Chitosan 70/1000 was purchased by Heppe Medical Chitosan GmbH (HMC+, Halle, Germany). All Fmoc protected amino acids, resins, coupling reagents 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (HBTU), and Oxima Pure, used for peptide synthesis were from Novabiochem (Merck KGaA, Darmstadt, Germany). Piperidine, diethyl ether, N, N-diisopropylethylamine (DIPEA), trifluoroacetic acid (TFA), and dichloromethane (DCM) were from Biosolve (Leenderweg, Valkenswaard, The Netherlands). All other solvents such as N, N-dimethylformamide (DMF) and reagents as sodium (meta)periodate (NaIO4) were from Sigma-Aldrich (Merck KGaA, Darmstadt, Germany) unless otherwise indicated.
Diethyl ether
Manufactured by Biosolve
Sourced in France, Germany
Diethyl ether is a colorless, highly volatile, and flammable liquid. It has a characteristic sweet odor. Diethyl ether is commonly used as a laboratory solvent and reagent in various chemical processes and analyses.
Automatically generated - may contain errors
Lab products found in correlation
Acetonitrile, by Biosolve (4 mentions)
Trifluoroacetic acid tfa, by Biosolve (2 mentions)
Lc ms grade water, by Biosolve (2 mentions)
Acetonitrile lc ms grade, by Biosolve (2 mentions)
Hydrochloric acid (hcl), by Merck Group (2 mentions)
Sodium hydroxide (naoh), by Merck Group (2 mentions)
Thiophenol, by Merck Group (2 mentions)
Heptane, by Biosolve (2 mentions)
2 1h benzotriazol 1 yl 1 1 3 3 tetramethyluronium fluorophosphate hbtu, by Iris Biotech (2 mentions)
N fmoc protected amino acids, by Iris Biotech (2 mentions)
Dichloromethane dcm, by Biosolve (1 mentions)
N dimethylformamide dmf, by Merck Group (1 mentions)
Fmoc protected amino acids, by Merck Group (1 mentions)
Piperidine, by Biosolve (1 mentions)
3 mercaptopropionic acid, by Merck Group (1 mentions)
Tris 2 carboxyethyl phosphine hydrochloride, by Merck Group (1 mentions)
Trifluoroacetic acid, by Biosolve (1 mentions)
Diisopropylcarbodiimide, by Iris Biotech (1 mentions)
N hydroxybenzotriazole, by Merck Group (1 mentions)
Piperidine, by Iris Biotech (1 mentions)
9 protocols using diethyl ether
1
Chitosan-Based Peptide Synthesis Protocol
2
Solid-Phase Peptide Synthesis Reagents
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1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium fluorophosphate (HBTU) and N-Fmoc-protected amino acids were obtained from Iris Biotech GmbH. Piperidine, diisopropylcarbodiimide (DIC), N-hydroxybenzotriazole (HOBt), MPAA (97%, MPAA), 3-mercaptopropionic acid (MPA), tris(2-carboxyethyl)phosphine hydrochloride (≥98%, TCEP·HCl), thiophenol, triisopropylsilane (TIS), guanidine hydrochloride (≥99%, Gn·HCl), hydrochloric acid (reagent grade, 37%), and sodium hydroxide (pellets, 97%) as well as other reagents were purchased from Sigma Aldrich, Acros Organics or Merck and were of the purest grade available. Peptide synthesis grade N,N-dimethylformamide (DMF), dichloromethane, diethyl ether, acetonitrile, heptane, LC-MS-grade acetonitrile (0.1% TFA), LC-MS grade water (0.1% TFA), N,N-diisopropylethylamine (DIEA), acetic anhydride (Ac2O), and trifluoroacetic acid (TFA) were purchased from Biosolve and Fisher-Chemical. NovaSyn TGR solid support was purchased from Sigma Aldrich. Bis(2-sulfenylethyl)amino trityl 1% divinylbenzene cross-linked polystyrene solid support (SEA PS) was produced on demand by Roowin. Solvents and reagents were used as received.
3
GC-MS analysis of bacterial SCFAs
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After measuring the optical density (OD600nm) of the overnight bacterial culture, supernatants were collected after centrifugation (15 min at 6000 rpm) and kept at −20 °C. SCFA were measured as previously described [35 (link),38 (link)] with slight modifications. Briefly, after the addition of the SCFA standards, each sample was acidified and then extracted using diethyl ether (Biosolve, Dieuze, France), with gentle stirring for 1 h and centrifugation for 2 min at 5000 rpm at 4 °C. The organic layers were derivatized using tert-butyldimethylsilyl imidazole (Sigma-Aldrich), and samples were incubated for 30 min at 60 °C before analysis by gas chromatography-mass spectrometry (GC-MS 7890A-5975C; Agilent Technologies, Montpellier, France) using a 30 m × 0.25 mm × 0.25 µm capillary column (HP1-MS; Agilent Technologies), as previously described [35 (link)]. The SCFA concentrations were reported at the mean concentrations divided by the optical density of the culture and expressed as mean ± SEM.
4
Synthesis of Cationic Surfactant C16H33-[1,2-dimethyl-3-imidazolium]
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In total,
0.013 mol of 1-bromohexadecane (Sigma-Aldrich, 98.0%) and 0.016 mol
of 1,2-dimethylimidazole (Sigma-Aldrich, 97.0%) were dissolved in
a 50 mL mixture of ethanol (Biosolve, 99.9%) and acetonitrile (Biosolve,
99.9%) (1:5 molar ratio) and heated at 70 °C for 16 h under nitrogen
atmosphere. After evaporation of the solvents and addition of diethyl
ether (Biosolve, 99.5%), a white powder precipitated out of solution.
This solid product was filtered and dried in a vacuum oven at 50 °C
for 12 h. The purity of the organic surfactant C16H33-[1,2-dimethyl-3-imidazolium] was analyzed by 1H, 13C, gHSQC, and gCOSY NMR after dissolution in CDCl3 (Figures S1–S4 ). The product
yield was 75%.
0.013 mol of 1-bromohexadecane (Sigma-Aldrich, 98.0%) and 0.016 mol
of 1,2-dimethylimidazole (Sigma-Aldrich, 97.0%) were dissolved in
a 50 mL mixture of ethanol (Biosolve, 99.9%) and acetonitrile (Biosolve,
99.9%) (1:5 molar ratio) and heated at 70 °C for 16 h under nitrogen
atmosphere. After evaporation of the solvents and addition of diethyl
ether (Biosolve, 99.5%), a white powder precipitated out of solution.
This solid product was filtered and dried in a vacuum oven at 50 °C
for 12 h. The purity of the organic surfactant C16H33-[1,2-dimethyl-3-imidazolium] was analyzed by 1H, 13C, gHSQC, and gCOSY NMR after dissolution in CDCl3 (
yield was 75%.
5
Synthesis and Characterization of Trimethylene Carbonate-Based Adhesives
6
Cellular Imaging with Fluorescent Probes
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All materials were obtained from Sigma-Aldrich (Zwijndrecht, The
Netherlands) and used as received unless indicated otherwise. Tetrahydrofuran
(THF), N,N-dimethylformamide (DMF),
and diethyl ether were purchased from Biosolve (Valkenswaard, The
Netherlands). PBS buffer pH 7.4 (8.2 g/L NaCl, 3.1 g/L Na2HPO4·12H2O, 0.3 g/L NaH2PO4·2H2O) was purchased from B. Braun (Melsungen,
Germany). Dulbecco’s modified Eagle’s medium (DMEM)
and fetal bovine serum (FBS) were purchased from Sigma-Aldrich (Zwijndrecht,
The Netherlands). Hoechst 33342 solution and phenol red free OptiMEM
medium were purchased from Thermo Fisher Scientific (Bleiswijk, The
Netherlands).
Netherlands) and used as received unless indicated otherwise. Tetrahydrofuran
(THF), N,N-dimethylformamide (DMF),
and diethyl ether were purchased from Biosolve (Valkenswaard, The
Netherlands). PBS buffer pH 7.4 (8.2 g/L NaCl, 3.1 g/L Na2HPO4·12H2O, 0.3 g/L NaH2PO4·2H2O) was purchased from B. Braun (Melsungen,
Germany). Dulbecco’s modified Eagle’s medium (DMEM)
and fetal bovine serum (FBS) were purchased from Sigma-Aldrich (Zwijndrecht,
The Netherlands). Hoechst 33342 solution and phenol red free OptiMEM
medium were purchased from Thermo Fisher Scientific (Bleiswijk, The
Netherlands).
7
Boc-NH-PEG5000-OH Synthesis and Characterization
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All materials were obtained
from Sigma-Aldrich (Zwijndrecht, The Netherlands) and used as received
unless otherwise noted. α-tert-Butyloxycarbonylamino-ω-hydroxypoly(ethylene
glycol) with PEG molecular weight of 5000 Da (Boc-NH-PEG5000-OH) was obtained from Iris Biotech GmbH (Marktredwitz, Germany)
and dried overnight in a vacuum oven at room temperature (RT) before
use. 4-(Dimethylamino)pyridinium-4-toluenesulfonate (DPTS) was
prepared according to a literature procedure.24 (link) Triethylamine (TEA) and 2,4,6-trinitrobenzenesulfonic acid
(TNBSA) solution in methanol (5% w/v) were obtained from Thermo Fisher
Scientific (Bleiswijk, The Netherlands). Peptide grade dichloromethane
(DCM), N,N-dimethylformamide (DMF), tetrahydrofuran (THF), and diethyl
ether were purchased from Biosolve (Valkenswaard, The Netherlands).
All solvents were dried by molecular sieves for 24 h before use. Prior
to use, 2-(dimethylamino)ethyl methacrylate (DMAEMA) was passed through
a column of alumina to remove the inhibitor. Slide-A-lyzer dialysis
cassettes (Mw cutoff: 3.5 and 10 kDa)
were obtained from Thermo Fisher Scientific (Bleiswijk, The Netherlands).
from Sigma-Aldrich (Zwijndrecht, The Netherlands) and used as received
unless otherwise noted. α-tert-Butyloxycarbonylamino-ω-hydroxypoly(ethylene
glycol) with PEG molecular weight of 5000 Da (Boc-NH-PEG5000-OH) was obtained from Iris Biotech GmbH (Marktredwitz, Germany)
and dried overnight in a vacuum oven at room temperature (RT) before
use. 4-(Dimethylamino)pyridinium-4-toluenesulfonate (DPTS) was
prepared according to a literature procedure.24 (link) Triethylamine (TEA) and 2,4,6-trinitrobenzenesulfonic acid
(TNBSA) solution in methanol (5% w/v) were obtained from Thermo Fisher
Scientific (Bleiswijk, The Netherlands). Peptide grade dichloromethane
(DCM), N,N-dimethylformamide (DMF), tetrahydrofuran (THF), and diethyl
ether were purchased from Biosolve (Valkenswaard, The Netherlands).
All solvents were dried by molecular sieves for 24 h before use. Prior
to use, 2-(dimethylamino)ethyl methacrylate (DMAEMA) was passed through
a column of alumina to remove the inhibitor. Slide-A-lyzer dialysis
cassettes (Mw cutoff: 3.5 and 10 kDa)
were obtained from Thermo Fisher Scientific (Bleiswijk, The Netherlands).
8
Peptide Synthesis with HBTU and Fmoc-Protected Amino Acids
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2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium fluorophosphate (HBTU) and N-Fmoc protected amino acids were obtained from Iris Biotech GmbH. 4-Mercaptophenylacetic acid (97%, MPAA), 3-mercaptopropionic acid (MPA), tris(2-carboxyethyl)phosphine hydrochloride (≥98%, TCEP), thiophenol, triisopropylsilane (TIS), guanidine hydrochloride (≥99%), sodium phosphate dibasic dihydrate (≥99%), hydrochloric acid (reagent grade, 37%), and sodium hydroxide (pellets, 97%) were purchased from Sigma-Aldrich. All other reagents were purchased from Acros Organics or Merck and were of the purest grade available. Peptide synthesis grade N,N-dimethylformamide, dichloromethane, diethylether, acetonitrile, heptane, LC–MS-grade acetonitrile (0.1% TFA), LC–MS-grade water (0.1% TFA), N,N-diisopropylethylamine (DIEA), and acetic anhydride were purchased from Biosolve and Fisher-Chemical. Trifluoroacetic acid (TFA) was obtained from Biosolve. Decane (synthesis grade) was purchased from Merck. Solvents and reagents were used as received. Water was purified with a Milli-Q UltraPure Water Purification System.
9
Synthesis of PLGA Nanoparticles with PVA
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FS10 as TFA salt was purchased from GenScript (Piscataway, NJ, USA). N-cyclohexyl-3-aminopropanesulfonic acid (CAPS), (4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid) (HEPES), phosphate buffer saline (PBS, pH 7.4), poly(vinyl alcohol) (PVA; MW 30,000–70,000; 88% hydrolyzed), tin(II) 2-ethylhexanoate (Sn(Oct)2) and poly(ethylene glycol) monomethyl ether (MePEG5000) were obtained from Sigma Aldrich (St. Louis, MO, USA). D,L-lactide, glycolide, and poly(lactic-co-glycolic acid) (25 kDa uncapped PLGA, lactide:glycolide 50:50) were obtained from Corbion (Amsterdam, The Netherlands). N,N-dimethylformamide (DMF), dichloromethane (DCM), chloroform, diethyl ether, and acetonitrile (ACN) were purchased from Biosolve (Valkenswaard, The Netherlands). Toluene obtained from Acros (Beerse, Belgium), was stored over 3 Å molecular sieves (Sigma Aldrich, St. Louis, MO, USA). Unless otherwise stated, all chemicals were used as received.
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