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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Main Authors:	Jian-Wei Wang, Ka-Xi Yu, Xin-Yuan Ji, Hongzhen Bai, Wen-Hua Zhang, Xiurong Hu, Guping Tang
Format:	Article
Language:	English
Published:	MDPI AG 2021-04-01
Series:	Molecules
Subjects:	cyclodextrin adamantane derivatives bio-conjugation host–guest interaction crystal structure
Online Access:	https://www.mdpi.com/1420-3049/26/9/2412

id	doaj-78736d6941b542919c86a06df5ea0c10
record_format	Article
spelling	doaj-78736d6941b542919c86a06df5ea0c102021-04-22T15:58:00ZengMDPI AGMolecules1420-30492021-04-01262412241210.3390/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
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Jian-Wei Wang Ka-Xi Yu Xin-Yuan Ji Hongzhen Bai Wen-Hua Zhang Xiurong Hu Guping Tang
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
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
title	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_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_sort	structural insights into the host–guest complexation between β-cyclodextrin and bio-conjugatable adamantane derivatives
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2021-04-01
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.
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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Structural Insights into the Host–Guest Complexation between β-Cyclodextrin and Bio-Conjugatable Adamantane Derivatives

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