Highly Water‐Soluble Amphiphilic Cyclodextrins Bearing Branched and Cyclic Oleic Grafts

Cocq, A.; Rousseau, Cyril; Bricout, H.; Oliva, E.; Bonnet, Véronique; Djedaïni‐Pilard, Florence; Monflier, Éric; Tilloy, S.

doi:10.1002/ejoc.201900789

Cited by 5 publications

(4 citation statements)

References 17 publications

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“…OS-CDs synthesis was conducted in two steps as previously reported by our group [31,32]. The first step involved the alkenylation of maleic anhydride by methyl oleate and oleic acid, leading to the formation of maleinised methyl oleate or maleinised oleic acid, respectively.…”

Section: Resultsmentioning

confidence: 99%

Rhodium-Catalyzed Aqueous Biphasic Olefin Hydroformylation Promoted by Amphiphilic Cyclodextrins

et al. 2020

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Hydroformylation is an industrial process that allows for the production of aldehydes from alkenes using transition metals. The reaction can be carried out in water, and the catalyst may be recycled at the end of the reaction. The industrial application of rhodium-catalyzed aqueous hydroformylation has been demonstrated for smaller olefins (propene and butene). Unfortunately, larger olefins are weakly soluble in water, which results in very low catalytic activity. In an attempt to counteract this, we investigated the use of amphiphilic oleic succinyl-cyclodextrins (OS-CDs) synthesized from oleic acid derivatives and maleic anhydride. OS-CDs were found to increase the catalytic activity of rhodium during the hydroformylation of water-insoluble olefins, such as 1-decene and 1-hexadecene, by promoting mass transfer. Recyclability of the catalytic system was also evaluated in the presence of these cyclodextrins.

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Section: Resultsmentioning

confidence: 99%

Rhodium-Catalyzed Aqueous Biphasic Olefin Hydroformylation Promoted by Amphiphilic Cyclodextrins

et al. 2020

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“…[114] The synthesis method of these highly water-soluble CDs, either Me-type 48 or Na-type 49, has recently been described. [41,115] Selected results in the hydroformylation of hexadec-1-ene are collected in Table 15. The nature of CDs does not significantly affect chemo-and regio-selectivity (entries 1-3 and 6-8), whereas conversions change considerably (9-94 %).…”

Section: Hydroformylationmentioning

confidence: 99%

“…This issue has recently been addressed by the Monflier group utilizing amphiphilic oleic succinyl‐cyclodextrins prepared from oleic acid derivatives and maleic anhydride promoting mass transfer [114] . The synthesis method of these highly water‐soluble CDs, either Me‐type 48 or Na‐type 49 , has recently been described [41,115] . Selected results in the hydroformylation of hexadec‐1‐ene are collected in Table 15.…”

Section: Hydroformylationmentioning

confidence: 99%

Synthetic Application of Cyclodextrins in Combination with Metal Ions, Complexes, and Metal Particles

Molnár

2020

ChemCatChem

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Cyclodextrins are green, environmentally benign products available through the enzymatic degradation of starch for a multitude of varied applications. This review attempts to collect useful information with respect to catalytic studies performed with the use of cyclodextrin and modified cyclodextrin preparations applied in combination of or loaded with varied catalytically active species including metal ions, complexes, and metal particles. Major sections are about their use in hydrogenation, reduction, oxidation, hydroformylation and coupling reactions. Additional sections include their utilization in ring formation and ring opening as well as degradation of pollutants. In the last part, examples about ester hydrolysis, hydroboration and hydrosilylation, as well as hydrogen production are treated. Data collected and analyzed indicate the importance and high potential of cyclodextrin-based catalysts in sustainable chemistry.

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“…以 HDI 扩链的聚四氢呋喃聚氨酯为臂, α-CD 为核, Maiti 等 [72] 合成了生物相容性好的 CD-聚氨酯星型聚合物并研究了其抗癌药物的负载和释放性能. Tilloy 等 [73] 通过酯化反应在 β-CD 上接枝上数量可控的线形或环化油酸(oleic acid), 极大提高了 β-CD 的水中溶解度(50～480 g/L)及其表面活性. 以全甲基化 β-CD 为核, Bonnet 等 [74] 通过酰胺化反应制备了各类脂肪酸接枝的多臂聚合物, 此聚合物能够形成直径约 120 nm 的纳米颗粒, 在 4 ℃能够长期稳定存在, 经 MD 模拟计算得到此 CD 多臂聚合物对阿扎那韦 (Atazanavir)具有优异的负载能力.…”

Section: 环糊精交联聚合物(Crosslinked 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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Highly Water‐Soluble Amphiphilic Cyclodextrins Bearing Branched and Cyclic Oleic Grafts

Cited by 5 publications

References 17 publications

Rhodium-Catalyzed Aqueous Biphasic Olefin Hydroformylation Promoted by Amphiphilic Cyclodextrins

Rhodium-Catalyzed Aqueous Biphasic Olefin Hydroformylation Promoted by Amphiphilic Cyclodextrins

Synthetic Application of Cyclodextrins in Combination with Metal Ions, Complexes, and Metal Particles

Advances in Cyclodextrin Polymers and Their Applications in Biomedicine

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