CN109535066B - 基于无氧条件下利用光敏剂三线态激发态的分子组及其制备方法 - Google Patents
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Abstract
本发明公开了基于无氧条件下利用光敏剂三线态激发态的分子组及其制备方法,其主要步骤是:制备有机金属配合物D作为敏化剂,制备受光激发能够释放具有治疗效果分子的湮灭剂A,在此基础上通过上转换理论将两者建立联系,当氧气耗尽或降低到一定阀值后,光敏剂的三线态能量会通过上转换方式传递给湮灭剂,从而使得湮灭剂被激发释放具有治疗效果的小分子。本发明能够充分利用光敏剂的三线态能量,在肿瘤的光疗领域具有非常重要的应用前景。
Description
技术领域
本发明涉及有机光电材料技术领域,具体涉及能够在无氧条件下充分利用光敏剂三线态激发态分子组的设计、合成及其在光动力治疗中的应用。
背景技术
光敏剂是指在光化学反应中,把光能转移到一些对可见光不敏感的反应物上以提高或扩大其感光性能的物质。金属配合物是一类常用的光敏剂,在有特定波长的光照和氧气分子的存在下,其可将光能转移至氧气分子,使氧气分子受激发而转变为单线态氧分子;而在无氧气分子存在下,受到光照激发的光敏剂将通过辐射或非辐射等形式将能量耗散。
目前,光敏剂的这一特殊性质主要应用于光疗。光疗是一种非侵入性光触发的肿瘤治疗方法,其主要包括光动力疗法和光热疗法。光动力疗法是利用光敏剂在光照和氧气存在的条件下产生单线态氧或活性氧,从而达到杀死肿瘤细胞的目的。而在肿瘤细胞内部是乏氧的环境,氧气耗尽即不会再产生单线态氧分子,使得光敏剂的三线态能量无法得到充分的利用。
基于上述背景,我们提出开发一种在无氧条件下仍能够利用光敏剂的三线态能量,并可以治疗肿瘤细胞的分子组,这一研究将具有重要的医学应用意义。
发明内容
本发明的目的在于解决现有技术中的不足,提供一种能够在无氧条件下利用光敏剂的三线态能量,并可以治疗肿瘤细胞的分子组。
本发明的技术方案为:基于无氧条件下利用光敏剂的三线态激发态的分子组,所涉及的光敏剂D和湮灭剂A的结构式分别如下,
其中,光敏剂D的结构式为:
其中,N^N配体为下列中任一个:
湮灭剂A具有如下能够在特定波长的光激发时释放CO分子的结构式:
其中,Ar为以下任意一个萘类或蒽类小分子:
所述无氧条件下利用光敏剂的三线态激发态的分子组的制备方法,具体包括如下步骤:
S1,制备有机金属配合物作为光敏剂D;
S2,制备能够在光激发下释放具有治疗效果分子的湮灭剂A;
S3,通过上转换理论将光敏剂D与湮灭剂A建立联系;在氧气存在下,光敏剂的三线态能量会传递给氧气生成单线态氧;当氧气耗尽或降低到一定阀值后,光敏剂的三线态能量会通过上转换方式传递给湮灭剂,从而使得湮灭剂被激发释放具有治疗效果的小分子。
进一步地,所述光敏剂D的合成路线为:
具体的合成步骤是:
1)化合物1的制备
称取二水合三氯化钌,N^N配体和氯化锂加入到装有搅拌子且接有冷凝管的双口烧瓶中;用锡箔纸包裹烧瓶,密封,抽真空然后充氮气,循环三次;注入N,N-二甲基甲酰胺,将双口烧瓶置于153℃油浴锅中搅拌并冷凝回流6h;反应结束后,冷却至室温,加入丙酮溶液,放入冰箱中冰冻过夜,抽滤得黑色固体;
2)化合物2的制备
将上述所得化合物1和2,2-联吡啶加入到装有搅拌子且接有冷凝管的双口烧瓶中;用锡箔纸包裹烧瓶,密封,抽真空然后充氮气,循环三次;注入乙醇和水,将双口烧瓶置于78℃油浴锅中搅拌并冷凝回流24h;反应结束后,冷却至室温,将反应液滴入饱和的六氟磷酸钾水溶液中,抽滤,用正己烷和乙醚洗涤;
3)化合物3的制备
将上述所得化合物1和2,2-联喹啉加入到装有搅拌子且接有冷凝管的双口烧瓶中;用锡箔纸包裹烧瓶,密封,抽真空然后充氮气,循环三次;注入乙醇和水,将双口烧瓶置于78℃油浴锅中搅拌并冷凝回流24h;反应结束后,冷却至室温,将反应液滴入饱和的六氟磷酸钾水溶液中,抽滤,用正己烷和乙醚洗涤。
进一步地,所述湮灭剂A的合成路线为:
具体的合成步骤为:
将装有搅拌子且接有冷凝管的双口烧瓶抽真空然后充氮气,循环三次;用锡箔纸包裹烧瓶,密封;向双口烧瓶中注入反应原料Ar和反应原料四氯环丙烯,于-78℃环境下搅拌2h,再放置常温环境下搅拌4h;通过TLC监测反应进程,反应结束后,待反应液冷却到室温,萃取,抽滤洗涤。
本发明的有益效果为:
本发明在制备光敏剂D和湮灭剂A的基础上通过上转换理论将两者建立联系;在氧气存在下,光敏剂的三线态能量会传递给氧气生成单线态氧;当氧气耗尽或降低到一定阀值后,光敏剂的三线态能量会通过上转换方式传递给湮灭剂,从而使得湮灭剂被激发释放具有治疗效果的小分子。本发明能够充分利用光敏剂的三线态能量,并在肿瘤的光疗领域具有非常重要的应用前景。
附图说明
图1是光敏剂Ru(bpy)3和湮灭剂DPCP-F的紫外-可见吸收光谱;
图2是湮灭剂DPCP-F在365nm,6W/cm2光源下紫外-可见吸收光谱变化;
图3是湮灭剂DPCP-F在475nm,30mW/cm2光源下紫外-可见吸收光谱变化;
图4是光敏剂Ru(bpy)3和湮灭剂DPCP-F混合液在475nm,30mW/cm2光源下紫外-可见吸收光谱变化。
具体实施方式
以下实施例进一步说明本发明的内容,但不应理解为对本发明的限制。在不背离本发明实质的情况下,对本发明方法、步骤或条件所作的修改和替换,均属于本发明的范围。
光敏剂、光照和氧气同时存在下可以产生单线态氧,并用于光动力治疗。但是当氧气耗尽,三线态的光敏剂将会通过辐射或非辐射等方式将能量耗散,此时光敏剂的三线态能量并没有得到利用。我们通过引入能够释放具有治疗效果的小分子的湮灭剂,并利用上转换理论,使得光敏剂的三线态能量得以充分利用。在氧气存在下,光敏剂的三线态能量会传递给氧气生成单线态氧;当氧气耗尽或降低到一定阀值后,光敏剂的三线态能量会通过上转换方式传递给湮灭剂,从而使得湮灭剂被激发释放具有治疗效果的小分子,其中,本发明公开的基于无氧条件下利用光敏剂三线态激发态的分子组中所涉及到的光敏剂D和湮灭剂A的制备方法如下:
一、光敏剂D的制备
光敏剂合成通用路线如下:
其中,N^N配体为下述中任一个:
1、化合物1的制备
称取二水合三氯化钌(243.5mg,1.0mmol),N^N配体(2.0mmol)和氯化锂(212.0mg,5.0mmol)加入到装有搅拌子且接有冷凝管的100mL双口烧瓶中;用锡箔纸包裹烧瓶进行避光处理,密封,抽真空然后充氮气,循环三次,保证反应在氮气保护下进行;注入N,N-二甲基甲酰胺(10mL),将双口烧瓶置于153℃油浴锅中搅拌并冷凝回流6h;反应结束后,冷却至室温,加入50mL丙酮溶液,放入冰箱中冰冻过夜,抽滤得黑色固体。
1.化合物2的制备
将上述所得化合物1(0.5mmol)和2,2-联吡啶(0.5mmol,78.0mg)加入到装有搅拌子且接有冷凝管的100mL双口烧瓶中;用锡箔纸包裹烧瓶进行避光处理,密封,抽真空然后充氮气,循环三次,保证反应在氮气保护下进行;注入乙醇(20mL)和水(10mL),将双口烧瓶置于78℃油浴锅中搅拌并冷凝回流24h;反应结束后,冷却至室温,将反应液滴入饱和的六氟磷酸钾水溶液中,抽滤,用正己烷和乙醚洗涤。
2.化合物3的制备
将上述所得化合物1(0.5mmol)和2,2-联喹啉(0.5mmol,128.1mg)加入到装有搅拌子且接有冷凝管的100mL双口烧瓶中;用锡箔纸包裹烧瓶进行避光处理,密封,抽真空然后充氮气,循环三次,保证反应在氮气保护下进行;注入乙醇(20mL)和水(10mL),将双口烧瓶置于78℃油浴锅中搅拌并冷凝回流24h;反应结束后,冷却至室温,将反应液滴入饱和的六氟磷酸钾水溶液中,抽滤,用正己烷和乙醚洗涤。
二、湮灭剂的制备
湮灭剂合成通用路线如下:
其中,Ar为下述中任一个:
1.化合物1的制备
将装有搅拌子且接有冷凝管的50mL双口烧瓶抽真空然后充氮气,循环三次,保证反应在氮气保护下进行;用锡箔纸包裹烧瓶进行避光处理,密封;向双口烧瓶中注入反应原料Ar(3.2mmol)和反应原料四氯环丙烯(0.3mL,1.6mmol),放置于-78℃环境下搅拌2h,再放置常温环境下搅拌4h;通过TLC监测反应进程。反应结束后,待反应液冷却到室温,萃取,抽滤洗涤。
根据本发明技术方案,我们设置了不同的体外实验组用于验证上述现象的发生,具体选用的光敏剂D和湮灭剂A的结构分别为:
(1)测定湮灭剂吸收光谱,用其最强吸收波长的光激发湮灭剂,得到其吸收光谱曲线的变化趋势,结果如图2,测试时光敏剂D的浓度为:C=5×10-6M;湮灭剂A的浓度为:C=2×10-4M。
(2)测定光敏剂吸收光谱,用其最强吸收波长的光激发湮灭剂(湮灭剂在其波长处无吸收),得到湮灭剂吸收光谱曲线无变化,结果如图3,测试时光敏剂D的浓度为:C=5×10-6M;湮灭剂A的浓度为:C=2×10-4M。
(3)将光敏剂与湮灭剂按一定的浓度配比配成混合溶液,测定其吸收光谱,用光敏剂最强吸收波长的光激发混合溶液,得到湮灭剂吸收曲线变化与(1)相同,结果如图4,测试时光敏剂D的浓度为:C=5×10-6M;湮灭剂A的浓度为:C=2×10-4M。
结果分析:
图1中测定了光敏剂Ru(bpy)3和湮灭剂DPCP-F的吸收光谱,其中光敏剂D的浓度为:C=1×10-5M;湮灭剂A的浓度为:C=1×10-5M,从结果可知光敏剂Ru(bpy)3的主要吸收峰为450nm;湮灭剂DPCP-F的主要吸收峰为365nm和380nm。
图2中测定了湮灭剂DPCP-F在波长365nm,功率为6W/cm2的手提式紫外灯照射激发下其吸收光谱的变化趋势,其在365nm和380nm的两个主要吸收峰逐渐下降直至消失,而产生两个新的主要吸收峰340nm和355nm。
图3中测定了湮灭剂DPCP-F在波长475nm,功率为30mW/cm2的氙灯照射激发下其吸收光谱的变化趋势。其吸收光谱峰型无明显变化,整体吸收曲线有一个上移的趋势,这是由于氙灯照射具有一定的热量,甲醇溶剂挥发,所导致其浓度的增大。所以证实在此波长光源下无法激发湮灭剂DPCP-F。
图4中测定了光敏剂D和湮灭剂A的混合溶液用波长475nm,功率为30mW/cm2的氙灯照射激发下其吸收光谱的变化趋势,发现其中湮灭剂A的吸收光谱峰型变化趋势与图2相同,由此证明湮灭剂A被激发了,而图三中单独湮灭剂DPCP-F在波长475nm,功率为30mW/cm2的氙灯照射下未被激发,由此证明了上转换的发生。
以上显示和描述了本发明的基本原理、主要特征及优点。但是以上所述仅为本发明的具体实施例,本发明的技术特征并不局限于此,任何本领域的技术人员在不脱离本发明的技术方案下得出的其他实施方式均应涵盖在本发明的专利范围之中。
Claims (3)
2.如权利要求1所述的无氧条件下利用光敏剂的三线态激发态的分子组的制备方法,其特征在于,具体包括如下步骤:
S1、制备有机金属配合物作为光敏剂D;
S2、制备能够在光激发下释放具有治疗效果分子的湮灭剂A;
S3、通过上转换理论将光敏剂D与湮灭剂A建立联系;在氧气存在下,光敏剂的三线态能量传递给氧气生成单线态氧;当氧气耗尽或降低到一定阀值后,光敏剂的三线态能量通过上转换方式传递给湮灭剂,从而使得湮灭剂被激发释放具有治疗效果的小分子。
3.如权利要求2所述的无氧条件下利用光敏剂的三线态激发态的分子组的制备方法,其特征在于,所述光敏剂D的合成路线为:
其中,N^N配体为
具体的合成步骤是:
1)化合物1的制备
称取二水合三氯化钌,N^N配体和氯化锂加入到装有搅拌子且接有冷凝管的双口烧瓶中;用锡箔纸包裹烧瓶,密封,抽真空然后充氮气,循环三次;注入N,N-二甲基甲酰胺,将双口烧瓶置于153℃油浴锅中搅拌并冷凝回流6h;反应结束后,冷却至室温,加入丙酮溶液,放入冰箱中冰冻过夜,抽滤得黑色固体;
2)化合物2的制备
将上述所得化合物1和2,2-联吡啶加入到装有搅拌子且接有冷凝管的双口烧瓶中;用锡箔纸包裹烧瓶,密封,抽真空然后充氮气,循环三次;注入乙醇和水,将双口烧瓶置于78℃油浴锅中搅拌并冷凝回流24h;反应结束后,冷却至室温,将反应液滴入饱和的六氟磷酸钾水溶液中,抽滤,用正己烷和乙醚洗涤。
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