CN111116672B - 一种靶向细胞核dna的铱配合物及其制备方法和用途 - Google Patents
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Abstract
本发明公开了一种靶向细胞核DNA的铱配合物及其制备方法和用途，其中铱配合物的结构式如下：
本发明通过分子设计获得了一种铱配合物，具有低毒性、水溶性，可实时观测细胞有丝分裂过程，能应用跟踪细胞核中的DNA以检测细胞是否癌变。
Description
技术领域
本发明涉及一种靶向细胞核DNA的铱配合物及其制备方法和用途，具有低毒性、水溶性、可实时观测细胞有丝分裂过程，能应用跟踪细胞核中的DNA以检测细胞是否癌变。
背景技术
细胞核作为真核细胞内最大的细胞器，控制着细胞的新陈代谢、遗传和增殖。其内部含有丰富的DNA，也即遗传信息的主要载体。因此，实时追踪细胞核内DNA动态过程在生命科学领域具有重要意义，受到科研工作者的广泛关注。目前常用的商业化细胞核染料DAPI、Hoechst等，大多是有机小分子，主要局限于单光子成像，同时伴随着水溶性差、细胞毒性大、光损伤大、光稳定性差等缺点，不利于长时间追踪，从而限制了这些染料在生物体内的应用和作用机理探究。此外，发射能量和激发能量间的斯托克斯位移小导致内源性荧光团的自发荧光而产生干扰。双光子荧光成像具有低能激发，高能发射，对细胞损伤小、高穿透性等特点。而近些年刚刚兴起的超分辨光学显微镜为在纳米分辨率的级别下观测细胞提供了可能。
铱(III)配合物由于其优良的磷光特性，如高的量子产量、大的斯托克斯位移、长寿命激发态、良好的抗光漂白性和卓越的发光波段可调特性等，作为荧光探针越来越广泛地应用于双光子及超分辨成像。铱(III)配合物的特性有利于靶向细胞核DNA，实时观测癌细胞分裂过程，跟踪细胞核中的DNA，避免遗传学上一些突变现象，具有重要的应用价值。据此，本发明设计合成了可用于双光子和超分辨成像具有细胞核DNA靶向性的铱(III)配合物。
发明内容
本发明提供了一种靶向细胞核DNA的铱配合物及其制备方法和用途，通过分子设计获得了一种铱配合物，具有低毒性、水溶性，可实时观测细胞有丝分裂过程，能应用跟踪细胞核中的DNA以检测细胞是否癌变。
本发明靶向细胞核DNA的铱配合物，简记为NIr，其结构式如下：
本发明铱配合物的制备方法，包括如下步骤：
在N2氛围下包裹锡箔纸的史莱克瓶中加入[Ir(L2)Cl]2(0.39g，0.2mmol)溶于混合溶剂50 mL(甲醇：二氯甲烷＝25：25)，再加9,10-双氨基邻菲罗啉(0.09g，0.44mmol)，NaPF6(0.34g， 2.0mmol)；升高温度至65℃，反应24h，冷却至室温，旋去溶剂，柱层析(二氯甲烷：甲醇＝20：1)得到紫红色固体NIr。产量：0.17g，产率：32.4％。
其中，[Ir(L2)Cl]2的合成参见相关参考文献。
本发明合成路线如下：
本发明铱配合物的用途，是作为靶向细胞核DNA的荧光探针使用。
本发明铱配合物可以实时观测细胞有丝分裂过程，可在双光子和超分辨成像过程中作为检测试剂使用。
本发明有益效果体现在：
1、本发明合成的配合物NIr对细胞核DNA具有特异靶向性，灵敏度高、选择性好，RNA、蛋白质等不产生干扰，如图1、图5、图6所示。
2、NIr在近红外区(770nm)波长处双光子荧光信号最强，具有对细胞损伤小、高穿透性的特点，如图2所示。
3、NIr具有优异的光稳定性，极低的细胞毒性，可以实时观测细胞有丝分裂过程，如图 3、图4、图6所示。
4、NIr原料易得，合成简单。综合性质优于商用细胞核DNA染料，不存在类似的物质作为荧光探针，具有较强的商业价值。
附图说明
图1(a)NIr荧光发射光谱滴定图，随着DNA的加入，配合物的荧光强度明显增强，说明NIr对DNA具有高灵敏性。(b)NIr对DNA具有高选择性，对RNA，蛋白质等其他底物均无明显荧光响应，说明NIr高的选择性。
图2配合物NIr在细胞中的双光子荧光显影，图(a)说明NIr在690-810nm波长范围，显示出明显的双光子荧光信号，且能够很好的靶向细胞核。图(b)和图(c)说明NIr双光子最佳激发波长在近红外区(770nm)，且在770nm波长处双光子荧光信号最强，双光子成像对生物体穿透性强，光损伤小。
图3为配合物NIr在HeLa细胞细内的荧光实时监测图。图(a)和(b)分别是5μM的NIr在37℃下孵育细胞24小时和6天，NIr依然能够着色细胞核，细胞的形态保存完好，说明NIr具有较低的细胞毒性，且能够稳定地靶向细胞核部位。
图4为NIr和细胞核商染在不同细胞分裂期的共聚焦显影情况。说明NIr和DAPI的着色部位和现象一致，即NIr可以靶向活细胞核内的DNA，且光稳定性好，能实时观察细胞核内DNA的动态过程。
图5为NIr在细胞中的TEM图。图(b)是被NIr作用的细胞，未用锇酸处理，作为对照；图(a)是被NIr作用的细胞，同时经过锇酸处理，两者对比，图(a)可以更加清楚地观察到亚细胞膜结构，包括线粒体、细胞膜和核膜。这些发现与共聚焦成像结果一致，说明了配合物NIr在活细胞的细胞核内高靶向性。
图6为NIr染色细胞核的受激发射损耗超分辨成像图。它的立体图、切面图以及立体深度图相辅相成，共同说明了NIr可以对细胞核进行高分辨成像，同时也说明NIr具有卓越的光稳定性、高穿透性和选择性。
具体实施方式
以下通过具体的实施例对本发明技术方案作进一步分析说明。
实施例1：
在N2氛围下包裹锡箔纸的史莱克瓶中加入[Ir(L2)Cl]2(0.39g，0.2mmol)溶于混合溶剂50 mL(甲醇：二氯甲烷＝25：25)，再加9,10-双氨基邻菲罗啉(0.09g，0.44mmol)，NaPF6(0.34g， 2.0mmol)；升高温度至65℃，反应24h，冷却至室温，旋去溶剂，柱层析(二氯甲烷：甲醇＝20：1)得到紫红色固体NIr。产量：0.17g，产率：32.4％。ESI-MS:m/z:[M-3PF6 -]+:285.11 (calculated:285.11)。IR(KBr,cm-1):3637.41(m),3371.63(s),2924.39(w),1609.99(s),1588.81(w), 1566.54(w),1479.92(vs),1430.70(m),1373.45(m),1310.01(w),1270.94(m),1231.74(w), 841.49(vs),757.21(w),557.03(vs).1H NMR(400MHz,CD3CN-d3)δ＝8.61(d,J＝8.5,2H),8.15 (d,J＝8.1,2H),8.08(d,J＝4.8,2H),7.94(d,J＝8.0,3H),7.88(t,J＝8.0,2H),7.75(dd,J＝8.5, 4.9,2H),7.45(d,J＝5.6,2H),7.19(d,J＝7.9,2H),6.97(t,J＝6.6,2H),6.36(s,1H),4.81(s,4H), 4.14(dd,J＝31.7,12.7,4H),2.88(s,18H).
实施例2：目标分子的生物学研究
1、利用激光共聚焦显微镜对NIr进行细胞成像研究。发现NIr在37℃下细胞中孵育30 min，展示出能够穿过细胞膜并对细胞核进行着色。
2、进一步研究NIr在细胞内的着色部位及细胞存活率，将5μM的NIr在37℃下分别孵育细胞24h和6d，NIr依然能够着色细胞核，从明场图中可以看出，细胞的形态保存完好，说明NIr具有较低的细胞毒性。NIr和细胞核商染DAPI在不同细胞分裂期的共聚焦显影实验表明，NIr着色的正在分裂的细胞的荧光较强，NIr和DAPI的着色部位一致，说明NIr可以靶向活细胞核内的DNA，且能够实时观察细胞核内DNA的动态。
参考文献：
Yi S.,Lu Z.,Zhang J.,Wang J.,Xie Z.,Hou L.Amphiphilic Gemini Iridium(III)Complex as a Mitochondria-Targeted Theranostic Agent for Tumor Imagingand Photodynamic Therapy,ACS Appl Mater Interfaces 2019:11:15276-15289。
Claims (6)
1.一种靶向细胞核DNA的铱配合物，简记为NIr，其特征在于其结构式如下：
2.一种权利要求1所述的铱配合物的制备方法，其特征在于包括如下步骤：
在N2氛围下包裹锡箔纸的史莱克瓶中加入[Ir(L2)Cl]2并溶于混合溶剂中，再加入9,10-双氨基邻菲罗啉和NaPF6；升高温度至65℃，反应24h，冷却至室温，旋去溶剂，柱层析分离，得到紫红色固体NIr；合成路线如下所示：
3.根据权利要求2所述的制备方法，其特征在于：
所述混合溶剂是由甲醇和二氯甲烷按体积比1:1构成。
4.根据权利要求2所述的制备方法，其特征在于：
柱层析分离的洗脱剂为二氯甲烷:甲醇＝20:1，v/v。
5.一种权利要求1所述的铱配合物用于制备靶向细胞核DNA的荧光探针的用途。
6.根据权利要求5所述的用途，其特征在于：
所述荧光探针在双光子和超分辨成像过程中作为检测试剂使用。
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| CN105694852A (zh) * | 2016-03-10 | 2016-06-22 | 安徽大学 | 一种邻菲罗啉钌配合物双光子吸收材料及其制备方法 |
| CN109486235A (zh) * | 2018-11-10 | 2019-03-19 | 大连理工大学 | 一类具有细胞核靶向功能的dna染料化合物及应用 |
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| CN109486235A (zh) * | 2018-11-10 | 2019-03-19 | 大连理工大学 | 一类具有细胞核靶向功能的dna染料化合物及应用 |
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| Water-soluble phosphorescent iridium(III) complexes as multicolor probes for imaging of homocysteine and cysteine in living cells;Yun Ma等;《J. Mater. Chem.》;20111102;第21卷;第18974-18982页 * |
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