Amphiphilic Poly(<i>N</i>‐propargylamide) with Galactose and Lauryloyl Groups: Synthesis and Properties

Suenaga, Masakazu; Kaneko, Yoshirō; Kadokawa, Jun‐ichi; Nishikawa, Takehiro; Mori, Hiromu; Tabata, Masayoshi

doi:10.1002/mabi.200600228

Cited by 10 publications

(8 citation statements)

References 18 publications

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“…For this assumption, specific investigations provided support. Both our additional experiments (Scheme S1 and Figure S11) and early report 49 proved that alkynylated glucose played the role of "sergeants" in driving the soldiers (achiral monomer M units) to arrange in the identical helicity along the copolymer chains. Thus, our investigations demonstrated that the molecular chirality of the glucose units in the alkynyl-CNCs served as the chiral origin, while the rodlike structure of alkynyl-CNCs played the role of stabilizing agent for forming the optically active microparticles.…”

Section: ■ Results and Discussionmentioning

confidence: 52%

Alkynylated Cellulose Nanocrystals Simultaneously Serving as Chiral Source and Stabilizing Agent for Constructing Optically Active Helical Polymer Particles

Deng

2016

Macromolecules

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To take advantage of the chirality of cellulose nanocrystals (CNCs) and to develop novel chiral polymer materials, alkynylated CNCs (alkynyl-CNCs) were prepared and copolymerized with an achiral acetylenic monomer through suspension polymerization in aqueous media. The chirality of the alkynyl-CNCs was efficiently transferred to racemic helical polymer chains, by which inducing predominantly one-handed polymer helicity. Moreover, alkynyl-CNCs simultaneously acted as a comonomer and stabilizing agent, directly providing optically active microparticles (400–800 μm) constructed by chirally helical polymer chains. So the alkynylated CNCs played triple roles in our strategy: chiral source, comonomer, and stabilizing agent for performing suspension polymerizations. SEM images showed the successful formation of microparticles with regular spherical morphology, while circular dichroism spectra demonstrated the formation of one-handed helical polymer chains and optical activity of the microparticles thereof. The present study opens new opportunities for using CNCs and for preparing novel optically active helical polymer materials.

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Section: ■ Results and Discussionmentioning

confidence: 52%

Alkynylated Cellulose Nanocrystals Simultaneously Serving as Chiral Source and Stabilizing Agent for Constructing Optically Active Helical Polymer Particles

Deng

2016

Macromolecules

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“…As has been recently reported by Suenaga et al for a copolymer carrier featuring hydrophobic lauryloyl groups (45), cold temperature induces a remarkable decrease in the copolymer-rhodamine uptake, indicating that the polymer is internalized Via an endocytosis mechanism. After a 10 h incubation at 4°C, labeled copolymers observed near unlabeled rhabdites are probably endocytotic vesicles that are about to fuse with rhabdites (Figure 8a-c).…”

Section: Resultsmentioning

confidence: 73%

Amphiphilic Copolymer for Delivery of Xenobiotics: In Vivo Studies in a Freshwater Invertebrate, a Mesostominae Flatworm

et al. 2008

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The synthesis of an amphiphilic polymethacrylate copolymer containing cholesterol hydrophobic moieties and rhodamine as a fluorescent probe, the formation of microspheres, and the uptake of these microspheres in an invertebrate are reported. The cholesterol-derived methacryloyl monomer, which was prepared via a one-step synthesis, was copolymerized with methacrylic acid and methacryloxyethyl thiocarbamoyl rhodamine B in the presence of AIBN as initiator. The obtained dye-labeled copolymer was characterized by (1)H NMR and UV-vis spectroscopy. Fluorescence and TEM microscopies studies show that this amphiphilic copolymer aggregates to give microspheres with diameters ranging from approximately 3 to 11 microm. The in vivo study in a freshwater invertebrate, a Mesostominae flatworm (Rhabdocoela, Thyphloplanidae), indicates that the microspheres enter the cells by endocytosis. The data collected demonstrate that the rhodamine B covalently attached to the amphiphilic copolymers is bioaccumulated without being translocated out of the cell by the multixenobiotic resistance (MXR) transporters. As the MXR system is similar to the multidrug resistance (MDR) first observed in tumor cell lines resistant to anticancer drugs, the present data confirm the significant role that amphiphilic copolymers can play in the ongoing development of drug delivery strategies to overcome multidrug resistance. These investigations illustrate a promising approach for the development of new medical and ecotoxicological tools that can deliver specific molecules within cells.

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“…The structure of the copolymer (left) and (right) the SEM80 image of the aggregated polymer particles (Reprinted from Ref 97. with permission from John Wiley and Sons).…”

mentioning

confidence: 99%

Particles of polyacetylene and its derivatives: preparation and applications

Huang

et al. 2014

Polym. Chem.

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How to prepare polymeric particles from acetylene and its derivatives, in particular in aqueous media, has remained as a challenging research topic for a rather long period. In recent years, this research area has achieved exciting progress and a variety of novel functional particles have been reported. However, there has not yet a review article exclusively summarizing the progress. This article presents an overview on the advanced particles with emphasis on the preparation and their applications. The state-of-the-art preparation methods fall into two major groups: emulsion, precipitation, suspension polymerization approaches by starting from monomers; and post-treatment of 10 pre-formed polymers (i.e. self-assembly). The polymer particles were investigated in such applications as circuits, sensors, drug release and chiral-related processes for instance asymmetric catalysis, enantioselective crystallization, enantioselective release, amongst many others. The review article is expected to stimulate more unprecedented functional particles derived from acetylene and its derivatives.

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Amphiphilic Poly(N‐propargylamide) with Galactose and Lauryloyl Groups: Synthesis and Properties

Cited by 10 publications

References 18 publications

Alkynylated Cellulose Nanocrystals Simultaneously Serving as Chiral Source and Stabilizing Agent for Constructing Optically Active Helical Polymer Particles

Alkynylated Cellulose Nanocrystals Simultaneously Serving as Chiral Source and Stabilizing Agent for Constructing Optically Active Helical Polymer Particles

Amphiphilic Copolymer for Delivery of Xenobiotics: In Vivo Studies in a Freshwater Invertebrate, a Mesostominae Flatworm

Particles of polyacetylene and its derivatives: preparation and applications

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