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新型吲哚螺吡喃与α-硫辛酸的分子杂合体作为潜在的光药理试剂:合成、结构、光致变色和生物性质。

Novel molecular hybrids of indoline spiropyrans and α-lipoic acid as potential photopharmacological agents: Synthesis, structure, photochromic and biological properties.

机构信息

Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka Ave., 344090 Rostov-on-Don, Russian Federation.

Academy of Biology and Biotechnology, Southern Federal University, 194/1 Stachka Ave., 344090 Rostov-on-Don, Russian Federation.

出版信息

Bioorg Med Chem Lett. 2021 Jan 1;31:127709. doi: 10.1016/j.bmcl.2020.127709. Epub 2020 Nov 23.

Abstract

Organic photochromic compounds are attracting great interest as photoswitchable components of various bioconjugates for using in photopharmacology, targeted drug delivery and bio-imaging. Here we report on the synthesis of two novel molecular hybrids of indoline spiropyrans and alpha-lipoic acid via an esterification reaction. Preliminary photochemical studies revealed photochromic activity of 5-methoxy-substituted spirocompounds in their acetonitrile solutions. Both hybrid spiropyrans along with their parent substances in the hybrids were tested for the short-term cytotoxicity on HeLa cell cultures. The results of cytotoxicity studies showed unpredictable biocompatibility of the hybrids in comparison with the parent hydroxyl-substituted spiropyrans and α-lipoic acid, especially at the relatively high concentration of 2 mM. Using flow cytometry, we demonstrated that the both hybrids induced antioxidant response in the model cells. After the 24 h treatment, the hybrids administered at lower (500 µM) concentration caused suppressed cytosolic ROS and/or induced cellular thiols. At higher concentration, one of the hybrids demonstrated properties qualitatively similar to alpha-lipoic acid, yet far more strong. Together, flow cytometry results suggested that both hybrids of spiropyrans possess emergent biochemical and signaling antioxidant properties, exceeding those of alpha-lipoic acid.

摘要

有机光致变色化合物作为各种生物缀合物的光开关组件,在光药理、靶向药物传递和生物成像中引起了极大的兴趣。在这里,我们通过酯化反应报告了吲哚啉螺吡喃和α-硫辛酸的两种新型分子杂化物的合成。初步光化学研究表明,5-甲氧基取代的螺化合物在其乙腈溶液中具有光致变色活性。两种混合螺吡喃及其母体物质在混合体中都在 HeLa 细胞培养物上进行了短期细胞毒性测试。细胞毒性研究的结果表明,与母体羟基取代的螺吡喃和α-硫辛酸相比,这些杂化物具有不可预测的生物相容性,特别是在相对较高的 2 mM 浓度下。通过流式细胞术,我们证明了这两种杂化物在模型细胞中诱导了抗氧化反应。经过 24 小时处理,在较低浓度(500 µM)下给药的杂化物会抑制细胞溶质 ROS 和/或诱导细胞硫醇。在较高浓度下,其中一种杂化物表现出与α-硫辛酸定性相似但更强的性质。总的来说,流式细胞术结果表明,两种螺吡喃杂化物都具有新兴的生化和信号抗氧化特性,超过了α-硫辛酸。

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