Acyclic Cucurbit[n]uril as Supramolecular Antagonist for Rapidly Reversing the Neuromuscular Blockade of Succinylcholine through Host-Guest Complexation

doi:10.6023/cjoc202601042

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (9): 3722-3730.DOI: 10.6023/cjoc202601042 Previous Articles Next Articles

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主客体络合驱动的开环葫芦脲对琥珀胆碱神经肌肉阻滞的快速拮抗

张丹维^a^,^*(), 高睿^a, 冯科^b, 余尚博^b, 王辉^a, 周伟^a^,^*(), 黎占亭^a^,^b^,^*()

^a 复旦大学化学系上海 200438
^b 中国科学院上海有机化学研究所金属有机化学全国重点实验室上海 200032

收稿日期:2026-01-26 修回日期:2026-04-06 发布日期:2026-05-07
通讯作者: 张丹维, 周伟, 黎占亭
基金资助:
国家自然科学基金(22531011); 国家自然科学基金(22271059)

Acyclic Cucurbit[n]uril as Supramolecular Antagonist for Rapidly Reversing the Neuromuscular Blockade of Succinylcholine through Host-Guest Complexation

Dan-Wei Zhang^a^,^*(), Rui Gao^a, Ke Feng^b, Shangbo Yu^b, Hui Wang^a, Wei Zhou^a^,^*(), Zhan-Ting Li^a^,^b^,^*()

^a Department of Chemistry, Fudan University, Shanghai 200438
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2026-01-26 Revised:2026-04-06 Published:2026-05-07
Contact: Dan-Wei Zhang, Wei Zhou, Zhan-Ting Li
About author:
Dedicated to the 100th anniversary of the birth of Professor Xikui Jiang.
Supported by:
National Natural Science Foundation of China(22531011); National Natural Science Foundation of China(22271059)

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Abstract

Seven new acyclic cucurbit[n]urils have been prepared. Compound ACB-p2 displays high water-solubility and high biocompatibility, with maximum tolerated dose reaching 1500 mg/kg for mice. The compound is revealed to have high binding affinity (K_a=1.7×10⁵ L•mol^－1) in water for succinylcholine (SCH), clinically used short-duration neuromuscular blocking agent. ¹H NMR and density functional theory calculation show that ACB-p2 binds to SCH mainly by encapsulating the choline segment of SCH in its hydrophobic cavity, which is stabilized by multiple intermolecular C—H…O hydrogen bonds. The high binding affinity of ACB-p2 for SCH leads to rapid antagonism of the neuromuscular blockade of SCH. For rats, compound ACB-p2 of the 80 and 160 mg/kg doses is capable of shortening the recovery time for spontaneous respiration averagely from 195 s to 38 and 23 s, respectively, corresponding to therapeutic an index of 11.8 and 5.9.

Key words: host-guest chemistry, acyclic cucurbit[n]uril, succinylcholine, antidote, neuromuscular blockade, supramolecular antagonism, drug design

Cite this article

Dan-Wei Zhang, Rui Gao, Ke Feng, Shangbo Yu, Hui Wang, Wei Zhou, Zhan-Ting Li. Acyclic Cucurbit[n]uril as Supramolecular Antagonist for Rapidly Reversing the Neuromuscular Blockade of Succinylcholine through Host-Guest Complexation[J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3722-3730.

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Fig. & Tab. 7

Scheme 1. Chemical structures of acyclic cucurbit[n]urils ACB-p1~ACB-p7, succinylcholine (SCH), decamethonium bromide (DCM), and mivacurium (MIV)

Scheme 2. Synthetic routes for compounds ACB-p1~ACB-p7

	Solubility/ (mg•mL^－1)	K_a^b/(×10³ L•mol^－1)
	Solubility/ (mg•mL^－1)	SCH	DCM	MIV
ACB-p1 ACB-p2 ACB-p3 ACB-p4 ACB-p5 ACB-p6 ACB-p7	65 225 62 75 78 124 216	230±9.1 150±7.7 12±0.98 1.0±0.099 130±5.1 67±2.6 79±12	210±8.7 170±6.6 —^c —^c 160±6.1 139±8.2 170±7.9	1.7±0.71 15±0.95 9.1±1.4 7.2±1.7 8.9±0.57 2.9±0.60 8.3±0.22

Table 1. Summary of water-solubility of ACB-p1~ACB-p7 and the binding constants (Ka) of their complexes with blocking agentsa

Figure 1. (a) ITC profile recorded by adding ACB-p2 (3.0 mmol/L) into the solution of SCH (0.3 mmol/L) in water (The solid line represents the best non-linear fit of the data to a 1∶1 binding model); (b) Chemical shift changes of H-a~H-d signals (Scheme 1) of SCH (1.0 mmol/L) with the addition of increasing amount of ACB-p2 (0~2.0 mmol/L) in 1H NMR spectra in D2O

Figure 2. DFT-optimized minimal-energy structures of complex ACB-p2·SCH, highlighting multiple intermolecular (SCH) C—H…O (carboxylate of ACB-p2) hydrogen bonds

Figure 3. (a) Viability of Hek293 cell lines treated with ACB-p2 of increasing concentration (0~256.0 μg/mL); (b) Relative body weight changes of mice versus the observation day after intravenous injection of ACB-p2 of different doses and saline; (c) H & E staining images of the tissues of the major organs (heart, liver, spleen, lung and kidney) collected from rats of the group treated with ACB-p2 of 1.5 g/kg dose and the saline group on the last observation day

Figure 4. Recovery time of rats (n=6, 3 female＋3 male) for spontaneous respiration from SCH-induced neuromuscular blockade by ACB-p2 The dose of SCH was 0.8 mg/kg. Intravenous injection of saline and ACB-p2 was given at T1=0.1. The recovery time was defined by the period from injection to TOF → 90%

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主客体络合驱动的开环葫芦脲对琥珀胆碱神经肌肉阻滞的快速拮抗

Acyclic Cucurbit[n]uril as Supramolecular Antagonist for Rapidly Reversing the Neuromuscular Blockade of Succinylcholine through Host-Guest Complexation

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