Correction: Wound healing properties of hyaluronan derivatives bearing ferulate residues

Correction for 'Wound healing properties of hyaluronan derivatives bearing ferulate residues' by Giuseppe Valacchi et al., J. Mater. Chem. B, 2015, DOI: 10.1039/c5tb00661a

Structural manipulation of the conjugated phenyl moiety in 3-phenylbenzofulvene monomers: Effects on spontaneous polymerization

Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a-h were synthesized in order to investigate the effects of differently substituted aromatic rings in position 3 of the benzofulvene scaffold on spontaneous polymerization. The newly synthesized monomers maintained the tendency toward spontaneous polymerization. However, monomer 1a, bearing an ortho-methoxy substituted phenyl, polymerized hardly, thus producing low polymerization yields, inhomogeneous structure, and low molecular weight of the obtained polymeric material. This result suggested the importance of the presence of hydrogen atoms in the 2'-position to achieve productive interactions among the monomers in the recognition step preluding the spontaneous polymerization and among the monomeric units in the polybenzofulvene backbones. Moreover, this study paves the way to modify the pendant rings in position 3 of the indene scaffold to synthesize new polybenzofulvene derivatives variously decorated

Design and development of hyaluronan-functionalized polybenzofulvene nanoparticles as CD44 receptor mediated drug delivery system

A tri-component polymer brush (TCPB), composed of a polybenzofulvene copolymer bearing low molecular weight hyaluronic acid (HA) on the surface of its cylindrical brush-like backbone and oligo-PEG fractions, was employed in the preparation of 350 nm nanostructured drug delivery systems capable of delivering the anticancer drug doxorubicin. The obtained drug delivery systems were characterized on the basis of drug loading and release, dimensions and zeta potential, morphology and in vitro cell activity, and uptake on three different human cell lines, namely the bronchial epithelial 16HBE, the breast adenocarcinoma MCF-7, and the colon cancer HCT116 cells. Finally, the ability of doxorubicin-loaded TCPB nanoparticles (DOXO-TCPB) to be internalized into cancer cells by CD44 receptor mediated uptake was assessed by means of uptake studies in HCT cells. These data were supported by anti-CD44-FITC staining assay. The proposed TCPB nanostructured drug delivery systems have many potential applications in nanomedicine, including cancer targeted drug delivery

Reversible polymerization techniques leading to π-stacked polymers

Serendipity has often played a pivotal role in research and, in harmony with this function, it has had a fundamental responsibility in the discovery of the thermoreversible spontaneous polymerization of benzofulvene derivatives. After a decade from the discovery of poly-BF1, the present chapter narrates the history of polybenzofulvene derivatives from the discovery to the latest developments. Now that more than 50 polymers belonging to this family have been synthesized and the relevant studies have been published in the most important journals dealing with polymer science, the spontaneous polymerization of benzofulvene monomers and the special features of the corresponding polymers appear to become a well-established topic. The chapter provides an in-depth analysis of the literature on the subject, from the preparation methods to the characterization of polybenzofulvene derivatives, the study of their properties, and the evaluation of the possible applications

π-Stacked polymers in drug delivery applications

Polybenzofulvenes are \u3c0-stacked polymers, which can be synthesized by spontaneous polymerization of the corresponding monomers without the use of catalysts or initiators. Therefore, they can be obtained completely free from byproducts, impurities, or harmful substances. The absence of any relevant toxic effects and cell viability impairments allows PEGylated polybenzofulvene brushes to be potentially functional in a wide range of biological, biomedical, and biotechnological applications. Moreover, the properties of these polymers, in terms of interaction with pharmacological active agents and the ability to self-assemble into nanoaggregates or a quite compact physical gel useful as drug delivery systems (DDSs), can be controlled by varying side chain moieties. Owing to the important role played by self-assembling DDS in the fields of the material and life sciences, the interaction and the delivery ability of polybenzofulvene polymers with model drug or protein molecules was definitively demonstrated. The present paper reviews the applications of polybenzofulvene derivatives in the drug delivery of a range of different drug molecules ranging from small molecules to peptides and proteins

Side chain engineering in π-stacked polybenzofulvene derivatives bearing electron-rich chromophores for OLED applications

In order to obtain new polymeric materials endowed with improved optoelectronic performances, suitable side chain engineering was designed to insert different chromophores showing electron donating ability [i.e. triphenylamine (TPA) and 9-methylcarbazole (MCBZ) residues] in two different key positions (i.e. 6 and 4′) of the 3-phenylindene scaffold of the polybenzofulvene monomeric units. Among the four newly-synthesized polybenzofulvene derivatives, those bearing triphenylamine moieties were found to show higher emissive properties with respect to the corresponding carbazole derivatives. Moreover, the preliminary OLED devices prepared with the triphenylamine-based polymers showed promising features, but the role of the aggregation process in affecting the emission properties of poly-6-TPA-BF3k suggested that extensive device development studies are required in order to maximize polybenzofulvene performances in OLED applications

Highly emissive supramolecular assemblies based on π-stacked polybenzofulvene hosts and a benzothiadiazole guest

Two new polymers envelop a benzothiadiazole dye by π-stacking interactions and a complete FRET is obtained.</p

Development of subnanomolar-affinity serotonin 5-HT4 receptor ligands based on quinoline structures

Two small series of quinoline derivatives were designed starting from previously published quinoline derivatives 7a and b in order to obtain information about their interaction with the 5-HT4R binding site. Initially, the structure of 7a and b was modified by replacing their basic moiety with that of partial agonist 4 (ML10302) or with that of reference ligand 6 (RS-67-333). Then, the aromatic moieties of 4-quinolinecarboxylates 7a, d-f, and h-k or 4-quinolinecarboxamides 7b, c, and g were modified into those of 2-quinolinecarboxamides 9a-e. Very interestingly, this structure-affinity relationship study led to the discovery of 7h-j as novel 5-HT4R ligands showing Ki values in the subnanomolar range. The structures of all these compounds contain the N-butyl-4-piperidinylmethyl substituent, which appear to behave as an optimized basic moiety in the interaction of these 4-quinolinecarboxylates with the 5-HT4R binding site. However, this basic moiety was ineffective in providing 5-HT4R affinity in the corresponding 4-quinolinecarboxamide 7g, but it did in 2-quinolinecarboxamide ligands 9c-e. Thus, a subtle interrelationship of several structural parameters appeared to play a major role in the interaction of the ligands with the 5-HT4R binding site. They include the kind of basic moiety, the position of the carbonyl linking group with respect to the aromatic moiety and its orientation, which could be affected by the presence of the intramolecular H-bond as in compounds 9c-e