Structure- and Mechanism-Based Research Progress of Anti-acquired Immune Deficiency Syndrome Drugs

doi:10.6023/cjoc202012036

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3015-3033.DOI: 10.6023/cjoc202012036 Previous Articles Next Articles

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基于靶标结构及作用机制的抗艾滋病药物研究进展

陈超^a^,^b, 胡晓东^b, 王春喜^b, 蓝文贤^b, 吴小余^a^,^*(), 曹春阳^b^,^*()

a 上海大学理学院化学系上海 200444
b 中国科学院上海有机化学研究所生命有机化学国家重点实验室上海 200032

收稿日期:2020-12-22 修回日期:2021-03-12 发布日期:2021-04-29
通讯作者: 吴小余, 曹春阳
基金资助:
科技部重点研发(2017YFE0108200); 科技部重点研发(2016YFA0502302); 中国科学院战略性先导科技专项(XDB20000000); 国家自然科学基金(21778065); 国家自然科学基金(21807105); 国家自然科学基金(21977110); 国家自然科学基金(91753119)

Structure- and Mechanism-Based Research Progress of Anti-acquired Immune Deficiency Syndrome Drugs

Chao Chen^a^,^b, Xiaodong Hu^b, Chunxi Wang^b, Wenxian Lan^b, Xiaoyu Wu^a(), Chunyang Cao^b()

a College of Science, Shanghai University, Shanghai 200444
b State Key Lab of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2020-12-22 Revised:2021-03-12 Published:2021-04-29
Contact: Xiaoyu Wu, Chunyang Cao
Supported by:
National Key Research and Development Program of Ministry of Science and Technology(2017YFE0108200); National Key Research and Development Program of Ministry of Science and Technology(2016YFA0502302); Chinese Academy of Sciences Strategic Priority Research Program(XDB20000000); National Natural Science Foundation of China(21778065); National Natural Science Foundation of China(21807105); National Natural Science Foundation of China(21977110); National Natural Science Foundation of China(91753119)

Human immunodeficiency virus (HIV) is a retrovirus that mainly targets immune cells such as CD4⁺T lymphocytes and macrophages, which eventually leads to acquired immunodeficiency syndrome (AIDS). HIV continues to be a major global public health challenege, having killed almost 33 million lives so far. Since the emergence of antiretroviral therapy (ART), the combination of antiretroviral drugs has transformed HIV-1 infection, once a fatal illness, into a manageable chronic condition. Based on different targets during the virus replication cycle, anti-AIDS drugs in recent years were classified with focus on the mechanism elucidation, current clinical application and future direction.

Key words: antiretroviral drug, human immunodeficiency virus (HIV), acquired immune deficiency syndrome (AIDS), long-acting inhibitor

Cite this article

Chao Chen, Xiaodong Hu, Chunxi Wang, Wenxian Lan, Xiaoyu Wu, Chunyang Cao. Structure- and Mechanism-Based Research Progress of Anti-acquired Immune Deficiency Syndrome Drugs[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3015-3033.

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Fig. & Tab. 29

Figure 1. Organization of the (a) HIV-1 and (b) HIV-2 genomes

Figure 2. Structure of the HIV-1 particle

Figure 3. HIV replication cycle in vivo

	药物类型	药物名称	研发状况	公司
	核苷类反转录酶抑制剂	EFdA (MK-8591, Islatravir )	Ⅲ期临床	Merck & Co
	核苷类反转录酶抑制剂	GS-9131 (Rovafovir Etalafenamide)	临床前期	Gilead Sciences
	非核苷类反转录酶抑制剂	Doravirine (MK-1439)	已上市	Merck & Co
	非核苷类反转录酶抑制剂	Elsulfavirine (VM1500)	Ⅱ/Ⅲ期临床	Viriom
	蛋白酶抑制剂	Darunavir	已上市	Tibotec
	整合酶抑制剂	Cabotegravir (GSK1265744)	已上市	ViiV Healthcare
侵入抑制剂	附着抑制剂	Fostemsavir (GSK-3684394, BMS-663068)	已上市	ViiV Healthcare
	附着后抑制剂	Trogarzo (ibalizumab-uiyk)	已上市	TaiMed Biologics
	趋化因子受体抑制剂	Thioraviroc	Ⅰ期临床	上海药物研究所昆明动物研究所
	融合抑制剂	Albuvirtide	已上市	前沿生物
	衣壳抑制剂	Lenacapavir (GS-6207)	Ⅱ/Ⅲ期临床	Gilead Sciences
	成熟抑制剂	GSK2838232	Ⅱ期临床	GlaxoSmithKline

Table 1. HIV antiretroviral drugs listed and in clinical development recently

Figure 4. Structures of FDA-approved NRTIs

Figure 5. (a) Chemical structure of EFdA and (b) crystal structure of EFdA-TP binding to reverse transcriptase-DNA complex[19] (PDB code 5J2M) DNA is in dark blue, Mg2+ ion is indicated by magenta sphere, and hydrogen bonds are depicted by black dashed lines

Scheme 1. Enantioselective synthesis of EFdA via enzymatic desymmetrization

Scheme 2. Nine-step stereoselective synthesis of EFdA from deoxyribose

Figure 6. (a) Chemical structure of d4AP, GS-9148, GS-9131 and GS-9148-DP, (b) crystal structure of GS-9148-DP binding to reverse transcriptase-DNA complex(PDB code 3KK1)[33] and (c) crystal structure of GS-9148-DP binding to reverse transcriptase Q151L mutant-DNA complex Nucleic acids is in dark blue, 2'-fluorine atom is indicated by light blue sphere.

Figure 7. Structures of FDA-approved NNRTIs

Figure 8. Crystal structure of Doravirine in complex with reverse transcriptase (PDB code 4NCG)[37] Hydrogen bonds are depicted by black dashed lines

Scheme 3. Highly efficient synthesis of doravirine

Figure 9. Chemical structure of Elsulfavirine

Figure 10. Structures of FDA-approved PIs

Figure 11. (a) Structure of Darunavir and (b) crystal structure of Darunavir in complex with protease (PDB code 4LL3)[50] Different proteases are coloured in cyan and light blue, respectively. Hydrogen bonds are depicted by black dashed lines

Figure 12. (a, c, e) Chemical structures of compounds 23~25 and (b, d, f) crystal structures of compounds 23~25 in complex with protease, respectively (PDB code 5AHA, 5AHB, 5AH8)[52] Different proteases are colored in cyan and light blue, respectively. Water molecule is indicated by magenta sphere, and hydrogen bonds are depicted by black dashed lines.

Figure 13. Fullerene-based inhibitors of HIV-1 protease

Figure 14. Chemical sructure of Ahmpatinin iBu

Figure 15. Structures of FDA-approved INSTIs

Scheme 4. Diastereoselective synthesis of Cabotegravir[63]

Figure 16. (a) Chemical structures of Temsavir and Fostemsavir and (b) crystal structure of Temsavir in complex with gp120 (PDB code 5U7O)[72] Hydrogen bonds are depicted by black dashed lines

Figure 17. Crystal structure of the complex of 2 domain CD4 and the Fab fragment of ibalizumab (PDB code 3O2D)[79] The heavy and light chains of ibalizumab are shown by surface representation in red and yellow, respectively, and the residues that make contacts with CD4 are also shown by stick model in the same color scheme. CD4 is in green in ribbon diagram and the residues interacting with ibalizumab are shown by stick model in green.

Figure 18. (a) Structure of Maraviroc and (b) crystal structure of Maraviroc in complex with CCR5 chemokine receptor (PDB code 4MBS)[85] Hydrogen bonds and salt bridge are depicted by black and red dashed lines, respectively

Scheme 5. Synthetic process for Maraviroc

Figure 19. (a) Chemical structure of Thioraviroc and (b) crystal structure of Thioraviroc in complex with CCR5 chemokine receptor (PDB code 6AKY)[87] Hydrogen bonds and salt bridge are depicted by black and red dashed lines, respectively

Figure 20. Structure of T-20

Figure 21. Sructure of ABT

Figure 22. (a) Chemcial structures of PF-3450074, GS-CA1 and GS-6207 and (b) crystal structure of GS-6207-CA hexamer complex (PDB code 6V2F)[96] CA monomers are coloured alternately in cyan and light blue, hydrogen bonds and cation-π interactions are depicted by black and red dashed lines, respectively.

Figure 23. Chemical sructure of GSK2838232

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基于靶标结构及作用机制的抗艾滋病药物研究进展

Structure- and Mechanism-Based Research Progress of Anti-acquired Immune Deficiency Syndrome Drugs

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