O-Benzyl-L-serine was purchased from Senn Chemicals AG (Dielsdorf, Switzerland). D,L-lactide was purchased from Purac (The Netherlands). Tin(II) 2-ethylhexanoate (SnOct 2 ), poly(vinyl alcohol) (PVA; M w = 13,000-23,000), dimethylsulfoxide (DMSO) and bovine serum albumin (BSA; A4503) with molecular weight of 66,776 Da, were obtained from Sigma-Aldrich (Germany). 1,4-Butanediol 99 + % was obtained from Acros Organics (Belgium). IRDye Ò 800CW -NHS ester (MW = 1166 Da) from LI-COR Biosciences was supplied by Westburg BV (Leusden, The Netherlands). Carboxymethyl cellulose (CMC, with viscosity of 2000 mPaÁs of a 1% solution in water) was obtained from Bufa B.V. (255611, The Netherlands). Halt™ Protease and phosphatase inhibitor cocktail, EDTA-free (78445) was obtained from Thermo Scientific (IL, USA). RIPA buffer (50 mM Tris-HCl, pH 7.5, 150 mM sodium chloride, 1% Triton X-100, 1% sodium deoxycholate, 0.1% SDS, 2 mM EDTA) was provided by Teknova (CA, USA). Sodium phosphate dibasic (Na 2 HPO 4 ) and sodium azide (NaN 3 ) were purchased from Fluka (The Netherlands). Dichloromethane (DCM), chloroform, tetrahydrofuran and methanol were purchased from Biosolve BV (The Netherlands). Sodium dihydrogen phosphate (NaH 2 PO 4 ) and sodium chloride (NaCl) were supplied from Merck (Germany).
Tetrahydrofuran
Manufactured by Biosolve
Sourced in France
Tetrahydrofuran is a colorless, volatile organic liquid commonly used as a solvent in the laboratory setting. It has a boiling point of approximately 66°C and is miscible with water and many organic solvents. Tetrahydrofuran is a versatile solvent due to its ability to dissolve a wide range of compounds, making it a valuable tool for various laboratory applications.
Automatically generated - may contain errors
Lab products found in correlation
Methanol, by Biosolve (2 mentions)
Dichloromethane, by Biosolve (2 mentions)
Sodium chloride (nacl), by Merck Group (1 mentions)
Irdye 800cw nhs ester, by LI COR (1 mentions)
Bovine serum albumin a4503, by Merck Group (1 mentions)
Sodium dihydrogen phosphate nah2po4, by Merck Group (1 mentions)
Ripa buffer, by Teknova (1 mentions)
Benzoic acid, by Merck Group (1 mentions)
1 4 diazabicyclo 2.2.2 octane, by Merck Group (1 mentions)
Jeffamine d230, by Merck Group (1 mentions)
Ethyl acetate, by Biosolve (1 mentions)
Pyridine, by Biosolve (1 mentions)
Chloroform, by Biosolve (1 mentions)
Penicillin streptomycin, by Thermo Fisher Scientific (1 mentions)
Trypsin edta, by Thermo Fisher Scientific (1 mentions)
Calcein am, by Thermo Fisher Scientific (1 mentions)
Propidium iodide, by Thermo Fisher Scientific (1 mentions)
Wheat germ agglutinin (wga), by Thermo Fisher Scientific (1 mentions)
Alexa fluor 488 conjugate, by Thermo Fisher Scientific (1 mentions)
No mycoplasma fetal bovine serum, by Thermo Fisher Scientific (1 mentions)
7 protocols using tetrahydrofuran
1
Synthesis and Characterization of Polymeric Nanoparticles
2
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.
3
Cytotoxicity Evaluation of Polymer-based Materials
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All materials were purchased from Sigma-Aldrich without further purification unless stated otherwise. Poly(ethylene glycol) methyl ether 2K was purchased from Rapp Polymers and freeze-dried before use. 1,4-Dioxane and tetrahydrofuran (THF) were obtained from Biosolve Chimie (Metz, France). Dialysis membranes MWCO (12,000–14,000 Da) were supplied by Spectra/Pro® (ThermoFisher, Waltham, MA, USA). Wheat germ agglutinin, Alexa FluorTM 488 conjugate, calcein-AM, propidium iodide (PI), Dulbecco’s modified eagle medium (DMEM), phosphate-buffered saline (PBS, pH 7.4), no-mycoplasma fetal bovine serum (FBS), trypsin-EDTA and penicillin–streptomycin was purchased from ThermoFisher (Waltham, MA, USA). Ultrapure Milli Q (St. Louis, MI, USA) water (18.2 MΩ·cm) was used in this work.
Information regarding the analytical equipment can be found in thesupporting information .
Information regarding the analytical equipment can be found in the
4
Synthesis and Characterization of BMAT-Terminated pNIPAm
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2,2′-Azobis(2-methylpropionitrile)
(AIBN, 98%), N-isopropylacrylamide (NIPAm,
97%), tert-butyl acrylate (tBuAc,
contains 10–20 ppm monomethyl ether hydroquinone as inhibitor,
98%), trioxane (⩾99.9%), trifluoroacetic acid (TFA, ⩾99%),
concentrated HCl (37% solution in water), and dioxane (anhydrous,
99.8%) were obtained from Sigma-Aldrich, Germany, and used without
further purification unless noted otherwise. NIPAm was recrystallized
twice from a mixture of hexane and acetone. tBuAc
was passed over a short column of Al2O3 to remove
the inhibitor. AIBN was recrystallized thrice from MeOH. Bis(2-methylpropionic
acid)trithiocarbonate20 (link),21 (link) (BMAT) and BMAT-terminated pNIPAm21 (link) were synthesized as described in the literature,
with NMR and SEC characterization described inTable S1 . Hexafluoroisopropanol (HFIP, AR), dichloromethane
(DCM, AR), tetrahydrofuran (THF, HPLC-grade), and methanol (MeOH,
HPLC) were obtained from Biosolve, France.
(AIBN, 98%), N-isopropylacrylamide (NIPAm,
97%), tert-butyl acrylate (tBuAc,
contains 10–20 ppm monomethyl ether hydroquinone as inhibitor,
98%), trioxane (⩾99.9%), trifluoroacetic acid (TFA, ⩾99%),
concentrated HCl (37% solution in water), and dioxane (anhydrous,
99.8%) were obtained from Sigma-Aldrich, Germany, and used without
further purification unless noted otherwise. NIPAm was recrystallized
twice from a mixture of hexane and acetone. tBuAc
was passed over a short column of Al2O3 to remove
the inhibitor. AIBN was recrystallized thrice from MeOH. Bis(2-methylpropionic
acid)trithiocarbonate20 (link),21 (link) (BMAT) and BMAT-terminated pNIPAm21 (link) were synthesized as described in the literature,
with NMR and SEC characterization described in
(DCM, AR), tetrahydrofuran (THF, HPLC-grade), and methanol (MeOH,
HPLC) were obtained from Biosolve, France.
5
Synthesis of Acrylate Emulsion Polymers
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Model acrylate emulsion polymers were synthesized using radical emulsion polymerization of methyl methacrylate (MMA, Sigma Aldrich), n-butyl acrylate (BA, Sigma Aldrich), n-butyl methacrylate (BMA, Sigma Aldrich) and acrylic or methacrylic acid (AA or MAA, Sigma Aldrich), as outlined in Table 1. Sodium lauryl sulphate (32% in water, VWR, Amsterdam, The Netherlands) was used as emulsifier and ammonium persulphate (Evonik, Marl, Germany) as initiator. The samples are dispersed in water to approximately 30% by weight. Ammonia (25% in water, VWR) was used in a stoichiometric equivalent of 0.7 to partly neutralize the acid groups.
n-Methylpyrrolidone (NMP, peptide synthesis grade) and tetrahydrofuran (THF, uLCMS grade) were purchased from Biosolve (Valkenswaard, The Netherlands). Triethylamine (TEA, 99.5%), hydrochloric acid (HCl, 37%), N-methylmorpholine (NMM, >99%), chloro-dimethoxytriazine (CDMT, >98%), ethyl chloroformate (ECF, >99%), propyl chloroformate (PCF, >99%), 3-nitrobenzyl chloroformate (NBCF, >96%), p-bromophenacyl bromide (pBPB, 99.8%), p-nitrophenacyl bromide (pNPB, >98%) and 2-bromoacetophenone (PB, 99%) were purchased from Sigma-Aldrich (Zwijndrecht, The Netherlands).
n-Methylpyrrolidone (NMP, peptide synthesis grade) and tetrahydrofuran (THF, uLCMS grade) were purchased from Biosolve (Valkenswaard, The Netherlands). Triethylamine (TEA, 99.5%), hydrochloric acid (HCl, 37%), N-methylmorpholine (NMM, >99%), chloro-dimethoxytriazine (CDMT, >98%), ethyl chloroformate (ECF, >99%), propyl chloroformate (PCF, >99%), 3-nitrobenzyl chloroformate (NBCF, >96%), p-bromophenacyl bromide (pBPB, 99.8%), p-nitrophenacyl bromide (pNPB, >98%) and 2-bromoacetophenone (PB, 99%) were purchased from Sigma-Aldrich (Zwijndrecht, The Netherlands).
6
Synthesis of Acryloyl-Based Compounds
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2-Methyl-1,4-phenylene bis(4-(3-(acryloyloxy)propoxy)benzoate)
[RM 257] (1 ) and 4-methoxyphenyl 4-((6-(acryloyloxy)hexyl)oxy)benzoate
[RM 105] (2 ) were obtained from Merck. 4-((6-(Acryloyloxy)hexyl)oxy)benzoic
acid (3 ) and 4-((6-(acryloyloxy)hexyl)oxy)-2-methylbenzoic
acid (4 ) were purchased from Synthon. Irgacure 369 (6 ) was purchased from CIBA. Chiral dopant (R)-(+)-3-methyladipic acid (5 ) and dimethylmethylphosphonate
(7 ) were from Sigma-Aldrich, as well as trimethylamine
and diisopropylamine. Solvents tetrahydrofuran and toluene were purchased
from Biosolve, and acetone was purchased from Sigma-Aldrich.
[RM 257] (
[RM 105] (
acid (
acid (
(
and diisopropylamine. Solvents tetrahydrofuran and toluene were purchased
from Biosolve, and acetone was purchased from Sigma-Aldrich.
7
Solvent Purification and Sample Preparation
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Acetone and methanol (MeOH) were from J.T. Baker® (Center Valley, USA). Tetrahydrofuran (THF) was acquired from Biosolve (Valkenswaard, The Netherlands). Dichloromethane (Picograde) was obtained from Promochem® (Wesel, Germany) and toluene came from Fisher Scientific (Loughborough, UK). Milli-Q water was obtained from ultrapure water purification Q-Pod system (Millipore, Bedford, USA). All solvents and reagents were of analytical grade and used as supplied.
For sample treatment, micro-centrifuge filters (0.2 μm, nylon) from Costar Spin-X obtained from Sigma-Aldrich were used for removing micro-particles from sample extracts when necessary.
For sample treatment, micro-centrifuge filters (0.2 μm, nylon) from Costar Spin-X obtained from Sigma-Aldrich were used for removing micro-particles from sample extracts when necessary.
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