Research Progress in Chemical Semi-synthetic Modification of Thiopeptide Antibiotics
Received date: 2022-06-27
Online published: 2022-08-10
Supported by
National Natural Science Foundation of China(31972850); Open Funding Project of State Key Laboratory of Microbial Metabolism(MMLKF21-09)
Thiopetheride antibiotics are a class of ribosomal peptides that are produced by microbial secondary metabolism, rich in sulfur, and highly modified amino acid residues. Thiopeptide antibiotics have a series of very important biological activities, including anti-infection, anti-tumor and immunosuppression, and their mechanism of action targeting ribosomes is different from those commonly used in clinical practice, which makes thiopeptide antibiotics have great development potential, but their poor water solubility and low bioavailability limit their clinical application. In order to improve the physicochemical properties of thiopeptide antibiotics, researchers tried to modified the structure of thiopeptide antibiotics by means of chemosemi-synthesis, combinatorial biosynthesis and precursors directed mutation biosynthesis. The complex structure of thiopeptide antibiotics provides many modification sites for its chemical semi-synthetic modification. In recent years, research on the chemical semi-synthetic modification of thiopeptide antibiotics has developed rapidly. In this paper, the research progress of thiopeptide antibiotic analogues obtained by chemical semi-synthetic modification in recent ten years is reviewed.
Fengqiao Zhu , Wengui Wang , Xudong Qu , Shoufeng Wang . Research Progress in Chemical Semi-synthetic Modification of Thiopeptide Antibiotics[J]. Acta Chimica Sinica, 2022 , 80(10) : 1448 -1462 . DOI: 10.6023/A22060276
| [1] | Furusawa, C.; Horinouchi, T.; Maeda, T. Curr. Opin. Biotechnol. 2018, 54, 45. |
| [2] | Arias, C. A.; Murray, B. E. Nat. Rev. Microbiol. 2012, 10, 266. |
| [3] | Isenman, H.; Fisher, D. Curr. Opin. Infect. Dis. 2016, 29, 577. |
| [4] | Su, T. L. Br. J. Exp. Pathol. 1948, 29, 473. |
| [5] | Nicolaou, K. C.; Dethe, D. H.; Chen, Y. K. Chem. Commun. 2008, 23, 2632. |
| [6] | Just-Baringo, X.; Bruno, P.; Ottesen, L. K.; Cañedo, L. M.; Albericio, F.; Álvarez, M. Angew. Chem., Int. Ed. 2013, 52, 7818. |
| [7] | Okumura, K.; Nakamura, Y.; Shin, C. Bull. Chem. Soc. Jpn. 1999, 72, 1561. |
| [8] | Wang, N.; Saidhareddy, P.; Jiang, X. Nat. Prod. Rep. 2020, 37, 246. |
| [9] | Liao, Y.; Jiang, X. Org. Lett. 2021, 23, 8862. |
| [10] | Luo, X.; Zambaldo, C.; Liu, T.; Zhang, Y.; Xuan, W.; Wang, C.; Reed, S. A.; Yang, P.-Y.; Wang, R. E.; Javahishvili, T. Proc. Natl. Acad. Sci. U. S. A. 2016, 113, 3615. |
| [11] | Bowers, A. A.; Acker, M. G.; Koglin, A.; Walsh, C. T. J. Am. Chem. Soc. 2010, 132, 7519. |
| [12] | Bowers, A. A.; Acker, M. G.; Young, T. S.; Walsh, C. T. J. Am. Chem. Soc. 2012, 134, 10313. |
| [13] | Zhang, Q.; Chen, D.; Lin, J.; Liao, R.; Tong, W.; Xu, Z.; Liu, W. J. Biol. Chem. 2011, 286, 21287. |
| [14] | Duan, L.; Wang, S.; Liao, R.; Liu, W. Chem. Biol. 2012, 19, 443. |
| [15] | Wang, S.; Zheng, Q.; Wang, J.; Zhao, Z.; Li, Q.; Yu, Y.; Wang, R.; Liu, W. Org. Chem. Front. 2015, 2, 106. |
| [16] | Bagley, M. C.; Dale, J. W.; Merritt, E. A.; Xiong, X. Chem. Rev. 2005, 105, 685. |
| [17] | Hensens, O. D.; Albers-Schonberg, G. J. Antibiot. 1983, 36, 814. |
| [18] | Miyairi, N.; Mlyoshi, T.; Aoki, H.; Kohsaka, M.; Ikushima, H.; Kunugita, K.; Sakai, H.; Imanaka, H. J. Antibiot. 1970, 23, 113. |
| [19] | Donovick, R.; Pagano, J.; Stout, H.; Weinstein, M. Antibiot. Annu. 1955, 3, 554. |
| [20] | Shoji, J. I.; Hinoo, H.; Wakisaka, Y.; Koizumi, K.; Mayama, M.; Matsuura, S.; Matsumoto, K. J. Antibiot. 1976, 29, 366. |
| [21] | Benazet, F.; Cartier, M.; Florent, J.; Godard, C.; Jung, G.; Lunel, J.; Mancy, D.; Pascal, C.; Renaut, J.; Tarridec, P. Experientia 1980, 36, 414. |
| [22] | Li, J.; Qu, X.; He, X.; Duan, L.; Wu, G.; Bi, D.; Deng, Z.; Liu, W.; Ou, H. Y. PLoS One 2012, 7, e45878. |
| [23] | Xing, Y.; Draper, D. E. Biochemistry 1996, 35, 1581. |
| [24] | Harms, J. M.; Wilson, D. N.; Schluenzen, F.; Connell, S. R.; Fucini, P. Mol. Cell 2008, 30, 26. |
| [25] | Anborgh, P. H.; Parmeggiani, A. EMBO J. 1991, 10, 779. |
| [26] | Parmeggiani, A.; Krab, I. M.; Okamura, S.; Nielsen, R. C.; Nissen, P. Biochemistry 2006, 45, 6846. |
| [27] | Zheng, Q.; Wang, Q.; Wang, S.; Wu, J.; Gao, Q.; Liu, W. Chem. Biol. 2015, 22, 1002. |
| [28] | Bhat, U. G.; Halasi, M.; Gartel, A. L. PLoS One 2009, 4, e6593. |
| [29] | Rogers, M. J.; Cundliffe, E.; Mccutchan, T. F. Antimicrob. Agents Chemother. 1998, 42, 715. |
| [30] | Key, H. M.; Miller, S. J. J. Am. Chem. Soc. 2017, 139, 15460. |
| [31] | Scamp, R. J.; Deramon, E.; Paulson, E. K.; Miller, S. J.; Ellman, J. A. Angew. Chem., Int. Ed. 2020, 59, 890. |
| [32] | Richter, M. F.; Drown, B. S.; Riley, A. P.; Garcia, A.; Shirai, T.; Svec, R. L.; Hergenrother, P. J. Nature 2017, 545, 299. |
| [33] | Bruijn, A. D.; Roelfes, G. Chem. Eur. J. 2018, 24, 11314. |
| [34] | Vries, R. H. D.; Viel, J. H.; Oudshoorn, R.; Kuipers, O. P.; Roelfes, G. Chem. Eur. J. 2019, 25, 12698. |
| [35] | Mortensen, M.; Husmann, R.; Veri, E.; Bolm, C. Chem. Soc. Rev. 2009, 38, 1002. |
| [36] | Rémond, E.; Martin, C.; Martinez, J.; Cavelier, F. Chem. Rev. 2016, 116, 11654. |
| [37] | Pujals, S.; Fernández-Carneado, J.; Kogan, M. J.; Martinez, J.; Cavelier, F.; Giralt, E. J. Am. Chem. Soc. 2006, 128, 8479. |
| [38] | Zhan, B.-B.; Fan, J.; Jin, L.; Shi, B.-F. ACS Catal. 2019, 9, 11058. |
| [39] | Vries, R. H. D.; Viel, J. H.; Kuipers, O. P.; Roelfes, G. Chem. Commun. 2020, 56, 11058. |
| [40] | Stubelius, A.; Lee, S.; Almutairi, A. Acc. Chem. Res. 2019, 52, 3108. |
| [41] | Vries, R. H. D.; Viel, J. H.; Kuipers, O. P.; Roelfes, G. Angew. Chem., Int. Ed. 2021, 60, 3946. |
| [42] | Jonker, H.; Baumann, S.; Wolf, M. A.; Schoof, S.; Hiller, D.; Schulte, K. W.; Kirschner, K. N.; Schwalbe, P.; Arndt, H. D. Angew. Chem., Int. Ed. 2011, 50, 3308. |
| [43] | Hegde, N. S.; Sanders, D.; Rodriguez, R.; Balasubramanian, S. Nat. Chem. 2011, 3, 829. |
| [44] | Clough, J.; Chen, S.; Gordon, E. M.; Hackbarth, C.; Lam, S.; Trias, J.; White, R. J.; Candiani, G.; Donadio, S.; Romanò, G.; Ciabatti, R.; Jacobs, J. W. Bioorg. Med. Chem. Lett. 2003, 13, 3409. |
| [45] | LaMarche, M. J.; Leeds, J. A.; Dzink-Fox, J.; Mullin, S.; Patane, M. A.; Rann, E. M.; Tiamfook, S. Bioorg. Med. Chem. Lett. 2011, 21, 3210. |
| [46] | LaMarche, M. J.; Leeds, J. A.; Amaral, K.; Brewer, J. T.; Bushell, S. M.; Dewhurst, J. M.; Dzink-Fox, J.; Gangl, E.; Goldovitz, J.; Jain, A. J. Med. Chem. 2011, 54, 8099. |
| [47] | LaMarche, M. J.; Leeds, J. A.; Amaral, A.; Brewer, J. T.; Bushell, S. M.; Deng, G.; Dewhurst, J. M.; Ding, J.; Dzink-Fox, J.; Gamber, G. J. Med. Chem. 2012, 55, 2376. |
| [48] | Fabbretti, A.; He, C.-G.; Gaspari, E.; Maffioli, S.; Brandi, L.; Spurio, R.; Sosio, M.; Jabes, D.; Donadio, S. Antimicrob. Agents Chemother. 2015, 59, 4560. |
| [49] | LaMarche, M. J.; Leeds, J. A.; Dzink-Fox, J.; Gangl, E.; Krastel, P.; Neckermann, G.; Palestrant, D.; Patane, M. A.; Rann, E. M.; Tiamfook, S. J. Med. Chem. 2012, 55, 6934. |
| [50] | Bower, J.; Drysdale, M.; Hebdon, R.; Jordan, A.; Lentzen, G.; Matassova, N.; Murchie, A.; Powles, J.; Roughley, S. Bioorg. Med. Chem. Lett. 2003, 13, 2455. |
| [51] | Naidu, B. N.; Sorenson, M. E.; Bronson, J. J.; Pucci, M. J.; Clark, J. M.; Ueda, Y. Bioorg. Med. Chem. Lett. 2005, 15, 2069. |
| [52] | Naidu, B. N.; Sorenson, M. E.; Matiskella, J. D.; Li, W.; Sausker, J. B.; Zhang, Y.; Connolly, T. P.; Lam, K. S.; Bronson, J. J.; Pucci, M. J. Bioorg. Med. Chem. Lett. 2006, 16, 3545. |
| [53] | Xu, L.; Farthing, A. K.; Shi, Y.-J.; Meinke, P. T.; Liu, K. J. Org. Chem. 2007, 72, 7447. |
| [54] | Xu, L.; Farthing, A. K.; Dropinski, J. F.; Meinke, P. T.; McCallum, C.; Leavitt, P. S.; Hickey, E. J.; Colwell, L.; Barrett, J.; Liu, K. Bioorg. Med. Chem. Lett. 2009, 19, 3531. |
| [55] | Sokolovsky, M.; Wilchek, M.; Patchornik, A. J. Am. Chem. Soc. 1964, 86, 1202. |
| [56] | Regueiro-Ren, A.; Ueda, Y. J. Org. Chem. 2002, 67, 8699. |
| [57] | Xu, L.; Farthing, A. K.; Dropinski, J. F.; Meinke, P. T.; McCallum, C.; Hickey, E.; Liu, K. Bioorg. Med. Chem. Lett. 2013, 23, 366. |
| [58] | Regueiro-Ren, A.; Naidu, B. N.; Zheng, X.; Hudyma, T. W.; Connolly, T. P.; Matiskella, J. D.; Zhang, Y.; Kim, O. K.; Sorenson, M. E.; Pucci, M. Bioorg. Med. Chem. Lett. 2004, 14, 171. |
| [59] | Connolly, T. P.; Regueiro-Ren, A.; Leet, J. E.; Springer, D. M.; Goodrich, J.; Huang, X.; Pucci, M. J.; Clark, J. M.; Bronson, J. J.; Ueda, Y. J. Nat. Prod. 2005, 68, 550. |
| [60] | Somei, M.; Tsuchiya, M. Chem. Pharm. Bull. 1981, 29, 3145. |
| [61] | Fan, Y.; Chen, H.; Mu, N.; Wang, W.; Zhu, K.; Ruan, Z.; Wang, S. Bioorg. Med. Chem. 2021, 31, 115970. |
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