A green route to synthesize poly(lactic acid)-based macromonomers in scCO2 for biodegradable nanoparticle production

Ferrari, Raffaele; Pecoraro, Claudio Maria; Storti, Giuseppe; Moscatelli, Davide

doi:10.1039/c4ra00333k

Cited by 10 publications

(9 citation statements)

References 40 publications

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“…HPMA was used as an initiator in the ROP of LT, which is similar to the previously described conditions. 21,22 For the HPMA-LA 8 macromonomers, 1 g of LT, 0.25 g of HPMA, 25 mg of Sn(Oct) 2 (i.e., Sn(Oct) 2 /HPMA molar ratio of 1 : 200) and 5 mg of sodium sulfate were added to the ask with stirring. The mixture was heated at 110 C for 18 hours while stirring.…”

Section: Methodsmentioning

confidence: 99%

Multiple strategies to produce lipophilic nanoparticles leaving water-soluble poly(HPMA)

2015

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N-(2-hydroxypropyl) methacrylamide (HPMA) can be used to produce watersoluble polymers with non-immumogenic properties that are widely used in drug delivery applications. In this study, an HPMA modification was proposed, which leads to lipophilic nanoparticle (NP) production. The ring opening polymerization of HPMA with a lactide (LT) was performed to obtain the reactive HPMA-LA n macromonomers with different average 2 chain lengths. The HPMA modification produced lipophilic macromonomer starting materials that were subsequently used to obtain polymer nanoparticles that are suitable for drug delivery applications of hydrophobic drugs. Different strategies were explored. First, emulsion-free radical polymerization was conducted to obtain the monodispersed PEGylated polymer NPs. Next, solvent polymerization was performed to produce a poly(HPMA-LA n )based polymer solution, which was used to produce the NPs via flash nanoprecipitation.Because these NPs are designed for drug delivery applications, their fast degradability in a biological medium was verified. Additionally, the ability to load and release a drug (i.e., dexamethasone) was verified for the NPs, which were synthesized using the proposed strategies, to demonstrate the effectiveness of the HPMA functionalization to obtain a system for delivering lipophilic drugs.To evaluate the release profile of the drug, 3 mL of the NP solution was loaded in a Slide-A-Lyzer cassette (Thermo Scientific, MW cutoff: 3.5 kDa) and dialyzed against 200 mL of PBS. The samples (0.2 µL) were withdrawn from the cassette after 1, 4, 8 and 24 h of dialysis and treated, as reported before, to determine the drug content in the NP solution. Figure 4. Evolution of NPs size (a), PDI (b) and relative scattered intensity (c) as a function of time in PBS for: poly-(HPMA-LA 4 -co-PEGMA 45 ) (■), poly-(HPMA-LA 6 -co-PEGMA 45 ) (•), and poly-(HPMA-LA 8 -co-PEGMA 45 ) (▲). The average particle size, shown in Figure 4a, remains almost constant during the time,despite the fact that the NPs that were based on HPMA-LA 6 and HPMA-LA 8 exhibited an increase (lower than 10% of the starting particle size), which is attributed to the swelling

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Section: Methodsmentioning

confidence: 99%

Multiple strategies to produce lipophilic nanoparticles leaving water-soluble poly(HPMA)

2015

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“…3-caprolactone, lactide, glycolide) exploiting a vinyl group bearing alcohol as the co-catalyst. 7,[21][22][23][24][25][26] Then, a direct synthesis exploiting HPMA as the co-catalyst in the ROP of the 3-caprolactone was tested using different HPMA/Sn(Oct) 2 mole ratios and a reaction temperature of 130 C. The conversion of both the HPMA and the caprolactone over time, evaluated via 1 H NMR, is reported in Fig. 1.…”

Section: Synthesis Of Hpma-cl5 Hydrophobic Macromonomermentioning

confidence: 99%

Poly(HPMA)-based copolymers with biodegradable side chains able to self assemble into nanoparticles

et al. 2017

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“…Supercritical fluid has tremendous potential in polymer modification and processing for its liquid‐like density and gas‐like diffusivity. In these processes, a micromolecule, as a supercritical fluid, dissolves, diffuses, and penetrates into polymer matrix, which will remarkably change the microenvironment of polymer, expand polymer volume, increase the ability of chain movement, plasticize polymer, and subsequently change thermodynamic properties of polymers, such as glass transition temperature depression, viscosity change, and tension decrease .…”

Section: Introductionmentioning

confidence: 99%

Diffusion and desorption of CO₂ in foamed polystyrene film

Qian

Cao

et al. 2017

J of Applied Polymer Sci

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Based on the existence of the pores in foamed polystyrene (PS), foamed-non-Fickian diffusion (FNFD) model was proposed, for the first time, to regress the desorption data obtained by gravimetric method. Results showed that FNFD model could accurately describe the diffusion behavior of CO 2 out of foamed PS, and well predict the solubility of CO 2 in foamed PS. The characterization of scanning electron microscopy indicated that there were abundant pores in the foamed PS, and the pores store most of CO 2 , which would diffuse in the pores, adsorb to the wall of the pores, penetrate across walls of the pores, diffuse in the matrix of PS, and desorb out of PS. The mass of CO 2 in the pores of foamed PS was expressed as a function of foaming pressure and temperature according to foaming kinetics. Results showed that the values calculated by this function agreed well with the values obtained from the FNFD model.

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A green route to synthesize poly(lactic acid)-based macromonomers in scCO2 for biodegradable nanoparticle production

Cited by 10 publications

References 40 publications

Multiple strategies to produce lipophilic nanoparticles leaving water-soluble poly(HPMA)

Multiple strategies to produce lipophilic nanoparticles leaving water-soluble poly(HPMA)

Poly(HPMA)-based copolymers with biodegradable side chains able to self assemble into nanoparticles

Diffusion and desorption of CO₂ in foamed polystyrene film

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A green route to synthesize poly(lactic acid)-based macromonomers in scCO2 for biodegradable nanoparticle production

Cited by 10 publications

References 40 publications

Multiple strategies to produce lipophilic nanoparticles leaving water-soluble poly(HPMA)

Multiple strategies to produce lipophilic nanoparticles leaving water-soluble poly(HPMA)

Poly(HPMA)-based copolymers with biodegradable side chains able to self assemble into nanoparticles

Diffusion and desorption of CO2 in foamed polystyrene film

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Diffusion and desorption of CO₂ in foamed polystyrene film