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18 protocols using chloroform

1

HPLC-MS Analytical Reagents

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Water (HPLC MS grade), ethanol, methanol,
and chloroform were obtained from Biosolve BV (Valkenswaard, Netherlands).
Ammonium sulfate and 2,5-dihydroxyacetophenone (2,5-DHA) were acquired
from Sigma-Aldrich (St. Louis, MI, USA).
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2

Enzymatic Assay for Angiotensin-Converting Enzyme Activity

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Chloroform, acetone, and acetonitrile (CAN) were purchased from Biosolve (Dieuze, France), methanol was obtained from Carlo Erba Reagent (Carlo Erba Reagent, Val-de-Reuil, France), ammonia was purchased from EMSURE (Fontnay-Sous-Bois, France), trifluoroacetic acid (TFA) was supplied by Thermo Fisher Scientific (Waltham, MA, USA). Alcalase® 2.4 L from Bacillus licheniformis, Neutrase® 0.8 L from Bacillus amyloliquefaciens, hexane, boron trifluoride-methanol solution, hippuryl histidyl-leucine (HHL), 2-(cyclohexylamino)ethanesulfonic acid (CHES), (ethylenediamino) tetraacetic acid (EDTA), angiotensin converting enzyme (ACE) derived from rabbit lung, C23, and all HPLC standards were purchased from Sigma-Aldrich (Munich, Germany). All other reagents used in this study were of analytical grade.
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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.
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4

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.
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5

Extraction and Analysis of ORURO Chia Seeds

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We chose to study the ORURO variety, which is a new genotype bred in France in 2017, adapted to the climatic conditions of the region [34 (link)]. ORURO chia seeds (Salvia hispanica L.) were purchased from the producer Agrofün, Occitania, France.
Purified rapeseed lecithin (Solae Europe SA society, Geneva, Switzerland), rapeseeds (NATUR-Haus Jurgen Kaiser, NK-Wiebelskirchen, Germany) and flax seeds (Linum usitatissimum L.) (Graines de Folie, La E Penell, Normandy, France) were used as for oil extractions (seeds) or NL preparation (rapeseed lecithin).
Ammonium molybdate, internal standard nonadecanoic acid (C19), boron trifluoride diethyl etherate and methanol were purchased from Sigma Aldrich (Saint-Quentin Fallavier, France). Formic acid was obtained from Fluka (Charlotte, NC, USA). Chloroform, hexane, diethyl and petroleum ethers were purchased from Biosolve (Dieuze, France).
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6

Chiral Lactide Polymerization Protocols

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All of the reactions and
manipulations were conducted using Schlenk techniques under nitrogen/vacuum
or in a glovebox (MBraun Unilab Plus). l-lactide and d-lactide ((S,S)-3,6-dimethyl-1,4-dioxane-2,5-dione and (R,R)-3,6-dimethyl-1,4-dioxane-2,5-dione,
respectively) were kindly donated by Purasorb (Corbion Co., Ltd.).
Toluene and tetrahydrofuran (THF) were purchased from LPS and purified
by SPS Compact (Mbraun Solvent Purification System). n-Butanol and benzyl alcohol were purchased from Sigma-Aldrich and
purified over molecular sieve under nitrogen. Chloroform (stabilized
with amylene) used for polymer dissolution was purchased from Biosolve,
while the Chloroform used for chromatogram analyses (HPLC grade) was
purchased from HiPerSolv and used as received. p-Toluenesulfonic
acid, 2,3,4,5,6-pentafluoroaniline, and 3-tert-butylsalicylaldheyde
were purchased from Acros Organics and used as received. CDCl3 was purchased from Cambridge Isotope Laboratories and used
as received. Aluminum trimethyl 2.0 M in toluene was purchased from
Sigma-Aldrich and used as received.
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7

Comprehensive Analytical Grade Solvent Acquisition

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Analytical grade solvents acetonitrile (MeCN), methanol (MeOH), ethanol (EtOH), chloroform and formic acid were purchased from Biosolve (Biosolve BV, Valkenswaard, The Netherlands), whereas ammonium formate, methyl tert-butyl ether (MTBE), and leucine-enkephalin were purchased from Sigma–Aldrich (Sigma–Aldrich, Burlington, WV, USA). Ultrapure water was obtained from an arium pro UF/VF water purification system with a Sartopore 0.2 μm filter (Sartorius Stedim, Amersfoort, The Netherlands). The majority of standards and deuterated internal standards were purchased from Sigma Aldrich (Sigma-Aldrich, Zwijndrecht, The Netherlands), Avanti (Avanti Polar Lipids, Alabaster, AL, USA), and Fluka (Honeywell, Netherlands). More detailed information regarding the standard suppliers and utilized concentration can be found in the Supplementary Information (Supplementary Table S1).
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8

Gefitinib Nanoformulation Development

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Gefitinib (GEF) was purchased from LC Laboratories, USA. Sodium alginate, fetal bovine serum (FBS), and L-glutamine were purchased from Sigma Aldrich, USA. Sodium acetate, acetic acid, trifluoroacetic acid (TFA), dimethyl sulfoxide (DMSO), calcium chloride, magnesium chloride, sodium chloride, 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES), Dulbecco’s Modified Eagle Medium (DMEM), ethylenediaminetetraacetic acid (EDTA), and phosphate buffered saline (PBS) were purchased from Carl Roth, Germany. Glucose monohydrate was purchased from Hänseler, Switzerland. Chloroform was purchased from Biosolve, Netherlands. S80 (LIPOID S 80; phospholipid with 73–79% phosphatidylcholine) and DPPC (1,2-dipalmitoyl-sn-glycero-3-phosphocholine) were purchased from Lipoid, Germany. DiD (1,1-dioctadecyl-3,3,3,3-tetramethylindodicarbocyanine), trypsin–EDTA, and Gibco penicilin-streptomycin were purchased from Thermo Fisher, Germany. Ultrapure water with a resistivity of 18.2 MΩ⋅cm was produced by a Barnstead Smart2pure device (Thermo Fisher Scientific, Germany).
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9

Block Copolymer Thin Film Fabrication

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PS-b-P2VP was purchased from Polymer Source, Inc. and used as received: P5742-S2VP, Mn (PS) = 133 kg mol−1, Mn (P2VP) = 132 kg mol−1, Mw/Mn = 1.15. Toluene Biosolve Chemicals (Biosolve BV, Valkenswaard, The Netherlands), >99.7%) and chloroform (Biosolve Chemicals, >99.9%) were used as received Silicon substrates (Prime CZ-Si wafer, thickness = 625 ± 20 μm, (100), 1-sidepolished, p-type (Boron) TTV < 10 μm, 15–25 Ohm) were supplied by Micro Chemicals GmbH, Ulm, Germany.
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10

Biological and Chemical Analysis Protocols

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For the biological test, bacto tryptone and bacto yeast extract were provided by Fisher Scientific (Illkirch, France). Potassium phosphate monobasic, potassium phosphate dibasic, and agar were purchased from Sigma-Aldrich (Saint-Quentin, Fallavier, France).
For extraction, purification, and chemical analysis, chloroform, ethyl acetate, methanol, formic acid, and water (of ULC-MS grade) were all purchased from Biosolve BV (Valkenswaard, The Netherlands). Hydrochloric acid solution (1M) was purchased from Sigma-Aldrich (Saint-Quentin, Fallavier, France). Deuterated reagent, such as deuterated chloroform (CDCl3), was purchased from Euriso-top (Saint-Aubin, France).
For organic synthesis, tropolone, 18-crown-6, iodomethane, N-bromosuccinimide, trifluoroacetic acid, and acetic anhydride were purchased form Thermo Scientific (Illkirch, France). Benzene and toluene were purchased from Sigma-Aldrich (Saint-Quentin, Fallavier, France).
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