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卟啉类第二代光敏剂的发展 总被引:19,自引:0,他引:19
马金石 《感光科学与光化学》2002,20(2):131-148
本文对目前用于光动力治疗的以卟啉为基础的第二代光敏剂进行了综述,这些光敏剂中的大部分已进入临床或临床前试验,光物理性质研究表明它们是很有前途的光动力药物。本文同样介绍了连接生物分子和硼烷的卟啉衍生物,作为光序剂,它们具有非常光明的前途。 相似文献
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卟啉类物质的基本合成方法 总被引:6,自引:1,他引:5
卟啉类化合物由于其独特的结构及性能,在抗癌、分析化学、模拟光合成、光电材料、催化氧化等方面具有广阔的应用前景。作者以典型物质四苯基卟啉的合成方法为例,对卟啉类物质的基本合成方法进行了比较、总结。 相似文献
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卟啉是一种具有良好光敏性的特殊大环共轭芳香化合物。文章利用活性自由基聚合的方法,以不对称羟基金属卟啉为原料,合成出具有温度响应性聚合物修饰的金属卟啉光敏剂,并通过核磁谱图分析证实了目标产物的结构。又以其作为光催化降解光敏剂,降解有机污染物亚甲基橙。考察不同光降解反应条件下,卟啉聚合物在氧化剂H_2O_2存在下,可见光照射下降解率最佳。同时也考察了不同温度、分子量、pH对光催化降解的影响。 相似文献
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以2-硝基四苯基卟啉及其Cu(Ⅱ)、Ni(Ⅱ)配合物为原料,分别与1-萘酚、2-萘酚反应,合成了4对β-萘酚基四苯基卟啉同分异构体,并通过1HNMR、UV、IR、MS对新化合物进行了结构表征。比较了两类卟啉同分异构体作为光动力治疗光敏剂在光敏抗菌及光敏切割DNA方面的活性差异,并利用Chem3D软件的MM2分子力场计算方法确定了卟啉同分异构体的空间优势结构。结果表明,β-萘酚基四苯基卟啉同分异构体空间结构的非平面程度相当,光敏活性差异也不明显,卟啉的非平面性与光敏活性具有一定的一致性。 相似文献
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Wenyu Wu Klingler Nadine Giger Lukas Schneider Vipin Babu Christiane Knig Patrick Spielmann Roland H. Wenger Stefano Ferrari Bernhard Spingler 《International journal of molecular sciences》2022,23(17)
Phthalocyanines (Pcs) are promising candidates for photodynamic therapy (PDT) due to their absorption in the phototherapeutic window. However, the highly aromatic Pc core leads to undesired aggregation and decreased reactive oxygen species (ROS) production. Therefore, short PEG chain functionalized A3B type asymmetric Pc photosensitizers (PSs) were designed in order to decrease aggregation and increase the aqueous solubility. Here we report the synthesis, characterization, optical properties, cellular localization, and cytotoxicity of three novel Pc-based agents (LC31, MLC31, and DMLC31Pt). The stepwise functionalization of the peripheral moieties has a strong effect on the distribution coefficient (logP), cellular uptake, and localization, as well as photocytotoxicity. Additional experiments have revealed that the presence of the malonic ester moiety in the reported agent series is indispensable in order to induce photocytotoxicity. The best-performing agent, MLC31, showed mitochondrial targeting and an impressive phototoxic index (p.i.) of 748 in the cisplatin-resistant A2780/CP70 cell line, after a low-dose irradiation of 6.95 J/cm2. This is the result of a high photocytotoxicity (IC50 = 157 nM) upon irradiation with near-infrared (NIR) light, and virtually no toxicity in the dark (IC50 = 117 μM). Photocytotoxicity was subsequently determined under hypoxic conditions. Additionally, a preliminarily pathway investigation of the mitochondrial membrane potential (MMP) disruption and induction of apoptosis by MLC31 was carried out. Our results underline how agent design involving both hydrophilic and lipophilic peripheral groups may serve as an effective way to improve the PDT efficiency of highly aromatic PSs for NIR light-mediated cancer therapy. 相似文献
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《精细化工》2016,(10)
以7-二芳氨基香豆素为电子给体,联噻吩或联苯噻吩为π桥,氰乙酸为电子受体设计合成了两个"D-π-A"型香豆素类光敏染料(Ⅴ1和Ⅴ2),通过核磁共振氢谱及高分辨质谱测定,确认其化学结构,测定了其紫外-可见吸收光谱、荧光发射光谱。采用密度泛函理论-高斯密度泛函〔DFT-B3LYP/6-31G(d)〕对化合物进行几何优化,并进一步用TD-DFT方法计算得到吸收光谱和发射光谱,分析了构效关系。结果表明,与7-二苯氨基香豆素光敏染料(Ⅴ_3和Ⅴ_4)相比,7-二芴氨基香豆素光敏染料(Ⅴ_1和Ⅴ_2)的基态能级差分别由2.49 eV和2.62 eV减小至2.31 eV和2.49 eV;激发态能级差也相应减小了0.52 eV和0.42 eV;与以联苯噻吩为π桥的光敏染料(Ⅴ_2和Ⅴ_4)相比,以联噻吩为π桥的光敏染料(Ⅴ_1和Ⅴ_3)具有更好的分子平面性,最大吸收波长分别红移4nm和19 nm,发射波长则分别红移9 nm和16 nm。 相似文献
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Osman Karaman Toghrul Almammadov M. Emre Gedik Dr. Gurcan Gunaydin Dr. Safacan Kolemen Dr. Gorkem Gunbas 《ChemMedChem》2019,14(22):1879-1886
Two red-absorbing, water-soluble and mitochondria (MT)-targeting selenophene-substituted BODIPY-based photosensitizers (PSs) were realized ( BOD − Se , BOD − Se − I ), and their potential as photodynamic therapy (PDT) agents were evaluated. BOD − Se − I showed higher 1O2 generation yield thanks to the enhanced heavy-atom effect, and this derivative was further tested in detail in cell culture studies under both normoxic and hypoxic conditions. BOD − Se − I not only effectively functioned under hypoxic conditions, but also showed highly selective photocytotoxicity towards cancer cells. The selectivity is believed to arise from differences in mitochondrial membrane potentials of healthy and cancerous cells. To the best of our knowledge, this marks the first example of a MT-targeted BODIPY PS that functions under hypoxic conditions. Remarkably, thanks to the design strategy, all these properties where realized by a compound that was synthesized in only five steps with 32 % overall yield. Hence, this material holds great promise for the realization of next-generation PDT drugs for the treatment of hypoxic solid tumors. 相似文献
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Taur Prakash Pandurang Bintu Kumar Narshimha Verma Debabrata Ghosh Dastidar Risa Yamada Tatsuya Nishihara Prof. Kazuhito Tanabe Prof. Dalip Kumar 《ChemMedChem》2023,18(1):e202200405
Six methyl pheophorbide-a derivatives were prepared by linking a tryptamine side chain at the C-13 1 , C-15 2 and C-17 3 positions of pheophorbide-a. P repared conjugates were characterized and evaluated for their photocytotoxicity against A549 cells. The conjugate 6 a with strong absorption at 413 nm (Soret band), 663–671 nm (Q bands) and comparable fluorescence quantum yield (0.26) was found to exhibit significant cytotoxicity (659 nM). Molecular integration of pheophorbide-a and tryptamines showed synergistic effects as the most potent conjugate 6 a was identified with enhanced photocytotoxicity when compared to methyl pheophorbide-a. T he conjugate 6 a was smoothly taken up by A549 cells and exhibited intracellular localization predominantly to lysosome in the cytoplasm. Upon photoirradiation 6 a generated singlet oxygen to show potent cytotoxicity toward A549 cells. 相似文献
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Bing Cun Cui Il Yoon Jia Zhu Li Woo Kyoung Lee Young Key Shim 《International journal of molecular sciences》2014,15(5):8091-8105
A series of novel purpurinimides with long wavelength absorption were designed and synthesized to develop novel and potential photosensitizers. These compounds were investigated through reduction, oxidation, rearrangement reaction and amidation reactions of methyl pheophorbide a. They demonstrated a considerable bathochromic shift of the major absorption band in the red region of the optical spectrum (695–704 nm). Newly synthesized purpurinimides were screened for their antitumor activities, and showed higher photodynamic efficiency against A549 cell lines as compared to purpurin-18 methyl ester. The results revealed the novel purpurinimides could be potential photosensitizers. 相似文献