CN111635438A - 多芳烃基修饰的双核铂(ii)配合物的制备方法和应用 - Google Patents
多芳烃基修饰的双核铂(ii)配合物的制备方法和应用 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及一类利用超分子自组装来合成对人体端粒G-四链体特异靶向性的多芳烃基修饰的双核铂(II)配合物的制备方法和应用,属于生物化学领域。
背景技术
肿瘤是严重威胁人类健康和生命的重大疾病,已成为人类死亡的第二大病因,也是21世纪世界范围内引起关注的重大主题之一。自2009年的诺贝尔生理学或医学奖颁发给在“端粒和端粒酶是如何保护染色体”领域有突出贡献的美国三位科学家(伊丽莎白·布莱克本、卡罗尔·格雷德和杰克·绍斯塔克),人们逐渐认识到端粒不仅与染色体的结构特点和稳定性相关,而且影响着细胞的寿命、衰老、死亡等。研究表明,核酸G-四链体结构的发现和现在生物学技术对其与癌症关系的揭示,为目前抗肿瘤药物研究提供了重要靶点。能够诱导DNA形成G-四链体结构,特异性结合并使之稳定的化合物,有望抑制肿瘤细胞的生长,从而达到抗肿瘤的作用。因此,此类核酸二级结构(G-四链体)的相关结构特点和生物学功能引起了各领域科学工作者的广泛关注。
众所周知,铂类抗肿瘤药物是临床治疗中的一线抗癌药物,顺铂及其衍生物在临床取得的成功使得制药公司和研究机构投入大量的人力、物力和经费支持金属配合物作为抗肿瘤药物的研究。而与此同时,金属配合物也拥有本身的优势,如合成步骤比较简单、刚柔相济的几何结构变化、丰富的电化学性质,同时还具有光学、磁学以及催化等多种性能。
桥联配体是具体芳香大π平面的系列含氮的杂环结构,可以通过改变桥联配体的取代基进而达到对整个配合物尺寸以及刚性/柔性结构调控的目的。
发明内容
本发明的目的在于针对现有技术的不足,提供一种靶向性诱导并稳定人体端粒G-四链体的多芳烃基修饰的双核铂(II)配合物,具有如化学式(1)所示的结构:
发明同时提供了该有机杂化多芳烃基修饰的双核铂(II)配合物的制备方法,是利用超分子自组装将侧臂铂(II)配合物与桥联配体组装成双核结构,得到的有机杂化多芳烃基修饰的双核铂(II)配合物。所述的侧臂铂(II)配合物是氯离子被硝酸根或水分子取代的侧臂铂(II)配合物。该类侧臂铂(II)配合物为式(2)、式(3)或式(4)中的一种。所述的表示同一类取代基是式(5)、式(6)、式(7)或式(8)中的一种。
具体来说反应步骤为:将原氯离子配位的侧臂铂(II)配合物溶于适量的DMF(二甲基甲酰胺)中再加入AgNO3,原氯离子配位的侧臂铂(II)配合物与AgNO3的物质的量的比为0.9-1:1-1.1,程序升温到60-150℃,在N2保护下避光反应1-4天,用低温离心机离心,弃去沉淀,保留清夜。在上述制备的清液中加入桥联配体,原氯离子配位的侧臂铂(II)配合物与桥联配体的物质的量比为1-2:1,程序升温到50-150℃,在N2保护下避光反应2-6天,反应结束后用脱脂棉对反应液过滤,得到澄清亮黄溶液(即到多芳烃基修饰的双核铂(II)配合物溶液),称取过量的NH4PF6加入到上述溶液中,加入的NH4PF6与多芳烃基修饰的双核铂(II)配合物溶液的物质的量比为3-8:1,大量白色沉淀立刻出现。常温避光搅拌约20 min,减压过滤,并用冰乙醇洗涤2-3次,所得产品在真空干燥箱中干燥离心得到浅色固体物质,即多芳烃基修饰的双核铂(II)配合物。
这个反应过程可以由以下反应式表示:
本发明所提供的多芳烃基修饰的双核铂(II)配合物可以作为G-四链体稳定剂,进而是一种潜在的以核酸为靶向的抗肿瘤药物。
本发明通过超分子自组装方法合成有机杂化多芳烃基修饰的双核铂(II)配合物,特异性靶向人体端粒(hTel)序列,诱导其形成并稳定G-四链体,可以作为G-四链体稳定剂,即潜在的抗肿瘤药物。
与现有技术相比,本发明具有以下有益效果:
本发明以来源丰富易得的K2PtCl4来合成系列侧臂铂(II)配合物如式(2)、式(3)或式(4),与相应的桥联配体,通过超分子自组装的方法合成和表征了一系列多芳烃修饰的双核Pt(II)配合物。通过对人体端粒序列(hTel)、启动子区域序列(c-myc、c-kit和bcl2)以及双链(duplex) DNA的FRET筛选,得到的数据表明该类配合物均具有优异的序列选择性。
附图说明
图1、双核铂(II)配合物与人体端粒序列(hTel)相互作用的FRET熔点曲线;
图2、双核铂(II)配合物与启动子区域序列(c-myc)相互作用的FRET熔点曲线;
图3、双核铂(II)配合物与启动子区域序列(c-kit) 相互作用的FRET熔点曲线;
图4、双核铂(II)配合物与启动子区域序列(bcl2) 相互作用的FRET熔点曲线;
图5、双核铂(II)配合物与双链(duplex) DNA相互作用的FRET熔点曲线。
具体实施方式
以下通过具体的实施例进一步说明本发明的技术方案。
实施例1
以侧臂铂(II)配合物式(2),与桥联配体为式(5)的有机杂化多芳烃基修饰的双核铂(II)配合物的合成:
称取氯离子配位的侧臂铂配合物式(2)(92.2 mg,0.2 mmol)溶于15 mL DMF溶剂中,加入AgNO3(34 mg,0.2 mmol)N2保护条件下,程序升温到100 ℃,加热、避光、搅拌约26h,反应结束后的反应液转移到高转速低温离心机(8000转,4 ℃)中,离心除去AgCl沉淀。将澄清的淡黄色液体转移到干净的反应瓶中,称取桥联配体式(5)(47.2 mg,0.1 mmol)加入到反应体系中,程序升温加热到120 ℃反应72 h,N2保护,整个反应过程都要在避光条件下进行。当桥联配体式(5)完全消失即反应结束,冷却至室温,用脱脂棉过滤,得到澄清亮黄溶液(即到多芳烃基修饰的双核铂(II)配合物溶液),称取过量的NH4PF6加入到上述溶液中,加入的NH4PF6与多芳烃基修饰的双核铂(II)配合物溶液的物质的量比为3~ 8:1,大量白色沉淀立刻出现,常温避光搅拌约20 min,减压过滤,并用冰乙醇洗涤2次,所得产品在真空干燥箱中干燥(0.12 g,0.77 mmol),产率77 %。元素分析(%):C51H37F12N11O3P2Pt2H2O(理论值,实验值):C(41.47,41.02),H(2.95,2.54),N(9.67,9.94)。
所合成的有机杂化多芳烃基修饰的双核铂(II)配合物结构式如下所示:
实施例2
实施例1所合成的双核铂(II)配合物对不同DNA序列选择性筛选实验及结果。
荧光共振能量转移实验(FRET):
1. 缓冲溶液的配制:配制60 mM砷酸钾(KH2AsO4),pH=7.4的缓冲溶液。
2. 双标记DNA样品的制备:双标记DNA为人体端粒重复序hTel、c-myc、c-kit、bcl2和duplex,其浓度按照商品自带说明书中方法来稀释确定,用缓冲溶液稀释到400 nM退火备用。
3. 按照前面所述方法将双核铂(II)配合物配成3.0 mM储备液,然后用缓冲溶液稀释至实验所需浓度。
4. 将12.5 μL,400 nM的双标记DNA样品分别与12.5 μL不同浓度(2×终浓度)的配合物混合均匀,然后取其中20 μL转移至罗氏(LightCycler)PCR管中,静置1小时后用罗氏实时荧光定量PCR仪(LightCycler2型荧光定量PCR仪)测试;固定激发波长为470 nm,对应监测的发射荧光强度为530 nm;温度变化范围30-100℃,升温间隔为1℃/min,升温后再平衡30s后采样,T m 值由仪器自带熔点分析程序给出;数据图是在Origin 8.0(OriginLabCorp.)中处理得到。
5. 重复上述实验,最终数据是三次平行实验的平均值。
表1 双核铂(II)配合物稳定不同DNA序列的解链温度(ΔT m)的变化。
从表1数据可以看出,所合成的有机杂化多芳烃基修饰的双核铂(II)配合物可以选择性的靶向人体端粒序列(hTel),诱导其形成G-四链体结构,对应的ΔT m值是34.2±1.1℃。相对而言,双核铂(II)配合物对启动子区域的序列(c-myc、c-kit以及bcl2)和双链(duplex)序列基本没有稳定作用。研究报道,在肿瘤细胞中,端粒酶活性被激活,端粒酶延长端粒;肿瘤细胞中的端粒要比正常细胞中更易形成G-四链体结构。所以双核铂(II)配合物具有潜在的抗肿瘤活性。
本发明以来源丰富易得的K2PtCl4来合成系列侧臂铂(II)配合物如式(2)、式(3)、式(4),与相应的桥联配体,通过超分子自组装的方法合成和表征了一系列多芳烃修饰的双核Pt(II)配合物;通过对人体端粒序列(hTel)、启动子区域序列(c-myc、c-kit和bcl2)以及双链(duplex) DNA的FRET筛选,得到的数据表明该类配合物均具有优异的序列选择性,即特异性靶向人体端粒序列(hTel),并诱导其形成G-四链体结构,使其熔点稳定升高约34.2℃;相比之下,该类配合物对启动子区域序列(c-myc、c-kit和bcl2)以及双链(duplex) DNA几乎没有稳定作用;研究报道,在肿瘤细胞中,端粒酶活性被激活,端粒酶延长端粒;肿瘤细胞中的端粒要比正常细胞中更易形成G-四链体结构;所以双核铂(II)配合物具有潜在的抗肿瘤活性。
本发明方案所公开的技术手段不仅限于上述实施方式所公开的技术手段,还包括由以上技术特征任意组合所组成的技术方案。应当指出,对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以做出若干改进和润饰,这些改进和润饰也视为本发明的保护范围。
Claims (10)
4.一种用于制备权利要求1-3中任一项所述的靶向性诱导并稳定人体端粒G-四链体的多芳烃基修饰的双核铂(II)配合物的方法,其特征在于,反应步骤如下:将原氯离子配位的侧臂铂(II)配合物和AgNO3反应进行脱氯处理,再加入桥联配体进行反应,即可得到多芳烃基修饰的双核铂(II)配合物。
5.根据权利要求4所述的制备方法,其特征在于:所述原氯离子配位的侧臂铂(II)配合物与AgNO3的物质的量的比为0.9-1:1-1.1。
6.根据权利要求4所述的制备方法,其特征在于:所述原氯离子配位的侧臂铂(II)配合物与桥联配体的物质的量比为1-2:1。
7.根据权利要求4所述的制备方法,其特征在于,脱氯处理的反应步骤如下:将原氯离子配位的侧臂铂(II)配合物和AgNO3进行混合后,升温至60-150℃,并在N2保护下进行避光反应1-4天。
8.根据权利要求4所述的制备方法,其特征在于,加入桥联配体进行反应的步骤如下:加入桥联配体后,升温至50-150℃,并在N2保护下进行避光反应2-6天。
9.根据权利要求1-3中任一项所述的靶向性诱导并稳定人体端粒G-四链体的多芳烃基修饰的双核铂(II)配合物在制备抗肿瘤药物中的应用。
10.根据权利要求9所述的应用,其特征在于:所述的药物含有药学上可接受的辅助剂。
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