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2 protocols using l histidine methyl ester dihydrochloride

1

Polyelectrolyte Multilayer Coatings

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Poly(isobutylene-alt-maleic anhydride) (PIAMA, Mw: 6 kDa), poly(allylamine hydrochloride) (PAH, Mw: 58 kDa), l-histidine methyl ester dihydrochloride, 3-aminopropyltrimethoxysilane (APTMS), N,N-diisopropylethylamine (DIPEA), copper(ii) nitrate trihydrate (Cu(NO3)2 × 3H2O), sodium chloride, sea salt and sodium hydroxide (all from Sigma Aldrich), N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), toluene, methanol, acetone and isopropanol (all from Tedia) were used directly as received without further purification. Dialysis membrane tubing (MWCO: 3.5 kD) was received from Fisher Scientific. Silicon wafers (Latech Scientific Supply Pte. Ltd) were 0.6 mm thick, with one side polished and with a natural silicon dioxide layer. QSX 303 Silicon dioxide 50 nm quartz crystal microbalance (QCM) chips were obtained from Analytical Technologies Pte Ltd. Deionized (DI) water with 18 MΩ cm–1 resistivity was obtained from a Millipore Nanopure system.
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2

Synthesis of Borane-Based Compounds

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Solvents (HPLC grade) and solids (Bu4N)CN (95%), L-histidine methyl ester dihydrochloride (97%), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (97%), 1-hydroxybenzotriazole (97%), 4-dimethylaminopyridine (99%), sodium tetraphenylborate (99%) were purchased from Sigma-Aldrich and used without additional purification. [Et3NH]2[B10H10] was prepared from decaborane-14 using the known synthetic procedure [52 (link)]. (Bu4N)[B10H11] was prepared by protonation of the [B10H10]2− anion in the CH3CN/CF3COOH system according to the method reported [53 ]. (Bu4N)[2-B10H9O(C4H8)] was synthesized from (Bu4N)[B10H11] and THF according to the known procedure [54 (link)]. The substitute was opened to give (Bu4N)2[2-B10H9OC4H8CN] when reacting with (Bu4N)CN in dichloromethane [55 (link)]; (Bu4N)2[2-B10H9OC4H8COOH] was obtained [55 (link)] by hydrolysis in boiled methanol with KOH.
Racemic rimantadine hydrochloride purchased from Zhejiang Kangyu Pharmaceutical Co (China) and hydroxychloroquine sulfate purchased from Promochem (Finland) were used as reference drugs.
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