A series of poly[N‐(2‐hydroxypropyl)methacrylamide] copolymers with anthracene‐derived fluorophores showing aggregation‐induced emission properties for bioimaging

Abstract

A series of new poly[N-(2-hydroxypropyl)methacrylamide]-based amphiphilic copolymers were synthesized through a radical copolymerization of a monomeric/hydrophobic fluorophore possessing aggregation-induced emission (AIE) property with N-(2-hydroxypropyl)methacrylamide. Photophysical properties were investigated using UV-Vis absorbance and fluorescence spectrophotometry. Influences of the polymer structures with different molar ratios of the AIE fluorophores on their photophysical properties were studied. Results show that the AIE fluorophores aggregate in the cores of the micelles formed from the amphiphilic random copolymers and polymers with more hydrophobic AIE fluorophores facilitate stronger aggregations of the AIE segments to obtain higher quantum efficiencies. The polymers reported herein have good water solubility, enabling the application of hydrophobic AIE materials in biological conditions. The polymers were endocytosed by two experimental cell lines, human brain glioblastoma U87MG cells and human esophagus premalignant CP-A, with a distribution into the cytoplasm. The polymers are non-cytotoxic to the two cell lines at a polymer concentration of 1 mg/mL.

Poly(ε-caprolactone)-containing graft copolymers for ratiometric extracellular oxygen sensing

“…2A). These phenomena were observed in other AIE materials [38,52] suggesting the typical AIE characteristics. The quantum yield of P3 in DMSO/H 2 O (2: 98 by volume) increased to 0.13, which is 6.5 times greater than that in pure DMSO.…”

“…Stannous octoate (J & K Scientific Ltd, Shanghai), Azodiisobutyronitrile (AIBN, Aladdin, Shanghai) and methacryloyl chloride, stabilized with MEHQ (TCI, Tokyo) were commercially available from different vendors. N-(2-Hydroxypropyl)methacrylamide (HPMA) was synthesized according to a known procedure and our publications [50,51], AIE fluorophore was synthesized according to our previous publication [52].…”

“…CMC of P3 was determined according our previous procedure by taking the advantage of the fluorophore's emission properties [52]; When the polymer concentration is extremely low, the polymers are in the form of unimers in the solutions. Under these conditions, the polymers did not self-assemble to form micelles.…”

Optical properties of amphiphilic copolymer-based self-assemblies

“…However, most luminescent polymers undergo the wellknown AIQ effect during the self-assembly process, which greatly limits the technological applications. To evading this obstacle, attempts to use the AIEE materials for bioimaging have been reported [128]. These fluorescent structures can be simply formed through self-assembly of polymers with fluorescent conjugated segments or polymers bearing AIEE-active molecules.…”

Synthesis, characterization, and micellar behaviors of hydroxyethyl cellulose-graft-poly(lactide/ε-caprolactone/p-dioxanone)

“…The self-assemblies based on amphiphilic polymers are excellent carriers of waterinsoluble drugs and functional materials (Guo et al 2012). To date, the amphiphilic polymeric materials have been applied in a broad range of fields, such as drug delivery (Chang et al 2008;Chen et al 2011b;Miller et al 2013;Wang et al 2014b), bioimaging (Lu et al 2012;Zhang et al 2013) and sensing (Gong et al 2014;Wang et al 2012a). Lately, in response to the shortage of petroleum resources and the growing need for sustainable development, the natural polysaccharide-based amphiphiles have received a great deal of interest because of their promising properties, e.g., ready availability, good biocompatibility, biodegradability and nontoxicity (Hassani et al 2012).…”