addtitle>Polymers (Basel)</addtitle><date>2021-11-23</date><risdate>2021</risdate><volume>13</volume><issue>23</issue><spage>4072</spage><pages>4072-</pages><issn>2073-4360</issn><eissn>2073-4360</eissn><abstract>The Poly(2-chloroquinyl methacrylate-
-2-hydroxyethyl methacrylate) (CQMA-
-HEMA) drug carrier system was prepared with different compositions through a free-radical copolymerization route involving 2-chloroquinyl methacrylate (CQMA) and 2-hydroxyethyl methacrylate) (HEMA) using azobisisobutyronitrile as the initiator. 2-Chloroquinyl methacrylate monomer (CQMA) was synthesized from 2-hydroxychloroquine (HCQ) and methacryloyl chloride by an esterification reaction using triethylenetetramine as the catalyst. The structure of the CQMA and CQMA-
-HEMA copolymers was confirmed by a CHN elementary analysis, Fourier transform infra-red (FTIR) and nuclear magnetic resonance (NMR) analysis. The absence of residual aggregates of HCQ or HCQMA particles in the copolymers prepared was confirmed by a differential scanning calorimeter (DSC) and XR-diffraction (XRD) analyses. The gingival epithelial cancer cell line (Ca9-22) toxicity examined by a lactate dehydrogenase (LDH) assay revealed that the grafting of HCQ onto PHEMA slightly affected (4.2-9.5%) the viability of the polymer carrier. The cell adhesion and growth on the CQMA-
-HEMA drug carrier specimens carried out by the (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) (MTT) assay revealed the best performance with the specimen containing 3.96 wt% HCQ. The diffusion of HCQ through the polymer matrix obeyed the Fickian model. The solubility of HCQ in different media was improved, in which more than 5.22 times of the solubility of HCQ powder in water was obtained. According to Belzer, the in vitro HCQ dynamic release revealed the best performance with the drug carrier system containing 4.70 wt% CQMA.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>34883576</pmid><doi>10.3390/polym13234072</doi><orcidid>https://orcid.org/0000-0002-5254-5665</orcidid><orcidid>https://orcid.org/0000-0002-1643-0377</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Polymers, 2021-11, Vol.13 (23), p.4072 |
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| source | PubMed Central Free; PubMed Central Open Access; MDPI - Multidisciplinary Digital Publishing Institute; EZB-FREE-00999 freely available EZB journals |
| subjects | Aqueous solutions Azobisisobutyronitrile Cell adhesion Chloride Copolymerization Copolymers Coronaviruses COVID-19 Drug carriers Drug dosages Esterification Fourier transforms Free radical polymerization Free radicals Lactate dehydrogenase Malaria Nitrogen NMR Nuclear magnetic resonance Polyhydroxyethyl methacrylate Polymerization Polymers Small intestine Solubility Stomach Toxicity |
| title | Copolymer Involving 2-Hydroxyethyl Methacrylate and 2-Chloroquinyl Methacrylate: Synthesis, Characterization and In Vitro 2-Hydroxychloroquine Delivery Application |
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