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(-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase.

Abstract：

:The natural dibenzylbutyrolactone type lignanolide (-)-arctigenin (2), an inhibitor of human immunodeficiency virus type-1 (HIV-1) replication in infected human cell systems, was found to suppress the integration of proviral DNA into the cellular DNA genome. In the present study 2 was tested with purified HIV-1 integrase and found to be inactive in the cleavage (3'-processing) and integration (strand transfer) assays. However, the semisynthetic 3-O-demethylated congener 9 characterized by a catechol substructure exhibited remarkable activities in both assays. Structure-activity relationship studies with 30 natural (1-6), semisynthetic (7-21), and synthetic (37-43, 45, 46) lignans revealed that (1) the lactone moiety is crucial since compounds with a butane-1,4-diol or tetrahydrofuran substructure and also lignanamide analogues lacked activity and (2) the number and arrangement of phenolic hydroxyl groups is important for the activity of lignanolides. The congener with two catechol substructures (7) was found to be the most active compound in this study. 7 was also a potent inhibitor of the "disintegration" reaction which models the reversal of the strand transfer reaction. The inhibitory activity of 7 with the core enzyme fragment consisting of amino acids 50-212 suggests that the binding site of 7 resides in the catalytic domain.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Eich E,Pertz H,Kaloga M,Schulz J,Fesen MR,Mazumder A,Pommier Y

doi

10.1021/jm950387u

subject

Has Abstract

pub_date

1996-01-05 00:00:00

pages

86-95

issue

1

eissn

0022-2623

issn

1520-4804

pii

jm950387u

journal_volume

39

pub_type

杂志文章

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