Construction and Chromatographic Performance of a Novel Triazole Bridged Hybrid Bilayer Cyclodextrin Chiral Stationary Phase

Zhang, Lifang; Jie, Zhao; Wang, Yong

doi:10.6023/a15080530

Cited by 5 publications

(6 citation statements)

References 4 publications

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“…BCDP had the ability of broad-spectrum resolution of all triazoles (11 kinds), and most triazoles were completely separated, which was superior to CDSP and other CD-based stationary phases. [24][25][26][27][28] This was related to two structural advantages. On the one hand, the propyl and bis-triazole bridged groups had certain flexibility and hydrophobicity, which could assist the bis-CD cavities of BCDP to encapsulate a wider range of analytes.…”

Section: Chiral Separation Of Triazole Pesticides By Reversed-phase C...mentioning

confidence: 99%

“…In 2008, Liang's group 24,25 prepared two native CD CSPs through the Click reaction, which were used for separating 11 chiral compounds, such as benzoin and flavanones, and various monosaccharides by hydrophilic chromatography. Wang's group [26][27][28][29] prepared stationary phases of natural cyclodextrin, full-methyl-derived cyclodextrin, and perphenylcarbamate cyclodextrin. At the same time, triazolyl was introduced into the cyclodextrin port by the Click reaction.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of a bis‐triazolyl bridged β‐cyclodextrin stationary phase and its application for enantioseparation of chiral compounds by HPLC

Zeng,

Huang,

et al. 2024

Chirality

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A novel bis‐triazolyl bridged β‐cyclodextrin was first synthesized by the Click reaction between azido‐β‐cyclodextrin and 1,6‐heptadiyne. Then it was bonded onto silica gel to obtain a bis‐triazolyl bridged β‐cyclodextrin‐based chiral stationary phase (BCDP). After structure characterization, the HPLC performance of BCDP was systematically evaluated by using different types of compounds as probes. The results showed that BCDP could well separate 18 kinds of achiral aromatic compounds (homologues, positional isomers, etc.) and 35 kinds of chiral drugs or pesticides, such as triazoles (Rs = 1.33–3.15), flavanones (Rs = 1.49–2.62), dansyl amino acids (Rs = 0.96–1.99), and β‐blocker drugs (Rs = 0.68–2.78). BCDP could separate a wider range of compounds (53 kinds); especially, some chiral substance pairs that were difficult to be resolved on the ordinary cyclodextrin CSPs, including triazoles containing two chiral carbons (triadimenol, bitertanol, metconazole, and triticonazole), strongly ionized amino acids (acidic Asp, alkalic Arg, and polar Thr) and β‐blockers with bulky groups (carvedilol, propranolol, and pindolol). Obviously, the unique synergistic inclusion effect of bridged cyclodextrin with double cavities and the bis‐triazole bridging group could provide multiple action sites, such as hydrogen bonding, π‐π stacking and acid–base action sites, thus improving its chiral chromatographic performance.

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Section: Chiral Separation Of Triazole Pesticides By Reversed-phase C...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation of a bis‐triazolyl bridged β‐cyclodextrin stationary phase and its application for enantioseparation of chiral compounds by HPLC

Zeng,

Huang,

et al. 2024

Chirality

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“…CD 接枝聚合物从结构上主要分为两种: 一种为图 1b 所示的侧链接枝型, 另一种为星型聚合物或支化聚合物端链上的接枝. 除此之外, CD 也被广泛用于固相界面的接枝修饰, 不在本综述所述的 CDP 范畴内 [52,53] .…”

Section: 环糊精接枝聚合物(Grafted-cdp)unclassified

Advances in Cyclodextrin Polymers and Their Applications in Biomedicine

Qie¹,

Hao²,

Liu³

et al. 2020

Acta Chim. Sinica

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Cyclodextrins (CDs) are a family of macrocyclic oligosaccharides composed of α-1,4-linked D-glucopyranose units. The most commonly used CDs are α-, β-, and γ-CD, which consist of 6, 7, and 8 D-glucose units, respectively. They possess a relative hydrophobic inner cavity and a hydrophilic outer surface and can form inclusion complexes with various small molecules, metal ions and polymers, tailoring the physicochemical property of the guests, and thus have been widely used in the fields of pharmacy, food, chemistry, chromatography, catalysis, biotechnology, agriculture, cosmetics, hygiene, medicine, textiles and the environment, etc. However, it is difficult to manipulate the native CDs in some specific applications, they are crystallized solid and soluble in water but insoluble in most organic solvents. CD polymers (CDPs), such as crosslinked CDs or CD based hydrogels with various crosslinkers by chemical reactions, and CD based supramolecular polymers formed by physical interactions, can achieve the integration effect and synergy effect of CDs, crosslinkers and guest polymers, not only possessing the inclusion capacity of CDs, but also endowing CDs with other properties introduced by crosslinkers. The CDPs can be easily manipulated and they exhibit unique features that native CDs are lack of. Hence, the design, synthesis and applications of CDPs have attracted broad interests in recent years. This review focuses on the recent progress in CDPs, and different types of CDPs are identified and classified based on the structures and functions, namely CD based polyrotaxane, grafted CDs, crosslinked CDs and linear CDs, etc. Besides, the synthetic methodologies of CDPs are highlighted. Particular attention is paid to the breakthrough on the CDPs in the past five years, and their applications in biomedicine, such as drug delivery, gene delivery, target delivery, controlled release and cell imaging are discussed in detail. The typical applications in other fields such as absorption, environment remediation, thermal insulation, catalysis and slid-ring gels are also discussed in brief. Finally, the review provides brief summary and prospect of CDPs. Keywords cyclodextrin; polymer; chemical crosslinking; drug carrier; supramolecular self-assembly 1 引言环糊精(cyclodextrin, 简称 CD)是一类由吡喃葡萄糖单元通过 α-1,4-糖苷键链接而成的大环分子, 具有疏水空腔和亲水外壁的中空圆台状立体结构, 能够通过包结作用(encapsulation)与多种小分子和聚合物形成主-客体(host-guest)包结物(inclusion complexes), 从而实现对客体分子物理和化学性能的调控, 被广泛用于制药、食

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“…In recent years, the emergence of bridged b-CD CSPs is a very promising candidate. 33 The Bridged bis(b-CD) is a supramolecular dimer connected by 2 single-derived CD units that has been widely used for molecular recognition and as a targeted drug carrier, photochemical, and asymmetric catalyst [34][35][36][37] because of its greater capacity for synergistic inclusion and molecular recognition compared to single b-CD. 38 In recent years, although the bridged b-CD has been widely used in many elds, the CSPs used for the separation of enantiomers are rarely reported.…”

Section: Introductionmentioning

confidence: 99%

Preparation of a novel bridged bis(β-cyclodextrin) chiral stationary phase by thiol–ene click chemistry for enhanced enantioseparation in HPLC

2021

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Construction and Chromatographic Performance of a Novel Triazole Bridged Hybrid Bilayer Cyclodextrin Chiral Stationary Phase

Cited by 5 publications

References 4 publications

Preparation of a bis‐triazolyl bridged β‐cyclodextrin stationary phase and its application for enantioseparation of chiral compounds by HPLC

Preparation of a bis‐triazolyl bridged β‐cyclodextrin stationary phase and its application for enantioseparation of chiral compounds by HPLC

Advances in Cyclodextrin Polymers and Their Applications in Biomedicine

Preparation of a novel bridged bis(β-cyclodextrin) chiral stationary phase by thiol–ene click chemistry for enhanced enantioseparation in HPLC

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