dimeric naphthoquinone 1

Dimeric naphthoquinone 1 is a naturally-derived small molecule compound isolated from Diospyros lotus and other plant sources, characterized structurally as 5,4′-dihydroxy-1′-methoxy-6,6′-dimethyl-7,3′-binaphthyl-1,4,5′,8′-tetraone. It represents a rare class of binaphthyl-linked naphthoquinones with demonstrated antiproliferative effects, notably by acting on multidrug resistance (MDR) efflux pumps in cells and showing moderate antagonism in combination index analysis for MDR modulation[2]. Mechanistically, dimeric naphthoquinones including this compound act through redox cycling, inhibition, and interaction with NAD(P)H dehydrogenase, quinone 1 (NQO1), leading to excessive production of reactive oxygen species (ROS), disruption of cellular oxidative balance, and mitochondrial dysfunction[1][3][6]. Its cytotoxicity has been most researched in highly proliferative cells such as leukemia, breast, and prostate cancer cell lines, with effects stemming from the induction of oxidative stress and selective targeting of NQO1 as a major cellular target[1][6].

Other names

5,4′-dihydroxy-1′-methoxy-6,6′-dimethyl-7,3′-binaphthyl-1,4,5′,8′-tetraone