Precise supramolecular control of surface coverage densities on polymer micro- and nanoparticles

Zhang, Shuai; Domínguez, Zoe; Assaf, Khaleel I.; Nilam, Mohamed; Thiele, Thomas; Pischel, Uwe; Schedler, Uwe; Nau, Werner M.; Hennig, Andréas

doi:10.1039/c8sc03150a

Cited by 17 publications

(11 citation statements)

References 74 publications

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“…The unique recognition properties and biocompatibility enables their implementation as excipients (Lim et al, 2002; Kuok et al, 2017). Recent achievements in the preparation of CB derivatives and analogs allow their incorporation into more intricate and applied research lines (Ayhan et al, 2015; Kim et al, 2018; Koc et al, 2018; Park et al, 2018; Sun et al, 2018; Zhang et al, 2018a, 2019a) in an effort to by-pass intrinsic limitations of the parent CBs, such as their stringent selectivity for guest binding and the low intrinsic solubility of CB6 and CB8. We contend that this account will provide a platform for understanding the potential of CBs toward applications in pharmaceutically and medicinally research and assist us in designing and creating new CB-based assemblies.…”

Section: Discussionmentioning

confidence: 99%

Applications of Cucurbiturils in Medicinal Chemistry and Chemical Biology

2019

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The supramolecular chemistry of cucurbit[n]urils (CBn) has been rapidly developing to encompass diverse medicinal applications, including drug formulation and delivery, controlled drug release, and sensing for bioanalytical purposes. This is made possible by their unique recognition properties and very low cytotoxicity. In this review, we summarize the host-guest complexation of biologically important molecules with CBn, and highlight their implementation in medicinal chemistry and chemical biology.

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Section: Discussionmentioning

confidence: 99%

Applications of Cucurbiturils in Medicinal Chemistry and Chemical Biology

2019

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“…Whereas a great deal of research in this direction concerns the use of CDs, CBs seem to have been underrated, probably due to legendary solubility and functionalisation issues. Several seminal recent papers have reported various methods for the functionalization of CBs, [51][52][53][54][55][56] and the difficult functionalisation of CBs is about to become a legend. As shown by the success of international conferences on CBs, this chemical structure appears to be more and more versatile in terms of functionalisation and uses.…”

Section: Discussionmentioning

confidence: 99%

Modelling haemoproteins: porphyrins and cyclodextrins as sources of inspiration

et al. 2019

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“…Meanwhile, propargyl modified CB[7] (CB[7]‐OPr) was prepared according to the previous literature. [ 29 ] Then, the hydrophilic host D18‐CB[7] was synthesized from CB[7]‐OPr and azide‐modified DNA through CuAAC reaction (Scheme S2, Supporting Information). The detail sequence of the azide‐modified DNA was 5′‐N 3 ‐TACTACACCACCACAACA‐3′.…”

Section: Methodsmentioning

confidence: 99%

Self‐Assembly of Supramolecular DNA Amphiphiles through Host–Guest Interaction and Their Stimuli‐Responsiveness

Yuan

Zhao

et al. 2020

Macromol. Rapid Commun.

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micelles, [6] nanofibers, [7] vesicles, [8] and nanosheets. [9] More interestingly, morphological shift of the DNA assemblies has been achieved through external stimuli, such as pH values, [10] temperature, [11] DNA-selective enzymatic activity, [12] and host-guest recognition. [13] Recently, supramolecular host-guest chemistry has been an effective strategy to construct supra-amphiphiles [14] by conjugating hydrophilic and hydrophobic segments. These supra-amphiphiles can assemble into diverse stimuli-responsive nanomaterials, applied in materials science, [15] supramolecular catalysis, [16] and biochemistry. [17] Doubtlessly, the hostguest approach could be an ideal alternative to construct DNA supra-amphiphiles. To date, the construction of DNA supra-amphiphiles through host-guest interactions has been rarely reported. [18] Moreover, the effect of such different topologic guests or stimuli-responsive guests on the assembled morphology is still unknown.Herein, we design and construct two DNA supra-amphiphiles via noncovalent recognition based on the host-guest interaction between cucurbit[7]uril (CB[7]) and the guests (ferrocene derivative or adamantane derivative). The host-guest interaction between CB[7] and guest (ferrocene or adamantane) has been widely investigated in the supramolecular chemistry due to their efficient molecular recognition with a strong association constant (K a = 10 4 -10 6 M −1 for CB [7] and ferrocene analogs, [19] K a = 10 8 -10 13 M −1 for CB [7] and adamantine derivates [20] ). Here, CB[7]-modified DNA (D18-CB[7]) is regarded as the hydrophilic host. Two types of molecules with different guest units and topologic structures are chosen to be the hydrophobic guests. One is ferrocene modified with second-generation poly(benzyl ether) dendron (G1) and the other is adamantane tailed with three 18-carbon alkyl chains (G2). Through host-guest interaction, the supramolecular DNA amphiphiles could be modularly constructed and then undergo their self-assembly process (Scheme 1). The self-assembly mechanism and application of the assembled nanostructures have been further demonstrated. Finally, the stimuli-responsiveness of assemblies induced by competitive guest or by the redox properties of ferrocene has been investigated.After having the host and two different guests obtained, we want to explore the construction of DNA-based supra-amphiphiles (D18-CB[7]/G1 and D18-CB[7]/G2) through host-guest 2000022 (5 of 5) www.advancedsciencenews.com www.mrc-journal.de

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Precise supramolecular control of surface coverage densities on polymer micro- and nanoparticles

Abstract: Competitive occupation of surface-bound supramolecular hosts allows precise control of surface coverage densities on particles.

Cited by 17 publications

References 74 publications

Applications of Cucurbiturils in Medicinal Chemistry and Chemical Biology

Applications of Cucurbiturils in Medicinal Chemistry and Chemical Biology

Modelling haemoproteins: porphyrins and cyclodextrins as sources of inspiration

Self‐Assembly of Supramolecular DNA Amphiphiles through Host–Guest Interaction and Their Stimuli‐Responsiveness

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