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26 protocols using propargyl bromide

1

Synthesis of Photoactive Dental Monomers

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1,3-Bis(2-isocyanatopropan-2-yl)benzene, dibutyltin dilaurate, tetrahydrofuran, 6-chloro-1-hexanol, sodium azide, 1,1,1-tris(hydroxymethyl)propane, propargyl bromide, propargyl alcohol, bisphenol A diglycidyl ether, ethanol, 3-(triethoxysilyl)propyl isocyanate, copper(II) chloride, N,N,N′,N′,N″-pentamethyldiethylenetriamine (PMDETA), camphorquinone (CQ), ethyl 4-(dimethylamino)benzoate (EDAB), and acetonitrile were used as received from Sigma Aldrich. Sodium hydroxide, ammonium chloride, dimethyl sulfoxide, dimethylformamide, methanol, and sodium sulfate were used as received from Fisher Scientific. BisGMA/TEGDMA (70/30) comonomers solution was used as received from ESSTECH. Fusion silane coupling agent was used as received from George Taub Products & Fusion Co., Inc. Bis(6-azidohexyl) (1,3-phenylenebis(propane-2,2-diyl))dicarbamate (BZ-AZ) and 1-(prop-2-yn-1-yloxy)-2,2-bis((prop-2-yn-1-yloxy)methyl)butane (AK) were synthesized according to a previously reported procedure [60 (link)]. All azides were synthesized according to the azide safety rules and handled with appropriate precaution when working with monomers, resins, and polymers in small quantities [62 ].
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2

Synthesis and Evaluation of Acridine-based Anticancer Agents

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2,7-Dimethylacridine-3,6-diamine
(acridine yellow, AY, L-1), 3,8-diamino-5-ethyl-6-phenyl-phenanthridin-5-ium
bromide (ethidium bromide, EB, L-2), pyrrole, trifluoroacetic acid,
2-/4-hydroxybenzaldehyde, 1,2-dibromoethane, sodium azide (NaN3), triethylamine, borontrifluoride diethyletherate (BF3·Et2O), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone,
potassium carbonate (K2CO3), propargyl bromide,
2-acetylpyridine, sodium hydroxide (NaOH), and ammonia (NH3, liq.) were purchased from Sigma-Aldrich Chemical Co., USA and used
as received. Solvents were purchased from Merck, and S D Fine-Chem
Ltd., Mumbai, India. The solvents were dried and distilled, following
the standard procedures prior to their use.67 Trypsin–ethylenediaminetetraacetic acid solution and MTT
were purchased from HiMedia, India, whereas DMSO from GeNie, Merck,
India. Dulbecco’s modified Eagle’s medium (DMEM), fetal
bovine serum, and antibiotic solution (10 000 units/mL penicillin
and 10.0 mg/mL streptomycin) were purchased from Cellclone, Genetix
Biotech Asia Pvt. Ltd. MDA-MB-231 a breast cancer cell line was procured
from National Centre for Cell Science (NCCS), Pune.
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3

Synthesis of Vanillyl Alcohol Derivatives

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Propargyl bromide, propargyl alcohol, vanillyl alcohol, ferulic acid, clove oil, sodium azide, N,N′-dicyclohexylcarbodiimide solution (DCC) and 4-(dimethylamino)pyridine (DMAP) and were purchased from Sigma-Aldrich St. Louis, USA. Vanillin (100% purity) was purchased from Eternal Pearl (The Zhonghua Chemical Factory, Zhejiang, China). Coniferaldehyde and vanillic acid were previously isolated from Cocos nucifera L., as reported.26 Eugenol was extracted and purified from clove oil using 30% aqueous KOH, according to the literature.27
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4

Synthesis of Functional Nanomaterials

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Copper(II) sulfate pentahydrate (CuSO4·5H2O), sodium tetrachloroaurate(III) dihydrate (NaAuCl4·2H2O), iron(III) chloride hexahydrate (FeCl3·6H2O), iron(II) chloride tetrahydrate (FeCl2·4H2O), silicon dioxide (SiO2), (3-glycidyloxypropyl)trimethoxysilane, polyvinylpyrrolidone (PVP, MW ~ 10,000), imidazole, propargyl bromide, chlorodiphenylphosphine, sodium borohydride (NaBH4), methyl orange (MO), sodium azide, 3-chloro-1,2-propanediol, ascorbic acid, rhodamine B (RhB), nitro compounds, methyl red (MR), and tetracycline (TC) were purchased from Sigma-Aldrich, Acros and Merck MilliporeSigma.
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5

Synthesis and Characterization of Azide-Functionalized Compounds

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Propargyl bromide (80 wt % solution in toluene)
and 4,4′-diazido-2,2′-stilbene disulfonic acid disodium
salt (≥99.0%) (SAZ) were purchased from Sigma-Aldrich, and
used as received. Hydroquinone sulfonic acid potassium salt (>98%)
was purchased from Alfa Aesar, India. Copper(I) iodide (>99%),
acetone,
potassium carbonate, and dimethyl sulfoxide (DMSO) were purchased
from Spectrochem, India. Potassium carbonate was dried at 120 °C
for overnight before use. DMSO and acetone were distilled prior to
use. Concentrated sulfuric acid (95%) and ammonia solution were purchased
from E. Merck, India. 4,4-Bis[3′-trifluoromethyl-4′(4-azidobenzoxy)benzyl]biphenyl
(QAZ) was synthesized according to the earlier reported procedure.30 (link)
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6

Synthesis and Characterization of PDMS-PEO Copolymers

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Hexamethylcyclotrisiloxane (D3) was purchased from Acros (Illkirch France) and purified on CaH2 before use. α-hydroxy-PEO were obtained from Polysciences (2000 g·mol−1, Niles, MI, USA), Creative Pegworks (1000 g·mol−1, Durham, NC, USA), Sigma Aldrich (750 and 550 g·mol−1, Haverhill, MA, USA), and Alfa Aesar (350 g·mol−1, Haverhill, MA, USA) and used without purification. Chloro-(3-chloropropyl)dimethylsilane was purchased from ABCR (Karlsruhe, Germany) and purified by distillation on CaH2. Sodium azide (NaN3), copper bromide, sec- or n-butyllithium, and propargylbromide were purchased from Sigma Aldrich (Haverhill, MA, USA) and used without purification. THF, purchased from VWR (Radnor, PA, USA), was dried over Na/benzophenone and cryo-distilled just before use. Cyclohexane and chloroform were purchased from VWR and used without purification.
All copolymers were characterized by 1H NMR in CDCl3 and size exclusion chromatography in THF. Synthesized PDMS polymers were characterized by 1H NMR in CDCl3 and by SEC in toluene.
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7

Chemoselective Ligation for Protein Labeling

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2,4-Dihydroxybenzaldehyde, 2,2-dimethyl-1,3-dioxane-4,6-dione, piperidinium acetate, 2-hydroxy-4-methoxybenzaldehyde, propargyl-PEG4-alcohol, and azidobenzoic acid were purchased from Tokyo Chemical Industry (Tokyo, Japan). K2CO3, propargyl-bromide, CuSO4, β-casein from bovine milk, rhodamine B isothiocyanate (RITC), and Tris–EDTA buffer solution (pH 7) were purchased from Sigma-Aldrich (St. Louis, MO). DBCO-s-s-amine was purchased from Conju-Probe LLC (San Diego, CA). The other chemicals were purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan). NH2-PEG-resin particles (10 μm) were purchased from Watanabe Chemical Industries (Hiroshima, Japan). Slide-A-Lyzer G2 dialysis cassettes (20k MWCO, 15 mL) and micro BCA protein assay were purchased from Thermo Fisher Scientific (Waltham, USA). High-quality deionized (DI) water (>15 MΩ cm) produced by an Elix-5 system (Millipore, Molsheim, France) was used in the experiments.
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8

Synthesis of Nickel Ferrite Nanoparticles

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Raw materials (nickel ferrites (NiFe2O4) (particle size ca. 30–70 nm and density
∼5.13 g/cc)) were purchased from Sigma-Aldrich Corp., India.
Malonic ester was procured from Alfa Aesar. Sodium hydride, propargyl
bromide, Hoveyda-Grubbs’ second-generation catalyst, and ethyl
vinyl ether were purchased from Sigma-Aldrich, India. Diethyl ether,
tetrahydrofuran (THF), ethyl acetate, hexane, chloroform, acetonitrile,
and anhydrous sodium sulfate were acquired from Merck India Ltd. Ethanol
(purity ∼99%) was purchased from Sigma-Aldrich, India. All
of the solvents were dried over calcium hydride before use, and all
raw materials and solvents were used as received without any further
purification.
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9

Synthesis and Purification of Novel Compounds

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Epichlorohydrin, sodium azide, propargyl bromide, paraformaldehyde, ammonium chloride and sodium chloride (Sigma, New York, NY, USA) were used for synthesis. Dialysis tubing, MWCO 12,000–14,000 from regenerated cellulose (RC), diameter 16 mm (SERVA LLC, Heidelberg, Germany), was used to remove byproducts.
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10

Azido-Functionalized Coumarin-PEG Conjugation

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The following materials
were used to carry out the different syntheses: 4-bromomethyl-7-methoxycoumarin
(97%, Sigma Aldrich), sodium azide (>99.5%, Sigma Aldrich), methoxy
polyethylene glycol (mPEG, Mn = 2000 g/mol, Sigma
Aldrich), propargyl bromide (80% in toluene, Sigma Aldrich), sodium
hydride (NaH, 60% in mineral oil, Sigma Aldrich), ethyl acetate (anhydrous,
99.8%, Sigma Aldrich), and carbon dioxide (industrial grade ≥99%,
Carburos Metálicos). The catalyst used to carry out the cycloaddition
reaction was copper(II) acetate monohydrate (Sigma Aldrich).
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