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5 protocols using 2 picolylamine

1

AIBN-Mediated Synthesis of Multifunctional Nanomaterials

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Azobis(isobutyronitrile) (AIBN), l-glutathione (GSH),
2,2′-dichloro-p-xylene,
2-picolylamine, 2,2′-dithiodiethanol, methacryloyl chloride,
triphosgene, and ethylenediamine tetraacetic acid (EDTA) were purchased
from Sigma-Aldrich. HPMA was purchased from Amadis Chemical (Hangzhou,
China). Human CXCL12 was from Shenandoah Biotechnology, Inc. (Warwick,
PA). miR-200c mimic (mature miRNA sequence: 5′-UAAUACUGCCGGGUAAUGAUGGA-3′)
and negative control miR-NC (mature miRNA sequence: 5′-UCACAACCUCCUAGAAAGAGUAGA-3′)
were purchased from GE Dharmacon (Lafayette, CO). Oligofectamine (OligoFT)
was from ThermoFisher Scientific. All the other regents were purchased
from Fisher Scientific unless specifically noted.
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2

Cobalt-catalyzed Borylation Reactions

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All experiments were carried out using dry solvents. The boronic acid, dialkyl phosphites, DIPEA, triethylamine, pyridine, 2,2′-dipyridylamine, 2-picolylamine, di-(2-picolyl)amine, and ter-pyridine, as well as the cobalt salts, were purchased from Sigma Aldrich. Silica gel for column chromatography and thin layer chromatography (TLC) plates (Silica gel 60 F254) were ordered from EMD/Merck. The analytical thin layer chromatography was eluted in the Ethylacetate/Hexane (30:70) solvent system. An ultra-violet lamp, iodine chamber, and PMA solution spray was used to visualize the product spots on thin layer chromatography (TLC). 1H-NMR and 13C-NMR spectra were recorded on Bruker Advance 400 and 100 MHz, respectively, and were referenced to residual protic solvent (CDCl3 1H [7.26 ppm] and CDCl3 13C [77.00 ppm]. Mass analyses were performed on the Joel GC-MS instrument (EI). The products were fully characterized using 1H-NMR, 13C-NMR, 31P-NMR, and GC-MS, and the relevant data has been provided in this section. All reagents were used as received from commercial sources without further purification.
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3

Lipid Derivatization and Quantification

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An AccQ•Tag Ultra derivatization kit (borate buffer and reagent) and AccQ•Tag Ultra eluents A and B were obtained from Waters (Milford, MA, USA). Ammonium formate, formic acid, and potassium hydroxide were acquired from Sigma-Aldrich (St. Louis, MO, USA). Hydrochloric acid solution and sodium hydroxide were purchased from Daejung (Seoul, Korea). HPLC-grade methanol, ethyl acetate, isopropyl alcohol, and chloroform were purchased from Burdick & Jackson (Muskegon, MI, USA). CHOL and the FFAs (C12, C14, C16, C16:1, C18, C18:1, C18:2, C20, C22, C22:1, C24, C24:1, C26, and C28) were obtained from Sigma-Aldrich. Deuterated FFAs C16-D3, C20-D3, and C18:1-D2 were purchased from Cambridge Isotope Laboratories (Andover, MA, USA). Synthetic CER-NP, CER-NDS, and CER-NS were purchased from Avanti Polar Lipids (Alabaster, AL, USA). Synthetic CER-AP was kindly provided by Evonik (Essen, Germany). 2,2′-dithiodipyridin, 2-picolylamine, and triphenylphosphine were purchased from Sigma-Aldrich. All other reagents used were of the highest grade available. The water used was ultra-pure deionized water (18.2 MΩ•cm) produced using a Milli-Q Gradient system (Millipore, Bedford, MA, USA).
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4

Copper(II) Pyridine-2,4-dicarboxylate Synthesis

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All chemicals and solvents used for the synthesis were of AR grade. Triethylamine, copper(II) nitrate trihydrate, were obtained from E. Merck, India. Pyridine-2,4dicarboxylic acid and 2-picolylamine (2-aminomethylpyridine) were purchased from Aldrich Chemical Co. All chemicals were used without further purification. Elemental analyses (carbon, hydrogen and nitrogen) were performed with a Perkin Elmer 2400 II Elemental Analyser. Copper(II) content of 1 has been estimated quantitatively by standard iodometric procedure. The Fourier transform infrared spectrum was recorded on a Perkin Elmer RX-I FT-IR spectrophotometer, with solid KBr disc, in the range 4000-400 cm -1 . Solid state UV-Vis spectrum of the title complex was recorded on a Perkin Elmer Lambda 35 UV-Vis system in the range 1100-200 nm. TG analysis was performed with a Perkin-Elmer (Singapore) Pyris Diamond TGA unit. Thermal study was performed at the temperature range 35-800 °C by maintaining the heating rate at 5 °C min -1 in a stream of nitrogen flowing at the rate of 50 mL min -1 with the sample in a platinum crucible. Powder X-ray diffraction was performed on a Bruker D8 instrument with Cu-Kα radiation. (2,4-
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5

Synthesis and Characterization of Heterocyclic Compounds

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N,N-Dimethylethylenediamine, 2-picolylamine, pyridine-2-carboxaldehyde, 1-methylimidazole-carboxaldehyde, sodium triacetoxyborohydride, adamantane, silver perchlorate monohydrate, 3-chlorosalicylic acid (Aldrich), 6-methylpyridine-2-carboxaldehyde and quinolin-2-carboxaldehyde (Alfa Aesar), tetraethylammonium chloride (Lancaster), cyclohexane (Ranbaxy, India), iron(iii) chloride hexahydrate (Loba, India), acetic acid, pentane (Merck, India) were used as received. The supporting electrolyte tetrabutylammonium perchlorate (NBu4ClO4, G. F. Smith, USA) was recrystallized twice from aqueous ethanol. Diethyl ether and tetrahydrofuran were dried over sodium metal with benzophenone indicator. Acetonitrile, dichloromethane (Merck, India) and methanol (Fisher Scientific, India) were distilled before use.
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