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

doi:10.6023/cjoc202506020

摘要/Abstract

大环内酯类抗生素(Macrolide)作为临床重要的常用药物, 凭借其广谱抗菌性与优良治疗效果得到了广泛应用, 如红霉素、克拉霉素和阿奇霉素都是世界卫生组织(WHO)推荐的基本药物. 然而, 细菌耐药问题的出现使其抗菌效力显著下降, 众多疾病的治疗面临无药可用的困境, 尤其是针对组成型erm金黄色葡萄球菌、组成型erm化脓链球菌以及A2058突变肺炎支原体引发的感染疾病, 包括第三、四代红霉素——泰利霉素、索利霉素在内的该类抗生素, 均难以发挥疗效. 为攻克大环内酯的细菌耐药难题, 进一步提升其对耐药菌的抗菌活性, 科研人员开展了大量新结构研究. 以大环内酯类抗生素的发展历程为时间脉络, 系统梳理2013~2024年该类药物在抗耐药菌领域的研究进展, 重点阐述其构效关系和药代动力学特征, 以及非天然大环内酯的全合成策略, 并总结了第5代大环内酯类抗生素在对抗细菌耐药性方面的关键突破, 以期为后续药物分子设计、耐药机制研究以及新型抗菌策略的开发指明方向.

关键词: 大环内酯, 耐药, 结构修饰, 构效关系, 全合成

As clinically important and widely used drugs, macrolide antibiotics exhibit broad-spectrum antimicrobial properties and excellent therapeutic efficacy, such as erythromycin, clarithromycin and azithromycin, all of which are 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 3rd-generation telithromycin and the 4th-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, extensive studies have been performed on new structures. Taking the development history of macrolide antibiotics as a chronological framework, the research progress of these drugs against drug-resistant bacteria from 2013 to 2024 is systematically summarized. This study 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 5th-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: macrolide, drug resistance, structural modification, structure-activity relationship, total synthesis

引用此文

崔心怡, 郭丽帆, 马聪璇, 李耘, 梁建华. 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[J]. 有机化学, 2026, 46(1): 39-73.

Xinyi Cui, Lifan Guo, Congxuan Ma, Yun Li, Jianhua Liang. Structural Modifications, Structure-Activity Relationships, and Total Synthesis Advances in Erythromycin Analogs against Resistant Pathogens[J]. Chinese Journal of Organic Chemistry, 2026, 46(1): 39-73.

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图/表 78

图1. 红霉素与核糖体靶点A2058的相互作用(粉色结构为红霉素(PDB: 4V7U))[12]

Figure 1. Interaction between erythromycin and the ribosomal base A2058 (The pink structure is erythromycin (PDB: 4V7U))[12]

图2. 大环内酯类抗生素代表化合物

Figure 2. Representative compounds of macrolide antibiotics

图式1. 红霉素A在酸性条件下降解的化学结构变化

Scheme 1. Chemical structural changes of erythromycin A during degradation under acidic conditions

图3. 红霉素A的二甲氨基通过水分子介导与A2058结合的示意图(PDB: 6XHY)[8]

Figure 3. Schematic diagram of the binding of dimethylamino group of erythromycin A to A2058 mediated by water molecules (PDB: 6XHY)[8]

Macrolide	Species	Res/Å	Method	PDB No.	Ref.
Erythromycin	E. coli	3.60	Electron microscopy	5JU8	[25]
Erythromycin	E. coli	3.60	Electron microscopy	5JTE	[25]
Telithromycin	B. subtilis	3.10	Electron microscopy	6HA1	[26]
Telithromycin	E. coli	3.50	Electron microscopy	6HA8	[26]
Erythromycin	Thermus thermophilus	2.85	X-Ray diffraction	6ND6	[27]
Erythromycin	Staphylococcus aureus	2.42	Electron microscopy	6S0X	[28]
Erythromycin	Thermus thermophilus	2.55	X-Ray diffraction	6XHX	[8]
Telithromycin	Thermus thermophilus	2.60	X-Ray diffraction	6XHY	[8]
Erythromycin	E. coli	2.90	Electron microscopy	7NSO	[29]
Erythromycin	E. coli	3.50	Electron microscopy	7NSP	[29]
Telithromycin	E. coli	3.10	Electron microscopy	7NSQ	[29]
Erythromycin	E. coli	3.00	Electron microscopy	7Q4K	[30]
Erythromycin	Thermus thermophilus	2.50	X-Ray diffraction	8FC1	[31]
Erythromycin	Thermus thermophilus	2.45	X-Ray diffraction	8FC4	[31]
Azithromycin	Thermus thermophilus	2.50	X-Ray diffraction	8FC2	[31]
Azithromycin	Thermus thermophilus	2.65	X-Ray diffraction	8FC5	[31]
Telithromycin	Thermus thermophilus	2.35	X-Ray diffraction	8FC6	[31]
Telithromycin	Thermus thermophilus	2.60	X-Ray diffraction	8FC3	[31]
MCX-66	Thermus thermophilus	2.40	X-Ray diffraction	8VTU	[32]
MCX-128	Thermus thermophilus	2.40	X-Ray diffraction	8VTX	[32]
MCX-128	Thermus thermophilus	2.35	X-Ray diffraction	8VTW	[32]
MCX-91	Thermus thermophilus	2.40	X-Ray diffraction	8VTV	[32]
MCX-190	Staphylococcus aureus	2.58	Electron microscopy	8Y38	[23]
MCX-190	Staphylococcus aureus	3.60	Electron microscopy	8Y39	[23]

表1. 2013~2024年大环内酯与70S核糖体复合物结构PDB汇总

Table 1. Summary of PDB structures of macrolide-70S ribosome complexes from 2013 to 2024

Macrolide	Species	Res/Å	Method	PDB No.	Ref.
Carbamolide 4d	Deinococcus radiodurans	3.20	X-Ray diffraction	4IO9	[33]
Carbamolide 4e	Deinococcus radiodurans	3.20	X-Ray diffraction	4IOA	[33]
Carbamolide 4f	Deinococcus radiodurans	3.60	X-Ray diffraction	4IOC	[33]
Erythromycin	E. coli	6.60	Cryo-electron microscopy	3J5L	[34]
Erythromycin	E. coli	3.90	Cryo-electron microscopy	3J7Z	[35]
Telithromycin	Staphylococcus aureus	3.43	X-Ray diffraction	4WF9	[36]
Erythromycin	Deinococcus radiodurans	3.54	X-Ray diffraction	4WFN	[37]
Erythromycin	Staphylococcus aureus	2.30	Electron microscopy	6S0Z	[28]
Clarithromycin	Mycobacterium tuberculosis	3.30	Electron microscopy	7F0D	[38]
Erythromycin	Mycobacterium smegmatis	3.60	Electron microscopy	8XZ3	[39]
MCX-190	Staphylococcus aureus	2.65	CElectron microscopy	8Y36	[23]
MCX-190	Staphylococcus aureus	2.53	Electron microscopy	8Y37	[23]

表2. 2013~2024年大环内酯与50S核糖体复合物结构PDB汇总

Table 2. Summary of PDB Structures of Macrolide-50S Ribosome Complexes from 2013 to 2024

图4. 酮内酯TE-802的结构

Figure 4. Structure of ketolide TE-802

图5. (A)泰利霉素与嗜热栖热菌核糖体靶点A752的相互作用[粉红色结构为泰利霉素(PDB: 4V7Z)][51]; (B)泰利霉素与金黄色葡萄球菌核糖体的复合物结构[泰利霉素在金黄色葡萄球菌中与A752不具有相互作用, 粉红色结构为泰利霉素(PDB: 4WF9)][36]

Figure 5. (A) Interaction between telithromycin and ribosomal target A752 of Thermus thermophilus (The pink structure is telithromycin (PDB: 4V7Z));[51] (B) Structure of the complex between telithromycin and ribosomes of S. aureus (Telithromycin does not interact with A752 in S. aureus. The pink structure is telithromycin (PDB: 4WF9))[36]

图6. 化合物3和4a~4e的结构

Figure 6. Structures of compounds 3 and 4a~4e

图7. 那非霉素结构

Figure 7. Structure of nafithromycin

图8. 化合物5a和5b结构

Figure 8. Structures of compounds 5a and 5b

图9. 化合物6a~6c结构

Figure 9. Structures of compounds 6a~6c

图10. 化合物7和8结构

Figure 10. Structures of compounds 7 and 8

图11. 化合物9结构

Figure 11. Structure of compound 9

图12. 化合物10和11a~11e的结构

Figure 12. Structures of compounds 10 and 11a~11e

图13. 化合物12a~12b结构

Figure 13. Structures of compounds 12a~12b

图14. 化合物13~15结构

Figure 14. Structures of compounds 13~15

Strain	Resistance phenotypes (genotypes)	MIC/(μg•mL^－1)
Strain	Resistance phenotypes (genotypes)	14	Clarithromycin
Streptococcus pneumoniae BAA1402	M (mef)	0.03	2
Staphylococcus aureus BAA976	M (mef)	0.03	64
Staphylococcus aureus BA977	iMLS (erm)	0.03	>64

表3. 化合物14的部分抗菌活性

Table 3. Antibacterial activity of compound 14

图15. TEA0777和FMA0122的结构

Figure 15. Structures of compounds TEA0777 and FMA0122

图16. 化合物16~20的结构

Figure 16. Structures of compounds 16~20

图17. 化合物21~23的结构

Figure 17. Structures of compounds 21~23

图18. 化合物24~27的结构

Figure 18. Structures of compounds 24~27

图19. 化合物28的结构

Figure 19. Structure of compound 28

图20. (A)化合物29a~29d结构及(B)化合物29d与D50S结合的X射线晶体结构(黄色结构为化合物29d(PDB: 4IO9))[33]

Figure 20. (A) Structures of compounds 29a~29d, and (B) X-ray crystal structure of compound 29d bound to D50S (The yellow structure is compound 29d (PDB: 4IO9))[33]

Strain	Resistance phenotypes	MIC/(mg•L^－1)
Strain	Resistance phenotypes	29a	29b	Clarithromycin
Streptococcus pneumoniae 1243-00	MLS_B	0.5	64	>64
Streptococcus pyogenes 1304-00	MLS_B	0.5	32	>64

表4. 化合物29a和29b的部分抗菌活性

Table 4. Antibacterial activity of compounds 29a and 29b

图21. 化合物30~33的结构

Figure 21. Structures of compounds 30~33

Compd.	Clearance/(mL•h^－1•kg^－1)	t_1/2/h	Mean resident time/h	c_max/(ng•mL^－1)
30	3034±600	2.9±0.4	4.5±0.6	1029±115
Telithromycin	21758±2748	1.2±0.3	3.3±0.5	204±20.5

表5. 化合物30的部分药代动力学数据[76]

Table 5. Pharmacokinetic data of compound 30

图22. 化合物34和35的结构

Figure 22. Structures of compounds 34 and 35

图23. 化合物36~38结构

Figure 23. Structures of compounds 36~38

图24. 化合物39a~39d和40的结构

Figure 24. Structures of compounds 39a~39d and 40

图25. 化合物41和42的结构

Figure 25. Structures of compounds 41 and 42

Strain	Resistance phenotypes	MIC/(μg•mL^－1)
Strain	Resistance phenotypes	41	42	Telithromycin	Clarithromycin
Staphylococcus epidermidis 12-4	MRSE^a	4	8	≤2	32
Staphylococcus epidermidis 12-11	MRSE	2	≤1	≤2	4

表6. 化合物41和42的部分抗菌活性

Table 6. Antibacterial activity of compounds 41 and 42

图26. 化合物43的结构

Figure 26. Structure of compound 43

Strain	Resistance phenotypes	MIC/(μg•mL^－1)
Strain	Resistance phenotypes	43	Azithromycin
Streptococcus pneumoniae 943	Sensitive	1	4
Streptococcus pneumoniae 746	Sensitive	2	8
MRSA-1	MRSA^a	16	16

表7. 化合物43的部分抗菌活性

Table 7. Antibacterial activity of compound 43

图27. 化合物44a和44b结构

Figure 27. Structures of compounds 44a and 44b

图28. 化合物45~47结构

Figure 28. Structures of compounds 45~47

图29. 化合物48~50的结构

Figure 29. Structures of compounds 48~50

Strain	Resistance genotypes	MIC/(μg•mL^－1)
Strain	Resistance genotypes	48	Azithromycin
Streptococcus pneumoniae B1	erm	0.25	128
Streptococcus pneumoniae AB11	mef, erm	2	256
Streptococcus pneumoniae A22072	mef	0.03	4

表8. 化合物48的部分抗菌活性

Table 8. Antibacterial activity of compound 48

图30. 化合物51的结构

Figure 30. Structure of compound 51

图31. 化合物52结构

Figure 31. Structure of compound 52

图32. 化合物53和54的结构

Figure 32. Structures of compounds 53 and 54

图33. 化合物55和56的结构

Figure 33. Structures of compounds 55 and 56

图34. 化合物57和58结构

Figure 34. Structures of compounds 57 and 58

图35. 索利霉素结构及其与靶点A752的相互作用(绿色结构为索利霉素(PDB: 4WWW))[97]

Figure 35. Structure of solithromycin and its interaction with base A752 (The green structure is solithromycin (PDB: 4WWW))[97]

图36. 化合物59结构

Figure 36. Structure of compound 59

图37. 化合物60a~60c结构

Figure 37. Structures of compounds 60a~60c

图38. 化合物61和62结构

Figure 38. Structures of compounds 61 and 62

图39. 化合物63a和63b结构

Figure 39. Structures of compounds 63a and 63b

图40. 化合物64结构

Figure 40. Structure of compound 64

图41. 化合物65a和65b结构

Figure 41. Structures of compounds 65a and 65b

图42. 化合物66结构式

Figure 42. Structure of compound 66

Strain	Resistant determinants	MIC/(μg•mL^－1)
Strain	Resistant determinants	66	Telithromycin
Streptococcus pneumoniae PU09	PSSP,^a mef	0.25	0.25
Streptococcus pyogenes 01-968	i-erm	0.062	0.062
Streptococcus pyogenes 12-207	mef	0.031	0.5

表9. 化合物66的抗菌活性

Table 9. Antibacterial activity of compound 66

图43. 化合物67~70结构

Figure 43. Structures of compounds 67~70

图式2. 分子内Nozaki-Hiyama-Kishi反应完成环化

Scheme 2. Intramolecular Nozaki-Hiyama-Kishi reaction completes cyclization Reagents and conditions: (a) Cl3PhCOCl, Et3N, DMAP, 75% yield; (b) TBAF, AcOH, 60% yield; (c) DMP, NaHCO3, 78% yield; (d) CrCl2, cat. NiCl2, DMSO, 50% yield; (e) DMP, 80% yield.

图式3. 分子内环化复分解反应完成环化

Scheme 3. Intramolecular ring-closing metathesis reaction completes cyclization Reagents and conditions: (a) Dess-Martin Periodinane, NaHCO3; (b) vinyl MgBr, THF; (c) Dess-Martin periodinane, CH2Cl2, 60% yield over three steps; (d) 20 mol% Grubbs II cat., 60% yield.

Strain	Resistant determinant	MIC/(μg•mL^－1)
Strain	Resistant determinant	67	68	69	70	Telithromycin
E. coli SQ171/2058G	A2058G	>512	>256	>256	>256	—
E. coli DK/PKK3535	wt	32	4	8	0.5	0.5
E. coliDK/2058G	A2058G	64	32	16	4	1
Staphylococcus aureus UCN14	A2058T	32	>256	>256	>256	>128
Staphylococcus aureus ATCC33591	ermA	>128	>64	>128	>128	>128

表10. 去甲基泰利霉素的抗菌活性

Table 10. Antibacterial activity of demethyltelithromycin

图式4. 14元氮杂酮内酯93的全合成路线

Scheme 4. Total synthesis route of 14-membered aza ketolide 93

图式5. 15元氮杂酮内酯100的全合成路线

Scheme 5. Total synthesis route of 15-membered aza ketolide 100

图式6. 索利霉素的的全合成路线

Scheme 6. Total synthesis route of solithromycin

图44. 化合物108的结构

Figure 44. Structure of compound 108

图45. 化合物109a~109f的结构

Figure 45. Structures of compounds 109a~109f

图46. 化合物110a~110c结构

Figure 46. Structures of compounds 110a~110c

图47. 化合物111a~111e结构

Figure 47. Structures of compounds 111a~111e

图48. 化合物112和113的结构

Figure 48. Structures of compounds 112 and 113

图49. 化合物114的结构

Figure 49. Structure of compound 114

图50. 化合物115的结构

Figure 50. Structure of compound 115

Strain	Resistant determinant	MIC/(μg•mL^－1)
Strain	Resistant determinant	115	Azithromycin	Telithromycin	Ciprofloxacin
Streptococcus pneumoniae 07P390	c-ermB	≤0.008	256	0.016	—
Streptococcus pyogenes 12-206	c-ermTR	0.016	>256	0.031	0.125
Staphylococcus aureus PU32	MRSA, i-ermA	0.25	32	0.125	64

表11. 化合物115的部分抗菌活性

Table 11. Antibacterial activity of compound 115

图51. 化合物116的结构

Figure 51. Structure of compound 116

图52. 化合物117和118的结构

Figure 52. Structures of compounds 117 and 118

图53. 化合物119的结构

Figure 53. Structure of compound 119

Strain	Resistant determinants	MIC/(μg•mL^－1)
Strain	Resistant determinants	119	Telithromycin
Streptococcus pneumoniae PU09	mef	≤0.008	0.5
Streptococcus pyogenes 12-206	c-ermTR	0.06	0.25
Haemophilus influenzae ATCC49247	sensitive	2	4

表12. 化合物119的部分抗菌活性

Table 12. Antibacterial activity of compound 119

图54. 化合物120~122的结构

Figure 54. Structures of compounds 120~122

图55. 化合物123的结构

Figure 55. Structure of compound 123

图56. 化合物124和125的结构

Figure 56. Structures of compounds 124 and 125

图57. 化合物126和127的结构

Figure 57. Structures of compounds 126 and 127

图58. (A)化合物MCX-219和190的结构及(B)化合物MCX-190与靶点的新作用模式[括号中是金黄色葡萄球菌rRNA编号, 粉色结构为化合物MCX-190 (PDB: 8Y36)][23]

Figure 58. (A) Structures of compounds MCX-219 and 190, and (B) new binding mode of compound MCX-190 with the target [The rRNA number of S. aureus is in parentheses. The pink structure represents compound MCX-190 (PDB: 8Y36)][23]

Strain	Resistant determinants	MIC/(μg•mL^－1)
Strain	Resistant determinants	MCX-190	MCX-219	Telithromycin
Staphylococcus aureus 15B196	c-ermB	8	1	32~>256
Staphylococcus aureus PU32	i-ermA	0.25~0.5	0.25	0.12~0.5
Mycoplasma pneumoniae	A2058G	1	0.25	256
Mycoplasma pneumoniae	A2059G	2	0.25	256
Mycoplasma pneumoniae	A2058T	0.5	0.06	256

表13. 化合物MCX-190和MCX-219的部分抗菌活性

Table 13. Antibacterial activity of compounds MCX-190 and MCX-190

图59. MCX-128结构及其与新靶点C2586的相互作用[黄色结构为化合物MCX-128(PDB: 8VTX)][32]

Figure 59. Structure of MCX-128 and its interaction with the new target C2586 [The yellow structure represents compound MCX-128 (PDB: 8VTX)][32]

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