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materials Article Quinoline- and Benzoselenazole-Derived Unsymmetrical Squaraine Cyanine Dyes: Design, Synthesis, Photophysicochemical Features and Light-Triggerable Antiproliferative Effects against Breast Cancer Cell Lines Eurico Lima 1 , Renato E. Boto 2 , Diana Ferreira 3 , José R. Fernandes 1 , Paulo Almeida 2, Luis F. V. Ferreira 3 , Eliana B. Souto 4,5 , Amélia M. Silva 6,* and Lucinda V. Reis 1,* 1 2 3 4 5 6 * Correspondence: amsilva@utad.pt (A.M.S.); lucinda.reis@utad.pt (L.V.R.) Received: 30 April 2020; Accepted: 8 June 2020; Published: 10 June 2020 Chemistry Centre of Vila Real (CQ-VR), University of Trás-os-Montes and Alto Douro, Quinta de Prados, 5001-801 Vila Real, Portugal; eurico_lima@icloud.com (E.L.); jraf@utad.pt (J.R.F.) Health Sciences Research Centre (CICS-UBI), University of Beira Interior, Av. Infante D. Henrique, 6201-001 Covilhã, Portugal; rboto@ubi.pt (R.E.B.); pjsa@ubi.pt (P.A.) Institute of Bioengineering and Biosciences (iBB), Higher Technical Institute, University of Lisbon, Av. Rovisco Pais, 1049-001 Lisbon, Portugal; diana.ferreira@det.uminho.pt (D.F.); luisfilipevf@ist.utl.pt (L.F.V.F.) Department of Pharmaceutical Technology, Faculty of Pharmacy, University of Coimbra, Pólo das Ciências da Saúde, Azinhaga de Santa Comba, 3000-548 Coimbra, Portugal; ebsouto@ff.uc.pt Centre of Biological Engineering (CEB), University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal Department of Biology and Environment (DeBA), and Centre for Research and Technology of Agro-Environmental and Biological Sciences (CITAB-UTAD), University of Trás-os-Montes and Alto Douro, Quinta de Prados, 5001-801 Vila Real, Portugal Abstract: Photodynamic therapy is an innovative treatment approach broadly directed towards oncological diseases. Its applicability and efficiency are closely related to the interaction of three main components, namely a photosensitizer, light and molecular triplet oxygen, which should drive cell death. Recently, several studies have demonstrated that squaraine cyanine dyes have a set of photophysical and photochemical properties that have made of these compounds’ potential photosensitizers for this therapeutic modality. In the present research work, we describe the synthesis and characterization of four quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes. Except for the precursor of aminosquaraine dyes, i.e., O-methylated derivative, all dyes were evaluated for their behavior and absorption capacity in different organic and aqueous solvents, their ability to form singlet oxygen, their light-stability, and in vitro phototherapeutic effects against two human breast cancer cell cultures (BT-474 and MCF-7). Regardless of the nature of the used solvents, the synthesized dyes showed intense absorption in the red and near-infrared spectral regions, despite the formation of aggregates in aqueous media. Dyes showed high light-stability against light exposure. Despite the low ability to produce singlet oxygen, aminosquaraine dyes demonstrated worthy in vitro phototherapeutic activity. Keywords: breast cancer; phototherapeutic effects; singlet oxygen; light-stability; quinoline; benzoselenazole; unsymmetrical squaraine dyes 1. Introduction Breast cancer is the most recurrently diagnosed cancer among women worldwide, currently accounting for 25% of cancers in women and 15% of cancer-related deaths [1]. Worldwide, the disease Materials 2020, 13, 2646; doi:10.3390/ma13112646 www.mdpi.com/journal/materialsPDF Image | Photophysicochemical Light Antiproliferative vs cancer
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