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5 protocols using phosphorus oxychloride

1

Synthesis and Purification of Heterocyclic Compounds

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2-Aminobenzylamine,
phosphorus oxychloride, 1-methylpiperazine, and iron powder were purchased
from Sigma-Aldrich (St. Louis, MO), while isatin, 5-nitroisatin, and
2-pyridinecarboxaldehyde were purchased from Acros (Geel, Belgium).
All chemicals, as well as the synthesized precursors, were used without
further purification. 2-Amino-5-nitrobenzylamine hydrochloride was
synthesized according to a procedure published elsewhere.46 The free amine was obtained by the dissolution
of the hydrochloride in a minimal amount of water, addition of 4 equiv
of aqueous ammonia, and collection of the formed precipitate by filtration.
Ethanol was dried over molecular sieves (3 Å), and tetrahydrofuran
(THF) was dried by using a standard procedure (Na/benzophenone).47
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2

Lipid Membrane Composition Analysis

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1,2-Dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and 1-(12-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]dodecanoyl)-2-hydroxy-sn-glycero-3-phosphocholine (NBD-LPC) were purchased from Avanti Polar Lipids, Inc. Chloroform was purchased from Macron Fine Chemicals and used as received. 2,4,6-collidine (99%), acetonitrile (HPLC), calcium chloride dihydrate (99%), and phosphorus oxychloride (99%), were purchased from Sigma Aldrich and used as received. Sodium chloride was used to maintain constant ionic strength in a 10 mM citric acid-sodium phosphate buffer (ACS grade). The buffer was used to maintain pH and tested prior to use in all experiments using a pH meter (Thermo Fisher). Water was obtained from a Barnstead water purification system and used for all experiments.
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3

Synthesis and Characterization of Organic Compounds

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P-phenylenediamine and 2-hydroxy-5-nitrobenzenaldehyde were purchased from Thermo Fisher Scientific (Morris Plains, NJ, USA). Shanghai Makclin Biochemical Co., Ltd. (Shanghai, China) provided the glycidyl trimethyl ammonium chloride (95%), AlCl3, and NaOH. Phosphorus oxychloride, sodium tungstate (Na2WO4⋅2H2O), NaCl, CHCl3, CDCl3, dimethyl sulfoxide, and CH3OH were purchased from Sigma-Aldrich (St. Louis, MO, USA). All chemicals were of a very high purity level and required no further processing before use. All the experimental solutions were prepared using ultrapure water of 18.2 MΩ·cm. Thin paper chromatography (PC) was utilized to explore the synthesis process. Furthermore, a basic UV lamp set to 250 nm and an eluent comprising a combination of 1:1 v/v ethanol and ethyl acetate were used to identify spots formed on the PC.
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4

Synthesis of Organic Compounds

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The chemicals used in this study, such as phenothiazine, allyl bromide, 2-pyridyl acetonitrile, and phosphorus oxychloride, were purchased from Sigma-Aldrich in Bangalore. Solvents, including dimethylformamide, chloroform, acetonitrile, acetone, tetrahydrofuran, hexane, and ethyl acetate, were purchased from Avra and used without further purification.
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5

Synthesis and Analysis of HQ-2P

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hydroquinone (HQ) and arbutin (Arb) were obtained from Wako Pure Chemical Industries, Ltd. (Osaka, Japan) . Phosphorus oxychloride and isostearyl alcohol were purchased from Sigma-Aldrich Co., Ltd., and from Nissan Chemical Industries, Ltd. (Tokyo, Japan) , respectively. Phosphatase inhibitor cocktail II (PIC II) was obtained from Merck Co. Disodium phenylene diphosphate (HQ-2P) was synthesized from hydroquinone and phosphoryl chloride.
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