Polyvinylpyrrolidone (PVP, MW 10, and 40 kDa), sulforhodamine B (SRB) and coumarin 314 fluorescence dyes were purchased from Sigma-Aldrich (St. Louis, MO, USA). Poly(DL-lactide-co-glycolide) (50:50 PLGA, ester-terminated, inherent viscosity 0.26–0.54 dL/g) was purchased from Lactel Absorbable Polymers (Birmingham, AL, USA). Poly(lactic acid) (PLA, Ingeo 4043D, 98% L-lactide, with weight average molecular weight of 111 kg/mol) was purchased from NatureWorks (Minnetonka, MN, USA). HRP (lyophilized powder, 85 unit/mg), ethyl acetate, dimethyl carbonate, ethanol, glycerol (all certified ACS grade) and tissue marking dye (Richard-Allen ScientificTM Mark-ItTM, blue) were purchased from Fisher Scientific (Waltham, MA, USA). Polydimethylsiloxane (PDMS, Sylgard 184) was purchased from Dow Corning (Midland, MI, USA). Multipurpose aluminum blocks (alloy 6061) were purchased from McMaster-Carr (Elmhurst, IL, USA). End mills were purchased from Ultra-Tool (Huntington Beach, CA, USA).
Dimethyl carbonate
Manufactured by Thermo Fisher Scientific
Sourced in Germany
Dimethyl carbonate is a colorless, volatile organic compound. It is a versatile chemical that can be used as a solvent, reagent, and fuel additive in various industrial and laboratory applications.
Automatically generated - may contain errors
Lab products found in correlation
Ethyl acetate, by Thermo Fisher Scientific (1 mentions)
Glycerol, by Thermo Fisher Scientific (1 mentions)
Ethanol, by Thermo Fisher Scientific (1 mentions)
Sulforhodamine b srb, by Merck Group (1 mentions)
Falcon tube, by BD (1 mentions)
Dimethyl carbonate, by Merck Group (1 mentions)
Syringe pump, by Harvard Apparatus (1 mentions)
Chloroform, by Scharlab (1 mentions)
Dichloromethane, by Scharlab (1 mentions)
1 4 dioxane, by Scharlab (1 mentions)
Polyethylene glycol peg, by Merck Group (1 mentions)
Dimethyl sulfoxide (dmso), by Scharlab (1 mentions)
6510 q tof lc ms spectrometer, by Agilent Technologies (1 mentions)
Elemental analyzer model 2400 chn, by PerkinElmer (1 mentions)
Cdcl3, by Merck Group (1 mentions)
Methyl acrylate, by Merck Group (1 mentions)
Sephadex lh 20, by Merck Group (1 mentions)
1 8 octanediol, by Merck Group (1 mentions)
Hexamethylene diisocyanate, by Merck Group (1 mentions)
Dimethyl sulfoxide (dmso), by Thermo Fisher Scientific (1 mentions)
6 protocols using dimethyl carbonate
1
Fabrication of Polymeric Nano-Micro Particles
2
PLGA TIPS Microcarrier Fabrication
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PLGA TIPS microcarriers were prepared as previously described (Ahmadi et al., 2011) . Poly (D, L-lactideco-glycolide) 75:25 (Purasorb PDLG7507, Purac Biomaterials, Gorinchem, Netherlands) was dissolved in dimethylcarbonate (1:24 (w/v)) (Sigma-Aldrich) using magnetic stirring overnight. The polymer solution was fed into a Nisco Encapsulator Unit (Nisco Engineering, Zurich, Switzerland) by a syringe pump (Harvard Apparatus, Kent, UK), connected by a silicone tube, at a constant rate of 3 mL min -1 . The vibration frequency of the nozzle was kept at 1.80 kHz and the amplitude of frequency at 100 %. The polymer droplets were delivered through a 150 µm sapphire nozzle.
Polymer droplets were collected in a polyethylene beaker containing 250 mL of liquid nitrogen. The frozen droplets were equilibrated in the liquid nitrogen, transferred to 50 mL Falcon™ tubes (BD Biosciences, Oxford, UK) and stored frozen at -80 °C for 10 min. Samples were freeze-dried (MicroModulyo, Fisher Scientific) for 24 h to allow sublimation of residual dimethylcarbonate. For the experiments conducted in the current study PLGA TIPS microcarriers were sieved to produce microspheres with a mean diameter of 337.5 ± 87.5 µm.
Polymer droplets were collected in a polyethylene beaker containing 250 mL of liquid nitrogen. The frozen droplets were equilibrated in the liquid nitrogen, transferred to 50 mL Falcon™ tubes (BD Biosciences, Oxford, UK) and stored frozen at -80 °C for 10 min. Samples were freeze-dried (MicroModulyo, Fisher Scientific) for 24 h to allow sublimation of residual dimethylcarbonate. For the experiments conducted in the current study PLGA TIPS microcarriers were sieved to produce microspheres with a mean diameter of 337.5 ± 87.5 µm.
3
Biobased Polymer Fabrication via PHBH and PEG
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Poly(3-hydroxybutyrate−co−3−hydroxyhexanoate) with 11% of hydroxyhexanoate (HH) content (PHBH) and molecular weights of 500–600 kDa was kindly gifted by Kaneka Co, Brussels, Belgium. Dichloromethane, chloroform, dimethyl sulfoxide, 1,4 dioxane, poly(ethylene glycol) (PEG) with molecular weights of 200, 400, and 600 g/mol, were purchased from Scharlau, Barcelona, Spain. poly(ethylene glycol) (PEG) with molecular weight of 100 kDa was purchased from Sigma Aldrich, Bavaria, Germany. Dimethyl carbonate was purchased from Alfa Aesar, Kandel, Germany. Isosorbide (C6H10O4) with a purity of 98% was purchased from Acros Organics, Geel, Belgium. Glycerol diacetomonolaurate (Biocizer ®) with purity ≥ 95% was kindly gifted by Riken Vitamin Co, Tokyo, Japan. All chemicals were used without further purification.
4
Grubbs Catalyst-Mediated Metathesis
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Methylacrylate was purchased from Sigma-Aldrich and stored over 3 Å molecular sieves under an inert atmosphere. Dimethyl carbonate was purchased from Alfa-Aesar and was distilled under an inert atmosphere of argon and stored over 3Å molecular sieves.
Hoveyda-Grubbs II catalyst M72 (C627) was provided by Umicore. Column chromatography (CC) was performed with silica gel (230-400 mesh, Merck) and Sephadex LH-20 (Aldrich), while thin layer chromatography (TLC) separations were carried out on silica gel 60 PF254 (Merck). 1 H and 13 C nuclear magnetic resonance (NMR) spectra were recorded, respectively, at 400 and 100 MHz on a Bruker Avance III Ascend 400 spectrometer using CDCl3 (Sigma-Aldrich) as the solvent and using the residual signal of CHCl3 as the internal standard ( 7.26 vs TMS). Electrospray ionization -high resolution mass spectrometry (ESI-HRMS) data were measured on an Agilent 6510 Q-TOF LC/MS spectrometer, using an ESI ion source operating at positive mode. Elemental analysis was obtained in a Perkin-Elmer Elemental Analyzer model 2400 CHN. Infrared (IR) spectra were recorded with a Shimadzu FT-IR Prestige-21 instrument.
Accepted manuscript / Clean copy
Hoveyda-Grubbs II catalyst M72 (C627) was provided by Umicore. Column chromatography (CC) was performed with silica gel (230-400 mesh, Merck) and Sephadex LH-20 (Aldrich), while thin layer chromatography (TLC) separations were carried out on silica gel 60 PF254 (Merck). 1 H and 13 C nuclear magnetic resonance (NMR) spectra were recorded, respectively, at 400 and 100 MHz on a Bruker Avance III Ascend 400 spectrometer using CDCl3 (Sigma-Aldrich) as the solvent and using the residual signal of CHCl3 as the internal standard ( 7.26 vs TMS). Electrospray ionization -high resolution mass spectrometry (ESI-HRMS) data were measured on an Agilent 6510 Q-TOF LC/MS spectrometer, using an ESI ion source operating at positive mode. Elemental analysis was obtained in a Perkin-Elmer Elemental Analyzer model 2400 CHN. Infrared (IR) spectra were recorded with a Shimadzu FT-IR Prestige-21 instrument.
Accepted manuscript / Clean copy
5
Synthesis of Biodegradable Polyester Polymers
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A detailed description of the applied experimental procedure and used chemicals is provided in the Supporting Information. Important chemicals included: rac-dilactide (Bio Invigor, Taiwan, recrystallized from ethyl acetate; the amount of meso-dilactide was considered to be neglectable), diglycolide (Boehringer Ingelheim GmbH, Germany), dimethyl carbonate (Alfa Aesar, USA) dibutyl tin dilaurate (Merck Schuhardt, Hohenbrunn, Germany), dibutyl tin (IV)oxide, hexamethylene diisocyanate (HDI), 2,2,4-and 2,4,4-trimethyl hexamethylene diisocyanate isomeric mixture (TMDI), and 1,8-octanediol (all from Fluka Analytical, Sigma-Aldrich), L-lysine diisocyanate ethyl ester (LDI; Shanghai Infinite Chemicals, China), and poly(vinyl alcohol) (PVA; Mowiol 4-88, Kuraray Europe GmbH, Frankfurt, Germany).
6
Diglycerol Synthesis and Characterization
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Diglycerol was kindly provided by Ivony S.A (Brussels, Belgium), dimethyl carbonate (99 %) from Alfa Aesar. Dimethylsulfoxide (99 %), potassium carbonate (>99 %) and triethylamine, NEt 3 , (>99 %) were supplied from Fisher Chemical. Deuterated DMSO (DMSO-d 6 , ≥ 99.9 %), 1, 5,
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