Optical properties and antiangiogenic activity of a chalcone derivate

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 204; pp. 685 - 695
• Main Authors: Lemes, Susy Ricardo, Júnior, Luizmar Adriano, da Silva Manoel, Diego, de Sousa, Maria Alice Montes, Fonseca, Ruben Dario, Lima, Rosa Silva, Noda-Perez, Caridad, de Melo Reis, Paulo Roberto, Cardoso, Clever Gomes, de Paula Silveira-Lacerda, Elisângela, Souza, Marcio Adriano Rodrigues, Mendonça, Cleber Renato, Gonçalves, Pablo José, de Boni, Leonardo, da Fonseca, Tertius Lima, da Silva Junior, Nelson Jorge
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 05.11.2018
• Subjects: Antiangiogic activity; Chalcona; Optical properties; Sarcoma; Chalcona; Sarcoma; Optical properties; Antiangiogic activity
• ISSN: 1386-1425; 1873-3557
• DOI: 10.1016/j.saa.2018.06.099

Chalcones and their derivatives exhibit numerous pharmacological activities such as antibacterial, antifungal, cytotoxic, antinociceptive and anti-inflammatory. Recently, they have been assessed aiming for novel application in nonlinear optics and in the treatment of immune diseases and cancers. In this study, we investigate the optical properties of synthetic chalcona 1E,4E-1-(4-chlorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one (CAB7β) and its antiangiogenic potential using the chorioallantoic membrane (CAM) with the S180 sarcoma cell line. Experimental and theoretical results show intense absorption in the UVA-UVC region, which is associated with a π → π* transition with intramolecular charge transfer from the trimethyl-cyclohexen-1-yl ring to the chlorophenyl ring. Quantum chemical calculations of the first hyperpolarizability, accounting for both solvent and frequency dispersion effects, are in very good concordance with hyper-Rayleigh scattering measurements. In addition, two-photon absorption allowed band centered at 650 nm was observed. Concerning antiangiogenic activity, CAB7β causes a significant reduction in the total number, junctions, length and caliber of blood vessels stimulated by S180 cells reducing the presence of blood vessels, inflammatory cells and others elements related to angiogenic process. It is found that CAB7β is a versatile compound and a promising candidate for linear and nonlinear optical applications, in therapy against sarcoma and phototherapy. [Display omitted] •CAB7β possesses absorption in UVA region which is associated with π → π* transition.•Two-photon absorption band and first hyperpolarizability were observed.•CAB7 reduces the number, junctions, length and caliber of blood vessels.•The antiangiogenic action of CAB7B is associated with its antiinflammatory activity.