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27 protocols using 1 1 carbonyldiimidazole

1

Functionalization of Silicone Oil for Biomedical Applications

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Poly[dimethylsiloxane-co-(3-aminopropyl)methylsiloxane] with a functional group equivalent weight of 4400 Da (silicone oil), N,N′-diisopropylcarbodiimide (DIC), N,N′-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole hydrate (HOBt), 1,1′-carbonyldiimidazole (CDI), 3-mercaptopropionic acid (MPA), l-cysteine hydrochloride monohydrate (cysteine), 4,4′-dithiodipyridine (DTDP), 2,4,6-trinitrobenzenesulphonic acid solution 5% (w/v) in demineralized water (TNBS), iodine, pyridine, triethylamine and 1-(2-methoxyphenylazo)-2-naphthol (sudan red G) were purchased from Sigma–Aldrich (Steinheim, Germany). All other chemicals, reagents and solvents were received from commercial sources.
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2

Biomaterial Synthesis and Characterization

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Cystamine dihydrochloride (CYS), 1.1 Carbonyldiimidazole (CDI), sodium alginate (Alginate, MW determined by viscosimetry was 140 kDa), dextran sulfate sodium salt (Dextran, MW 40 kDa), carboxymethyl-dextran sodium salt (CM-Dextran-MW 70 kDa), hyaluronic acid (low MW HA, 20–70 kDa), Rhodamine B isothiocyanate (RITC), DL-Dithiothreitol 99% (DTT), bovine serum albumin, 96% (BSA), dimethyl sulfoxide (DMSO), and lysozyme from chicken egg white, 90% were purchased from Sigma-Aldrich (St. Louis, MO, USA).
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3

Synthesis and Preparation of NAI

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NAI was synthesized as previously described (20 (link)). Briefly, 137.14 mg of 2-methylpyridine-3-carboxylic acid (Sigma Aldrich, cat. 325228) were resuspended in 500 μl DMSO anhydrous (Sigma Aldrich, cat. 276855). ∼162.15 mg of 1,1’-carbonyldiimidazole (Sigma Aldrich, cat. 115533) were resuspended in 500 μl DMSO anhydrous and added dropwise to the 2-methylpyridine-3-carboxylic acid solution while constantly stirring, over a period of 5 minutes. The reaction mixture was then incubated at room temperature with constant stirring for 2 h. This mixture (assumed to represent a 1 M stock) was aliquoted in 50 μl aliquots and stored at −80°C.
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4

Cyclic Nigerosyl-1-6-Nigerose and α-Cyclodextrin Protocol

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α-Cyclodextrin (α-CD, Mw = 972.846 g/mol) was a gift from Roquette Frères SA (Lestrem, France). Cyclic nigerosyl-1-6-nigerose (CNN, Mw = 648.564 g/mol) was obtained from Hayashibara (Tokyo, Japan). CNN and α-CD were desiccated in an oven at 80 °C up to constant weight before their usage to remove any traces of absorbed moisture. Additionally, 1,1′-Carbonyldiimidazole (CDI, ≥97.0%), 2′,7′-dichlorodihydrofluorescein diacetate (H2DCFDA fluorescent probe), and 2′,7′-dichlorofluorescein (DCF), N,N-dimethylformamide (DMF, ≥99.8%), acetone (≥99% (GC)), and ethanol (96.0–97.2%) were purchased from Sigma-Aldrich (Munich, Germany). Deionized and MilliQ® water was obtained using a Millipore Direct-QTM 5 production system. All other chemicals used to prepare the cardioplegic solution (CS) were commercially available as analytical-grade products.
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5

Multifunctional Nanomedicine Synthesis

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2,6-Dimethyl-1-nitrobenzene (99%; Sigma-Aldrich),
potassium permanganate (KMnO4, ≥99.0%; Alfa Aesar), borane
tetrahydrofuran complex solution (1.0 M in tetrahydrofuran (THF);
Sigma-Aldrich), 1,1′-carbonyldiimidazole (Sigma-Aldrich), acetonitrile
(99.8%; Sigma-Aldrich), ethyl alcohol (99.8%, Sigma-Aldrich), zinc
nitrate hexahydrate (Alfa Aesar), tetracycline (TCN) (TCI Chemicals),
fluorescein (TCI Chemicals), DOX was obtained from DOX hydrochloride
(TCI Chemicals). THF (≥99.9%; Sigma-Aldrich) was refluxed with
sodium and a small amount of benzophenone and distilled prior to use.
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6

Synthesis of Polyurethane Biomaterials

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DHBA (3,4-Dihydroxybenzoic acid), 1,1′-carbonyldiimidazole (CDI), thionyl chloride (SOCl2), triethyl orthoformate (TEOF), resin Amberlyst 15, polycaprolactone diol with molecular weight of 2037 (PCL-2000), 1,4-butanediol (BD), ε-caprolactone (ε-CL), tin(II) 2-ethylhexanoate (Sn(Oct)2), N,N-dimethyl-acetamide (DMAc), and 1,6-diisocyanatohexane (HDI) were purchased from Sigma-Aldrich (Madrid, Spain). The diisocyanate product was freshly distilled at low pressure before use, and the rest of the products were used as received. AMPD (2-Amino-2-methyl-1,3-propanediol) and N,N-diethanolamine (DEA) were purchased from Merck (Madrid, Spain) and used as received.
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7

Hyaluronic Acid-based Biomaterial Synthesis

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The sodium salt of hyaluronic acid (Mw ∼5 kDa, Purity 99%) was purchased from Freda Biopharm Co., Ltd. (China). Agarose (AG, Mw ∼3 kDa) was prepared following an H2O2 degradation protocol [27] . PEI with Mw of 1.2 kDa (Purity 99%) and 25 kDa (Purity 99%), N-(3-dimethylpropyl)-N-ethylcarbodiimide hydrochloride (EDC, Purity ≥99%), N-hydroxysulfo-succinimide sodium salt (sulfo-NHS, Purity 98%), and 1, 1-Carbonyldiimidazole (CDI, Purity 97%) were obtained from Sigma-Aldrich (USA). PX458 plasmid was obtained from Addgene (Cambridge, USA). All other commercial reagents are analytical grade and were used without further purification.
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8

Cyclodextrin-Resveratrol Conjugate for Cancer

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The β-cyclodextrin (β-CD) was a kind gift from Roquette Italia (Cassano Spinola, Italy). Resveratrol and 1,1′-carbonyldiimidazole (CDI) were purchased from Sigma-Aldrich (Milan, Italy). OxyResveratrol was purchased from TCI Europe. DU-145 prostate cancer cell lines were purchased from ATCC (Manassas, VA, USA) and Cell culture reagents were purchased from Gibco/Invitrogen (Life Technologies, Paisley, UK). Unless otherwise specified, all other chemicals and reagents used were of analytical grade.
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9

Engineered Nanoparticles for Targeted Gene Delivery

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Branched polyethylenimine (PEI, Mw ~ 25 kDa), ethylenediamine (EDA, 99.5%), methyl acrylate (MA, 99.0%), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDAC, 98%), 1,1′-carbonyldiimidazole (CDI, 97%), 3-(4,5-dimethylthiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT), fluorescein diacetate (FDA, >98%), propidium iodinate (PI, >98%), D-mannitol (>99%), and 5-fluorocytosine (5-FC) were obtained from Sigma-Aldrich Chemical (St. Louis, MO, USA). Female Balb/c-nu mice were purchased from Institute of Laboratory Animal Sciences (ILAS). The plasmid DNAs (pDNA), including pRL-CMV encoding renilla luciferase (Promega Co., Cergy Pontoise, France), pEGFP-N1 encoding enhancedgreen fluorescent protein (EGFP) (BD Biosciences, San Jose, CA, USA), and pAdTrack-CMV-CD (pCMV-CD) encoding Escherichia coli cytosine deaminase (ECD) were amplified in Escherichia coli and purified according to the supplier’s protocol (Qiagen GmbH, Hilden, Germany). The quality and concentration of the purified pDNA were assessed by measuring its absorption at 260 nm and 280 nm, and by agarose gel electrophoresis. HepG2 and COS7 cell lines were purchased from the American Type Culture Collection (ATCC, Rockville, MD, USA).
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10

Multifunctional Polymer-based Anticancer Therapy

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PEI, MW 600 Da and 25 kDa, HP-β-CD, FA, 1,1-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (NHS), 3-(4,5-dimethyl-thiazol-2-yl)-2, 5-diphenyl tetrazolium bromide (MTT), and Hoechst 33258 were obtained from Sigma-Aldrich (St Louis, MO, USA) and used without additional purification. Drug-fast MCF-7/Adr cells (resistant to 1 μg/mL DOX) were obtained from Kaiji Biology (Nanjing, People’s Republic of China [PRC]). The cells were routinely grown at 37°C in a humidified atmosphere with 5% CO2 (in air) in 25 cm2 culture flasks (Corning, New York, NY, USA) with Dulbecco’s Modified Eagle’s Medium (HyClone, Logan, UT, USA), and 10% fetal bovine serum (HyClone) and 1% penicillin streptomycin solution (HyClone) were added to the medium for optimal growth. The BCL2 siRNA duplexes were provided by Genpharm (Shanghai, PRC), and the sequences were 5′-AAGGC-CACAATCCTCCCCCAGCCTGTCTC-3′ and (anti-sense) 5′-AACTGGGGGAG-GATTGTGGCCCCTGTCTC-3′. Other siRNA, including siRNAFAM (siRNA link with FAM green fluorescent dye) were also provided by Genpharm. The anti-BCL2 monoclonal antibody and β-actin monoclonal antibody were obtained from Abgent (San Diego, CA, USA).
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