CN106588939B - 酞菁-芳基钌化合物及其制备方法和用途 - Google Patents
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Abstract
本发明公开了一种酞菁‑芳基钌化合物，为一氯化一氯一β‑一羧基缩二乙胺‑酞菁一甲基异丙基苯合钌(Ⅰ)。本发明还公开了酞菁‑芳基钌化合物的制备方法，包括：1)将RuCl3·xH2O和γ‑松油烯溶于无水乙醇中，加热回流，静置析出得到二氯化二氯‑二‑甲基异丙基苯合二钌(II)；2)取β‑一羧基‑酞菁和乙二胺溶于DMF溶液，氮气保护下80℃反应后，静置析出得到β‑一羧基缩二乙胺‑酞菁；3)将β‑一羧基缩二乙胺‑酞菁和二氯化二氯‑二‑甲基异丙基苯合二钌(II)溶于无水乙醇，加热搅拌回流，反应完成后把溶液蒸发剩2ml液体，加入正己烷，析出红色晶体，即为一氯化一氯一β‑一羧基缩二乙胺‑酞菁一甲基异丙基苯合钌(II)。本发明还公开了酞菁‑芳基钌化合物的用途。
Description
技术领域
本发明属于药物技术领域，涉及一种酞菁-芳基钌化合物及其制备方法和用途，特别涉及一种一氯化一氯一β-一羧基缩二乙胺-酞菁一甲基异丙基苯合钌(II)及制备方法和用途。
背景技术
目前，顺铂已成为世界上用于治疗癌症最为广泛的3种药物之一，在美国的年销售额达到近5亿美元。但顺铂的使用也存在有一定的不足，它对某些肿瘤没有抑制作用，且易与其他铂制剂产生交叉耐药性。此外，顺铂有多种副作用，如肾毒性、外周神经毒性、骨髓毒性、血液学毒性以及催吐性等。因此，寻找高效、低毒且无交叉耐药性的新型抗肿瘤药物一直是科研工作者的研究热点。
芳基钌配合物由于其毒性低，抗肿瘤活性高的特点而受到人们的关注。卟啉类化合物由于其稳定无毒的性质，以及其良好的发光性能而令人瞩目。以卟啉类化合物芳基钌配合物结合得到卟啉连芳基钌钌化合物，由于芳基钌与卟啉化合物的协同作用，能够使其在具备良好抗肿瘤活性的基础上具备光毒性，达到增强其细胞抑制活性的效果。
发明内容
本发明的一个目的是解决至少上述问题和/或缺陷，并提供至少后面将说明的优点。
本发明另有一个目的是提供一种酞菁-芳基钌化合物。
本发明再有一个目的是提供一种酞菁-芳基钌化合物的制备方法。
本发明还有一个目的是提供所述的酞菁-芳基钌化合物的用途。
为此，本发明提供的技术方案为：
一种酞菁-芳基钌化合物，所述酞菁-芳基钌化合物的化学名称为一氯化一氯一β-一羧基缩二乙胺-酞菁一甲基异丙基苯合钌(Ⅰ)，结构式如下所示：
所述的酞菁-芳基钌化合物的制备方法，包括如下步骤：
1)将钌重量含量为37％的RuCl3·xH2O和纯度为95％的γ-松油烯溶于无水乙醇中，加热回流搅拌，静置析出得到二氯化二氯-二-甲基异丙基苯合二钌(II)；
2)取β-一羧基-酞菁和乙二胺溶于DMF溶液，氮气保护下80℃反应后，静置析出得到β-一羧基缩二乙胺-酞菁；
3)将β-一羧基缩二乙胺-酞菁和二氯化二氯-二-甲基异丙基苯合二钌(II)溶于无水乙醇，加热搅拌回流，反应完成后把溶液蒸发剩2ml液体，加入30ml正己烷，析出红色晶体，即为一氯化一氯一β-一羧基缩二乙胺-酞菁一甲基异丙基苯合钌(Ⅰ)。
优选的是，所述的的酞菁-芳基钌化合物的制备方法中，步骤1)中，各组分用量为：所述RuCl3·xH2O为0.366g，所述γ-松油烯为3ml，所述无水乙醇为10ml；
所述加热回流搅拌时间为6小时。
优选的是，所述的的酞菁-芳基钌化合物的制备方法中，步骤2)中，各组分用量为：所述β-一羧基-酞菁为0.12g，所述乙二胺为0.12g，所述DMF溶液为10ml；
于所述氮气保护下80℃反应6小时。
优选的是，所述的的酞菁-芳基钌化合物的制备方法中，步骤3)中，各组分用量为：所述β-一羧基缩二乙胺-酞菁为20mg，所述二氯化二氯-二-甲基异丙基苯合二钌(II)为12mg，所述无水乙醇为8ml；
所述加热搅拌回流时间为6小时。
所述的酞菁-芳基钌化合物的用途，利用所述酞菁-芳基钌化合物制备用于治疗卵巢癌的药物。
本发明至少包括以下有益效果：
本发明的有机金属钌化合物可用于制备治疗癌症的药物，可制成注射剂、片剂、丸剂、胶囊剂、悬浮剂或乳剂的形式使用。
本发明有机金属钌化合物的制备方法简单，原料易得，具有成本低的优势。
本发明的其它优点、目标和特征将部分通过下面的说明体现，部分还将通过对本发明的研究和实践而为本领域的技术人员所理解。
具体实施方式
下面结合实施例对本发明做进一步的详细说明，以令本领域技术人员参照说明书文字能够据以实施。
应当理解，本文所使用的诸如“具有”、“包含”以及“包括”术语并不配出一个或多个其它元件或其组合的存在或添加。
实施例1
一种酞菁-芳基钌化合物，该酞菁-芳基钌化合物的化学名称为一氯化一氯一β-一羧基缩二乙胺-酞菁一甲基异丙基苯合钌(Ⅰ)；
结构式：
2)理化性质：一氯化一氯一β-一羧基缩二乙胺-酞菁一甲基异丙基苯合钌(II)，为红色晶体，易溶于水和有机溶剂，其核磁共振氢谱数据为1H NMR:(ppm,CDCl3)δ＝0.90(3H,s)，1.30(6H,d,J＝6.9Hz),2.36(3H,s)，2.75-2.87(4H,m,J＝6.1Hz)，3.12(1H,m,J＝6.9Hz)，3.35(3H,d,J＝5.9Hz)，6.77-7.90(15H,m,J＝6.1Hz)。
实施例2
一氯化一氯一β-一羧基缩二乙胺-酞菁一甲基异丙基苯合钌(Ⅰ)的制备方法，包括以下步骤：
1)将0.366g钌重量含量为37％的RuCl3·xH2O和3ml纯度为95％的γ-松油烯溶于10ml无水乙醇，加热回流搅拌6小时，静置析出得到二氯化二氯-二-甲基异丙基苯合二钌(II)。
2)称取0.095gβ-一羧基-酞菁,0.12g乙二胺,溶于10ml DMF溶液，氮气保护下80℃反应6小时后，静置析出得到β-一羧基缩二乙胺-酞菁。
3)将20mg的β-一羧基缩二乙胺-酞菁和12mg二氯化二氯-二-甲基异丙基苯合二钌(II)溶于8ml无水乙醇，加热搅拌回流6小时，反应完成后把溶液蒸发剩2ml液体，加入30ml正己烷，析出红色晶体，即为产物一氯化一氯一β-一羧基缩二乙胺-酞菁一甲基异丙基苯合钌(Ⅰ。
实施例3
采用MTT方法，进行体外细胞毒性测定。将实施例1得到的有机金属钌化合物与卵巢癌A2780细胞株分别作用时间72小时，结果如表1所示。
表1有机金属钌化合物对肿瘤细胞株的半数有效浓度(IC50)
| 细胞株 | A2780(避光) | A2780(光照) |
| IC50(μmol/mL) | 7.3±1.1 | 1.3±0.2 |
通过体外肿瘤细胞抑制活性实验表明，本发明的一氯化一氯一β-一羧基缩二乙胺-酞菁一甲基异丙基苯合钌(II)化合物对卵巢癌A2780细胞株具有显著的抑制作用,并且在可见光照射下其抑制作用明显增强。
从上述结果可以看出，本发明的有机金属钌化合物经体外抗肿瘤实验表明，该化合物具有强的抗肿瘤活性以及较好的细胞光毒性。本发明为研究开发新的抗肿瘤药物提供了新的思路。
这里说明的模块数量和处理规模是用来简化本发明的说明的。对本发明的酞菁-芳基钌化合物及其制备方法和用途的应用、修改和变化对本领域的技术人员来说是显而易见的。
尽管本发明的实施方案已公开如上，但其并不仅仅限于说明书和实施方式中所列运用，它完全可以被适用于各种适合本发明的领域，对于熟悉本领域的人员而言，可容易地实现另外的修改，因此在不背离权利要求及等同范围所限定的一般概念下，本发明并不限于特定的细节和这里示出与描述的实施例。
Claims (6)
1.一种酞菁-芳基钌化合物，其特征在于，所述酞菁-芳基钌化合物的化学名称为一氯化一氯一β-一羧基缩二乙胺-酞菁一甲基异丙基苯合钌(Ⅰ)，结构式如下所示：
2.如权利要求1所述的酞菁-芳基钌化合物的制备方法，其特征在于，包括如下步骤：
1)将钌重量含量为37％的RuCl3·xH2O和纯度为95％的γ-松油烯溶于无水乙醇中，加热回流搅拌，静置析出得到二氯化二氯-二-甲基异丙基苯合二钌(II)；
2)取β-一羧基-酞菁和乙二胺溶于DMF溶液，氮气保护下80℃反应后，静置析出得到β-一羧基缩二乙胺-酞菁；
3)将β-一羧基缩二乙胺-酞菁和二氯化二氯-二-甲基异丙基苯合二钌(II)溶于无水乙醇，加热搅拌回流，反应完成后把溶液蒸发剩2ml液体，加入30ml正己烷，析出红色晶体，即为一氯化一氯一β-一羧基缩二乙胺-酞菁一甲基异丙基苯合钌(Ⅰ)。
3.如权利要求2所述的的酞菁-芳基钌化合物的制备方法，其特征在于，步骤1)中，各组分用量为：所述RuCl3·xH2O为0.366g，所述γ-松油烯为3ml，所述无水乙醇为10ml；
所述加热回流搅拌时间为6小时。
4.如权利要求2所述的的酞菁-芳基钌化合物的制备方法，其特征在于，步骤2)中，各组分用量为：所述β-一羧基-酞菁为0.12g，所述乙二胺为0.12g，所述DMF溶液为10ml；
于所述氮气保护下80℃反应6小时。
5.如权利要求2所述的酞菁-芳基钌化合物的制备方法，其特征在于，步骤3)中，各组分用量为：所述β-一羧基缩二乙胺-酞菁为20mg，所述二氯化二氯-二-甲基异丙基苯合二钌(II)为12mg，所述无水乙醇为8ml；
所述加热搅拌回流时间为6小时。
6.权利要求1所述的酞菁-芳基钌化合物的用途，其特征在于，利用所述酞菁-芳基钌化合物制备用于治疗卵巢癌的药物。
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