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Materials 2020, 13, 2646 7 of 24 6.07 (1H, s, C=CH), 5.94 (1H, s, C=CH), 5.85 (1H, s, C=CH), 4.36 (4H, br s, NCH2(CH2)4CH3), 4.21 (2H, br t, J = 7.2, NCH2(CH2)4CH3), 4.14 (2H, br t, J = 7.2, NCH2(CH2)4CH3), 3.30 (3H, br s, NHCH3), 3.29 (3H, br s, NHCH3), 1.77–1.71 (4H, m, NCH2CH2(CH2)3CH3), 1.67 (4H, br qt, NCH2CH2(CH2)3CH3), 1.52 (2H, br qt, N(CH2)2CH2(CH2)2CH3), 1.48 (2H, br qt, N(CH2)2CH2(CH2)2CH3), 1.39 (4H, br qt, N(CH2)2CH2(CH2)2CH3), 1.36–1.24 (16H, m, N(CH2)3(CH2)2CH3), 0.90–0.84 (12 H, m, N(CH2)5CH3) ppm. 13C NMR (150.90 MHz, DMSO-d6) δ: 174.59, 174.43, 165.80, 165.66, 163.51, 161.06, 157.64, 157.29, 154.74, 153.45, 151.45, 150.58, 142.37, 142.21, 138.90, 138.60, 136.67 (ArCH), 135.38 (ArCH), 132.83 (ArCH), 132.51 (ArCH), 129.25 (ArCH), 128.99 (ArCH), 128.26, 128.08, 127.54 (ArCH), 127.37 (ArCH), 125.94 (ArCH), 125.70 (ArCH), 125.67 (ArCH), 125.19 (ArCH), 124.73 (ArCH), 124.42 (ArCH), 124.15 (ArCH), 123.93 (ArCH), 121.73, 119.60, 116.53 (ArCH), 116.18 (ArCH), 114.41 (ArCH), 113.99 (ArCH), 94.44 (C=CH), 93.99 (C=CH), 89.86 (C=CH), 89.30 (C=CH), 48.36 (NCH2(CH2)4CH3), 48.26 (NCH2(CH2)4CH3), 46.72 (NCH2(CH2)4CH3), 46.07 (NCH2(CH2)4CH3), 31.05 (CH2), 30.97 (CH2), 30.89 (CH2), 30.81 (CH2), 30.28 (NHCH3), 30.09 (NHCH3), 27.08, (CH2), 26.98 (CH2), 26.60 (CH2), 25.76 (CH2), 25.72 (CH2), 25.70 (CH2), 25.60 (CH2), 22.17 (CH2), 22.08 (CH2), 22.01 (CH2), 13.90 (CH3), 13.86 (CH3), 13.83 (CH3), 13.81 (CH3) ppm. HRESI-TOFMS m/z: 600.24826 [M-I]+ (C35H42N3OSe+, calc. 600.24900). 2.2. Photostability Assessment From dimethyl sulfoxide dye stock solutions at 1 mM, working solutions of each studied compound at a concentration of 25 μM were prepared by diluting them in the same solvent or in phosphate-buffered saline. Two hundred microliters of each diluted dye solution were added to each well of a 96-well plate, and these treatments were performed in quadruplicate. The dyes 9–12 were repeatedly irradiated for periods of 1 min with a light-emitting diode system, the characteristics of which are found in Section 2.4, and their absorbance was measured at a wavelength close to that of maximum absorption in dimethyl sulfoxide for 20 min using a Multiscan Go spectrophotometer microplate reader (Thermo Fisher Scientific, Vantaa, Finland). Finally, a graph was made with the variation of the normalized absorbance of the dyes as a function of the irradiation time. For comparison, the commercially known methylene blue (Merck, Darmstadt, Germany) was used, which displays an absorption wavelength close to the prepared squaraine dyes herein presented. 2.3. Dyes’ Singlet Oxygen Quantum Yields Determination Singlet oxygen quantum yields of squaraine dyes 9, 11 and 12 were measured as earlier described by our research group [48]. In summary, a system equipped with a OBB OL-401 nitrogen laser (Horiba Scientific, Piscataway, NJ, USA) exiting at 337 nm with 0.60 ns pulses and 1.1 mJ/pulse, and a detection system with an indium gallium arsenide charge-coupled device (model iDus from Andor Technology Limited, Belfast, UK) working at −60 ◦C coupled to a fixed spectrograph (model Shamrock 163i also from Andor). During the quantum yield determinations, long pass filters were used to exclude the radiation from reaching the LFP1100 detector (CVI Laser Optics, Albuquerque, NM, USA). Phenazine (Φ∆ = 0.84) was used as a standard at an optical density of 0.6. The comparison of the total areas of the emission spectra displayed for the standard sample with those displayed by the prepared squaraine dyes, using the same optical density at the excitation wavelength, allowed the calculation of their singlet oxygen quantum yields. 2.4. In Vitro Photobiological Assays BT-474 and MCF-7 breast cancer cell lines were used for the evaluation of the photocytotoxicity of squaraine cyanine dyes 9, 11 and 12. Cells were maintained in Dulbecco’s modified Eagle medium (Nutrient Mixture F12; 1:1) (DMEM) containing 25 mM glucose and supplemented with 10% (v/v) FBS, 2 mM L-glutamine, 100 U/mL penicillin and 100 μg/mL streptomycin, in an incubator at 37 ◦C in controlled humidity atmosphere containing 5% CO2 in the air environment. Cell culture medium was renewed every two days and cells were sub-cultured before reaching 95% of confluence [49].PDF Image | Photophysicochemical Light Antiproliferative vs cancer
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