葫芦状有机金属配位笼的合成及其对两种药物分子的选择性结合

doi:10.6023/A22120511

摘要/Abstract

自1998年第一个设计并合成的Pd₂L₄型配位笼分子被报道以来, Pd₂L₄型笼被不断深入研究, 目前已广泛应用到催化、药物传递、分子识别等领域. 本工作介绍了一个葫芦状Pd₂L₄型有机金属配位笼(C1)的合成, 且经核磁共振氢谱(¹H NMR)和高分辨质谱(HR-MS)表征, 并用¹H NMR研究了C1与两种药物分子磺胺胍(G1)和顺铂(G2)的主客体化学行为. ¹H NMR结果显示C1的两个不同空腔内能够选择性分别结合G1和G2. 无论G1和G2是同时加入还是分步加入, 都能得到相同的主客体复合物. 这一实验结果为后续的靶向给药相关研究奠定了基础, 为联合用药提供了新思路.

关键词: 双空腔笼, 磺胺胍, 顺铂, 主客体化学, 选择性结合

The Pd₂L₄ type coordination cage has been extensively studied and widely applied in catalysis, drug delivery, molecular recognition and other research fields since the seminal report in 1998. In this work, a gourd-shaped Pd₂L₄ type coordination cage (C1) was synthesized and characterized by proton nuclear magnetic resonance spectroscopy (¹H NMR) and high resolution mass spectrum (HR-MS). The host-guest chemistry of C1 was studied by ¹H NMR with two drug molecules, sulfaguanidine (G1) and cisplatin (G2). ¹H NMR results show that G1 and G2 can be selectively combined in two different cavities of C1. The same host-guest complex could be obtained, whether G1 and G2 were added at the same time or in a stepwise fashion. This work laid a foundation for drug delivery and provided a new inspiration for concomitant drugs.

Key words: double cavity cage, sulfaguanidine, cisplatin, host-guest chemistry, selective bonding

引用此文

黄秀清, 张琦. 葫芦状有机金属配位笼的合成及其对两种药物分子的选择性结合[J]. 化学学报, 2023, 81(3): 217-221.

Xiuqing Huang, Qi Zhang. A Gourd-shaped Organometallic Coordination Cage: Synthesis and Selective Binding of Two Drug Molecules[J]. Acta Chimica Sinica, 2023, 81(3): 217-221.

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图/表 6

图1. C1、C2和C3的结构示意图

Figure 1. Structures of C1, C2 and C3

图2. 配体L1 (a)和化合物C1 (b)的局部核磁共振氢谱图(400 MHz, DMSO-d6)

Figure 2. Partial 1H NMR spectra (400 MHz, DMSO-d6) of (a) L1 and (b) C1

图3. 化合物C1的1H DOSY谱图(400 MHz, DMSO-d6)

Figure 3. 1H DOSY spectrum of C1 (400 MHz, DMSO-d6)

图4. 化合物C1的HR-MS图

Figure 4. HR-MS of C1

图5. C2 (a)、C2与过量G1 (b)和G1 (c)的局部核磁共振氢谱图(400 MHz, CD3CN)

Figure 5. Partial 1H NMR spectra (400 MHz, CD3CN) of (a) C2 only, (b) a mixture of C2 with excess G1 and (c) sulfaguanidine G1, only

图6. C1 (a, g)、C1和过量G2混合物(b)、G1(约2.0 equiv.)与C1@G2混合物(c)、C1与约2.0 equiv. G1, 过量G2同时混合(d)、过量G2与C1@G1混合物(e)、C1与约2.0 equiv. G1混合物(f)的局部核磁共振氢谱图(400 MHz, CD3CN)

Figure 6. Partial 1H NMR spectra of C1 only (a, g), mixture of C1 and excess G2 (b), mixture of G1 (about 2.0 equiv.) and complex C1@G2 (c), mixture of C1, G1 (about 2.0 equiv.) and excess G2 (d), mixture of excess G2 and complex C1@G1 (e), mixture of G1 (about 2.0 equiv.) and C1 (f)

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