A versatile and modular approach to functionalisation of deep-cavity cavitands via“click” chemistry

Li, Yejia; Giles, Marco D.; Liu, Simin; Laurent, Boyd A.; Hoskins, Jessica N.; Cortez, Mallory A.; Sreerama, Subramanya Gupta; Gibb, Bruce C.; Grayson, Scott M.

doi:10.1039/c1cc11259g

Cited by 19 publications

(11 citation statements)

References 29 publications

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“…The double hydrophilic block assembly showed thermoresponsive behavior with heat-induced hydrophilic-hydrophobic switching. Azido-semitelechelic pEtOx was coupled to a (former octaol) alkyne-functionalized "deep-cavity cavitand" using azide-alkyne click-coupling by Grayson et al [82]. The resulting macromolecular cavitand exhibited tuneable solubility, while its ability to encapsulate guest molecules was maintained.…”

Section: Covalent Attachment To/supramolecular Assembly With Cyclodexmentioning

confidence: 99%

Design Strategies for Functionalized Poly(2-oxazoline)s and Derived Materials

2013

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Abstract:The polymer class of poly(2-oxazoline)s currently is under intensive investigation due to the versatile properties that can be tailor-made by the variation and manipulation of the functional groups they bear. In particular their utilization in the biomedic(in)al field is the subject of numerous studies. Given the mechanism of the cationic ring-opening polymerization, a plethora of synthetic strategies exists for the preparation of poly(2-oxazoline)s with dedicated functionality patterns, comprising among others the functionalization by telechelic end-groups, the incorporation of substituted monomers into (co)poly(2-oxazoline)s, and polymeranalogous reactions. This review summarizes the current state-of-the-art of poly(2-oxazoline) preparation and showcases prominent examples of poly(2-oxazoline)-based materials, which are retraced to the desktop-planned synthetic strategy and the variability of their properties for dedicated applications.

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Section: Covalent Attachment To/supramolecular Assembly With Cyclodexmentioning

confidence: 99%

Design Strategies for Functionalized Poly(2-oxazoline)s and Derived Materials

2013

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“…2-Propylsulfanylthiocarbonylsulfanyl-2-methyl propionic acid (PTPA), [14] azido-terminated polyethylene oxide (PEO 113 -N 3 ), [15] and 2-nitro-5-(prop-2-ynyloxy)benzyl alcohol [16] were synthesized according to literature procedures. 2-Propylsulfanylthiocarbonylsulfanyl-2-methyl propionic acid (PTPA), [14] azido-terminated polyethylene oxide (PEO 113 -N 3 ), [15] and 2-nitro-5-(prop-2-ynyloxy)benzyl alcohol [16] were synthesized according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

“…Sinopharm Chemical Reagent Co. Ltd. and used as received. 2-Propylsulfanylthiocarbonylsulfanyl-2-methyl propionic acid (PTPA), [14] azido-terminated polyethylene oxide (PEO 113 -N 3 ), [15] and 2-nitro-5-(prop-2-ynyloxy)benzyl alcohol [16] were synthesized according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Photodegradable Neutral–Cationic Brush Block Copolymers for Nonviral Gene Delivery

Yang

Liu

et al. 2014

Chemistry An Asian Journal

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We report on the fabrication of a photodegradable gene-delivery vector based on PEO-b-P(GMA-g-PDMAEMA) neutral-cationic brush block copolymers that possess cationic poly(N,N-dimethylaminoethyl methacrylate) (PDMAEMA) brushes for DNA compaction, poly(ethylene oxide) (PEO) as a hydrophilic block, and poly(glycidyl methacrylate) (PGMA) as the backbone. The PEO-b-P(GMA-g-PDMAEMA) copolymers were synthesized through the combination of reversible addition-fragmentation transfer (RAFT) polymerization and postmodification. A photocleavable PEO-based macroRAFT agent was first synthesized; next, the PEO-b-PGMA block copolymer was prepared by RAFT polymerization of GMA; this was followed by a click reaction to introduce the RAFT initiators on the side chains of the PGMA block; then, RAFT polymerization of DMAEMA afforded the PEO-b-P(GMA-g-PDMAEMA) copolymer. The obtained neutral-cationic brush block copolymer could effectively complex plasmid DNA (pDNA) into nanoparticles at an N/P ratio (i.e., the number of nitrogen residues per DNA phosphate) of 4. Upon UV irradiation, pDNA could be released owing to cleavage of the pDNA-binding cationic PDMAEMA side chains as well as the nitrobenzyl ester linkages at the diblock junction point. In addition, in vitro gene transfection results demonstrated that the polyplexes could be effectively internalized by cells with good transfection efficiency, and the UV irradiation protocol could considerably enhance the efficiency of gene transfection.

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“…For example, working with Scott Grayson across town at Tulane University we successfully formed the dendrimer–coated host shown in Fig. 8 [ 36 ], as well as wide series of polymer coated derivatives coupled using “Click” chemistry [ 37 ].…”

Section: Reviewmentioning

confidence: 99%