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11 protocols using 2 nitrobenzaldehyde

1

Synthesis and Characterization of Hydrazones

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Ethyl acetoacetate (EAA), phenylhydrazine,
2,4-dinitrophenylhydrazine (DNP), hydrazine hydrate, p-aminoacetophenone, sodium nitrite, benzaldehyde, 3,5-dimethoxybenzaldehyde,
4-(N,N-dimethylamino)benzaldehyde,
4-hydroxybenzaldehyde, 2-nitrobenzaldehyde, cinnamaldehyde, 4-(N,N-dimethylamino)cinnamaldehyde, sodium
hydroxide, ethyl alcohol, glacial acetic acid, trichloroacetic acid
(TCA), sodium pyrophosphate, reduced glutathione (GSH), and thiobarbituric
acid (TBA) were obtained from Sigma-Aldrich Chemical Co. (St. Louis,
MO, USA). Doxorubicin HCl injection, USP, was purchased from Pfizer
injectables.
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2

Radiolabeled 2-Nitrobenzaldehyde Synthesis

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A solution of kryptofix/K18F was received from the cyclotron and transferred into a crimped V-vial for drying. Acetonitrile (0.4 mL) was added to the mixture, and it was dried under a stream of argon at 105°C. A solution of 2-nitrobenzaldehyde (8 mg, Sigma, Milwaukee, WI) in dry DMSO (0.4 mL) was added to the dried kryptofix/K18F, and the mixture was heated to 120°C and stirred under argon for 20 min. The reaction was cooled, passed through a silica-gel cartridge (Alltech, Nicholas-ville, KY, 900 mg), and eluted with 30% methanol in dichloromethane (2 mL). Afterward, the solvent was evaporated under a stream of argon to a volume <0.5 mL, and the product was purified by semipreparative HPLC. The desired compound was isolated with 50% MeCN in water at 20 min. This product was injected into an analytical HPLC with the authentic nonradiolabeled compound (used as purchased from Sigma, Milwaukee, WI) to assess the identity and purity of the desired compound. The compound was obtained in 11% radiochemical yield and >95% purity as determined by HPLC. For more details, see the Supporting Information.
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3

Chitosan-ZnO Nanocomposite Synthesis

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Cs (1.0–3.0 × 105 g mol−1 molecular weight and 98% degree of deacetylation) was made from the shell of shrimps and crabs Pandalus borealis and purchased from Acros Organics (USA). ZnONPs (product No. NCZ4701, powder, and 20 nm particle size) were supplied by nanochemazone (Canada). Epichlorohydrin was obtained from PanReac. AppliChem-ITW Reagent (USA). 6-Amino-1,3-dimethyluracil, benzaldehyde, 2-chlorobenzaldehyde, 4-chlorobenzaldehyde, 2-methoxybenzaldehyde, formaldehyde, and 2-nitrobenzaldehyde were purchased from Sigma-Aldrich (Germany). XTT (2, 3-bis [2-methyloxy-4-nitro-5-sulfophenyl]-2H-tetrazolium-5-carboxanilide) was obtained from Sigma (St. Louis, MO, USA).
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4

Synthesis and Characterization of 2-Nitrobenzaldehyde Compound

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2-Nitrobenzaldehyde, iron powder, pyrrolidine etc were procured from Sigma-Aldrich (USA) and used as received. The FT-IR spectra of the compound was recorded on Agilent FT-IR spectrometer in KBr discs (4000–400 cm−1). 1H, 13C NMR spectra were recorded on a Bruker Spectrospin DPX-400 NMR spectrometer at 400.13 and 100.47 respectively using TMS as an internal standard. Mass analysis was carried out using Nexera UHPLC at 130 MPa with SIL-30 AC Nexera autosampler coupled to an LC-MS 8030 tandem mass spectrometer manufactured by Shimadzu Corporation, Kyoto, Japan. The software SADABS was used for absorption correction and SHELXTL for space group, structure determination and refinements. All non-hydrogen atoms were refined anisotropically. All the computations have been carried out at DFT/B3LYP/6-31G (d,p) level of theory using GAUSSIAN 09 software.
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5

Synthesis of Copper Nanoparticles

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All the chemicals used were of analytical reagent grade and were used without any further purification. PVP (MW 10 000) was provided by Sigma-Aldrich (USA). Copper nitrate trihydrate (98%, Cu(NO3)2·3H2O) and sodium hydroxide (99.5%, NaOH) granules were purchased from Merck (Germany). 4-Nitrophenol (4-NP), 4-nitroaniline (4-NA) 4-nitrobenzaldehyde, 2-nitrobenzaldehyde, and 5-amino-2-hydroxybenzoic acid (5-ASA) were purchased from Sigma Aldrich (Germany).
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6

Analytical Ranking of Chemicals

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The chemicals of analytical ranking for example 2-Nitrobenzaldehyde, 3-Nitrobenzaldehyde, 4-Nitrobenzaldehyde, 4-Methyl-benzenesulfonylhydrazine, AgNO3, AuCl3, CdSO4, Co(NO3)2, Cr(NO3)3, HgCl2, NiCl2, Y(NO3)3, ZnSO4, EtOH, MeOH, NaH2PO4, Na2HPO4, and nafion (5% ethanolic solution) were purchased from the Sigma Aldrich company, and used as received. A mother solution of Y3+ (100.0 mM) was prepared from the purchased chemical, Y(NO3)3. A Stuart scientific SMP3 (version 5.0) melting point apparatus (Bibby Scientific Limited, Staffordshire, UK) was used to record the melting point (m.p.), and the reported m.p. was not corrected. 1H-NMR, and 13C-NMR spectra were recorded on an AVANCE-III instrument (400 MHz, Bruker, Fallanden, Switzerland) at 300 k, and chemical shifts were reported in ppm with reference with residual solvent signal. FTIR spectra were recorded as neat on a Thermo scientific NICOLET iS50 FTIR spectrometer (Madison, WI, USA). UV-V is study was conducted using Evolution 300 UV-Vis spectrophotometer (Thermo scientific). I-V method was carried out in order to detect Y3+ at a selective point using the modified 2-MNBBSH/GCE by Keithley electrometer (6517A, USA). Warning! Yttrium is poisonous. So, a minute amount of this chemical can be used for the preparation of the essential solution with care.
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7

Immunoaffinity-based detection of nitrofuran metabolites

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Furaltadone, furazolidone, nitrofurantoin, Furaltadone, AMOZ, AOZ, AHD, SEM, 2-NP-AMOZ, 2-NP-AOZ, 2-NP-AHD, 2-NP-SEM, 2-nitrobenzaldehyde, 4-carboxybenzaldehyle, and horseradish peroxidase-labeled goat anti-mouse IgG were purchased from Sigma-Aldrich (St. Louis, MO, USA). Goat anti-mouse IgG conjugated with 655 nm QDs was obtained from Invitrogen Corp (Carlsbad, CA, USA). N,N-dicyclohexylcarbodiimide (DCC), N,N-dimethylformamide (DMF), N-hydroxysuccinimide (NHS), dimethyl sulfoxide (DMSO), ethyl acetate, and all other chemicals were of analytical grade and purchased from Sinopharm Chemical Reagent Co. Ltd. (Beijing, China) unless indicated otherwise.
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8

Synthesis of Substituted Benzophenones

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Reagents and materials 4-Hydroxybenzophenone (4BPOH, 98%), benzophenone (BP, 99%), furfuryl alcohol (FFA, 98%), 2-propanol (99.8%), 2-nitrobenzaldehyde (98%), acetonitrile (gradient grade), HClO 4 (70% in water), NaOH (98%) and methanol (gradient grade) were purchased from Sigma-Aldrich, and nitrogen (5.5, 99.9995%), argon (5.5, 99.9995%) and oxygen (6.0, 99.9999%) from SAPIO. Water used was of Milli-Q quality.
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9

Photosensitizer Synthesis and Characterization

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Anthracene, oleic acid, linoleic acid, acetonitrile, methylene blue (MB), DABCO, BHT, BHA, TBHQ, 2-nitrobenzaldehyde, 3-nitrobenzaldehyde, and 4-nitrobenzaldehyde were purchased from Merck or Sigma-Aldrich (Vienna, Austria) and Alfa Aesar (Karlsruhe, Germany) without further purification. 5,10,15,20-Tetrakis(tolyl)porphyrin (H2TTP) and its ferric complex TTPFeCl were synthesized according to the literature [13 (link),14 (link)].
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10

Analytical Characterization of Semicarbazide

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Methanol, ammonium acetate, ethyl acetate, dimethyl sulfoxide, 2-nitrobenzaldehyde were of high-performance liquid chromatography (HPLC) grade and purchased from Merck Corporation (Darmstadt, Germany). Dipotassium hydrogen phosphate and hydrochloric acid were of superior pure grade and purchased from Sinopharm Chemical Reagent (Shanghai, China). Semicarbazide HCl and semicarbazide HCl-13C,15N2 analytical standards were obtained from Dr.Ehrenstorfer GmbH (Augsburg, Germany). Water was purified in a Milli-Q system (Millipore, Burlington, MA, USA). Semicarbazide crude drug (99% purity) was obtained from Aladdin (Shanghai, China).
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