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Novel HIV-1 capsid-targeting small molecules of the PF74 binding site.

Abstract：

:The PF74 binding site in HIV-1 capsid protein (CA) is a compelling antiviral drug target. Although PF74 confers mechanistically distinct antiviral phenotypes by competing against host factors for CA binding, it suffers from prohibitively low metabolic stability. Therefore, there has been increasing interest in designing novel sub-chemotypes of PF74 with similar binding mode and improved metabolic stability. We report herein our efforts to explore the inter-domain interacting indole moiety for designing novel CA-targeting small molecules. Our design includes simple substitution on the indole ring, and more importantly, novel sub-chemotypes with the indole moiety replaced with a few less electron-rich rings. All 56 novel analogs were synthesized and evaluated for antiviral activity, cytotoxicity, and impact on CA hexamer stability. Selected analogs were tested for metabolic stability in liver microsomes. Molecular modeling was performed to verify compound binding to the PF74 site. In the end, 5-hydroxyindole analogs (8,9 and 12) showed improved potency (up to 20-fold) over PF74. Of the novel sub-chemotypes, α- and β-naphthyl analogs (33 and 27) exhibited sub micromolar antiviral potencies comparable to that of PF74. Interestingly, although only moderately inhibiting HIV-1 (single-digit micromolar EC50s), analogs of the 2-indolone sub-chemotype consistently lowered the melting point (Tm) of CA hexamers, some with improved metabolic stability over PF74.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Wang L,Casey MC,Vernekar SKV,Sahani RL,Kankanala J,Kirby KA,Du H,Hachiya A,Zhang H,Tedbury PR,Xie J,Sarafianos SG,Wang Z

doi

10.1016/j.ejmech.2020.112626

subject

Has Abstract

pub_date

2020-10-15 00:00:00

pages

112626

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(20)30598-5

journal_volume

204

pub_type

杂志文章

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