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Materials 2020, 13, 2646 17 of 24 Materials 2020, 13, x FOR PEER REVIEW 17 of 25 Figure 5. Antiproliferative effects of photodynamic treatment on MCF-7 cells. MCF-7 cells were Figure 5. Antiproliferative effects of photodynamic treatment on MCF-7 cells. MCF-7 cells were exposed for 24 h to the quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine exposed for 24 h to the quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes dyes 9, 11 and 12, at indicated concentrations, and then subjected to light-treatment using a 9, 11 and 12, at indicated concentrations, and then subjected to light-treatment using a light-emitting light-emitting diode system 0, 7, or 14 min (see methods for details). After contact with the irradiated diodesystemdye0s,f7o,ro1rh1o4rmforin24(she,ecemll veitahboilidtyswfoars dasesteassielsd)..CAelfltveirabciolitnietsaacrtewexipthretshsediarsrathdeiapetercdendtaygesofor1horfor control, non-treated cells (0 μM), and presented as mean value ± standard error of three independent 24 h, cell viability was assessed. Cell viabilities are expressed as the percentage of control, non-treated experiments (each one in quadruplicates). Student’s t-test statistical significant treatments related to cells (0 μM), and presented as mean value ± standard error of three independent experiments (each one the non-treated condition (p-value < 0.05) are evidenced by an asterisk (*) of the color relative to the in quadruplicates). Student’s t-test statistical significant treatments related to the non-treated condition irradiation time. (p-value < 0.05) are evidenced by an asterisk (*) of the color relative to the irradiation time. The recorded half-inhibitory concentration values (which translate the pharmacological potency of a drug and the required concentration to produce a 50% reduction in cell viability) are shown in 4. Discussion Table 4. Similarly to what was previously reported [25], the zwitterionic dye 9 presented weak and The syintchonesiissteonft uefnfescytsmonmberteraisctaclanmceorlceecluls,leas,itinshtohweecdahsieghofhathlf-eindhyibeitsorpyrecosnecnetnetrdatinonthvaislusetsuindy, aimed at all tested conditions. However, aminosquaraines 11 and 12 were only able to significantly reduce combining photophysicochemical properties which, according to some of our previous works, would these values in irradiated treatments (Table 4). These differences in potency of irradiated and be of particular interest in the formulation of novel photosensitizer candidates for photodynamic non-irradiated aminosquaraine dyes suggest their potential application as photosensitizers for breast cancertheracapnyc.erTpheotcodhyoniacmeiocfthqeuraipnyo.lTihneehaignhdcobeeffniczieonstseloefnvalzuoesl’edhetetremrioncatyiocnle(s≥0w.95a)sabreasuegdgeostnivtehefactthat the dyes with quinoline units display a much higher red shift in their absorption than other heterocycle nuclei [39], and those of benzoselenazole, as it has a heavy atom in their structure, can positively influence the production of reactive oxygen species by the so-called “heavy atom effect” [40]. All dyes, regardless of the polarity of the organic solvents studied, displayed narrow and intense absorption bands in the red and near-infrared regions, one of the most critical properties, since the light from these electromagnetic regions can better permeate living tissues, as well as making sure that energy can reach the photosensitizing molecule to be activated. Their molar absorptivity coefficients also show the high capacity of these dyes to capture energy from radiation. Compared to symmetrical quinoline-derived squaraine dyes, previously synthesized and reported by some of us [42], these unsymmetrical dyes displayed similar maximum absorption wavelengths. However, compared to thePDF Image | Photophysicochemical Light Antiproliferative vs cancer
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