Supramolecular Organic Framework Loading for Camptothecin Open-Ring Carboxylates and Their Lactonization Kinetics

doi:10.6023/cjoc201903071

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2567-2573.DOI: 10.6023/cjoc201903071 Previous Articles Next Articles

Special Issue: 有机超分子化学合辑

ARTICLE

超分子有机框架对喜树碱类开环羧酸盐的负载及其内酯化动力学

闫萌, 彭文昶, 王辉, 张丹维, 黎占亭

复旦大学化学系上海 200438

收稿日期:2019-03-29 修回日期:2019-04-19 发布日期:2019-04-26
通讯作者: 黎占亭 E-mail:ztli@fudan.edu.cn
基金资助:
国家自然科学基金（Nos.21432004，21529201，21890732）资助项目.

Supramolecular Organic Framework Loading for Camptothecin Open-Ring Carboxylates and Their Lactonization Kinetics

Yan Meng, Peng Wenchang, Wang Hui, Zhang Danwei, Li Zhanting

Department of Chemistry, Fudan University, Shanghai 200438

Received:2019-03-29 Revised:2019-04-19 Published:2019-04-26
Contact: 10.6023/cjoc201903071 E-mail:ztli@fudan.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21432004, 21529201, 21890732).

1. Supramolecular Organic Framework Loading for Camptothecin Open-Ring Carboxylates and Their Lactonization Kinetics.PDF(479KB)

Abstract

Camptothecin derivatives exist mainly as inactive open ring carboxylates in physiological media. Tumor microenvironment is generally weakly acidic, whereas supramolecular organic frameworks can adsorb and deliver anionic antitumor drugs into tumor cells. In principle, supramolecular organic frameworks (SOFs) can adsorb and deliver camptothecin open ring carboxylates to tumor microenvironment and the delivered carboxylates can undergo lactonization to afford active molecules due to the weak acid character of the tumor microenvironment, which may lead to efficient utilization of the carboxylates as predrugs. To explore this potential, dialysis experiments for the open ring carboxylates of camptothecin, SN-38 and 10-hydroxycamptothecin in the presence of two SOFs were conducted, which revealed important adsorption and retaining capacity of the SOFs for the carboxylates. Absorption spectroscopy was also utilized to evaluate the lactonization kinetics of the three carboxylates in weakly acidic saline solution. The result reveals that at pH=6.5, the half lives of the conversion are 120, 22 and 31 h, respectively, which are considerably shorter than the time gap for repeated administrations of clinically used irinotican (14 d) or topotecan (21 d), which provides the experimental basis for further study.

Key words: camptothecin, SN-38, 10-hydroxycamptothecin, open ring carboxylate, supramolecular organic frameworks, loading, lactonization kinetics

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Yan Meng, Peng Wenchang, Wang Hui, Zhang Danwei, Li Zhanting. Supramolecular Organic Framework Loading for Camptothecin Open-Ring Carboxylates and Their Lactonization Kinetics[J]. Chin. J. Org. Chem., 2019, 39(9): 2567-2573.

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超分子有机框架对喜树碱类开环羧酸盐的负载及其内酯化动力学

Supramolecular Organic Framework Loading for Camptothecin Open-Ring Carboxylates and Their Lactonization Kinetics

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