A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water
P-tert-butyldihomooxacalix[4]arene is a well-known calix[4]arene analog in which one CH2 bridge is replaced by one -CH2OCH2- group. Thus, dihomooxacalix[4]arene has a slightly larger cavity than that of calix[4]arene and usually possesses a more flexible cone conformation, and the bridged oxygen ato...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2020-02-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2020.00033/full |
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| author | Hao Guo Hao Guo Runmiao Zhang Runmiao Zhang Ying Han Jin Wang Chaoguo Yan |
| author_facet | Hao Guo Hao Guo Runmiao Zhang Runmiao Zhang Ying Han Jin Wang Chaoguo Yan |
| author_sort | Hao Guo |
| collection | DOAJ |
| description | P-tert-butyldihomooxacalix[4]arene is a well-known calix[4]arene analog in which one CH2 bridge is replaced by one -CH2OCH2- group. Thus, dihomooxacalix[4]arene has a slightly larger cavity than that of calix[4]arene and usually possesses a more flexible cone conformation, and the bridged oxygen atom might provide additional binding sites. Here, we synthesized a new functional p-tert-butyldihomooxacalix[4]arene 1 through Ugi reaction with good yield (70%), starting from condensed p-tert-butyldihomooxacalix[4]arene O-alkoxy–substituted benzaldehydes, benzoic acid, benzylamine, and cyclohexyl isocyanide. Proton nuclear magnetic resonance spectroscopy (1H NMR), 13C NMR, IR, and diffusion-ordered 1H NMR spectroscopy (DOSY) methods were used to characterize the structure of 1. Then soft gel was prepared by adding 1 into cyclohexane directly. It shows remarkable thermoreversibility and can be demonstrated for several cycles. As is revealed by scanning electron microscopy (SEM) images, xerogel showed highly interconnected and homogeneous porous network structures, and hence, the gel is suitable for storage and controlled release. |
| first_indexed | 2024-12-11T05:54:28Z |
| format | Article |
| id | doaj.art-6a9c305fd7694a1eaf2abbd153f31c29 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-11T05:54:28Z |
| publishDate | 2020-02-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-6a9c305fd7694a1eaf2abbd153f31c292022-12-22T01:18:42ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462020-02-01810.3389/fchem.2020.00033513189A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in WaterHao Guo0Hao Guo1Runmiao Zhang2Runmiao Zhang3Ying Han4Jin Wang5Chaoguo Yan6School of Chemistry and Chemical Engineer, Yangzhou University, Yangzhou, ChinaSchool of Chemistry and Chemical Engineer, Nantong University, Nantong, ChinaSchool of Chemistry and Chemical Engineer, Yangzhou University, Yangzhou, ChinaSchool of Chemistry and Chemical Engineer, Nantong University, Nantong, ChinaSchool of Chemistry and Chemical Engineer, Yangzhou University, Yangzhou, ChinaSchool of Chemistry and Chemical Engineer, Nantong University, Nantong, ChinaSchool of Chemistry and Chemical Engineer, Yangzhou University, Yangzhou, ChinaP-tert-butyldihomooxacalix[4]arene is a well-known calix[4]arene analog in which one CH2 bridge is replaced by one -CH2OCH2- group. Thus, dihomooxacalix[4]arene has a slightly larger cavity than that of calix[4]arene and usually possesses a more flexible cone conformation, and the bridged oxygen atom might provide additional binding sites. Here, we synthesized a new functional p-tert-butyldihomooxacalix[4]arene 1 through Ugi reaction with good yield (70%), starting from condensed p-tert-butyldihomooxacalix[4]arene O-alkoxy–substituted benzaldehydes, benzoic acid, benzylamine, and cyclohexyl isocyanide. Proton nuclear magnetic resonance spectroscopy (1H NMR), 13C NMR, IR, and diffusion-ordered 1H NMR spectroscopy (DOSY) methods were used to characterize the structure of 1. Then soft gel was prepared by adding 1 into cyclohexane directly. It shows remarkable thermoreversibility and can be demonstrated for several cycles. As is revealed by scanning electron microscopy (SEM) images, xerogel showed highly interconnected and homogeneous porous network structures, and hence, the gel is suitable for storage and controlled release.https://www.frontiersin.org/article/10.3389/fchem.2020.00033/fullcalixarenesgelcontrolled releasemacrocyclic compoundsUgi reaction |
| spellingShingle | Hao Guo Hao Guo Runmiao Zhang Runmiao Zhang Ying Han Jin Wang Chaoguo Yan A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water Frontiers in Chemistry calixarenes gel controlled release macrocyclic compounds Ugi reaction |
| title | A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water |
| title_full | A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water |
| title_fullStr | A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water |
| title_full_unstemmed | A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water |
| title_short | A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water |
| title_sort | p tert butyldihomooxacalix 4 arene based soft gel for sustained drug release in water |
| topic | calixarenes gel controlled release macrocyclic compounds Ugi reaction |
| url | https://www.frontiersin.org/article/10.3389/fchem.2020.00033/full |
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