Research Progress of Tetralactam Macrocycle-Based Molecular Recognition and Applications

doi:10.6023/cjoc202401021

Abstract

Molecular recognition is ubiquitous in nature and plays a crucial role in numerous biological processes and supramolecular chemistry. Due to the significant weakening of specific non-covalent interactions (e.g., hydrogen bonding) by the polar environment of water, the use of artificial macrocyclic hosts for molecular identification in the water is challenging. Tetralactam macrocycles are artificial macrocyclic hosts with polar binding sites inside the hydrophobic cavity, which can realize the recognition of hydrophilic molecules in the water by mimicking the molecular recognition of bioreceptors. Through the synergistic effect of hydrophobic effect and hydrogen bonds, it can selectively recognize drug molecules, saccharides, dyes, organic pollutants, disease markers and other substances in the aqueous environment. The research advances of tetralactam macrocycles in molecular recognition and application over the last 30 years are summarized, with a particular emphasis on its molecular recognition and application in the water, hoping to provide a reference for the development of tetralactam macrocycles in the future.

Key words: supramolecular chemistry, tetralactam macrocycle, molecular recognition, hydrogen bond

Cite this article

Jing Guo, Shiyao Li, Huan Yao, Liupan Yang, Lili Wang. Research Progress of Tetralactam Macrocycle-Based Molecular Recognition and Applications[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1777-1785.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

Figure 1. Chemical structures of (a) aryl-extended calix[4]pyrroles, (b) cage-like artificial lectin and (c) amide naphthotubes[22?-24]

Figure 2. Chemical structures of the tetralactam macrocycles covered by this review

Figure 3. (a) Chemical structures of macrocyclic host H1 and H2, (b) chemical structures of dicarbonyl substrates 1~8 and (c) potential sites for recognition of p-benzoquinone[37,47,51]

Figure 4. (a) Chemical structures of macrocyclic host H3 and H4, (b) enzyme-triggered release of Met-enkephalin from [2]rotaxane, (c) formation of a stable complex by squaraine dye with tetralactam macrocycle through guest back-folding and aromatic stacking and (d) chemical structure of macrocyclic host H6, graphical illustration of the molecular temple and its principle of binding a glucose substrate[39,41,52-53]

Figure 5. (a) Chemical structures of macrocyclic host H7~H12, (b) energy-minimized structure of phenazine@H7 by using Spartan’14 and (c) schematic illustration of the tetralactam macrocycle based dual-mode colorimetric and fluorescence indicator displacement assay for UA[44,56]

Figure 6. (a) Chemical structure of macrocyclic host H13~H16, (b) crystal structure of β-glucopyranose@H14, (c) binding model of hypoxanthin@H14, (d) chemical structure of macrocyclic host H17 and binding model of squaraine dye@H17, and (e) multivalent probes unfold on the anionic membrane surface and emite strong fluoresce for imaging of microbial and mammalian cells, as well as in rats tumor model[58???-62]

References 65

[1]	Wagner, B. D. Host-Guest Chemistry-Supramolecular Inclusion in Solution, De Gruyter, 2020.
[2]	Li, D.-H.; Smith, B. D. Beilstein J. Org. Chem. 2019, 15, 1086.
[3]	Liu, W.; Samanta, S. K.; Smith, B. D.; Isaacs, L. Chem. Soc. Rev. 2017, 46, 2391.
[4]	Luo, Q. H. Macrocyclic Chemistry-Host-Guest Compound and Supramolecular, Science Press, Beijing, 2009. (in Chinese)
	(罗勤慧, 大环化学- -主-客体化合物和超分子, 科学出版社, 北京, 2009.)
[5]	Yazaki, K.; Sei, Y.; Akita, M.; Yoshizawa, M. Nat. Commun. 2014, 5, 5179. doi: 10.1038/ncomms6179 pmid: 25322998
[6]	Biedermann, F.; Schneider, H.-J. Chem. Rev. 2016, 116, 5216. doi: 10.1021/acs.chemrev.5b00583 pmid: 27136957
[7]	Persch, E.; Dumele, O.; Diederich, F. Angew. Chem., Int. Ed. 2015, 54, 3290.
[8]	Livnah, O.; Bayer, E. A.; Wilchek, M.; Sussman, J. L. Proc. Natl. Acad. Sci. U. S. A. 1993, 90, 5076.
[9]	Escobar, L.; Ballester, P. Chem. Rev. 2021, 121, 2445. doi: 10.1021/acs.chemrev.0c00522 pmid: 33472000
[10]	Yang, L.-P.; Wang, X.; Yao, H.; Jiang, W. Acc. Chem. Res. 2019, 53, 198.
[11]	Shen, Z.-Y.; Li, S.-Y.; Yang, L.-P.; Wang, L.-L.; Yao, H. Chin. J. Org. Chem. 2024, 44, 1151. (in Chinese)
	(谌泽亚, 李诗瑶, 杨留攀, 王力立, 姚欢, 有机化学, 2024, 44, 1151.) doi: 10.6023/cjoc202310017
[12]	Huang, G.; Chen, Z.; Wei, X.; Chen, Y.; Li, X.; Zhong, H.; Tan, M. Chin. J. Org. Chem. 2020, 40, 614. (in Chinese)
	(黄国保, 陈志林, 韦贤生, 陈钰, 李秀英, 仲辉, 谭明雄, 有机化学, 2020, 40, 614.) doi: 10.6023/cjoc201909029
[13]	Purse, B. W.; Rebek, J. Jr, Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 10777.
[14]	Adriaenssensa, L.; Ballester, P. Chem. Soc. Rev. 2013, 42, 3261. doi: 10.1039/c2cs35461f pmid: 23321897
[15]	Butterfield, S. M.; Rebek, J., Jr. J. Am. Chem. Soc. 2006, 128, 15366. pmid: 17131990
[16]	Gassensmith, J. J.; Arunkumar, E.; Barr, L.; Baumes, J. M.; DiVittorio, K. M.; Johnson, J. R.; Noll, B. C.; Smith, B. D. J. Am. Chem. Soc. 2007, 129, 15054. doi: 10.1021/ja075567v pmid: 17994746
[17]	Wang, Y.-F.; Wang, S.-M.; Zhang, X.; Nian, H.; Zheng, L.-S.; Wang, X.; Schreckenbach, G.; Jiang, W.; Yang, L.-P.; Wang, L.-L. Angew. Chem., Int. Ed. 2023, 62, e202310115.
[18]	Allen, W. E.; Gale, P. A.; Brown, C. T.; Lynch, V. M.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 12471.
[19]	Escobar, L.; Sun, Q.; Ballester, P. Acc. Chem. Res. 2023, 56, 500.
[20]	Verdejo, B.; Gil-Ramírez, G.; Ballester, P. J. Am. Chem. Soc. 2009, 131, 3178. doi: 10.1021/ja900151u pmid: 19216565
[21]	Hernández-Alonso, D.; Zankowski, S.; Adriaenssens, L.; Ballester, P. Org. Biomol. Chem. 2013, 13, 1022.
[22]	Peñuelas-Haro, G.; Ballester, P. Chem. Sci. 2019, 10, 2413. doi: 10.1039/c8sc05034a pmid: 30931096
[23]	Xiong, Y.; Li, M.; Xiong, P.; Yang, M.; Qing, G.; Sun, T. Prog. Chem. 2014, 26, 48. (in Chinese)
	(熊雨婷, 李闵闵, 熊鹏, 杨梦, 卿光焱, 孙涛垒, 化学进展, 2014, 26, 48.) doi: 10.7536/PC130631
[24]	Klein, E.; Crump, M. P.; Davis, A. P. Angew. Chem., Int. Ed. 2005, 44, 298.
[25]	Shorthill, B. J.; Avetta, C. T.; Glass, T. E. J. Am. Chem. Soc. 2004, 126, 12732. pmid: 15469241
[26]	Ferrand, Y.; Crump, M. P.; Davis, A. P. Science 2007, 318, 619. pmid: 17962557
[27]	Ríos, P.; Mooibroek, T. J.; Carter, T. S.; Williams, C.; Wilson, M. R.; Crump, M. P.; Davis, A. P. Chem. Sci. 2017, 8, 4056.
[28]	Davis, A. P. Chem. Soc. Rev. 2020, 49, 2531.
[29]	Tromans, R. A.; Samanta, S. K.; Chapman, A. M.; Davis, A. P. Chem. Sci. 2020, 11, 3223. doi: 10.1039/c9sc05406e pmid: 34122828
[30]	Huang, G.-B.; Wang, S.-H.; Ke, H.; Yang, L.-P.; Jiang, W. J. Am. Chem. Soc. 2016, 138, 14550.
[31]	Wang, L.-L.; Chen, Z.; Liu, W.-E.; Ke, H.; Wang, S.-H.; Jiang, W. J. Am. Chem. Soc. 2017, 139, 8436. doi: 10.1021/jacs.7b05021 pmid: 28609613
[32]	Liu, W.-E.; Chen, Z.; Yang, L.-P.; Au-Yeung, H. Y.; Jiang, W. Chem. Commun. 2019, 55, 9797.
[33]	Yang, L. P.; Ke, H.; Yao, H.; Jiang, W. Angew. Chem., Int. Ed. 2021, 60, 21404.
[34]	Li, S.-Y.; Wang, D.; Qiu, Y.; Wang, L.-L.; Yang, L.-P. Curr. Opin. Green Sustainable Chem. 2023, 40.
[35]	Yao, H.; Ke, H.; Zhang, X.; Pan, S.-J.; Li, M.; Yang, L.-P.; Schreckenbach, G.; Jiang, W. J. Am. Chem. Soc. 2018, 140, 13466.
[36]	Zhao, C.-D.; Yao, H.; Li, S.-Y.; Du, F.; Wang, L.-L.; Yang, L.-P. Chin. Chem. Lett. 2024, 35, 108879.
[37]	Hunter, C. A. J. Chem. Soc.,Chem. Commun. 1991, 749.
[38]	Johnston, A. G.; Leigh, D. A.; Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209.
[39]	Johnston, A. G.; Leigh, D. A.; Murphy, A.; Smart, J. P.; Deegan, M, D., J. Am. Chem. Soc. 1996, 118, 10662.
[40]	Biscarini, F.; Cavallini, M.; Leigh, D. A.; León, S.; Teat, S. J.; Wong, J. K. Y.; Zerbetto, F. J. Am. Chem. Soc. 2002, 124, 225. pmid: 11782174
[41]	Zhai, C.; Xu, C.; Cui, Y.; Wojtas, L.; Liu, W. Chem.-Eur. J. 2023, 29, e202300524.
[42]	Liu, W.; Oliver, A. G.; Smith, B. D. J. Am. Chem. Soc. 2018, 140, 6810.
[43]	Wang, L.-L.; Tu, Y.-K.; Yao, H.; Jiang, W. Beilstein J. Org. Chem. 2019, 15, 1460.
[44]	Wang, L.-L.; Tu, Y.-K.; Valkonen, A.; Rissanen, K.; Jiang, W. Chin. J. Chem. 2019, 37, 892.
[45]	Ke, C.; Destecroix, H.; Crump, M. P.; Davis, A. P. Nat. Chem. 2012, 4, 718.
[46]	Peck, E. M.; Liu, W.; Spence, G. T.; Shaw, S. K.; Davis, A. P.; Destecroix, H.; Smith, B. D. J. Am. Chem. Soc. 2015, 137, 8668.
[47]	Allott, C.; Adams, H.; Bernad, P. L. Jr; Hunter, C. A.; Rotgerc, C.; Thomasa, J. A. Chem. Commun. 1998, 2449.
[48]	Destecroix, H.; Renney, C. M.; Mooibroek, T. J.; Carter, T. S.; Stewart, P. F. N.; Crump, M. P.; Davis, A. P. Angew. Chem., Int. Ed. 2015, 54, 2057.
[49]	Fernandes, A.; Viterisi, A.; Aucagne, V.; Leigh, D. A.; Papot, S. Chem. Commun. 2012, 48, 2083.
[50]	Dong, J.; Davis, A. P. Angew. Chem., Int. Ed. 2020, 60, 8035.
[51]	Fiona, H. A.; Carver, J.; Hunter, C. A.; Osborne, N. J. Chem. Commun. 1996, 2529.
[52]	Fernandes, A.; Viterisi, A.; Coutrot, F.; Potok, S.; Leigh, D. A.; Aucagne, V.; Papot, S. Angew. Chem., Int. Ed. 2009, 48, 6443.
[53]	Dempsey, J. M.; Zhai, C.; McGarraugh, H. H.; Schreiber, C. L.; Stoffel, S. E.; Johnson, A.; Smith, B. D. Chem. Commun. 2019, 55, 12793.
[54]	Zhang, H.; Wang, L.-L.; Pang, X.-Y.; Yang, L.-P.; Jiang, W. Chem. Commun. 2021, 57, 13724.
[55]	Li, S.-Y.; Yao, H.; Hu, H.; Chen, W.-J.; Yang, L.-P.; Wang, L.-L. Chem. Commun. 2023, 59, 7204.
[56]	Yao, H.; Li, S.-Y.; Zhang, H.; Pang, X.-Y.; Lu, J.-L.; Chen, C.; Jiang, W.; Yang, L.-P.; Wang, L.-L. Chem. Commun. 2023, 59, 5411.
[57]	Yao, H.; Qin, J.; Wang, Y.-F.; Wang, S.-M.; Yi, L.-H.; Li, S.-Y.; Du, F.; Yang, L.-P.; Wang, L.-L. Chin. Chem. Lett. 2024, 35, 109154.
[58]	Mandal, P. K.; Kauffmann, B.; Destecroix, H.; Ferrand, Y.; Davis, A. P.; Huc, I. Chem. Commun. 2016, 52, 9355.
[59]	Van Eker, D.; Samanta, S. K.; Davis, A. P. Chem. Commun. 2020, 56, 9268.
[60]	Liu, W.; Johnson, A.; Smith, B. D. J. Am. Chem. Soc. 2018, 140, 3361.
[61]	Federica, B.; Patrick, S.; Soumen, S.; Tiddo, M.; Thomas, H.-J.; Kejia, S.; Bradley, S.; Davis, A. P.; Balduzzi, F.; Stewart, P.; Samanta, S. K.; Mooibroek, T. J.; Hoeg-Jensen, T.; Shi, K.; Smith, B. D.; Davis, A. P. Angew. Chem., Int. Ed. 2023, 62, e202314373.
[62]	Roland, F. M.; Peck, E. M.; Rice, D. R.; Smith, B. D. Bioconjugate Chem. 2017, 28, 1093.
[63]	Liu, W.; Gómez-Durán, C. F. A.; Smith, B. D. J. Am. Chem. Soc. 2017, 139, 6390.
[64]	Shaw, S. K.; Liu, W.; Gómez Durán, C. F. A.; Schreiber, C. L.; Betancourt Mendiola, M. L.; Zhai, C.; Roland, F. M.; Padanilam, S. J.; Smith, B. D. Chem.-Eur. J. 2018, 24, 13821.
[65]	Dharmarwardana, M.; Dempsey, J. M.; Padilla-Coley, S.; Jarvis, T. S.; Shi, K.; Atkinson, K. M.; Smith, B. D. Chem. Commun. 2021, 57, 13518.

四内酰胺大环的分子识别与应用研究进展