The 8-arm poly(ethylene glycol) (8-arm PEG, hexaglycerol core, Mw = 20,000) was acquired from Jenkem Technology (Allen, Texas, USA) and purified before use by dissolution in dichloromethane and precipitation in cold diethyl ether. Hyaluronic acid sodium salt (Mw = 15–25 kg/mol) was purchased from Contipro. The polymer was dried by lyophilization overnight before use. p-Nitrophenyl chloroformate (PNC, 96%) was purchased from Sigma-Aldrich (Zwijndrecht, the Netherlands) and was sublimated before use. Anhydrous dimethylformamide (DMF, 99.8%), tyramine (99%), anhydrous pyridine (99.8%), hydrogen peroxide (H2O2, 30 wt% in H2O), lithium chloride and HRP (261 U/mg) were obtained from Sigma-Aldrich and used without further purification. dichloromethane (stabilized by Amylene, ≥99.9%), ethanol (99.8%) and diethyl ether (stabilized by BHT, ≥99.5%) were obtained from Biosolve (Valkenswaard, The Netherlands) and used as received. Dialysis membranes (Spectra/Por molecular porous membrane tubing 6, MWCO: 1 kDa) were acquired from Spectrum Laboratories, Inc. (Breda, The Netherlands) and rinsed with distilled water before use. Deuterated solvents were purchased from Aldrich. Phosphate buffered saline (PBS, 150 mM, pH 7.4) was purchased from Gibco Life Technologies Ltd (Paisley, UK).
Dichloromethane
Manufactured by Biosolve
Sourced in Netherlands, France
Dichloromethane is a colorless, volatile organic compound commonly used as a solvent in laboratory applications. It has a low boiling point and is miscible with a wide range of organic solvents, making it a versatile tool for various extraction and purification processes.
Automatically generated - may contain errors
Lab products found in correlation
Methanol, by Biosolve (4 mentions)
Ethyl acetate, by Biosolve (3 mentions)
Piperidine, by Biosolve (3 mentions)
N n diisopropylethylamine diea, by Biosolve (3 mentions)
Acetonitrile, by Biosolve (3 mentions)
Tetrahydrofuran, by Biosolve (2 mentions)
Chloroform, by Biosolve (2 mentions)
Acetonitrile, by Merck Group (2 mentions)
Triethoxysilane tes, by Merck Group (2 mentions)
Hydrochloric acid (hcl), by Merck Group (2 mentions)
Hplc grade acetonitrile, by Biosolve (2 mentions)
Peptide grade n n dimethylformamide dmf, by Biosolve (2 mentions)
1 3 dioxolane, by Thermo Fisher Scientific (2 mentions)
Anhydrous pyridine, by Merck Group (1 mentions)
Deuterated solvent, by Merck Group (1 mentions)
Hydrogen peroxide, by Merck Group (1 mentions)
Lithium chloride (licl), by Merck Group (1 mentions)
Anhydrous dimethylformamide, by Merck Group (1 mentions)
Tyramine, by Merck Group (1 mentions)
P nitrophenyl chloroformate, by Merck Group (1 mentions)
18 protocols using dichloromethane
1
Hyaluronic Acid-PEG Hydrogel Synthesis
2
Sunitinib-Loaded Polymeric Nanoparticles
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Sunitinib malate was obtained from LC laboratories, USA. Poly(vinyl alcohol) (PVA; M w 30,000-70,000; 88% hydrolyzed), Tween 20, stannous octoate and dimethyl sulfoxide (DMSO) were obtained from Sigma Aldrich, Germany. Dichloromethane (DCM), acetonitrile and tetrahydrofuran (THF) were purchased from Biosolve (Valkenswaard, The Netherlands). PEG1000, 1,4-butanediol and 1,4 dioxane were purchased from Acros (Geel, Belgium), 1,4butanediisocyanate was purchased from Bayer (Leverkusen, Germany) and DL-lactide and L-lactide were purchased from Corbion Purac (Gorinchem, The Netherlands). Polystyrene standards were purchased from Agilent technologies (Santa Clara, USA). Fertilized white Leghorn eggs were obtained from Het Anker company (Ochten, The Netherlands).
3
Synthesis and Characterization of Polyurethane Precursors
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5-Hydroxymethylfurfural (HMF, 98%) was procured
from Manchester Organics and used without further purification. Lauroyl
chloride (98%), p-tolylisocyanate (99%), 1,4-diazabicyclo
[2.2.2]octane (DABCO, ≥99%), Jeffamine D230 (Mn ∼ 230), Jeffamine T403 (Mn ∼ 440), isophorone diamine (IPDA, ≥99%), 1,5-diamino-2-methylpentane
(99%), and benzoic acid (≥99.5%) were purchased from Merck.
Deuterated CDCl3 was obtained from Cambridge Isotope Laboratories;
THF-d8 was from Merck. Ethyl acetate,
chloroform, dichloromethane, tetrahydrofuran, and pyridine were procured
from Biosolve B.V. and used without further purification. Methylene
diphenyl diisocyanate (4,4′-MDI, Lupranat ME), Lupranol 1005/1
(polypropylene glycol with an average molecular weight of 4000 and
OH number of 28 mg KOH/g), and Lupranol 2095 (trifunctional reactive
polyether polyol containing primary hydroxyl groups with OH number
of 35 mg KOH/g) were obtained from BASF (Germany) and used as received.
The amine functionalities of Jeffamine D230 and Jeffamine T403 were
determined to be 1.7 and 2.2, respectively, using titrimetric 1H NMR analysis. The amine values of Jeffamine D230 and T403
amounted to 414.7 and 280.5 mg of KOH/g, respectively.
from Manchester Organics and used without further purification. Lauroyl
chloride (98%), p-tolylisocyanate (99%), 1,4-diazabicyclo
[2.2.2]octane (DABCO, ≥99%), Jeffamine D230 (Mn ∼ 230), Jeffamine T403 (Mn ∼ 440), isophorone diamine (IPDA, ≥99%), 1,5-diamino-2-methylpentane
(99%), and benzoic acid (≥99.5%) were purchased from Merck.
Deuterated CDCl3 was obtained from Cambridge Isotope Laboratories;
THF-d8 was from Merck. Ethyl acetate,
chloroform, dichloromethane, tetrahydrofuran, and pyridine were procured
from Biosolve B.V. and used without further purification. Methylene
diphenyl diisocyanate (4,4′-MDI, Lupranat ME), Lupranol 1005/1
(polypropylene glycol with an average molecular weight of 4000 and
OH number of 28 mg KOH/g), and Lupranol 2095 (trifunctional reactive
polyether polyol containing primary hydroxyl groups with OH number
of 35 mg KOH/g) were obtained from BASF (Germany) and used as received.
The amine functionalities of Jeffamine D230 and Jeffamine T403 were
determined to be 1.7 and 2.2, respectively, using titrimetric 1H NMR analysis. The amine values of Jeffamine D230 and T403
amounted to 414.7 and 280.5 mg of KOH/g, respectively.
4
Retinoid Isomer Synthesis and Purification
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The reagents were of biochemical or reagent grade purity, obtained from Sigma-Aldrich (USA) and Component-Reactive Ltd (Russia). Solvents hexane, dichloromethane, ethyl acetate, and methanol of HPLC-grade purity were purchased from Biosolve (The Netherlands). All-trans retinal (A1) was obtained from Sigma-Aldrich (USA). All-trans, 11-cis and 13-cis isomers of retinol were obtained from Sigma (USA).
5
Hyaluronic Acid Peptide Synthesis Protocols
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Hyaluronic acid (MW = 100–1250 kDa) was obtained from Contipro Biotech s.r.o. (Dolni Dobrouc, Czech Republic). 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) and triethoxysilane (TES) were obtained from Sigma Aldrich (Steinheim, Germany), and ethanol was procured from VWR Chemicals Prolab (Fontenay-sous-Bois, France). The Rink Amide MBHA resin and the 9-fluorenylmethoxycarbonyl (Fmoc) protected amino acids were purchased from Novabiochem (Merck KGaA, Darmstadt, Germany). The coupling reagents 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) and 1-hydroxybenzotriazole (HOBt) were obtained from Advanced Biotech (Seveso, MI, Italy). N,N-diisopropylethylamine (DIEA) and piperidine were purchased from Biosolve (Leenderweg, Valkenswaard, The Netherlands). N,N-dimethylformamide (DMF), trifluoroacetic acid (TFA), N-methyl-2-pyrrolidone (NMP), and dichloromethane (DCM) were procured from Biosolve (Leenderweg, Valkenswaard, The Netherlands). Acetonitrile and TFA were obtained from Sigma-Aldrich, Saint Louis, MO, USA.
6
Synthesis of Functional Polymeric Materials
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11-Bromoundecyl methacrylate30 and 11-(4-hydroxyphenoxy)undecyl acrylate31 (link) were kindly provided by Philips Research. 4,4′-Biphenol,
sodium iodide, anhydrous N,N-dimethylformamide,
anhydrous Chloroform, thionyl chloride, anhydrous tetrahydrofuran
(THF), t-butyl-hydroquinone, 4-carboxybenzo-15-crown-5,
terephthaloyl chloride, magnesium sulfate, hydrochloric acid (37%),
and silica were purchased from Merck Life Science. Potassium carbonate
and ethanol were obtained from VWR Chemicals. Chloroform and triethylamine
were purchased from Merck KGaA. Dichloromethane and ethyl acetate
were obtained from Biosolve. Irgacure 819 was supplied by Ciba. For
permeation and sorption measurements, the gasses He (5.0 grade), CO2 (4.5 grade), N2 (5.0 grade), and Ar (5.0 grade)
were purchased from Linde gas (the Netherlands). All reagents were
used as received, without further purification.
sodium iodide, anhydrous N,N-dimethylformamide,
anhydrous Chloroform, thionyl chloride, anhydrous tetrahydrofuran
(THF), t-butyl-hydroquinone, 4-carboxybenzo-15-crown-5,
terephthaloyl chloride, magnesium sulfate, hydrochloric acid (37%),
and silica were purchased from Merck Life Science. Potassium carbonate
and ethanol were obtained from VWR Chemicals. Chloroform and triethylamine
were purchased from Merck KGaA. Dichloromethane and ethyl acetate
were obtained from Biosolve. Irgacure 819 was supplied by Ciba. For
permeation and sorption measurements, the gasses He (5.0 grade), CO2 (4.5 grade), N2 (5.0 grade), and Ar (5.0 grade)
were purchased from Linde gas (the Netherlands). All reagents were
used as received, without further purification.
7
Peptide Synthesis and Polymer Scaffold Fabrication
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The solid support resins Sasrin and Amide MBHA were from Novabiochem (Merck KGaA, Darmstadt, Germany). The Fmoc protected amino acids were from Novabiochem (Merck KGaA, Darmstadt, Germany). The coupling reagents 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) and 1-hydroxybenzotriazole (HOBt) were from Advanced Biotech (Seveso, MI, Italy). N,N-Diisopropylethylamine (DIEA) and piperidine were from Biosolve (Leenderweg, Valkenswaard, Netherlands). Triethoxysilane (TES) was from Sigma-Aldrich (Steinheim, Germany). Solvents such as N,N-dimethylformamide (DMF), trifluoroaceticacid (TFA), N-methyl-2-pyrrolidone (NMP), and dichloromethane (DCM) were from Biosolve (Leenderweg, Valkenswaard, Netherlands). Poly-ɛ-caprolactone (Mn = 60 KDa), acetonitrile, and 1,1,1-3,3,3-hexafluoro-2-propanol (HFIP) were purchased from Sigma-Aldrich (Steinheim, Germany). The copolymer poly(L-lactic acid-co-ɛ-caprolactone) (70 : 30) was purchased by PURAC biochem (Gorinchen, Holland).
Phosphate-buffered saline (PBS) tablets were purchased from Gibco Invitrogen Corp. (Paisley, UK). The Endothelial Cell Growth Medium MV2 was purchased from PromoCell GmbH (Heidelberg, Germany). Cell strainer, tissue culture-treated dishes, and fibronectin were from BD Biosciences (San Jose, CA, USA), whereas 3-(4,5-
Phosphate-buffered saline (PBS) tablets were purchased from Gibco Invitrogen Corp. (Paisley, UK). The Endothelial Cell Growth Medium MV2 was purchased from PromoCell GmbH (Heidelberg, Germany). Cell strainer, tissue culture-treated dishes, and fibronectin were from BD Biosciences (San Jose, CA, USA), whereas 3-(4,5-
8
Solid-Phase Peptide Synthesis with Fmoc-Lys(Boc) Wang Resin
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The Fmoc-Lys(Boc) Wang resin, Acetonitrile (CH3CN), acetic anhydride, N, N-dimethylformamide (DMF), diethyl ether, 2,6-Lutidine, and triethylsilane (TES) were purchased from Sigma-Aldrich (Steinheim, Germany). N-hydroxybentrizol (HOBt) and 3-hydroxytriazolo[4,5-b]pyridine (HOAt) were purchased from Advanced Biotech Italia (Milan, Italy). All the Fmoc protected amino acids (AA), (E)-(((1-Cyano-2-ethoxy-2-oxyethylene)amino)oxy)tri(pyrrolidine-1-yl)phosphonium hexafluorophosphate(V) (PyOxim), 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), and N,N,N′,N′-Tetramethyl-O-(1H-benzotriazole-1-yl)uronium hexafluorophosphate (HBTU), were purchased from Novabiochem (Merck KGaA, Darmstadt, Germany). Trifluoroacetic acid (TFA), N-methyl-2-pyrrolidone (NMP), piperidine, N, N-Diisopropylethylamine (DIPEA), and Dichloromethane were purchased from Biosolve Chimie (Valkenswaard, The Netherlands).
9
Analytical standards for chemical characterization
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Neat certified standards of acetophenone (AP, 99%) benzophenone (BP, purity 99.9%), benzyl butyl phthalate (BBP, 98%), dibutyl phthalate (DBP, 99%), dibutyl sebacate (DBS, 97%), 2,6-diisopropylnaphthalene (DiPN, CPR), 2,2-dimethoxy-2-phenyl acetophenone (DMPA, 99%), trans,trans-1,4-diphenyl-1,3-butadiene (DPBD, 98%), 2,6-di-tert-butylphenol (DTBP, 99%), 2-ethylhexyl-4-dimethylaminobenzoate (EDB , 98%), 4-methylbenzophenone (MBP, 99.9%), methyl stearate (MS, 99%), naphthalene (NPT, 99%), 4-phenylbenzophenone (PBZ, 99.8%) were purchased from Sigma-Aldrich (Bornem, Belgium). 2-Isopropyl-9H-thioxanthen-9-one (ITX, 100%) was supplied by Rahn (Zürich, Switzerland). Chemical structures are given in Figure 1.
Tenax ® (60/80 Mesh) was also purchased from Sigma-Aldrich (Bornem, Belgium).
Acetonitrile, chloroform, dichloromethane and methanol were purchased from Biosolve (Valkenswaard, Netherlands). All solvents were HPLC-grade.
All stock solutions were prepared in methanol at a concentration of 1 mg mL -1 and stored at -20°C for 6 months.
Tenax ® (60/80 Mesh) was also purchased from Sigma-Aldrich (Bornem, Belgium).
Acetonitrile, chloroform, dichloromethane and methanol were purchased from Biosolve (Valkenswaard, Netherlands). All solvents were HPLC-grade.
All stock solutions were prepared in methanol at a concentration of 1 mg mL -1 and stored at -20°C for 6 months.
10
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.
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