CN110745781B - 一种蓝光或近红外光激发小分子蒽醌电荷转移态产生单线态氧的方法 - Google Patents
一种蓝光或近红外光激发小分子蒽醌电荷转移态产生单线态氧的方法 Download PDFInfo
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Abstract
本发明涉及一种蓝光或近红外光激发小分子蒽醌电荷转移态产生单线态氧的方法，主要包括：将蒽醌和叔丁醇碱混合物溶解在溶剂中，再利用蓝光LED灯光照或近红外的飞秒脉冲激光聚焦光照生成三重态的CT双自由基，三重态的CT双自由基与溶液中的氧气发生能量转移产生单线态氧。本发明利用价格低廉小分子，简单易操作的策略，只需将小分子蒽醌和叔丁醇碱金属混合就能使小分子的吸收从紫外区红移到蓝光和黄光区。蒽醌的吸收波长从340 nm红移到560 nm，并且形成的三重态的CT双自由基中间体同时兼具发射红光（600 nm）和产生单线态氧两种特性，可同时产生一定的光热效应，发射红色的荧光，可用于荧光成像定位、可用于光催化，非线性光学等领域。
Description
技术领域
本发明属于单线态氧领域，尤其涉及一种蓝光或近红外光激发小分子蒽醌电荷转移态产生单线态氧的方法。
背景技术
单线态氧( 1O2 )是一种处于激发态的分子氧，与超氧自由基( O2 -·)、羟基自由基(·OH )、硫酸根自由基( SO4 ·- )等活性氧物种类似，化学性质活泼、不稳定，在自然界中广泛存在，是化学、环境、医学等领域最长涉及的活性氧之一，具有氧化能力强、反应活性高、存活时间短、氧化后不产生有毒有害副产物等特点，属于绿色、环境友好型氧化剂。
目前产生单线态氧的方法是合成大的共轭有机大分子或有机金属配合物作为光敏剂，利用可见光激发光敏剂生成三重态再与氧气发生反应生成单线态氧，产生活性氧中间体（ROS），ROS能杀死细菌或癌细胞等。但是有机共轭大分子和有机金属配合物试剂合成工序繁琐，含有金属的有机试剂价格昂贵，如果用有机小分子光敏剂则共轭度较小，需要用高能量的紫外光激发生成三重态，较难实现同时兼具可见光激发、长波长发光成像及产生单线态氧的特性。
发明内容
本发明的目的在于提供一种通过较低的能量（蓝光或近红外光）激发小分子蒽醌与叔丁醇碱金属（钾，钠或锂）形成的电荷转移态（CT）双自由基中间体，该中间体在氧气条件下能高效产生单线态氧，能进行光热转化，可进行光热治疗。同时，形成的三重态的CT双自由基中间体能发射红光，有利于跟踪成像，实现诊断治疗一体化设计；有望被利用在癌细胞动力学治疗与定位研究当中，以解决现有技术存在的问题。
一种蓝光或近红外光激发小分子蒽醌电荷转移态产生单线态氧的方法，主要包括：将含羰基的芳香化合物和叔丁醇碱混合溶解在溶剂中，再利用蓝光LED灯光照或近红外的飞秒脉冲激光聚焦光照生成三重态的CT双自由基，三重态的CT双自由基与溶液中的氧气发生能量转移产生单线态氧。
优选的，所述羰基的芳香化合物为蒽醌，所述叔丁醇碱为叔丁醇钾、叔丁醇钠、叔丁醇锂中的一种或者多种。
优选的，所述蒽醌和叔丁醇碱的摩尔比为1：2-5。
优选的，所述溶剂为DMF、DMSO、CH3CN中的一种或者多种。主要考虑的是叔丁醇钾的溶解性问题。
优选的，所述蓝光LED灯的为30W，波长为400-460 nm。
优选的，所述近红外的飞秒脉冲激光的波长为800 nm、功率为100 mW、脉宽100fs。
上述的方法生成的三重态的CT双自由基。
上述的方法生成的单线态氧。
上述的三重态的CT双自由基的应用，可用于跟踪成像。
上述的单线态氧的应用，可用于光热治疗。光热治疗即利用光能转化热能，通过加热达到杀死癌细胞或病原体的目的。
与传统的有机光敏分子相比，由于有机小分子的吸收光谱一般都处于紫外区，而紫外光的组织穿透深度比较浅，并且紫外光对人体的伤害比较大。因此小分子光敏剂并不适合应用于光动力学治疗。
与现有技术相比，本发明利用价格低廉小分子，简单易操作的策略，只需将小分子蒽醌和叔丁醇碱金属混合就能使小分子的吸收从紫外区红移到蓝光和黄光区(如图1)。蒽醌的吸收波长从紫外340 nm红移到560 nm，并且形成的三重态的CT双自由基中间体同时兼具发射红光（600 nm）和产生单线态氧两种特性，可同时产生一定的光热效应杀伤癌细胞；发射红色的荧光，可用于荧光成像定位；具备同时成像和动力学治疗两种功能，实现诊断和治疗一体化。还可用于光催化，非线性光学等领域。而且本发明激发所需能量小；制备蒽醌和叔丁醇钾复合物方法简单易操作。
附图说明
图1为传统产生单线态氧的策略以及本发明的蓝光或近红外光激发小分子蒽醌电荷转移态产生单线态氧的方法的对比；
图2中的(1)为5种物质的紫外可见光谱图，(2)为蒽醌，蒽醌与叔丁醇钾混合（光照前）和蒽醌与叔丁醇钾混合（光照后）的Z-扫描双光子截面测试结果；
图3为利用100 mW的800 nm激光双光子激发蒽醌和叔丁醇钾混合物的紫外可见光谱的变化过程；
图4中的（1）为SOSG单线态氧探针547 nm处的荧光增加曲线，（2）光照后的物种（T0(2)）稳定性循环测试；
图5为蒽醌与叔丁醇钾混合后的在298K的荧光发射光谱图，图中的小图为298K下，600 nm发光峰的动力学曲线。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚，下面将结合附图对本发明作进一步地详细描述。
实施例1
一种蓝光或近红外光激发小分子蒽醌电荷转移态产生单线态氧的方法，主要包括：将摩尔比（1:5）蒽醌和叔丁醇碱混合物溶解在DMF溶剂中，利用波长为420 nm的蓝光LED灯（30 W）光照蒽醌和叔丁醇钾混合溶液或功率为100 mW的800 nm近红外的飞秒脉冲激光（脉宽100 fs）聚焦光照蒽醌和叔丁醇钾混合溶液，生成红色的三重态的CT双自由基，该中间体可与溶液中的氧气发生能量转移产生单线态氧。
如图2（1）所示，蒽醌分子在紫外区（340 nm）有很强的吸收光谱，而在可见区的吸收光谱非常弱。但与叔丁醇钾相互作用之后，以及被蓝光光照激发后，在400 nm附近和550nm附近有两个非常强的吸收峰，这是由于蒽醌分子与叔丁醇钾混合形成非共价的分子间CT态显著地将蒽醌的吸收光谱从紫外区红移到了可见区。由于蒽醌和叔丁醇钾之间CT态存在双自由基的特性，通过Z-扫描光谱仪对蒽醌，蒽醌与叔丁醇钾混合（光照前）和蒽醌与叔丁醇钾混合（光照后）三个物种的双光子截面进行了测定，如图2（2）所示，光照之前（T0(1)）的双光子吸收截面是4394 GM，光照后（T0(2)）的截面是16852 GM，与母体蒽醌（AQ）2246 GM相比，双光子吸收截面增加了将近8倍。因此通过蒽醌与叔丁醇钾形成CT态中间体后，不仅可以利用可见光激发复合物，甚至可以利用近红外光对样品进行双光子激发，如图3，这可能使该体系将来用于动力学治疗时具有更深的组织穿透深度和很低的细胞光毒性，而且还能降低细胞背景的荧光影响，增加了时间空间的控制性和分辨率。
本发明利用蒽醌和叔丁醇钾混合产生双自由基三重态的复合物，该复合物可被可见光（波长范围400 nm到460nm）或者近红外波长即800 nm脉冲光双光子激发，激发后的复合物与氧气作用能产生单线态氧。如图4（1）所示，用400 nm LED激发样品后，通过荧光光谱检测并记录单线态氧探针的荧光强度变化，从图可得，探针SOSG的荧光强度在不断上升，说明SOSG与单线态氧作用后荧光被打开，证实复合物样品确实可以产生单线态氧。蒽醌和叔丁醇钾的非共价的分子间CT态被可见光或近红外光激发后能发射红光，如图5所示。所以可通过荧光光谱记录下样品发出的荧光，以600 nm处的荧光强度作为衡量样品稳定性循环的标度（如图4（2））。每一次循环都对样品溶液施加光照和通入氧气，同时记录该点处的荧光强度，可见该样品能够重复多次循环而不被破坏，因此该种方法可适合光动力学治疗。
Claims (3)
1.一种蓝光或近红外光激发小分子蒽醌电荷转移态产生单线态氧的方法，其特征在于，主要包括：将含羰基的芳香化合物和叔丁醇碱混合溶解在溶剂中，再利用蓝光LED灯光照或近红外的飞秒脉冲激光聚焦光照生成三重态的CT双自由基，三重态的CT双自由基与溶液中的氧气发生能量转移产生单线态氧；所述羰基的芳香化合物为蒽醌，所述叔丁醇碱为叔丁醇钾、叔丁醇钠、叔丁醇锂中的一种或者多种；所述蓝光LED灯为30W，波长为400-460nm；所述近红外的飞秒脉冲激光的波长为800 nm、功率为100 mW、脉宽100 fs。
2.根据权利要求1所述的方法，其特征在于，所述蒽醌和叔丁醇碱的摩尔比为1：2-5。
3.根据权利要求1所述的方法，其特征在于，所述溶剂为DMF、DMSO、CH3CN中的一种或者多种。
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