Supramolecular Drug Inclusion Complex Constructed from Tetrame-thyl-cucurbit[6]uril and Capecitabine via the Host-Guest Interactions
- Corresponding author: Xiao Xin, gyhxxiaoxin@163.com
Citation:
Zhang Zhirui, Kan Jinglan, Feng Huaming, Liu Qingyun, Tao Zhu, Xiao Xin. Supramolecular Drug Inclusion Complex Constructed from Tetrame-thyl-cucurbit[6]uril and Capecitabine via the Host-Guest Interactions[J]. Chinese Journal of Organic Chemistry,
;2018, 38(8): 1972-1976.
doi:
10.6023/cjoc201804008
Greef, T. F. A.; Smulders, M. M. J.; Wolffs, M.; Schenning, A. P. H. J.; Sijbesma, R. P.; Meijer, E. W. Chem. Rev. 2009, 109, 5687.
doi: 10.1021/cr900181u
Webber, M. J.; Langer, R. Chem. Soc. Rev. 2017, 46, 6600.
doi: 10.1039/C7CS00391A
Webber, M. J.; Appel, E. A.; Meijer, E. W.; Langer, R. Nat. Mater. 2016, 15, 13.
doi: 10.1038/nmat4474
Schmaljohann, D. Adv. Drug Delivery Rev. 2006, 58, 1655.
doi: 10.1016/j.addr.2006.09.020
Meng, F. H.; Zhong, Z. Y.; Feijen, J. Biomacromolecules 2009, 10, 197.
doi: 10.1021/bm801127d
Rosler, A.; Vandermeulen, G. W. M.; Klok, H. A. Adv. Drug Delivery Rev. 2012, 64, 270.
doi: 10.1016/j.addr.2012.09.026
Allen, T. M.; Cullis, P. R. Adv. Drug Delivery. Rev. 2013, 65, 36.
doi: 10.1016/j.addr.2012.09.037
Yang, Y.; Wang, S. P.; Wang, Y. T.; Wang, X. H.; Wang, Q.; Chen, M. W. Biotechnol. Adv. 2014, 32, 1301.
doi: 10.1016/j.biotechadv.2014.07.007
Davis, M. E.; Brewster, M. E. Nat. Rev. Drug Discovery 2004, 3, 102.
Brewster, M. E.; Loftsson, T. Adv. Drug Delivery Rev. 2007, 59, 645.
doi: 10.1016/j.addr.2007.05.012
Hirayama, F.; Uekama, K. Adv. Drug Delivery Rev. 1999, 36, 125.
doi: 10.1016/S0169-409X(98)00058-1
Liu, Q. Y.; Yang, Y. T.; Li, H.; Zhu, R. R.; Shao, Q.; Yang, S. G.; Xu, J. J. Biosens. Bioelectron. 2015, 64, 147.
doi: 10.1016/j.bios.2014.08.062
Liu, Q. Y.; Yang, Y. T.; Lv, X. T.; Ding, Y. A.; Zhang, Y. Z.; Jing, J. J.; Xu, C. X. Sens. Actuators, B 2017, 240, 726.
doi: 10.1016/j.snb.2016.09.049
Liu, Q. Y.; Chen, P. P.; Xu, Z.; Chen, M. M.; Ding, Y. A.; Yue, K.; Xu, J. Sensor Actuators, B 2017, 251, 339.
doi: 10.1016/j.snb.2017.05.069
Liu, Q. Y.; Zhu, J. Q.; Sun, T.; Zhou, H. Y.; Shao, Q.; Li, G. J.; Liu, X. D.; Yin, Y. S. RSC Adv. 2013, 3, 2765.
doi: 10.1039/c2ra21364h
Zhou, Y.; Li, H.; Yang, Y. W. Chin. Chem. Lett. 2015, 26, 825.
doi: 10.1016/j.cclet.2015.01.038
Wheate, N. J.; Dickson, K. A.; Kim, R. R.; Nematollahi, A.; Macquart, R. B.; Kayser, V.; Yu, G. C.; Church, W. B. Marsh, D. J. J. Pharm. Sci. 2016, 105, 3615.
doi: 10.1016/j.xphs.2016.09.008
Veesar, I. A.; Memon, S.; Syed, M. N. Biochem. Eng. J. 2013, 79, 71.
doi: 10.1016/j.bej.2013.07.002
Duan, Q.; Cao, Y.; Li, Y.; Hu, X.; Xiao, T.; Lin, C.; Pan, Y.; Wang, L. J. Am. Chem. Soc. 2013, 135, 10542.
doi: 10.1021/ja405014r
Gokel, G. W.; Leevy, W. M.; Weber, M. E. Chem. Rev. 2014, 104, 2723.
Zhang, M.; Saha, M. L.; Wang, M.; Zhou, Z.; Song, B.; Lu, C.; Yan, X.; Li, X.; Huang, F.; Yin, S.; Stang, P. J. J. Am. Chem. Soc. 2017, 139, 5067.
doi: 10.1021/jacs.6b12536
Chi, X.; Ji, X.; Shao, L.; Huang, F. Macromol. Rapid Commun. 2017, 38, 1600626.
doi: 10.1002/marc.v38.4
Yu, G.; Yu, W.; Shao, L.; Zhang, Z.; Chi, X.; Mao, Z.; Gao, C.; Huang, F. Adv. Funct. Mater. 2016, 26, 8999.
doi: 10.1002/adfm.v26.48
Yao, Y.; Wang, Y.; Zhao, R.; Shao, L.; Tang, R.; Huang, F. J. Mater. Chem. B 2016, 4, 2691.
Yu, G.; Zhou, J.; Shen, J.; Tang, G.; Huang, F. Chem. Sci. 2016, 7, 4073.
doi: 10.1039/C6SC00531D
Jie, K.; Zhou, Y.; Yao, Y.; Huang, F. Chem. Soc. Rev. 2015, 44, 3568.
doi: 10.1039/C4CS00390J
Yu, G.; Jie, K.; Huang, F. Chem. Rev. 2015, 115, 7240.
doi: 10.1021/cr5005315
Yu, G.; Yu, W.; Mao, Z.; Gao, C.; Huang, F. Small 2015, 11, 919.
doi: 10.1002/smll.v11.8
Wang, Q.; Cheng, M.; Cao, Y.; Jiang, J.; Wang L. Acta Chim. Sinica 2016, 74, 9(in Chinese).
Gao, Y.; Hu J.; Ju Y. Acta Chim. Sinica 2016, 74, 312(in Chi-nese).
Li, W.; Qu, W.; Zhang, H.; Li, X.; Lin, Q.; Yao, H.; Zhang, Y.; Wei, T. Chin. J. Org. Chem. 2017, 37, 2619(in Chinese).
Li, B.; Li, X.; Sun, X.; Wang, N. Chin. J. Chem. 2016, 34, 1114.
doi: 10.1002/cjoc.v34.11
Kim, J.; Jung, I. S.; Kim, S. Y.; Kang, E.; Sakamoto, J. K.; Yamaguchi, S.; Kim, K.; Am, K. J. Chem. Soc. 2000, 122, 540.
doi: 10.1021/ja993376p
Day, A. I.; Blanch, R. J.; Arnold, A. P. Angew. Chem. 2002, 114, 285.
doi: 10.1002/(ISSN)1521-3757
Cheng, X. J.; Liang, L. L.; Chen, K.; Ji, N. N.; Xiao, X.; Zhang, J. X.; Zhang, Y. Q.; Xue, S. F.; Zhu, Q. J.; Ni, X. L.; Tao, Z. Angew. Chem., Int. Ed. 2003, 52, 7393.
Li, Q.; Qiu, S. C.; Zhang, J.; Chen, K.; Huang, Y.; Xiao, X.; Zhang, Y.; Li, F.; Zhang, Y. Q.; Xue, S. F.; Zhu, Q. J.; Tao, Z.; Lindoy, L. F.; Wei, G. Org. Lett. 2016, 18, 4020.
doi: 10.1021/acs.orglett.6b01842
Gao, R. H.; Chen, L. X.; Chen, K.; Tao, Z.; Xiao, X. Coord. Chem. Rev. 2017, 348, 1.
doi: 10.1016/j.ccr.2017.07.017
Gao, Z. Z.; Kan, J. L.; Chen, L. X.; Bai, D.; Wang, H. Y.; Tao, Z.; Xiao, X. ACS Omega 2017, 2, 5633.
doi: 10.1021/acsomega.7b00429
Wang, X. X.; Chen, K.; Shen, F. F.; Hua, Z. Y.; Qiu, S. C.; Zhang, Y. Q.; Cong, H.; Liu, Q. Y.; Tao, Z.; Xiao, X. Chem.-Eur. J. 2017, 23, 16953.
doi: 10.1002/chem.201704069
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
Gao, Z. Z.; Bai, D.; Chen, L.X.; Tao, Z.; Xiao, X.; Priorb, T. J.; Redshaw, C. RSC Adv. 2017, 7, 461.
doi: 10.1039/C6RA24780F
Assaf, K. I.; Nau, W. M. Chem. Soc. Rev. 2015, 44, 394.
doi: 10.1039/C4CS00273C
Kaifer, A. E. Acc. Chem. Res. 2014, 47, 2160.
doi: 10.1021/ar5001204
Gao, Z. Z.; Yang, L. G.; Bai, D.; Chen, L. X.; Tao, Z.; Xiao, X. Chem. J. Chin. Univ. 2017, 38, 212(in Chinese).
doi: 10.7503/cjcu20160458
Chen, L. X.; J. L. Kan, Cong, H.; Prior, T. J.; Tao, Z.; Xiao, X.; Redshaw, C. Molecules 2017, 22, 1147.
doi: 10.3390/molecules22071147
Ji, L.; Yang, L.; Yu, Z.Y.; Tan, C. S. Y.; Parker, R. M.; Abell, C.; Scherman, O. A. Acc. Chem. Res. 2017, 50, 208.
doi: 10.1021/acs.accounts.6b00429
Xiao, X.; Sun, J. S.; Jiang, J. Z. Chem.-Eur. J. 2013, 19, 16891.
doi: 10.1002/chem.v19.50
Yang, B.; Gao, Z. Z.; Lu, J. H.; Zhu, Q. J.; Xue, S. F.; Tao, Z.; Prior, T. J.; Redshaw, C.; Wei, G.; Xiao, X. CrystEngComm 2016, 18, 5028.
doi: 10.1039/C6CE00134C
Uzunova, V. D.; Cullinane, C.; Brix, K.; Nau, W. M.; Day, A. I. Org. Biomol. Chem. 2010, 8, 2037.
doi: 10.1039/b925555a
Walker, S.; Oun, R.; McInnes, F. J.; Wheate, N. J. Isr. J. Chem. 2011, 51, 616.
doi: 10.1002/ijch.201100033
Wheate, N. J.; Limantoro, C. Supramol. Chem. 2016, 28, 849-856.
doi: 10.1080/10610278.2016.1178746
Walker, S.; Oun, R.; McInnes, F. J.; Wheate, N. J. Isr. J. Chem. 2011, 51, 616.
doi: 10.1002/ijch.201100033
Saleh, N. I.; Ghosh, I.; Nau, W. M. Supramolecular Systems in Biomedical Fields, RSC Publishing, Cambridge UK, 2013, pp. 164~212.
Zhao, Y. J.; Xue, S. F.; Zhu, Q. J.; Tao, Z.; Zhang, J. X.; Wei, Z. B.; Long, L. S.; Hu, M. L.; Xiao, H. P.; Day, A. I. Chin. Sci. Bull. 2004, 49, 1111.
doi: 10.1360/04wb0031
Gao, Z. Z.; Bai, D.; Xiao, Z. Y.; Zhu, Q. J.; Xue, S. F.; Tao, Z.; Xiao, X. Inorg. Chem. Commun. 2016, 71, 68.
doi: 10.1016/j.inoche.2016.07.005
Bai, D.; Wang, X.; Gao, Z.; Qiu, S.; Tao, Z.; Zhang, J.; Xiao, X. Chin. J. Org. Chem. 2017, 37, 2022(in Chinese).
Negreira, N.; Mastroianni, N.; Alda, M. L.; de Barcelo, D. Talanta 2013, 116, 290.
doi: 10.1016/j.talanta.2013.04.070
Walko, C. M.; Lindley, C. Clin. Ther. 2005, 27, 23.
doi: 10.1016/j.clinthera.2005.01.005
Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd6(L)4]8+-type macrocyclic complexes for fluorescent sensing of HSO3-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
Shengyong Liu , Hui Li , Wei Zhang , Yan Zhang , Yan Dong , Wei Tian . Multiple host-guest and metal coordination interactions induce supramolecular assembly and structural transition. Chinese Chemical Letters, 2025, 36(6): 110465-. doi: 10.1016/j.cclet.2024.110465
Cheng He , Renlan Huang , Lingling Wei , Qiuhui He , Jinbo Liu , Jiao Chen , Ge Gao , Cheng Yang , Wanhua Wu . Uncovering the mask of sensitizers to switch on the TTA-UC emission by supramolecular host-guest complexation. Chinese Chemical Letters, 2025, 36(4): 110103-. doi: 10.1016/j.cclet.2024.110103
Qian Ren , Xue Dai , Ran Cen , Yang Luo , Mingyang Li , Ziyun Zhang , Qinghong Bai , Zhu Tao , Xin Xiao . A cucurbit[8]uril-based supramolecular phosphorescent assembly: Cell imaging and sensing of amino acids in aqueous solution. Chinese Chemical Letters, 2024, 35(12): 110022-. doi: 10.1016/j.cclet.2024.110022
Ran Cen , Yan-Yan Tang , Li-Xia Chen , Zhu Tao , Xin Xiao . A novel supramolecular assembly based on nor-seco-cucurbit[10]uril for spermine sensing and artificial light-harvesting. Chinese Chemical Letters, 2025, 36(1): 109744-. doi: 10.1016/j.cclet.2024.109744
Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
Xianchen Hu , Junli Yang , Fang Gao , Zhiyong Zhao , Simin Liu . Highly selective [4+4] cross-photodimerization of (4a-azonia)anthracenes driven by confinement of D-A hetero-guest pair in cucurbit[10]uril host. Chinese Chemical Letters, 2025, 36(3): 109967-. doi: 10.1016/j.cclet.2024.109967
Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
Xingwen Cheng , Haoran Ren , Jiangshan Luo . Boosting the self-trapped exciton emission in vacancy-ordered double perovskites via supramolecular assembly. Chinese Journal of Structural Chemistry, 2024, 43(6): 100306-100306. doi: 10.1016/j.cjsc.2024.100306
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Jie Yang , Xin-Yue Lou , Dihua Dai , Jingwei Shi , Ying-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818
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Xinguo Mao , Shuo Zhang , Qiang Shi , Hua Cheng , Leyong Wang . Macrocyclic host molecules: Rising as a promising supramolecular material. Chinese Chemical Letters, 2025, 36(6): 110950-. doi: 10.1016/j.cclet.2025.110950
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