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探究两种具有抗增殖作用的苯并二氮杂吡咯衍生物的光动力性质。

Exploring the Photodynamic Properties of Two Antiproliferative Benzodiazopyrrole Derivatives.

机构信息

Department of Pharmacy, University of Naples Federico II, 80131 Naples, Italy.

Department of Physics "Ettore Pancini", University of Naples Federico II, 80126 Naples, Italy.

出版信息

Int J Mol Sci. 2020 Feb 13;21(4):1246. doi: 10.3390/ijms21041246.

DOI:10.3390/ijms21041246
PMID:32069905
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7072997/
Abstract

The identification of molecules whose biological activity can be properly modulated by light is a promising therapeutic approach aimed to improve drug selectivity and efficacy on the molecular target and to limit the side effects compared to traditional drugs. Recently, two photo-switchable diastereomeric benzodiazopyrrole derivatives and have been reported as microtubules targeting agents (MTAs) on human colorectal carcinoma p53 null cell line (HCT 116 p53-/-). Their IC was enhanced upon Light Emitting Diode (LED) irradiation at 435 nm and was related to their form. Here we have investigated the photo-responsive behavior of the acid derivatives of and , namely, and , in phosphate buffer solutions at different pH. The comparison of the UV spectra, acquired before and after LED irradiation, indicated that the conversion of and is affected by the degree of ionization. The apparent rate constants were calculated from the kinetic data by means of fast UV spectroscopy and the conformers of the putative ionic species present in solution (pH range: 5.7-8.0) were modelled. Taken together, our experimental and theoretical results suggest that the photo-conversions of / into the corresponding forms and the thermal decay of / are dependent on the presence of diazonium form of /. Finally, a photo-reaction was detected only for after prolonged LED irradiation in acidic medium, and the resulting product was characterized by means of Liquid Chromatography coupled to High resolution Mass Spectrometry (LC-HRMS) and Nuclear Magnetic Resonance (NMR) spectroscopy.

摘要

光活性分子的鉴定是一种很有前途的治疗方法，旨在提高药物对分子靶点的选择性和疗效，并限制与传统药物相比的副作用。最近，两种光可切换的非对映体苯并二氮杂吡咯衍生物和 被报道为针对人类结直肠癌细胞 p53 缺失细胞系（HCT 116 p53-/-）的微管靶向剂（MTAs）。它们的 IC 在 435nm 的发光二极管（LED）照射下增强，这与它们的 形式有关。在这里，我们研究了酸衍生物 和 的光响应行为，即 和 ，在不同 pH 值的磷酸盐缓冲溶液中。比较 LED 照射前后的紫外光谱表明， 和 的 转换受离解度的影响。通过快速紫外光谱法从动力学数据计算出表观速率常数，并对溶液中存在的假定离子物种的构象进行建模（pH 范围：5.7-8.0）。总之，我们的实验和理论结果表明， / 向相应的 形式的光转化以及 / 的热衰减取决于 的重氮形式的存在。最后，仅在酸性介质中长时间 LED 照射后才检测到 的光反应，并用液相色谱-高分辨率质谱（LC-HRMS）和核磁共振（NMR）光谱对所得产物进行了表征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6df/7072997/d35fe9e23f95/ijms-21-01246-g009.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6df/7072997/d7831d47e30d/ijms-21-01246-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6df/7072997/6899e33931f6/ijms-21-01246-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6df/7072997/58fdf13d217d/ijms-21-01246-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6df/7072997/7df5da637a8e/ijms-21-01246-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6df/7072997/a9566e816a34/ijms-21-01246-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6df/7072997/9102ce7fc67e/ijms-21-01246-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f6df/7072997/d35fe9e23f95/ijms-21-01246-g009.jpg

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