Synthesis of Amphiphilic Diblock Poly-amido-saccharides and Self-Assembly of Polymeric Nanostructures

Abstract

We report the synthesis of diblock poly-amido-saccharides (PASs) by sequential addition of variably protected glucose and galactose monomers via living anionic ring-opening polymerization. Diblock polymers with varied polymer length, hydrophobic to hydrophilic ratio, and stereochemistry of hydrophilic component were synthesized, characterized by NMR, IR, and GPC. These amphiphilic polymers self-assemble in water to form nanoparticles as determined by DLS, SEM, and cryo-TEM. Amphiphilic polymers with glucose-PAS hydrophobic and galactose-PAS hydrophilic blocks and degree of polymerization of 100 (100-EtGlc1-OHGal3diblock PAS) form spherical nanostructures and are non-cytotoxic.

Multifunctional Alternating “Bitter-Sweet” Macromolecular Architecture

“…The fluorescence spectra of pyrene recorded at increasing concentrations of P5GC10 (from 0.00025 to 1.0 mg/mL) are shown in Figure B, while the dependence of the I 384 / I 372 intensity ratio as a function of the concentration of the copolymer is reported in Figure C. The I 384 / I 372 was found to increase abruptly above a given concentration of P5GC1 0, signaling the onset of the aggregation process . The crossing point of the two straight lines in Figure C denoted the CAC value of P5GC10 as 63 μg/mL.…”

“…The I 384 /I 372 was found to increase abruptly above a given concentration of P5GC10, signaling the onset of the aggregation process. 46 The crossing point of the two straight lines in Figure 2C denoted the CAC value of P5GC10 as 63 μg/mL. Similarly, CAC values of P5GC5 and P5GC15 were determined as 56 and 69 μg/mL, respectively (Figure S11).…”

Glycopolymers based on carbohydrate or vinyl backbones and their biomedical applications

“…3b, the majority of current studies on ROP monomers focus on several five- and six-membered rings with high ring strain, such as the cyclic carbonates/phosphates reported by the Wooley group, 60–69 the cyclic ethers reported by the Buchard group 8–10,70,71 and the cyclic lactam reported by the Grinstaff group. 72–75 However, the field has developed slowly because the construction of a new ring often requires tedious protection and deprotection processes.…”

“…17). 75 β-Peptides with promising biological activities were introduced as part of the block sugar-based polymer to increase the antibacterial properties. Pethe and Chan-Park et al prepared a hydrophilic block polymer composed of PAS and poly(β-lysine) by anionic ROCOP.…”

“…This journal is © The Royal Society of Chemistry 2023 ethers reported by the Buchard group [8][9][10]70,71 and the cyclic lactam reported by the Grinstaff group. [72][73][74][75] However, the field has developed slowly because the construction of a new ring often requires tedious protection and deprotection processes. 2.2.1 Bicyclic sugar-based carbonate monomers.…”