Monocarbonyl curcuminoids as potential photosensitizers in photodynamic therapy against skin cancer

IF 3.9 2区 生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY
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Abstract

Two monocarbonyl dimethylamino curcuminoids, one derived from acetone (C3) and the second one from cyclohexane (C6), were synthesized aiming to study their photophysical properties and anticancer photodynamic potential. Compound C6 exhibited lower absorbance and fluorescence than C3. Photobleaching studies showed that C3 and C6 photostability behavior in DMSO differ significantly. C3 was completely photoconverted into a new species absorbing at lower wavelength than the parent compound, whereas, C6, upon a 30 min irradiation at λ = 440 nm with 15 mW/cm2 reached a photostationary phase where a smaller amount of the initial compound coexists with some photoproducts of higher and lower absorbance. Both compounds were able to generate significant amounts of ROS upon irradiation in an aqueous environment and exhibited successful intracellular localization in skin cancer cells (A431 cells). After dark cytotoxicity studies the concentrations of 5 μM and 1 μM for C3 and C6, respectively, were selected for the PDT assessment. C3 presented light dose-dependent photodynamic activity against A431 cells, resulting in 40 % cell viability after 12 min of light irradiation (440 nm, 15 mW/cm2). On the other side, C6 showed a biphasic light dose PDT effect with cell viability gradually decreasing up to 50 % after 5 min of light exposure, and then increasing again after 8 and 12 min of light exposure. The photodynamic performance of C6 may provide a new insight into the development of PSs with reduced prolonged photosensitivity.

Abstract Image

单羰基姜黄素作为潜在的光敏剂用于皮肤癌的光动力疗法。
研究人员合成了两种单羰基二甲基氨基姜黄素,一种来自丙酮(C3),另一种来自环己烷(C6),旨在研究它们的光物理特性和抗癌光动力潜力。化合物 C6 的吸光度和荧光度均低于 C3。光漂白研究表明,C3 和 C6 在二甲基亚砜中的光稳定性有显著差异。C3 被完全光转化成一种吸收波长低于母体化合物的新物种,而 C6 在 λ = 440 nm 处以 15 mW/cm2 照射 30 分钟后进入光稳定阶段,在这一阶段,少量的初始化合物与一些吸收率较高或较低的光产物共存。这两种化合物在水环境中照射后都能产生大量的 ROS,并在皮肤癌细胞(A431 细胞)中成功地进行了细胞内定位。经过暗细胞毒性研究后,C3 和 C6 的浓度分别为 5 μM 和 1 μM,被选定用于光导放疗评估。C3 对 A431 细胞具有光剂量依赖性光动力活性,在光照射(440 纳米,15 毫瓦/平方厘米)12 分钟后,细胞存活率为 40%。另一方面,C6 显示出双相光剂量光动力疗法效应,细胞存活率在光照射 5 分钟后逐渐下降至 50%,在光照射 8 分钟和 12 分钟后再次上升。C6 的光动力性能可能为开发具有较低光敏感性的 PS 提供了新的思路。
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来源期刊
CiteScore
12.10
自引率
1.90%
发文量
161
审稿时长
37 days
期刊介绍: The Journal of Photochemistry and Photobiology B: Biology provides a forum for the publication of papers relating to the various aspects of photobiology, as well as a means for communication in this multidisciplinary field. The scope includes: - Bioluminescence - Chronobiology - DNA repair - Environmental photobiology - Nanotechnology in photobiology - Photocarcinogenesis - Photochemistry of biomolecules - Photodynamic therapy - Photomedicine - Photomorphogenesis - Photomovement - Photoreception - Photosensitization - Photosynthesis - Phototechnology - Spectroscopy of biological systems - UV and visible radiation effects and vision.
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