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Hydrazone- and imine-containing [PdPtL4]4+ cages: a comparative study of the stability and host–guest chemistry
Dalton Transactions ( IF 3.5 ) Pub Date : 2022-11-15 , DOI: 10.1039/d2dt02720h Lynn S Lisboa 1 , Mie Riisom 2 , Henry J Dunne 1 , Dan Preston 3 , Stephen M F Jamieson 4 , L James Wright 2 , Christian G Hartinger 2 , James D Crowley 1
Dalton Transactions ( IF 3.5 ) Pub Date : 2022-11-15 , DOI: 10.1039/d2dt02720h Lynn S Lisboa 1 , Mie Riisom 2 , Henry J Dunne 1 , Dan Preston 3 , Stephen M F Jamieson 4 , L James Wright 2 , Christian G Hartinger 2 , James D Crowley 1
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A new [PdPtL4]4+ heterobimetallic cage containing hydrazone linkages has been synthesised using the sub-component self-assembly approach. 1H and DOSY nuclear magnetic resonance (NMR) spectroscopy and electrospray ionisation mass spectrometry (ESIMS) data were consistent with the formation of the [PdPtL4]4+ architecture. The cage was stimulus-responsive and could be partially disassembled and reassembled by the addition of dimethylaminopyridine (DMAP) and p-tolenesulfonic acid (TsOH), respectively. Additionally, the stability of the hydrazone cage against hydrolysis in the presence of water and nucleophilic decomposition in the presence of guest molecules was compared to a previously synthesised imine-containing [PdPtL4]4+ cage. It was established that the hydrazone linkage was more resistant to hydrolysis. Furthermore, the host–guest (HG) chemistry with a series of drug and drug-like molecules was examined. The hydrazone cage was shown to interact with cisplatin while the smaller imine cage was shown to interact with 5-fluorouracil and oxaliplatin in CD3CN. No HG interactions were observed in the more polar d6-DMSO. In vitro antiproliferative activity studies demonstrated both cages were active against the cancer cell lines tested and displayed half-maximal inhibitory (IC50) values in the range of 25–35 μM. Most [PdPtL4]4+-drug mixtures tested had higher IC50 values than the hosts. However, the [PdPtL4]4+ cages, and [PdPtL4]4+:drug mixtures were less cytotoxic than the well established anticancer drugs cisplatin, oxaliplatin and 5-fluorouracil.
中文翻译：
含腙和亚胺的 [PdPtL4]4+ 笼：稳定性和主客体化学的比较研究
使用子组件自组装方法合成了一种新的 [PdPtL 4 ] 4+异双金属笼，其中包含腙键。1 H 和 DOSY 核磁共振 (NMR) 光谱和电喷雾电离质谱 (ESIMS) 数据与 [PdPtL 4 ] 4+结构的形成一致。笼子对刺激有反应，可以通过添加二甲基氨基吡啶 (DMAP) 和p进行部分拆卸和重新组装-甲苯磺酸（TsOH），分别。此外，将腙笼在水存在下的水解和客体分子存在下的亲核分解的稳定性与先前合成的含亚胺的 [PdPtL 4 ] 4+笼进行了比较。确定腙键更耐水解。此外，还检查了具有一系列药物和类药物分子的主客体 (HG) 化学。腙笼显示与顺铂相互作用，而较小的亚胺笼显示与 CD 3 CN中的 5-氟尿嘧啶和奥沙利铂相互作用。在极性更强的d 6 -DMSO中未观察到 HG 相互作用。体外抗增殖活性研究表明，两种笼子均对测试的癌细胞系具有活性，并显示 25–35 μM 范围内的半数最大抑制 (IC 50 ) 值。大多数测试的 [PdPtL 4 ] 4+ -药物混合物具有比宿主更高的IC 50值。然而，[PdPtL 4 ] 4+笼和[PdPtL 4 ] 4+：药物混合物的细胞毒性低于公认的抗癌药物顺铂、奥沙利铂和5-氟尿嘧啶。
更新日期：2022-11-15
中文翻译：
含腙和亚胺的 [PdPtL4]4+ 笼：稳定性和主客体化学的比较研究
使用子组件自组装方法合成了一种新的 [PdPtL 4 ] 4+异双金属笼，其中包含腙键。1 H 和 DOSY 核磁共振 (NMR) 光谱和电喷雾电离质谱 (ESIMS) 数据与 [PdPtL 4 ] 4+结构的形成一致。笼子对刺激有反应，可以通过添加二甲基氨基吡啶 (DMAP) 和p进行部分拆卸和重新组装-甲苯磺酸（TsOH），分别。此外，将腙笼在水存在下的水解和客体分子存在下的亲核分解的稳定性与先前合成的含亚胺的 [PdPtL 4 ] 4+笼进行了比较。确定腙键更耐水解。此外，还检查了具有一系列药物和类药物分子的主客体 (HG) 化学。腙笼显示与顺铂相互作用，而较小的亚胺笼显示与 CD 3 CN中的 5-氟尿嘧啶和奥沙利铂相互作用。在极性更强的d 6 -DMSO中未观察到 HG 相互作用。体外抗增殖活性研究表明，两种笼子均对测试的癌细胞系具有活性，并显示 25–35 μM 范围内的半数最大抑制 (IC 50 ) 值。大多数测试的 [PdPtL 4 ] 4+ -药物混合物具有比宿主更高的IC 50值。然而，[PdPtL 4 ] 4+笼和[PdPtL 4 ] 4+：药物混合物的细胞毒性低于公认的抗癌药物顺铂、奥沙利铂和5-氟尿嘧啶。
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