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23 protocols using succinic anhydride

1

Synthesis and Characterization of Functionalized Silica Nanoparticles

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The chemicals were reagent grade from commercial sources. Iron (III) sulfate hydrate, iron (II) sulfate heptahydrate (99+%), citric acid (99+%), tetraethoxysilane (99.9%), 3-(2-aminoethylamino)propylmethyldimethoxysilane (97%), N,N-dimethylformamide (99%), and succinic anhydride (99%) were purchased from Alfa Aesar, Ward Hill, MA, USA. The acetone (AppliChem GmbH, Darmstadt, Germany), ethanol absolute (Carlo Erba, Val de Reuil, France, reagent – USP), NH4OH (aq) (Fluka, pa, 25%), and HCl 1 M (pa, Riedl-de-Haën) were used as received. The lipids POPC and DPPC were purchased from Avanti Polar Lipids Inc., Alabaster, AL, USA. The fluorophores 1,6-diphenyl-1,3,5-hexatriene (DPH), (1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5-hexatriene p-toluenesulfonate) (TMA-DPH) and other chemicals such as 4-(2-hydroxyethyl) piperazine-1-ethanesulfonic acid (HEPES), sepharose CL-4B, potassium thiocyanate (KSCN), Triton X-100, chloroform and methanol were obtained from Sigma-Aldrich Chemie GmbH (Steinheim, Germany).
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2

Synthesis of Superparamagnetic Nanochains

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The chemicals used for the synthesis of the superparamagnetic nanochains were of reagent grade quality and were obtained from commercial sources. Primary magnetic nanoparticle clusters were provided by Nanos SCI company (Ljubljana, Slovenia), and are commercially sold as iNANOvative™ (Nanos SCI, Ljubljana, Slovenia). Succinic anhydride (SA, 99%) and NH4OH (28–30%) were supplied by Alfa Aesar (Lancashire, UK). Acetone (AppliChem GmbH, Darmstadt, Germany) and ethanol absolute (Carlo Erba, reagent—USP, Milano, Italy) were used without further processing. Hydroxy (polyethyleneoxy) propyl triethoxysilane (silane-PEG, 50% in ethanol) was supplied by Gelest Inc. (Morrisville, PA, USA). Tetraethoxysilane (TEOS; 98%), rhodamine B isothiocyanate (RB), (3-aminopropyl) triethoxysilane (APS; silane-NH2, 99%), dichloromethane (DCM), dimethylformamide (DMF), Keiser test kit, and polyvinyl pyrrolidone (PVP, 40 kDa) were obtained from Sigma Aldrich (St. Louis, MO, USA).
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3

Tocotrienol-rich Palm Oil Fractionation

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Vitamin E isomers for the current work were isolated from Tocotrol™ L50P, a viscous tocotrienol-rich fraction of palm fruit oil, that contains approximately 43% tocotrienol isomers (Fuji Health Science Inc., Burlington, NJ). Silica Gel with a 230–400 mesh size, which is suitable for flash (low pressure) chromatography, was from Natland International Corporation (Research Triangle Park, NC). 10 cm d × 60 cm L LG-0000 chromatography column with a fritted disc/PTFE stopcock was custom made by Wilmad-LabGlass Inc. (Vineland, NJ). Ethyl Acetate (EtOAc) from Pharmco-AAPER (Shelbyville, KY). Methoxy polyethylene glycols (mPEG 1000 and 350) were from INEOS Oxide (Antwerp, Belgium). Triethylamine and succinic anhydride were from Alfa Aesar (Ward Hill, MA). Toluene and Chloroform-d (CDCL3) were from Acros (Bridgewater, NJ). Hexanes, AR®, p-Toluenesulfonic acid monohydrate (p-TsOH), sodium sulfate anhydrous (Na2SO4) and sodium bicarbonate (NaHCO3) were from Avantor (Center Valley,PA). Acetonitrile and dichloromethane were from EMD Millipore (Temecula, CA). All chemicals and solvents were of reagent grade or higher and were used as supplied without further modification.
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4

Characterization of Ferruginous Beidellite Clay

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Mineralogical and physico-chemical textural and structural characterizations of raw ferruginous beidellite clay (BDT) from the area of Agadir (Morocco) were reported in details by Bouna et al.45 (link) Sodium beidellite (Na-BDT), having particle size <2 μm, was isolated from the raw clay according to the procedure described in ref. 45 (link) and found to be made up of 93% of beidellite, and 7% of kaolinite. Its cation exchange capacity (CEC), BET specific surface area and total pore volume were assessed to be around 58.2 meq/100 g, 82.2 m2 g−1 and 0.136 cm3 g−1, respectively. Succinic anhydride (SuAh; 99%), 1,4-butanediol (1,4-BD, 99%), were purchased from Alfa Aesar. Bismuth chloride (BiCl3), hexadecyltrimethylammonium bromide (CTAB, cetyltrimethylammonium bromide), and lithium chloride were supplied from Sigma-Aldrich. Chloroform and decalin were used as received without any further purification. Tetrahydrofuran (THF) was distilled prior to use.
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5

Surface Functionalization of Stainless Steel

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Foils (100 mm × 100 mm) of 316 SS and 316L polished SS (Goodfellow, Pittsburgh, PA, USA) were cut into 10 mm × 10 mm coupons and a 0.8 mm hole was drilled in one corner. 316L SS 20-gauge wire was obtained from Beadlon (Valley Township, PA, USA). Oligo(ethylene glycol) methacrylate (OEGMA), Cu(I)Br, 2,2′-bipyridyl, ethyl 2-bromoisobutyrate, dopamine hydrochloride, anhydrous pyridine, hydrogen hexachloroplatinate (IV) hexahydrate, anhydrous dimethylformamide (DMF), 10-undecen-1-ol, dimethylchlorosilane, 1-ethyl-3-(3-N,N-dimethylaminopropyl)carbodiimide hydrochloride, 2-bromoisobutyryl bromide and N-hydroxysuccinimide (NHS) were purchased from Sigma-Aldrich (Milwaukee, WI, USA). Succinic anhydride was purchased from Alfa Aesar (Wardhill, MA, USA). For the polymerization of OEGMA, DI H2O and methanol (MeOH) (VWR, Atlanta, GA, USA) were degassed by bubbling a stream of argon through the solvents for 3 h. Peptide ligands (RGD (GRGDSPC) or RDG (GRDGSPC) or RGD-FITC (GRGDSPK conjugated to fluorescein isothiocyanate(FITC))) were custom synthesized by GenScript (Piscataway, NJ, USA)
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6

Cellulose Paper Pretreatment Protocol

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Cellulose filter papers (diameter 125 mm, Whatman, Hangzhou, China) were cut into (2 × 5 mm) pieces and dried overnight at 105 °C before use. Tetrabutylammonium acetate (Sigma-Aldrich, Santa Clara, CA, USA, 97%), Dimethyl sulfoxide (BDH, 99.7%), Succinic anhydride (Alfa Aesar, Shanghai, China, 99%), and Isopropyl Alcohol (BDH, Radmanovic, PA, USA, 99.5%) were used without further purification. All other chemicals were purchased from commercial sources and were of reagent grade.
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7

Synthesis and Characterization of MPEG-Succinic Acid Conjugates

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Methoxypoly(ethylene glycol) (MPEG, Mn=2,000, Aldrich), succinic anhydride (SA, 99%, Alfa Aesar), 3-amino-1-propanol (AP, 99%, Alfa Aesar), hexane-1,6-dioldiacrylate (HDD, 99%), methylthiazoltetrazolium (MTT), and phosphate-buffered saline (PBS) were purchased from Sigma Chemical Co., and 1st BASE (Malaysia), respectively. N,N′-dicyclohexylcarbodiimide (DCC, 99%, Alfa Aesar), 4-(dimethyl amino)pyridine (DMAP, 99%, Alfa Aesar), cholesteryl chloroformate (Chol, 99%, Alfa Aesar), anhydrous dichloromethane (DCM), anhydrous triethylamine (TEA), 1,4-dioxane, and other materials were received and prepared as described in previous work.31 (link)
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8

Synthesis of Tocotrienol Derivatives

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Gemcitabine HCL was obtained from LC Laboratories (Woburn, MA). α-T and γ-T3 isomers were extracted from Tocotrol L50P, a Tocotrienol-rich fraction from palm oil (Fuji Health Science, Inc., Burlington, NJ). Stearoyl chloride, linoleoyl chloride, Di-tert-butyl dicarbonate (Boc2O), and dioxane were from TCI America Inc. (Portland, OR). 4-Dimethylaminopyridine (DMAP), Dimethylformamide (DMF), dichloromethane (DCM), trifluoroacetic acid (TFA), and pyridine were obtained from EMD Chemical Inc, (Gibbstown, NJ). Triethylamine, succinic anhydride, and oxalyl chloride were from Alfa Aesar (Ward Hill, MA). Ethyl acetate (EtOAc) was from Pharmco-AAPER (Brookfield, CT). Potassium hydroxide (KOH) was from BDH, VWR International LLC (West Chester, PA). Sodium sulfate (Na2SO4) was from AMRESCO LLC (Solon, OH). All chemicals and solvents were of reagent grade or higher and were used as supplied without further modification.
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9

Epsilon-poly-L-lysine Hydrogel Synthesis

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Epsilon‐poly‐l‐lysine (EPL; MW ≈ 3900) was purchased from BOC Sciences (Shirly, NY). Ninhydrin agent, hyaluronic acid (100 kDa), and succinic anhydride (SA) were purchased from Acros Organics (Morris Plains, NJ). Ethyl acetate (EA), deuterium oxide (D2O), anhydrous dimethyl sulfoxide (DMSO), pluronic F127, 4‐(4,6‐dimethoxy‐1,3,5‐triazin‐2‐yl)‐4‐methyl‐morpholinium chloride (DMTMM), ferric chloride, sodium acetate, and sodium hydroxide were purchased from Sigma‐Aldrich (Saint Louis, MO). DFO and assay reagent kits (for aspartate aminotransferase, alanine aminotransferase, and serum creatinine) were purchased from Cayman Chemical (Ann Arbor, MI).
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10

Synthesis of Di-carboxylated Polyethylene Glycol

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Hydroxyl groups in polyethylene glycol (Sigma, MW 10000 g/mol) were converted to carboxy groups to obtain di-carboxylated polyethylene glycol by ring opening polymerization of succinic anhydride (99 % Acros organics) in the presence of DMAP (4-Dimethylaminopyridine, 99%, Fisher). In brief, 8 g of PEG were dissolved in 100 mL of 1,4-dioxane (Certified ACS, Fisher). Then, 0.39 g of 4-DMAP and 0.43 mL of triethyl amine (Fisher, 99% pure) were added to catalyze the ring opening reaction of 0.32 g of succinic acid (4 times molar excess relative to PEG) with PEG. The solvents from di-carboxylated PEG solution were removed in a rotary evaporator. The reduced solution was mixed with 1 M hydrochloric acid (40 w/v %) and washed with ethyl ether in a separatory funnel to remove the DMAP. The aqueous layer containing oxidized PEG was collected and extracted using methylene chloride. The organic solution was then dried in a rotovap, washed with cold diethyl ether and dried in a vacuum oven at room temperature.
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