Optical Properties And Antiangiogenic Activity Of A Chalcone Derivate

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

Theoretical study of electrical properties of retinal derivatives solution

Submitted by Erika Demachki ([email protected]) on 2014-11-10T16:30:55Z No. of bitstreams: 2 Dissertação - Luizmar Adriano Júnior - 2011.pdf: 4167499 bytes, checksum: 4e36a5a1dc0e88a79a75b9cc835c5185 (MD5) license_rdf: 23148 bytes, checksum: 9da0b6dfac957114c6a7714714b86306 (MD5)Approved for entry into archive by Erika Demachki ([email protected]) on 2014-11-10T16:31:04Z (GMT) No. of bitstreams: 2 Dissertação - Luizmar Adriano Júnior - 2011.pdf: 4167499 bytes, checksum: 4e36a5a1dc0e88a79a75b9cc835c5185 (MD5) license_rdf: 23148 bytes, checksum: 9da0b6dfac957114c6a7714714b86306 (MD5)Made available in DSpace on 2014-11-10T16:31:04Z (GMT). No. of bitstreams: 2 Dissertação - Luizmar Adriano Júnior - 2011.pdf: 4167499 bytes, checksum: 4e36a5a1dc0e88a79a75b9cc835c5185 (MD5) license_rdf: 23148 bytes, checksum: 9da0b6dfac957114c6a7714714b86306 (MD5) Previous issue date: 2011-03-03Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqIn this work we study the dipole moment, linear polarizability and first hiperpolarizability of 09cis, 11cis, 13cis and all-trans retinal derivatives in the gaseous phase and in different solvents. The solvent effects were modelled using the sequential Quantum Mechanics/Molecular Mechanics – S-QM/MM – methodology and the electric properties were calculated numerically with the finite field method. We use an average solvent electrostatic configuration – ASEC – to obtain the same statistical average with just one quantum mechanics calculation, instead of performing several quantum mechanics calculations for each one of the configurations of liquid. The second-order Møller–Plesset perturbation theory – MP2 – were used to describe the electronic structure. Our results show that the presence of the solvent increases the first hyperpolarizability of molecules of retinal [retinoic acid] by 17%-120% [5%-65%] when compared with corresponding gas phase results. It is found, in addition, that the dipole moment and the first hyperpolarizability are particularly affected by changes in the polarity and nature of solvent. A comparative analysis between cis and trans retinal derivatives shows that the isomerization effects have a marked influence on both the dipole moment and the average first hyperpolarizability.Neste trabalho estudamos o momento de dipolo, a polarizabilidade linear, e a primeira hiperpolarizabilidade de derivados de retinal 09cis, 11cis, 13cis e todo-trans em fase gasosa e diferentes solventes. Os efeitos de solvente foram modelados usando a metodologia seqüencial Mecânica Quântica/Mecânica Molecular - S-QM/MM - e as propriedades elétricas foram calculadas numericamente com o método de campo finito. Usamos uma configuração eletrostática média de solvente – ASEC – para obter a mesma média estatística com apenas um cálculo de mecânica quântica, ao invés de realizar diversos cálculos de mecânica quântica para cada uma das configurações de líquido. A teoria de perturbação de Møller–Plesset de segunda ordem - MP2 - foi usada para descrever a estrutura eletrônica. Nossos resultados mostram que a presença do solvente aumenta a primeira hiperpolarizabilidade de moléculas de retinal [ácido retinóico] em 17%-120% [5%-65%] quando comparados com os correspondentes resultados de fase gasosa. É encontrado, além disso, que o momento de dipolo e a primeira hiperpolarizabilidade são particularmente afetados pela mudança na polaridade e natureza do solvente. Uma análise comparativa entre derivados de retinal cis e trans mostra que os efeitos de isomerização têm uma influência marcante sobre ambos, o momento de dipolo e a primeira hiperpolarizabilidade média