Structural Modifications, Structure-Activity Relationships, and Total Synthesis Advances in Erythromycin Analogs against Resistant Pathogens

doi:10.6023/cjoc202506020

Abstract

Macrolide antibiotics (Macrolide) as clinically important and widely used drugs, by virtue of its broad-spectrum antimicrobial properties and excellent therapeutic efficacy, such as erythromycin, clarithromycin and azithromycin, the essential medicines recommended by the World Health Organization (WHO). However, the emergence of bacterial resistance has significantly reduced their antibacterial efficacy, leaving the treatment of numerous diseases facing a dilemma of no effective drugs available. In particular, macrolide antibiotics, the 3^rd-generation telithromycin and 4^th-generation solithromycin included, are difficult to exert therapeutic effects against infectious diseases caused by constitutive erm-carrying Staphylococcus aureus, constitutive erm-carrying Streptococcus pyogenes, and Mycoplasma pneumoniae with A2058 mutation. To overcome the problem of bacterial resistance to macrolide antibiotics and further enhance their antibacterial activity against drug-resistant bacteria, researchers have carried out extensive studies on new structures. This review takes the development history of macrolide antibiotics as a chronological framework, systematically summarizing the research progress of these drugs against drug-resistant bacteria from 2013 to 2024. It focuses on elaborating the structure-activity relationships of new structures, pharmacokinetic characteristics, and total synthesis strategies of non-natural macrolides, and summarizes the key breakthroughs of 5^th-generation macrolide antibiotics in combating bacterial resistance. This review will provide guidance for subsequent drug design, research on resistance mechanisms, and the development of novel antibacterial strategies.

Key words: macrolides, drug resistance, structural modification, structure-activity relationship, total synthesis

Cite this article

Cui, Xinyi, Guo, Lifan, Ma, Congxuan, Li, Yun, Liang, Jianhua. Structural Modifications, Structure-Activity Relationships, and Total Synthesis Advances in Erythromycin Analogs against Resistant Pathogens[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202506020.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Bryskier A.;Bergogne‐Bérézin, E. Macrolides, Ed.: Bryskier, A., ASM Press, Washington, DC, 2005, p. 475.
[2] Kurath P.; Jones P. H.; Egan R. S.; Perun T. J.Experientia. 1971, 27, 362.
[3] Alvarez-Elcoro, S.; Enzler, M. J. Mayo Clin. Proc. 1999, 74(6), 613.
[4] Wellington K.; Noble S. Drugs. 2004, 64, 1683.
[5] Woodward, R. Angew.Chem. 1957, 69(1‐2), 50.
[6] Mazzei T.; Mini E.; Novelli A.; Periti P. J. Antimicrob. Chemother. 1993, 31, 1.
[7] Periti P.; Mazzei T.; Mini E.; Novelli A. Clin.Pharmacokinet. 1989, 16, 193.
[8] Svetlov M. S.; Syroegin E. A.; Aleksandrova E. V.; Atkinson G. C.; Gregory S. T.; Mankin A. S.; Polikanov Y. S. Nat. Chem. Biol. 2021, 17(4), 412.
[9] Jelić D.; Antolović R. Antibiotics. 2016, 5(3), 29.
[10] (a) Vázquez-Laslop, N.; Mankin, A. S. Trends Biochem. Sci. 2018, 43(9), 668.
(b) Kannan, K.; Kanabar, P.; Schryer, D.; Florin, T.; Oh, E.; Bahroos, N.; Tenson, T.; Weissman, J. S.; Mankin, A. S. Proc. Natl. Acad. Sci. 2014, 111(45), 15958.
[11] Dinos, G. P. Br. J. Pharmacol. 2017, 174(18), 2967.
[12] Mcguire J. M.; Bunch R. L.; Anderson R. C.; Boaz H. E.; Smith J. W.Antibiot Chemother. 1952, 2(41), 1064.
[13] Lee H.; Yun K. W.; Lee H. J.; Choi E. H.Expert Rev. Anti-Infect. Ther. 2018, 16(1), 23.
[14] Dunkle J. A.; Xiong L.; Mankin A. S.; Cate J. H. Proc. Natl. Acad.Sci. 2010, 107(40), 17152.
[15] Biradar S. V.; Patil A. R.; Sudarsan G. V.; Pokharkar V. B.Powder Technol. 2006, 169(1), 22.
[16] Gaynor M.; Mankin A. S. Curr. Top. Med.Chem. 2003, 3(9), 949.
[17] Allen, N. E. Antimicrob. Agents Chemother. 1977, 11(4), 669.
[18] Wilson, D. N. Nat. Rev. Microbiol. 2014, 12(1), 35.
[19] Fyfe C.; Grossman T. H.; Kerstein K.; Sutcliffe J.Cold Spring Harbor Perspect. Med. 2016, 6(10), a025395.
[20] Jalava J.; Vaara M.; Huovinen P. Ann. Clin. Microbiol. Antimicrob. 2004, 3(1), 1.
[21] Amdan N. A.N.; Shahrulzamri, N. A.; Hashim, R.; Jamil, N. M. J. Global Antimicrob. Resist. 2024, 38, 368.
[22] (a) Denis, A.; Agouridas, C.; Auger, J.-M.; Benedetti, Y.; Bonnefoy, A.; Bretin, F.; Chantot, J.-F.; Dussarat, A.; Fromentin, C.; D'Ambrières, S. G. Bioorg. Med. Chem. Lett. 1999, 9(21), 3075.
(b) Bemer-Melchior, P.; Juvin, M.-E.; Tassin, S.; Bryskier, A.; Schito, G. C.; Drugeon, H.-B. Antimicrob. Agents Chemother. 2000, 44(11), 2999.
[23] Ma C. X.; Li Y.; Liu W. T.; Li Y.; Zhao F.; Lian X. T.; Ding J.; Liu S. M.; Liu X. P.; Fan B. Z.Cell Discovery. 2024, 10(1), 75.
[24] Liang J. H.; Han X. Curr. Top. Med. Chem. 2013, 13(24), 3131.
[25] Arenz S.; Bock L. V.; Graf M.; Innis C. A.; Beckmann R.; Grubmüller H.; Vaiana A. C.; Wilson D. N. Nat. Commun. 2016, 7(1), 12026.
[26] Crowe-McAuliffe, C.; Graf, M.; Huter, P.; Takada, H.; Abdelshahid, M.; Nováček, J.; Murina, V.; Atkinson, G. C.; Hauryliuk, V.; Wilson, D. N. Proc. Natl. Acad. Sci. 2018, 115(36), 8978.
[27] Svetlov M. S.; Plessa E.; Chen C.-W.; Bougas A.; Krokidis M. G.; Dinos G. P.; Polikanov Y. S.Rna. 2019, 25(5), 600.
[28] Halfon Y.; Matzov D.; Eyal Z.; Bashan A.; Zimmerman E.; Kjeldgaard J.; Ingmer H.; Yonath A. Sci.Rep. 2019, 9(1), 11460.
[29] Beckert B.; Leroy E. C.; Sothiselvam S.; Bock L. V.; Svetlov M. S.; Graf M.; Arenz S.; Abdelshahid M.; Seip B.; Grubmüller H.; Mankin A. S.; Innis C. A.; Vázquez-Laslop, N.; Wilson, D. N. Nat. Commun. 2021, 12(1), 4466.
[30] Fostier C. R.; Ousalem F.; Leroy E. C.; Ngo S.; Soufari H.; Innis C. A.; Hashem Y.; Boël G. Nat.Commun. 2023, 14(1), 3891.
[31] Chen C. W.; Leimer N.; Syroegin E. A.; Dunand C.; Bulman Z. P.; Lewis K.; Polikanov Y. S.; Svetlov M. S. Nat. Commun. 2023, 14(1), 4196.
[32] Aleksandrova E. V.; Ma C. X.; Klepacki D.; Alizadeh F.; Vázquez-Laslop, N.; Liang, J. H.; Polikanov, Y. S.; Mankin, A. S. Nat. Chem. Biol. 2024, 20(12), 1680.
[33] Magee T. V.; Han S.; McCurdy, S. P.; Nguyen, T.-T.; Granskog, K.; Marr, E. S.; Maguire, B. A.; Huband, M. D.; Chen, J. M.; Subashi, T. A. Bioorg. Med. Chem. Lett. 2013, 23(6), 1727.
[34] Arenz S.; Ramu H.; Gupta P.; Berninghausen O.; Beckmann R.; Vázquez-Laslop, N.; Mankin, A. S.; Wilson, D. N. Nat. Commun. 2014, 5(1), 3501.
[35] Arenz S.; Meydan S.; Starosta Agata L.; Berninghausen O.; Beckmann R.; Vázquez-Laslop, N.; Wilson, Daniel N. Mol. Cell. 2014, 56(3), 446.
[36] Eyal Z.; Matzov D.; Krupkin M.; Wekselman I.; Paukner S.; Zimmerman E.; Rozenberg H.; Bashan A.; Yonath A. Proc. Natl. Acad. Sci. 2015, 112(43), E5805.
[37] Wekselman I.; Zimmerman E.; Davidovich C.; Belousoff M.; Matzov D.; Krupkin M.; Rozenberg H.; Bashan A.; Friedlander G.; Kjeldgaard J.; Ingmer H.; Lindahl L.; Zengel J. M.; Yonath A. Structure. 2017, 25(8), 1233.
[38] Zhang W.; Li Z. F.; Sun Y. F.; Cui P.; Liang J. H.; Xing Q. H.; Wu J.; Xu Y. H.; Zhang W. H.; Zhang Y.; Lin H.; Ning G.Emerging Microbes Infect. 2022, 11(1), 293.
[39] Srinivasan K.; Banerjee A.; Sengupta J. Structure. 2024, 32(9), 1443.
[40] LeMahieu, R. A.; Carson, M.; Kierstead, R. W.; Fern, L. M.; Grunberg, E. J. Med. Chem. 1974, 17(9), 953.
[41] Douthwaite S.; Champney W. S.J. Antimicrob. Chemother. 2001, 48, 1.
[42] (a) Kashimura, M.; Asaka, T.; Misawa, Y.; Matsumoto, K.; Morimoto, S. J. Antibiot. 2001, 54(8), 664.
(b) Ono, T.; Kashimura, M.; Suzuki, K.; Oyauchi, R.; Miyachi, J.; Ikuta, H.; Kawauchi, H.; Akashi, T.; Asaka, T.; Morimoto, S. J. Antibiot. 2004, 57(8), 518.
[43] Zhanel G. G.; Walters M.; Noreddin A.; Vercaigne L. M.; Wierzbowski A.; Embil J. M.; Gin A. S.; Douthwaite S.; Hoban D. J.Drugs. 2002, 62, 1771.
[44] Douthwaite S.; Hansen L. H.; Mauvais P. Mol.Microbiol. 2000, 36(1), 183.
[45] Chancey S. T.; Zhou X.; Zähner D.; Stephens D. S. Antimicrob. Agents Chemother. 2011, 55(7), 3413.
[46] Shlaes D. M.; Moellering R. C.Lancet Infect. Dis. 2008, 8(2), 83.
[47] Fernandes P.; Fernandes P.; Martens E.; Martens E.; Bertrand D.; Bertrand D.; Pereira D.; Pereira D. Bioorg. Med. Chem. 2016, 24(24), 6420.
[48] Douthwaite S.; Jalava J.; Jakobsen L. Mol.Microbiol. 2005, 58(2), 613.
[49] Zheng Z. H.; Du D. P.; Cao L. L.; Liu J.; Chen X. F.J. Antibiot. 2016, 69(11), 811.
[50] Zhao Z. H.; Zhang X. X.; Jin L. L.; Yang S.; Lei P. S. Bioorg. Med. Chem.Lett. 2018, 28(14), 2358.
[51] Bulkley D.; Innis C. A.; Blaha G.; Steitz T. A. Proc. Natl. Acad.Sci. 2010, 107(40), 17158.
[52] Bhawsar S.; Tadiparthi R.; Kayastha A. K.; Dixit P.; Pavase L.; Mishra A.; Chavan V.; Birajdar S.; Shaikh M.; Yeole R. Med. Chem. Res. 2024, 33(10), 1715.
[53] Bhavsar S.; Tadiparthi R.; Gupta S.; Pawar S.; Yeole R.; Kayastha A. K.; Deshpande P.; Bhagwat S.; Patel M. Chem.Pap. 2023, 77(7), 3629.
[54] Bhavsar S.; Ravikumar T.; Gupta S.; Pawar S.; Dabhade S.; Kayastha A. K.; Deshpande P.; Yeole R.; Nandanwar M.; Bhagwat S.Results Chem. 2023, 5, 100757.
[55] Nandanwar M.; Chavan R.; Kansagara A.; Patel M. A.; Patel A.; Yeole R.; Patel M. Regul. Toxicol. Pharm. 2021, 122, 104889.
[56] Iwanowski P.; Bhatia A.; Gupta M.; Patel A.; Chavan R.; Yeole R.; Friedland D. Antimicrob.Agents Chemother. 2019, 63(12), 01253.
[57] Jia L.; Yan M.; Shen Y.; Qin Y. H.; Qiang S. S.; Ma S. T. Bioorg. Med. Chem.Lett. 2017, 27(16), 3693.
[58] Jia L.; Wang Y. H.; Wang Y. X.; Qin Y. H.; Hu C. Y.; Sheng J. Z.; Ma S. T. Bioorg. Med. Chem.Lett. 2018, 28(14), 2471.
[59] Bai B. F.; Bi F. C.; Qin Y. H.; Teng Y. T.; Ma S. T. Bioorg. Med. Chem.Lett. 2021, 43, 128110.
[60] Teng Y. T.; Qin Y. H.; Song D.; Liu X. B.; Ma Y. A.; Zhang P. P.; Ma S. T. Bioorg. Med. Chem.Lett. 2020, 30(2), 126850.
[61] Liang J. H.; Lv W.; Li X. L.; An K.; Cushman M.; Wang H.; Xu Y. C. Bioorg. Med. Chem.Lett. 2013, 23(5), 1387.
[62] Liang J. H.; An K.; Lv W.; Cushman M.; Wang H.; Xu Y. C. Eur. J. Med.Chem. 2013, 59, 54.
[63] Chen X. Z.; Xu P.; Xu Y. P.; Liu L.; Liu Y.; Zhu D.; Lei P. S. Bioorg. Med. Chem.Lett. 2012, 22(24), 7402.
[64] Xu Y. P.; Chen X. Z.; Zhu D.; Liu Y.; Zhao Z. H.; Jin L. L.; Liu C.; Lei P. S. Eur. J. Med.Chem. 2013, 69, 174.
[65] Chen X. Z.; Xu Y. P.; Zhao Z. H.; Lei P. S.Tetrahedron Lett. 2014, 55(44), 6128.
[66] (a) Wang, A. P.; Liu, C.; Yang, S.; Zhao, Z. H.; Lei, P. S. Tetrahedron. 2016, 72(2).
(b) Zhao, Z. H.; Wang, A. P.; Zhang, X. X.; Yang, S.; Luo, Z. G.; Lei, P. S. Chin. Chem. Lett. 2019, 30(2), 425.
[67] Zhao Z. H.; Wang A. P.; Zhang X. X.; Yang S.; Luo Z. G.; Lei P. S.J. Asian Nat. Prod. Res. 2019, 21(5), 456.
[68] Anwar H. F.; Andrei M.; Undheim K. Bioorg. Med. Chem. 2017, 25(8), 2313.
[69] Andrei M.; Undheim K. Phytochem.Lett. 2022, 50, 128.
[70] Tanikawa T.; Asaka T.; Kashimura M.; Misawa Y.; Suzuki K.; Sato M.; Kameo K.; Morimoto S.; Nishida A. J. Med. Chem. 2001, 44(24), 4027.
[71] Tanikawa T.; Asaka T.; Kashimura M.; Suzuki K.; Sugiyama H.; Sato M.; Kameo K.; Morimoto S.; Nishida A. J. Med. Chem. 2003, 46(13), 2706.
[72] (a) Pandya, M.; Chakrabarti, A.; Rathy, S.; Katoch, R.; Venkataraman, R.; Bhateja, P.; Mathur, T.; Kumar, G. R.; Malhotra, S.; Rao, M. Int. J. Antimicrob. Agents. 2010, 36(2), 169.
(b) Kumar, R.; Rathy, S.; Hajare, A. K.; Surase, Y. B.; Dullu, J.; Jadhav, J. S.; Venkataramanan, R.; Chakrabarti, A.; Pandya, M.; Bhateja, P. Bioorg. Med. Chem. Lett. 2012, 22(1), 476.
[73] Han X.; Lv W.; Guo S. Y.; Cushman M.; Liang J. H. Bioorg. Med. Chem. 2015, 23(19), 6437.
[74] Tian J. C.; Han X.; Lv W.; Li Y. X.; Wang H.; Fan B. Z.; Cushman M.; Liang J. H. Bioorg. Med. Chem.Lett. 2017, 27(7), 1513.
[75] Sugiyama H.; Yoshida I.; Ueki M.; Tanabe K.; Manaka A.; Hiramatsu K. J.Antibiot. 2017, 70(3), 264.
[76] Li X. M.; Lv W.; Guo S. Y.; Li Y. X.; Fan B. Z.; Cushman M.; Kong F. S.; Zhang J.; Liang J. H. Eur. J. Med.Chem. 2019, 171, 235.
[77] Qin Y. H.; Qiang S. S.; Ji S. L.; Liu Z. Y.; Hu C. Y.; Ma S. T. Bioorg. Med. Chem.Lett. 2018, 28(20), 3324.
[78] Yan M.; Ma R. X.; Jia L.; Venter H.; Ma S. T. Eur. J. Med.Chem. 2017, 127, 874.
[79] Qin Y. H.; Xu L. L.; Teng Y. T.; Yang Y.; Wang Y. H.; Ma P. Z. Bioorg. Med. Chem.Lett. 2021, 49, 128330.
[80] (a) Liang, J. H.; Li, X. L.; Wang, H.; An, K.; Wang, Y. Y.; Xu, Y. C.; Yao, G. W. Eur. J. Med. Chem. 2012, 49, 289.
(b) Liang, J. H.; Wang, Y. Y.; Wang, H.; Li, X. L.; An, K.; Xu, Y. C.; Yao, G. W. Bioorg. Med. Chem. Lett. 2010, 20(9), 2880.
(c) Liang, J. H.; Wang, Y. Y.; Zhu, D. Y.; Dong, L. J.; An, M. M.; Wang, R.; Yao, G. W. J. Antibiot. 2009, 62(11), 605.
[81] Grgičević I.; Mikulandra I.; Bukvić M.; Banjanac M.; Radovanović V.; Habinovec I.; Bertoša B.; Novak P. Int.J. Antimicrob. Agents. 2020, 56(5), 106147.
[82] (a) Ju, Y. J.; Xian, R. Q.; Zhang, L.; Ma, R. X.; Cao, J. C.; Ma, S. T. Bioorg. Med. Chem. Lett. 2010, 20(11), 3272.
(b) Qi, Y. K.; Jiao, B.; Ma, X. D.; Cui, W. P.; Ma, S. T. Arch. Pharm. 2010, 343(8), 458.
[83] Zhu D.; Xu Y. P.; Liu Y.; Chen X. Z.; Zhao Z. H.; Lei P. S. Bioorg. Med. Chem.Lett. 2013, 23(23), 6274.
[84] Ma S. T.; Jiao B.; Liu Z. P.; Wang H.; Xian R. Q.; Zheng M. J.; Lou H. X. Bioorg. Med. Chem.Lett. 2009, 19(6), 1698.
[85] Zhang L.; Chai X. Y.; Wang B. G.; Yu S. C.; Hu H. G.; Zou Y.; Zhao Q. J.; Meng Q. G.; Wu Q. Y. Bioorg. Med. Chem.Lett. 2013, 23(18), 5057.
[86] Qin Y. H.; Sun M.; Zhang N.; Yang Y.; Ma P. Z. Bioorg. Chem. 2022, 127, 106020.
[87] Yan M.; Ma X. D.; Dong R. Q.; Li X.; Zhao C.; Guo Z. Z.; Shen Y.; Liu F.; Ma R. X.; Ma S. T. Eur. J. Med.Chem. 2015, 103, 506.
[88] Wang Y. H.; Cong C.; Chai W. C.; Dong R. Q.; Jia L.; Song D.; Zhou Z. T.; Ma S. T. Bioorg. Med. Chem.Lett. 2017, 27(16), 3872.
[89] Tevyashova A. N.; Korolev A. M.; Mirchink E. P.; Isakova E. B.; Osterman I. A.J. Antibiot. 2019, 72(1), 22.
[90] Li X.; Ma S. T.; Yan M.; Wang Y. Z.; Ma S. T. Eur. J. Med.Chem. 2013, 59, 209.
[91] Klahn P.; Brönstrup, M. Nat. Prod. Rep. 2017, 34(7), 832.
[92] Tevyashova A. N.; Bychkova E. N.; Korolev A. M.; Isakova E. B.; Mirchink E. P.; Osterman I. A.; Erdei R.; Szücs Z.; Batta G. Bioorg. Med. Chem. Lett. 2019, 29(2), 276.
[93] Volynkina I. A.; Bychkova E. N.; Karakchieva A. O.; Tikhomirov A. S.; Zatonsky G. V.; Solovieva S. E.; Martynov M. M.; Grammatikova N. E.; Tereshchenkov A. G.; Paleskava A.; Konevega A. L.; Sergiev P. V.; Dontsova O. A.; Osterman I. A.; Shchekotikhin A. E.; Tevyashova A. N.Pharmaceuticals. 2024, 17(2), 187.
[94] Janas A.; Pecyna P.; Gajecka M.; Bartl F.; Przybylski P.ChemMedChem. 2020, 15(16), 1529.
[95] Yu J.; Cen D. W.; Chen Y. C.; Zhao H. L.; Xu M. Y.; Wu S. L.; Wang S.; Jin Q.; Shen T. RSC Adv. 2023, 13(27), 18651.
[96] Zhanel G. G.; Hartel E.; Adam H.; Zelenitsky S.; Zhanel M. A.; Golden A.; Schweizer F.; Gorityala B.; Lagacé-Wiens, P. R.; Walkty, A. J. Drugs. 2016, 76, 1737.
[97] Llano-Sotelo, B.; Dunkle, J.; Klepacki, D.; Zhang, W.; Fernandes, P.; Cate Jamie, H. D.; Mankin Alexander, S. Antimicrob. Agents Chemother. 2010, 54(12), 4961.
[98] (a) Rodgers, W.; Frazier, A. D.; Champney, W. S. Antimicrob. Agents Chemother. 2013, 57(4), 1632.
(b) Putnam, S. D.; Sader, H. S.; Farrell, D. J.; Biedenbach, D. J.; Castanheira, M. Int. J. Antimicrob. Agents. 2011, 37(1), 39.
[99] Kobayashi Y.; Wada H.; Rossios C.; Takagi D.; Higaki M.; Mikura, S. i.; Goto, H.; Barnes, P. J.; Ito, K. J Pharmacol Exp Ther. 2013, 345(1), 76.
[100] Jamieson B. D.; Ciric S.; Fernandes P. Antimicrob.Agents Chemother. 2015, 59(8), 4379.
[101] MacLauchlin, C.; Schneider, S. E.; Keedy, K.; Fernandes, P.; Jamieson, B. D. Antimicrob. Agents Chemother. 2018, 62(5), 01474.
[102] Buege M. J.; Brown J. E.; Aitken S. L. Am. J.Health-Syst. Pharm. 2017, 74(12), 875.
[103] Raj V. S.; Barman T. K.; Kalia V.; Purnapatre K.; Dube S.; Bhateja P.; Mathur T.; Chaira T.; Upadhyay D. J.; Surase Y. B. Antimicrob. Agents Chemother. 2014, 58(8), 4283.
[104] Daher S. S.; Jin X.; Patel J.; Freundlich J. S.; Buttaro B.; Andrade R. B. Bioorg. Med. Chem.Lett. 2019, 29(11), 1386.
[105] Daher S. S.; Lee M.; Jin X.; Teijaro C. N.; Barnett P. R.; Freundlich J. S.; Andrade R. B. Eur. J. Med.Chem. 2022, 233, 114213.
[106] Jin L. L.; Zhang X. X.; Luo Z. G.; Wu X. F.; Zhao Z. H. Bioorg. Med. Chem.Lett. 2023, 80, 129115.
[107] Bian C.; Zhang J.; Zheng X.; Qiao M. Q.; Li Y.; Chen X. F.; Si S. Y. Eur. J. Med.Chem. 2024, 267, 116181.
[108] Tu D.; Blaha G.; Moore P. B.; Steitz T. A.Cell. 2005, 121(2), 257.
[109] Velvadapu V.; Paul T.; Wagh B.; Klepacki D.; Guvench O.; MacKerell, A., Jr.; Andrade, R. B. ACS Med. Chem. Lett. 2011, 2(1), 68.
[110] Zhang J. M.; Yuan G. Y.; Zou Y. Nat. Prod. Rep. 2025, 42(2), 298.
[111] (a) Driedger, D.; Wilson, D. M.; Britton, R. Chem. Sci. 2025, 16(14), 5918.
(b) Velvadapu, V.; Paul, T.; Wagh, B.; Glassford, I.; DeBrosse, C.; Andrade, R. B. J. Org. Chem. 2011, 76(18), 7516.
[112] Sutro J. L.;Fürstner, A. J. Am. Chem. Soc. 2024, 146(4), 2345.
[113] (a) Wagh, B.; Paul, T.; Glassford, I.; DeBrosse, C.; Klepacki, D.; Small, M. C.; MacKerell, A. D., Jr.; Andrade, R. B. ACS Med. Chem. Lett. 2012, 3(12), 1013.
(b) Velvadapu, V.; Glassford, I.; Lee, M.; Paul, T.; DeBrosse, C.; Klepacki, D.; Small, M. C.; MacKerell, A. D., Jr.; Andrade, R. B. ACS Med. Chem. Lett. 2012, 3(3), 211.
(c) Glassford, I.; Lee, M.; Wagh, B.; Velvadapu, V.; Paul, T.; Sandelin, G.; DeBrosse, C.; Klepacki, D.; Small, M. C.; MacKerell, A. D., Jr.; Andrade, R. B. ACS Med. Chem. Lett. 2014, 5(9), 1021.
[114] Andrade R. B.Synlett. 2015, 26(16), 2199.
[115] Seiple I. B.; Zhang Z.; Jakubec P.; Langlois-Mercier, A.; Wright, P. M.; Hog, D. T.; Yabu, K.; Allu, S. R.; Fukuzaki, T.; Carlsen, P. N. Nature. 2016, 533(7603), 338.
[116] Hutinec A.; Đerek M.; Lazarevski G.; Šunjić V.; Paljetak H. Č.; Alihodžić S.; Haber V. E.; Dumić M.; Maršić N.; Mutak S. Bioorg. Med. Chem. Lett. 2010, 20(11), 3244.
[117] (a) Pavlovic, D.; Mutak, S. ACS Med. Chem. Lett. 2011, 2(5), 331.
(b) Čipčić Paljetak, H.; Verbanac, D.; Padovan, J.; Dominis -Kramarić, M.; Kelnerić, Ž.; Perić, M.; Banjanac, M.; Ergović, G.; Simon, N.; Broskey, J.; Holmes David, J.; Eraković Haber, V. Antimicrob. Agents Chemother. 2016, 60(9), 5337.
[118] Kos V. M.; Koštrun S.; Fajdetić A.; Bosnar M.; Kelnerić Ž.; Stepanić V.; Haber V. E. Eur. J. Pharm.Sci. 2013, 49(2), 206.
[119] Pavlović D.; Mutak S. Bioorg. Med. Chem. 2016, 24(6), 1255.
[120] Pavlović D.; Fajdetić A.; Mutak S. Bioorg. Med. Chem. 2010, 18(24), 8566.
[121] Ma C. X.; Lv W.; Li Y. X.; Fan B. Z.; Han X.; Kong F. S.; Tian J. C.; Cushman M.; Liang J. H. Eur. J. Med.Chem. 2019, 169, 1.
[122] Fan B. Z.; Hiasa H.; Lv W.; Brody S.; Yang Z. Y.; Aldrich C.; Cushman M.; Liang J. H. Eur. J. Med.Chem. 2020, 193, 112222.
[123] Ma C. X.; Liu W. T.; Li X. M.; Ding J.; Liu S. M.; Xue F.; Li Y.; Liang J. H. Eur. J. Med.Chem. 2024, 276, 116630.
[124] Pavlović D.; Kimmins S.; Mutak S. Eur.J. Med. Chem. 2017, 125, 210.
[125] Zhang N.; Liu W. T.; Cui X. Y.; Liu S. M.; Ma C. X.; Liang J. H. Bioorg. Chem. 2024, 151, 107712.
[126] Liu X. P.; Lv W.; Zhao F.; Ding J.; Zhang J. R.; Xue F.; Zhang J. Z.; Liu L. Y.; Cushman M.; Li Y.; Liang J. H. Bioorg. Med. Chem.Lett. 2022, 68, 128761.
[127] Barmada M. I.; Conn G. L. Nat. Chem. Biol. 2024, 20(12), 1555.

抗耐药菌红霉素的结构修饰策略、构效关系及全合成研究进展