Gradient Enhancement of Supramolecular Organic Framework for Solubilization of Hydrophobic Molecules by Two Molecular Containers in Water

doi:10.6023/cjoc202202038

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 2236-2242.DOI: 10.6023/cjoc202202038 Previous Articles Next Articles

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超分子有机框架对分子容器的水相增溶的梯度增强效应

王泽坤^a, 徐子悦^a, 李娟娟^b, 余尚博^c, 王辉^a, 郭东升^b, 张丹维^a, 黎占亭^a^,^c^,^*()

^a复旦大学化学系上海市分子催化和功能材料重点实验室上海 200438
^b南开大学化学学院元素有机化学国家重点实验室天津 300071
^c中国科学院上海有机化学研究所有机功能分子合成与组装化学重点实验室上海 200032

收稿日期:2022-02-28 修回日期:2022-03-13 发布日期:2022-08-09
通讯作者: 黎占亭
基金资助:
国家自然科学基金(21921003); 国家自然科学基金(21890730); 国家自然科学基金(21890732)

Gradient Enhancement of Supramolecular Organic Framework for Solubilization of Hydrophobic Molecules by Two Molecular Containers in Water

Ze-Kun Wang^a, Zi-Yue Xu^a, Juan-Juan Li^b, Shang-Bo Yu^c, Hui Wang^a, Dong-Sheng Guo^b, Dan-Wei Zhang^a, Zhan-Ting Li^a^,^c()

^aDepartment of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai 200438
^bCollege of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071
^cKey Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2022-02-28 Revised:2022-03-13 Published:2022-08-09
Contact: Zhan-Ting Li
Supported by:
National Natural Science Foundation of China(21921003); National Natural Science Foundation of China(21890730); National Natural Science Foundation of China(21890732)

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Abstract

Many functional organic molecules have very low water-solubility, which remarkably limits their practical applications. The inclusion of water-soluble hosts has been demonstrated as an important strategy to increase the water solubility of organic molecules. However, this strategy usually requires high concentration for the hosts to realize efficient solubilization of guest molecules. Herein a new strategy of gradient solubilization by utilizing a water-soluble porous supramolecular polymer to adsorb or enrich molecular containers to increase their efficient concentration in a confined space is reported. For this aim, a cationic water-soluble supramolecular organic framework was used to include an anionic calix[5]arene or an anionic acyclic cucurbituril. In this way, the supramolecular organic framework was revealed to exhibit significant gradient enhancement for the solubilization of the calix[5]arene host for C₆₀, C₇₀, ferrocene, 1,1'-dimethylferrocene and 1,1'-dibromoferrocene, and the solubilization of the acyclic cucurbituril host for paclitaxel, docetaxel and cabazitaxel.

Key words: supramolecular organic framework, host-guest chemistry, calixarene, acyclic cucurbituril, gradient solubilization, fullerene, ferrocene, paclitaxel

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Ze-Kun Wang, Zi-Yue Xu, Juan-Juan Li, Shang-Bo Yu, Hui Wang, Dong-Sheng Guo, Dan-Wei Zhang, Zhan-Ting Li. Gradient Enhancement of Supramolecular Organic Framework for Solubilization of Hydrophobic Molecules by Two Molecular Containers in Water[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2236-2242.

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Fig. & Tab. 5

Figure 1. Formation of SOF-1 from T1 and CB[8], and the structures of compounds T1, CB[8], M1, CLX and ACB

Figure 2. Change of the fluorescence spectra (450 mmol/L) of SOF-1 ([T1]=62.5 μmol/L) with the addition of (a) CLX and (b) ACB in water at 25 °C [Anion]: the anionic concentration of CLX and ACB, [Cation]: the cationic concentration of monomer T1 in SOF-1

Figure 3. Zeta potential of SOF-1 versus [Anion]/[Cation] [Anion] and [Cation] represent the ionic concentration of CLX, ACB or SOF-1

Figure 4. UV-Vis spectra of the solutions of SOF-1 ([T1]=5 mmol/L) and CLX (1 mmol/L) and their mixtures with saturated (a) C60 or (b) C70 in water at 25 °C

Figure 5. (a) Solubility of C60, C70, ferrocene (Fc), 1,1'-dimethylferrocene (DMFc) and 1,1'-dibromoferrocene (DBFc) in the aqueous solutions of SOF-1 ([T1]=5.0 mmol/L)/CLX (1.0 mmol/L), T1 (5.0 mmol/L)/CLX (1.0 mmol/L), SOF-1 ([T1]=5.0 mmol/L)+PPSS (p-phenolsulfonic sodium, 5.0 mmol/L) and NaCl (40 mmol/L)/CLX (1.0 mmol/L). (b) Solubility of Paclitaxel (PTX), Docetaxel (DTX), Cabazitaxel (CTX) in SOF-1 ([T1]=0.5 mmol/L)/ACB (0.5 mmol/L), ACB (1.0 mmol/L) and water

References 17

[1]	(a) Brewster, M. E.; Loftsson, T. Adv. Drug Delivery Rev. 2007, 59, 645. doi: 10.1016/j.addr.2007.05.012
	(b) Rao, V. M.; Stella, V. J. J. Pharm. Sci. 2003, 92, 927. doi: 10.1002/jps.10341
[2]	(a) Hu, Y.; Qiu, C.; Qin, Y.; Xu, X.; Fan, L. Wang, J.; Jin, Z. Trend. Food Sci. Technol. 2021, 109, 398. doi: 10.1016/j.tifs.2020.12.023
	(b) Jambhekar, S. S.; Breen, P. Drug Delivery Today 2016, 21, 363.
	(c) Qie, S.; Hao, Y.; Liu, Z.; Wang, J.; Xi, J. Acta Chim. Sin. 2020, 78, 232. (in Chinese)
	( 郄淑燕, 郝莹, 刘宗建, 王锦, 席家宁, 化学学报, 2020, 78, 232.) doi: 10.6023/A20010006
[3]	(a) Nakahata, M.; Takashima, Y.; Harada, A. Chem. Pharm. Bull. 2017, 65, 330. doi: 10.1248/cpb.c16-00778
	(b) Qi, W.; Ma, C.; Yan, Y.; Huang, J. Curr. Opin. Colloid Interface Sci. 2021, 56, 101526. doi: 10.1016/j.cocis.2021.101526
	(c) Xu, W.; Li, X.; Wang, L.; Li, S.; Chu, S.; Wang, J.; Li, Y.; Hou, J.; Luo, Q.; Liu, J. Front. Chem. 2021, 9, 635507. doi: 10.3389/fchem.2021.635507
	(d) Zhou, W.-L.; Chen, Y.; Liu, Y. Acta Chim. Sin. 2020, 78, 1164. (in Chinese)
	( 周维磊, 陈湧, 刘育, 化学学报, 2020, 78, 1164.) doi: 10.6023/A20100486
[4]	(a) Yu, Y.; Rebek, R. Acc. Chem. Res. 2018, 51, 3031. doi: 10.1021/acs.accounts.8b00269
	(b) Zhu, H.; Li, Q.; Khalil-Cruz, L. E.; Khashab, N. M.; Yu, G.; Huang, F. Sci. China Chem. 2021, 64, 688. doi: 10.1007/s11426-020-9932-9
	(c) Yin, H.; Wang, R. Isr. J. Chem. 2018, 58, 188. doi: 10.1002/ijch.201700092
	(d) Gu, A.; Wheate, N. J. J. Inclus. Phenom. Macrocycl. Chem. 2021, 100, 55. doi: 10.1007/s10847-021-01055-9
	(e) Yang, K.; Zhang, Z.; Du, J.; Li, W.; Pei, Z. Chem. Commun. 2020, 56, 5865. doi: 10.1039/D0CC02001J
	(f) Zheng, Z.; Geng, W.-C.; Xu, Z.; Guo, D.-S. Isr. J. Chem. 2019, 59, 913. doi: 10.1002/ijch.201900032
	(g) Yang, X.; Chen, M.; Wang, F.; Jin, X.-Y.; Cong, H.; Tao, Z. Mini-Rev. Org. Chem. 2018, 15, 274. doi: 10.2174/1570193X15666171228150315
	(h) Sathiyajith, C.; Shaikh, R. R.; Han, Q.; Zhang, Y.; Meguellati, K.; Yang, Y.-W. Chem. Commun. 2017, 53, 677. doi: 10.1039/C6CC08967D
	(i) Yin, H.; Bardelang, D.; Wang, R. Trends Chem. 2021, 3, 1. doi: 10.1016/j.trechm.2020.08.008
	(j) Li, Z.; Wang, H.; Zhang, D. Chem. J. Chin. Univ. 2020, 41, 1139. (in Chinese)
	( 黎占亭, 王辉, 张丹维, 高等学校化学学报, 2020, 41, 1139.)
	(k) Shi, Q.; Wang, X.; Liu, B.; Qiao, P.; Li, J.; Wang, L. Chem. Commun. 2021, 57, 12379. doi: 10.1039/D1CC04400A
	(l) Zhang, S.; Boussouar, I.; Li, H. Chin. Chem. Lett. 2021, 32, 642. doi: 10.1016/j.cclet.2020.06.035
	(m) Li, S.; Gao, Y.; Ding, Y.; Xu, A.; Tan, H. Chin. Chem. Lett. 2021, 32, 313. doi: 10.1016/j.cclet.2020.04.049
	(n) Xiao, T.; Zhou, L.; Sun, X.-Q.; Huang, F.; Lin, C.; Wang, L. Chin. Chem. Lett. 2020, 31, 1. doi: 10.1016/j.cclet.2019.05.011
	(o) Li, R.-H.; Ma, J.; Sun, Y.; Li, H. Chin. Chem. Lett. 2020, 31, 3095. doi: 10.1016/j.cclet.2020.06.041
	(p) Duan, Z.; Xu, F.; Huang, X.; Qian, Y.; Li, H.; Tian, W. Macromol. Rapid Commun. 2021, e2100775.
[5]	(a) Hussain, A. M.; Ashraf, U. M.; Muhammad, G.; Tahir, N. M.; Bukhari, N. A. S. Curr. Pharm. Des. 2017, 23, 2377.
	(b) Pan, Y. C.; X. Y. Hu, X. Y.; Guo, D.-S. Angew. Chem., Int. Ed. 2021, 60, 2768. doi: 10.1002/anie.201916380
	(c) Li, P.; Chen, Y.; Liu, Y. Chin. Chem. Lett. 2019, 30, 1190. doi: 10.1016/j.cclet.2019.03.035
	(d) Guo, D.-S.; Liu, Y. Acc. Chem. Res. 2014, 47, 1925. doi: 10.1021/ar500009g
	(e) Perret, F.; Coleman, A. W. Chem. Commun. 2011, 47, 7303. doi: 10.1039/c1cc11541c
	(f) Zhou, Y.; Li, H.; Yang, Y.-W. Chin. Chem. Lett. 2015, 26, 825. doi: 10.1016/j.cclet.2015.01.038
[6]	(a) Macartney, D. H. Future Med. Chem. 2013, 5, 2075. doi: 10.4155/fmc.13.164 pmid: 24215347
	(b) Yin, H.; Zhang, X.; Wei, J.; Lu, S.; Bardelang, D.; Wang, R. Theranostics 2021, 11, 1513. doi: 10.7150/thno.53459 pmid: 24215347
	(c) Ma, D.; Hettiarachchi, G.; Nguyen, D.; Zhang, B.; Wittenberg, J. B.; Zavalij, P. Y.; Briken, V.; Isaacs, L. Nat. Chem. 2012, 4, 503. doi: 10.1038/nchem.1326 pmid: 24215347
	(d) Mao, D.; Liang, Y.; Liu, Y.; Zhou, X.; Ma, J.; Jiang, B.; Liu, J.; Ma, D. Angew. Chem. Int. Ed. 2017, 56, 12614. doi: 10.1002/anie.201707164 pmid: 24215347
	(e) Liu, J.; Chen, L.; Dong, G.; Yang, J.; Zhu, P.; Liao, X.; Wang, B.; Yang, B. J. Inclus. Phenom. Macrocycl. Chem. 2021, 100, 197. doi: 10.1007/s10847-021-01073-7 pmid: 24215347
	(f) Deng, C.-L.; Murkli, S. L.; Isaacs, L. Chem. Soc. Rev. 2020, 49, 7516-7532. doi: 10.1039/D0CS00454E pmid: 24215347
	(g) Lu, X.; Isaacs, L. Angew. Chem. Int. Ed. 2016, 55, 8076-8080. doi: 10.1002/anie.201602671 pmid: 24215347
[7]	(a) Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844. doi: 10.1002/anie.200460675
	(b) Barrow, S. J.; Kasera, S.; Rowland, M. J.; del Barrio, J.; Scherman, O. A. Chem. Rev. 2015, 115, 12320. doi: 10.1021/acs.chemrev.5b00341
	(c) Kim, K. Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, D.; Kim, J. Chem. Soc. Rev. 2007, 36, 267. doi: 10.1039/B603088M
	(d) Yao, Y. Q.; Chen, K.; Hua, Z. Y.; Zhu, Q. J.; Xue, S. F.; Tao, Z. J. Inclusion Phenom. Macrocyclic Chem. 2017, 89, 1. doi: 10.1007/s10847-017-0733-5
[8]	(a) Yu, S.-B.; Lin, F.; Tian, T.; Yu, J.; Zhang, D.-W.; Li, Z.-T. Chem. Soc. Rev. 2022, 51, 434. doi: 10.1039/D1CS00862E pmid: 25470406
	(b) Tian, J.; Chen, L.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Chem. Commun. 2016, 52, 6351. doi: 10.1039/C6CC02331B pmid: 25470406
	(c) Tian, J.; Wang, H.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Natl. Sci. Rev. 2017, 4, 426. doi: 10.1093/nsr/nwx030 pmid: 25470406
	(d) Yang, B.; Wang, H.; Zhang, D.-W.; Li, Z.-T. Chin. J. Chem. 2020, 38, 970. doi: 10.1002/cjoc.202000085 pmid: 25470406
	(e) Tian, J.; Zhou, T.-C.; Zhang, S.-C.; Aloni, S.; Altoe, M. V.; Xie, S.-H.; Wang, H.; Zhang, D.-W.; Zhao, X.; Liu, Y.; Li, Z.-T. Nat. Commun. 2014, 5, 5574. doi: 10.1038/ncomms6574 pmid: 25470406
	(f) Wang, H.; Zhang, D.; Li, Z. Chem. J. Chin. Univ. 2020, 41, 1139. (in Chinese) pmid: 25470406
	( 王辉, 张丹维, 黎占亭, 高等学校化学学报, 2020, 41, 1139.) pmid: 25470406
[9]	(a) Xu, Z.-Y.; Mao, W.; Zhao, Z.; Wang, Z.-K.; Liu, Y.-Y.; Wu, Y.; Wang, H.; Zhang, D.-W.; Li, Z.-T.; Ma, D. J. Mater. Chem. B 2022, 10, 899. doi: 10.1039/D1TB02601A
	(b) Liu, Y.; Liu, C.-Z.; Wang, Z.-K.; Zhou, W.; Wang, H.; Zhang, Y.-C.; Zhang, D.-W.; Ma, D.; Li, Z.-T. Biomaterials 2022, 284, 121467. doi: 10.1016/j.biomaterials.2022.121467
[10]	(a) Yao, C.; Tian, J.; Wang, H.; Zhang, D.-W.; Liu, Y.; Zhang, F.; Li, Z.-T. Chin. Chem. Lett. 2017, 28, 893. doi: 10.1016/j.cclet.2017.01.005
	(b) Tian, J.; Yao, C.; Yang, W.-L.; Zhang, L.; Zhang, D.-W.; Wang, H.; Zhang, F.; Liu, Y.; Li, Z.-T. Chin. Chem. Lett. 2017, 28, 798. doi: 10.1016/j.cclet.2017.01.010
	(c) Zhang, Y.-C.; Zeng, P.-Y.; Ma, Z.-Q.; Xu, Z.-Y.; Wang, Z.-K.; Guo, B.; Yang, F.; Li, Z.-T. Drug Delivery 2022, 29, 128. doi: 10.1080/10717544.2021.2021325
[11]	Yang, B.; Zhang, X.-D.; Li, J.; Tian, J.; Wu, Y.-P.; Yu, F.-X.; Wang, R.; Wang, H.; Zhang, D.-W.; Liu, Y.; Zhou, L.; Li, Z.-T. CCS Chem. 2019, 1, 156. doi: 10.31635/ccschem.019.20180011
[12]	(a) Guo, D.-S.; Jiang, B.-P.; Wang, X.; Liu, Y. Org. Biomol. Chem. 2012, 10, 720. doi: 10.1039/C2OB06973C
	(b) Ma, D.; Zavalij, P. Y.; Isaacs, L. J. Org. Chem. 2010, 75, 4786. doi: 10.1021/jo100760g
[13]	Yu, S.-B.; Qi, Q.; Yang, B.; Wang, H.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Small 2018, 14, 1801037.
[14]	Haino, T.; Yanase, M.; Fukunaga, C.; Fukazawa, Y. Tetrahedron 2006, 62, 2025. doi: 10.1016/j.tet.2005.07.121
[15]	(a) Sun, W.; Wang, Y.; Ma, L.; Zheng, L.; Fang, W.; Chen, X.; Jiang, H. J. Org. Chem. 2018, 83, 14667. doi: 10.1021/acs.joc.8b02674
	(b) Han, Y.; Tian, Y.; Li, Z.; Wang, F. Chem. Soc. Rev. 2018, 47, 5165. doi: 10.1039/C7CS00802C
[16]	Hardie, M. J. Supramol. Chem. 2002, 14, 7. doi: 10.1080/10610270290006529
[17]	Lim, S.; Pang, Z.; Hweiyuin, T.; Shaikh, M.; Adinarayana, G.; Garg, S. Drug Dev. Ind. Pharm. Drug Develop. Ind. Pharm. 2015, 41, 1.

超分子有机框架对分子容器的水相增溶的梯度增强效应

Gradient Enhancement of Supramolecular Organic Framework for Solubilization of Hydrophobic Molecules by Two Molecular Containers in Water

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