Sugar decorated star-shaped (co)polymers with resveratrol-based core – physicochemical and biological properties

Abstract

Star-shaped glycopolymers due to the attractive combination of the physicochemical, morphological, self-assembly properties along with biological activity have gained increased attention as innovative agents in novel cancer therapies. Unfortunately, the production of these highly desirable biomaterials remains a challenge in modern macromolecular chemistry. The main reason for that is the low polymerizability of ionic glycomonomers originated from their steric congestion and the occurrence of ionic interactions that generally negatively influence the polymerization progress and hinder controllable reaction pathway. In this work, the new ionic sugar monomer was (co)polymerized for the first time via Activator Generated by Electron Transfer Atom Transfer Radical Polymerization (AGET ATRP) using a three-arm resveratrol-based core to obtain star-like (co)polymers. The obtained products were examined in terms of their physicochemical properties and morphology. Aside from the synthesis of these new glycopolymers, also a thorough description of their thermal properties, ability to self-assembly, the formation of stable superstructures was studied in detail. It was found that examined (co)polymers did not show any heterogeneities and phase separation, while their variation of glass transition temperature (Tg) was strictly related to the change in the number of glycomonomer. Also, the stability and shapes of formed superstructures strictly depend on their composition and topology. Finally, we have shown that synthesized carbohydrate-based polymers revealed high antiproliferative activity against several cancer cell lines (i.e., breast, colon, glioma, and lung cancer). The cytotoxic activity was particularly observed for star-shaped polymers that were systematically enhanced with the growing concentration of amine moieties and molecular weight. The results presented herein suggest that synthesized star-shaped glyco(co)polymers are promising as drug or gene carriers in anticancer therapies or anti-tumor agents, depending on their cytotoxicity. Graphical abstract

Sustainable Design of New Ionic Forms of Vitamin B3 and Their Utilization as Plant Protection Agents

“…Thus, the use of substances of natural origin as substrates has become a common strategy in recent years. Natural compounds that do not adversely affect human health, such as terpenes, , glycosides, − essential oil components, , or vitamins, are considered favorable raw materials in sustainable chemical processes. It should also be noted that the newly developed chemicals must also be obtained in an efficient and environmentally friendly manner.…”

Swelling Behavior of Novel Hydrogels Produced from Glucose-Based Ionic Monomers with Varying Cross-Linkers

“… 8 Using polymerizable ionic liquids as starting materials furthermore leads to either anionic, cationic, or zwitterionic hydrogels, which bear interesting possibilities in the medical field due to their ion exchange-controlled drug release. 9 In the case of carbohydrates, notable work has been done on glucose- and mannose-based acryl esters, 15 , 16 on carbohydrate vinyl ethers, 17 and even on cationic glucose-based monomers, 18 all of which bear isopropylidene or acetyl protecting groups and have been used for copolymerizations. However, hydrogels produced from carbohydrate-based monomers have, to the best of our knowledge, not been produced and investigated before.…”

Hydroxypropyl methacrylate stars as versatile carriers of therapeutic agents

“…A solution is to encapsulate them in the hydrophobic domain of amphiphilic nanocarriers, with the hydrophilic part as a stabilizer. Thus, researchers have made amphiphilic block copolymers with drugs in the self‐assembled structures in water and phosphate buffer saline (PBS) 6–11 . Others have used liposomes with drugs in the hydrophobic bilayer 12,13 …”

“…Thus, researchers have made amphiphilic block copolymers with drugs in the self-assembled structures in water and phosphate buffer saline (PBS). [6][7][8][9][10][11] Others have used liposomes with drugs in the hydrophobic bilayer. 12,13 Rhodamine B is a fluorescent dye and an anticancer agent.…”

“…It can reduce insulin sensitivity, combat atherosclerosis, and prevent or treat cancer. [20][21][22][23][24][25] Bielas et al 6 synthesized hybrid sugar/poly(2-dimethylamino ethyl methacrylate) star copolymers with a resveratrol-like core. They showed their cytotoxicity against various cancer cells.…”