Monofunctionalised cucurbit[6]uril synthesis using imidazolium host–guest complexation

Zhao, Nan; Lloyd, Gareth O.; Scherman, Oren A.

doi:10.1039/c2cc17433b

Cited by 117 publications

(379 citation statements)

References 25 publications

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“…32 In order to facilitate the confirmation of copolymerization and the detection of supramolecular interaction, NIPAA was firstly chosen as a co-monomer to copolymerize with 4VBOCB [7]. The polymerization was conducted using redox initiate polymerization in water under 30 C. C 8 bim, which was used to increase the solubility of 4VBOCB [7], becomes a problem after the polymerization as it demonstrates high binding affinity with the copolymer and therefore cannot be removed easily through conventional methods. An alternate method was designed where the polymer was firstly subject to dialysis in CB [7] solution allowing C 8 bim to be competitively removed from polymeric CB [7].…”

Section: -7mentioning

confidence: 99%

“…The method for the synthesis of mono-functionalized CB [6] reported recently offers an approach for the synthesis of such a CB based monomer. 30 Hence a CB [7] based monomer, 4-vinylbenzyloxy CB [7] (4VBOCB [7]), was designed and synthesized in a two-step synthesis. The precursor of CB [7] monomer, mono-hydroxyl CB [7] (HOCB [7]), was synthesized through firstly dissolving CB [7] in deionized water with the support of 3,3…”

Section: -7mentioning

confidence: 99%

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Synthesis of linear cucurbit[7]uril pendent copolymers through radical polymerization: Polymers with ultra‐high binding affinity

Chen

Tan

2015

J. Polym. Sci. Part A: Polym. Chem.

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Cucurbiturils (CBs) are a family of macrocyclic molecules with high binding affinity and high binding selectivity. [1][2][3][4][5][6][7] They have been intensively researched for the past decade and have applications in a wide range of fields including molecular recognition, catalysis, drug delivery, bioassays, nanoparticle synthesis and modification, and molecular devices.1-3 Their anchoring onto macromolecules offers further opportunities to expand their applications, [8][9][10] however there are currently few examples of such reports.11-16 The relatively few reports are likely as a result of the difficulties encountered in the modification of CBs; this problem persisted until Kim's group reported the functionalization of CBs with a facile oxidation method in 2003.17 Through oxidization of CBs with persulfate, hydroxyl groups -which are suitable for further functionalization-could be introduced at their peripheries. Following that a series of polymer nanocapsules constructed with perallyloxy-CB[6] and dithiols have been reported. [11][12][13] The eminent binding properties of CB[6] allow these polymer nanocapsules to be decorated easily with targeting and labeling groups through host-guest interactions. Recently, allyl functionalized CB[6] and CB [7] were grafted on to hyaluronate through a thiol-ene click reaction, [14][15][16] and where employed for theranostic systems and tissue engineering applications. In addition of the oxidation method, Isaacs's group developed a different method to synthesize CB derivatives. In their works, CB [6] and CB [7] derivatives were synthesized by the condensation glycoluril hexamer with phthalaldehydes and glycoluril bis(cyclic ethers), respectively.18-20 Despite these, there is still an unmet need for new and facile methods for the construction of CB covalently linked polymers to broaden their portfolio of potential applications.The binding properties of the covalently linked macrocycle polymers are one of the key considerations in their design for specific applications. 21,22 Although their binding properties are usually determined by the binding properties of the macrocycle moieties; the structure of polymers also has a profound and sophisticated effect. Based on the research on polymeric cyclodextrins (CDs), if the CD moieties are spatially isolated, their binding affinity to guest molecules decreases slightly; 23-25 while if they are in close proximity, adjacent two CD moieties may have a cooperation effect and both the binding affinity and binding stoichiometry will be affected. [24][25][26][27][28] To the best of our knowledge, there have been no studies on the binding property of polymeric CBs prior to this work. Here, we present a universal method for the synthesis of linear CB [7] pendent copolymers through free radical polymerization (Scheme 1). The binding properties of the obtained copolymers were studied using turbidity measurement, isothermal titration calorimetry (ITC) and NMR.Free radical polymerization is a universal polymerization method which is suitable f...

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Section: -7mentioning

confidence: 99%

Section: -7mentioning

confidence: 99%

Synthesis of linear cucurbit[7]uril pendent copolymers through radical polymerization: Polymers with ultra‐high binding affinity

Chen

Tan

2015

J. Polym. Sci. Part A: Polym. Chem.

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“…理论上这三部分都可以发生反应(或转化), 即腰位偕二次甲基 C-H 键和桥联亚甲基 C-H 键的功能化; 脲羰基的还原或水解 (Scheme 1), 特别是酰胺一般易水解 [12] , 但葫芦脲的弧形偕环结构使得其非常稳定, 能够耐受 370 ℃的高温而不分解, 即使是 100℃的浓盐酸, CB [5], CB [6], CB [7] 也不分解 [4] . [19,20] . 我们在相关的羟基化研…”

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Oxidation of Cucurbituril and Its Analogues

Lü¹,

Shi²,

Zhang³

et al. 2015

Chin. J. Org. Chem.

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“…Despite the great effort to introduce functional moieties on CB [6], 21 mono-amination of CB [6] is still difficult and complicated. 22,23 We previously reported the method to synthesize CB [6]-HA derivative via Michael addition between thiol (SH) modied HA and mono-allyloxy CB [6]. However, there were unreacted thiol groups on HA backbone, resulting in selfcrosslinking by disulde bonding.…”

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confidence: 99%

Supramolecular hydrogels encapsulating bioengineered mesenchymal stem cells for ischemic therapy

Hwang

Kim

Kim³

et al. 2018

RSC Adv.

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We developed supramolecular hyaluronate (HA) hydrogels to encapsulate genetically engineered mesenchymal stem cells (MSCs) for the treatment of limb ischemia. In vivo angiogenic factors could be produced stably by the bioengineered MSCs (BMSCs) within the supramolecular hydrogels showing effective vascular repair and enhanced blood perfusion.Clinical limb ischemia (CLI) is the severe manifestation of peripheral arterial disease, which is one of the most common diseases in the population over 70 years old, up to 20%.

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Monofunctionalised cucurbit[6]uril synthesis using imidazolium host–guest complexation

Cited by 117 publications

References 25 publications

Synthesis of linear cucurbit[7]uril pendent copolymers through radical polymerization: Polymers with ultra‐high binding affinity

Synthesis of linear cucurbit[7]uril pendent copolymers through radical polymerization: Polymers with ultra‐high binding affinity

Oxidation of Cucurbituril and Its Analogues

Supramolecular hydrogels encapsulating bioengineered mesenchymal stem cells for ischemic therapy

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