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Materials 2020, 13, 2646 4 of 24 BT-474 cells were acquired from Cell Lines Service (CLS, Eppelheim, Germany) and MCF-7 cells from American Type Culture Collection (ATCC, Rockville, MA, USA). Dulbecco’s modified Eagle medium, trypsin-ethylenediamine tetraacetic acid, antibiotics (penicillin and streptomycin), L-glutamine amino acid, fetal bovine serum (FBS), Alamar Blue, and other consumables used in the in vitro photobiological assays were obtained from Gibco (Alfagene, Lisbon, Portugal). 2.1. Chemistry 2.1.1. Synthesis of 3-Butoxy-4-[(1-hexylquinolin-2(1H)-ylidene)methyl]-cyclobut-3-en-1,2-dione (5) A mixture of 2 (5.70 g, 16.1 mmol) and 4 (3.60 g, 16.4 mmol) in ethanol (180 mL) was heated under reflux for 4 h 30 min, in the presence of triethylamine (2.45 mL, 17.6 mmol). After cooling at room temperature, the mixture was kept in an ice bath, allowing the product to precipitate. The crude product was filtered under reduced pressure, washed with petroleum ether and dried on a vacuum pump. Orange crystals. Yield 63%. M.p. 158–159 ◦C. IR (KBr) νmax: 2955 (w, CH), 2930 (w, CH), 1758 (w, C=O), 1691 (m, C=O), 1626 (w), 1526 (s, ArC=C), 1481 (s), 1446 (m), 1405 (w), 1343 (s), 1171 (s), 831 (w), 749 (w) cm−1. 1H NMR (600 MHz, CDCl3) δ: 8.51 (1H, br s, ArH), 7.52 (1H, t, J = 7.8, ArH), 7.46 (1H, d, J = 7.8, ArH), 7.36 (1H, d, J = 9.6, ArH), 7.31 (1H, d, J = 8.4, ArH), 7.22 (1H, t, J = 7.5, ArH), 5.22 (1H, s, C=CH), 4.81 (2H, t, J = 6.6, OCH2(CH2)2CH3), 4.06 (2H, br s, NCH2(CH2)4CH3), 1.87–1.80 (4H, m, OCH2CH2CH2CH3 + NCH2CH2(CH2)3CH3), 1.57–1.47 (4H, m, O(CH2)2CH2CH3 + N(CH2)2CH2(CH2)2CH3), 1.46–1.37 (4H, m, N(CH2)3(CH2)2CH3), 1.00 (3H, t, J = 7.2, O(CH2)3CH3), 0.95 (3H, t, J = 6.9, N(CH2)5CH3) ppm. 13C NMR (150.90 MHz, CDCl3) δ: 193.05, 186.19, 184.78, 173.64, 150.50, 139.21, 132.92 (ArCH), 131.04 (ArCH), 128.70 (ArCH), 124.11 (ArCH), 123.79, 123.30 (ArCH), 114.05 (ArCH), 85.82 (C=CH), 73.40 (OCH2(CH2)2CH3), 47.76 (NCH2(CH2)4CH3), 32.05 (CH2), 31.19 (CH2), 26.34 (CH2), 25.76 (CH2), 22.50 (CH2), 18.66 (CH2), 13.90 (CH3), 13.68 (CH3) ppm. HRESI-TOFMS m/z: 380.22202 [M+H]+ (C24H30NO3+, calc. 380.22202). 2.1.2. Synthesis of 3-[(1-Hexylquinolin-2(1H)-ylidene)methyl]-4-hydroxycyclobut-3-ene-1,3-dione (6) To a solution of semisquaraine dye 5 (1.24 g, 3.30 mmol) in ethanol (65 mL) at 90 ◦C, 0.80 mL of a 40% (w/v) sodium hydroxide aqueous solution was added, and the reaction mixture was kept for further 15 min. After cooling at room temperature, 4.10 mL of a 2 M aqueous hydrochloric acid solution was added to the mixture. Then, the reaction mixture was neutralized, and it was placed into a separating funnel that contained dichloromethane. The organic phase was separated, washed twice with cold distilled water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the obtained residue was recrystallized from dichloromethane/petroleum ether. After the crude product was filtered under reduced pressure, the obtained residue was then washed with cold petroleum ether and dried under vacuum pressure. The resulting reddish crystals (75% yield) were used in the next reaction without further purification. 2.1.3. Synthesis of 2-[(3-Hexylbenzoselenazol-2(3H)-ylidene)methyl]-4-[(1-hexylquinolin-1-ium- 2-yl)methylidene]-3-oxocyclobut-1-en-1-olate (9) A mixture of semisquaraine dye 6 (2.40 g, 7.43 mmol) and benzoselenazole-based ammonium salt 8 (3.04 g, 7.45 mmol) in a solution of 10% of n-butanol/pyridine (150 mL) was heated under reflux for 4 h. After cooling at room temperature, the mixture was placed into a separating funnel that contained dichloromethane (100 mL). The organic layer was washed several times with distilled water before separation by decantation, dried with anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The resulting solid was recrystallized first from methanol/diethyl ether/petroleum ether and then from dichloromethane/diethyl ether to remove some impurities. Finally, the crystals were filtered under reduced pressure, washed with heated acetonitrile, and dried in a vacuum pump. Red crystals. Yield 33%. M.p. 280–281 ◦C (dec). Vis-NIR λmax (ACN): 686 nm, log ε = 5.11; Vis-NIR λmax (ACT): 692 nm, log ε = 5.24; Vis-NIR λmax (DCM): 694 nm, log ε = 5.18;PDF Image | Photophysicochemical Light Antiproliferative vs cancer
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