Structural Insights into the Host–Guest Complexation between β-Cyclodextrin and Bio-Conjugatable Adamantane Derivatives
Understanding the host–guest chemistry of α-/β-/γ- cyclodextrins (CDs) and a wide range of organic species are fundamentally attractive, and are finding broad contemporary applications toward developing efficient drug delivery systems. With the widely used β-CD as the host, we herein demonstrate tha...
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MDPI AG
2021-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/9/2412 |
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| author | Jian-Wei Wang Ka-Xi Yu Xin-Yuan Ji Hongzhen Bai Wen-Hua Zhang Xiurong Hu Guping Tang |
| author_facet | Jian-Wei Wang Ka-Xi Yu Xin-Yuan Ji Hongzhen Bai Wen-Hua Zhang Xiurong Hu Guping Tang |
| author_sort | Jian-Wei Wang |
| collection | DOAJ |
| description | Understanding the host–guest chemistry of α-/β-/γ- cyclodextrins (CDs) and a wide range of organic species are fundamentally attractive, and are finding broad contemporary applications toward developing efficient drug delivery systems. With the widely used β-CD as the host, we herein demonstrate that its inclusion behaviors toward an array of six simple and bio-conjugatable adamantane derivatives, namely, 1-adamantanol (adm-1-OH), 2-adamantanol (adm-2-OH), adamantan-1-amine (adm-1-NH<sub>2</sub>), 1-adamantanecarboxylic acid (adm-1-COOH), 1,3-adamantanedicarboxylic acid (adm-1,3-diCOOH), and 2-[3-(carboxymethyl)-1-adamantyl]acetic acid (adm-1,3-diCH<sub>2</sub>COOH), offer inclusion adducts with diverse adamantane-to-CD ratios and spatial guest locations. In all six cases, β-CD crystallizes as a pair supported by face-to-face hydrogen bonding between hydroxyl groups on C2 and C3 and their adjacent equivalents, giving rise to a truncated-cone-shaped cavity to accommodate one, two, or three adamantane derivatives. These inclusion complexes can be terminated as (adm-1-OH)<sub>2</sub>⊂CD<sub>2</sub> (<b>1</b>, 2:2), (adm-2-OH)<sub>3</sub>⊂CD<sub>2</sub> (<b>2</b>, 3:2), (adm-1-NH<sub>2</sub>)<sub>3</sub>⊂CD<sub>2</sub> (<b>3</b>, 3:2), (adm-1-COOH)<sub>2</sub>⊂CD<sub>2</sub> (<b>4</b>, 2:2), (adm-1,3-diCOOH)⊂CD<sub>2</sub> (<b>5</b>, 1:2), and (adm-1,3-diCH<sub>2</sub>COOH)⊂CD<sub>2</sub> (<b>6</b>, 1:2). This work may shed light on the design of nanomedicine with hierarchical structures, mediated by delicate cyclodextrin-based hosts and adamantane-appended drugs as the guests. |
| first_indexed | 2024-03-10T12:05:47Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T12:05:47Z |
| publishDate | 2021-04-01 |
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| series | Molecules |
| spelling | doaj.art-78736d6941b542919c86a06df5ea0c102023-11-21T16:35:03ZengMDPI AGMolecules1420-30492021-04-01269241210.3390/molecules26092412Structural Insights into the Host–Guest Complexation between β-Cyclodextrin and Bio-Conjugatable Adamantane DerivativesJian-Wei Wang0Ka-Xi Yu1Xin-Yuan Ji2Hongzhen Bai3Wen-Hua Zhang4Xiurong Hu5Guping Tang6Department of Chemistry, Zhejiang University, Hangzhou 310028, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou 310028, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou 310028, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou 310028, ChinaDepartment of Materials, Chemistry and Chemical Engineering, Soochow University, Suzhou 215123, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou 310028, ChinaDepartment of Chemistry, Zhejiang University, Hangzhou 310028, ChinaUnderstanding the host–guest chemistry of α-/β-/γ- cyclodextrins (CDs) and a wide range of organic species are fundamentally attractive, and are finding broad contemporary applications toward developing efficient drug delivery systems. With the widely used β-CD as the host, we herein demonstrate that its inclusion behaviors toward an array of six simple and bio-conjugatable adamantane derivatives, namely, 1-adamantanol (adm-1-OH), 2-adamantanol (adm-2-OH), adamantan-1-amine (adm-1-NH<sub>2</sub>), 1-adamantanecarboxylic acid (adm-1-COOH), 1,3-adamantanedicarboxylic acid (adm-1,3-diCOOH), and 2-[3-(carboxymethyl)-1-adamantyl]acetic acid (adm-1,3-diCH<sub>2</sub>COOH), offer inclusion adducts with diverse adamantane-to-CD ratios and spatial guest locations. In all six cases, β-CD crystallizes as a pair supported by face-to-face hydrogen bonding between hydroxyl groups on C2 and C3 and their adjacent equivalents, giving rise to a truncated-cone-shaped cavity to accommodate one, two, or three adamantane derivatives. These inclusion complexes can be terminated as (adm-1-OH)<sub>2</sub>⊂CD<sub>2</sub> (<b>1</b>, 2:2), (adm-2-OH)<sub>3</sub>⊂CD<sub>2</sub> (<b>2</b>, 3:2), (adm-1-NH<sub>2</sub>)<sub>3</sub>⊂CD<sub>2</sub> (<b>3</b>, 3:2), (adm-1-COOH)<sub>2</sub>⊂CD<sub>2</sub> (<b>4</b>, 2:2), (adm-1,3-diCOOH)⊂CD<sub>2</sub> (<b>5</b>, 1:2), and (adm-1,3-diCH<sub>2</sub>COOH)⊂CD<sub>2</sub> (<b>6</b>, 1:2). This work may shed light on the design of nanomedicine with hierarchical structures, mediated by delicate cyclodextrin-based hosts and adamantane-appended drugs as the guests.https://www.mdpi.com/1420-3049/26/9/2412cyclodextrinadamantane derivativesbio-conjugationhost–guest interactioncrystal structure |
| spellingShingle | Jian-Wei Wang Ka-Xi Yu Xin-Yuan Ji Hongzhen Bai Wen-Hua Zhang Xiurong Hu Guping Tang Structural Insights into the Host–Guest Complexation between β-Cyclodextrin and Bio-Conjugatable Adamantane Derivatives Molecules cyclodextrin adamantane derivatives bio-conjugation host–guest interaction crystal structure |
| title | Structural Insights into the Host–Guest Complexation between β-Cyclodextrin and Bio-Conjugatable Adamantane Derivatives |
| title_full | Structural Insights into the Host–Guest Complexation between β-Cyclodextrin and Bio-Conjugatable Adamantane Derivatives |
| title_fullStr | Structural Insights into the Host–Guest Complexation between β-Cyclodextrin and Bio-Conjugatable Adamantane Derivatives |
| title_full_unstemmed | Structural Insights into the Host–Guest Complexation between β-Cyclodextrin and Bio-Conjugatable Adamantane Derivatives |
| title_short | Structural Insights into the Host–Guest Complexation between β-Cyclodextrin and Bio-Conjugatable Adamantane Derivatives |
| title_sort | structural insights into the host guest complexation between β cyclodextrin and bio conjugatable adamantane derivatives |
| topic | cyclodextrin adamantane derivatives bio-conjugation host–guest interaction crystal structure |
| url | https://www.mdpi.com/1420-3049/26/9/2412 |
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