An overview of the chemistry and pharmacology of naphthoquinones with emphasis on beta-lapachone and derivatives

Quimica nova

Ferreira, Vítor F.¹  Souza, Maria Cecília B. V. de¹  Silva, Milton N. da¹ 

[1] Universidade Federal Fluminense, Niterói

关键词: beta-Lapachone;    naphthoquinone;    pyranaphthoquinone;    apoptosis.;   

DOI  :  10.1590/S0100-40422003000300019

学科分类：化学（综合）

来源: Sociedade Brasileira de Quimica

【 摘 要 】

Naphthoquinoneshave been extensively studied due to their activity as topoisomerase inhibitors.These enzymes are critical to DNA replication in cells. In addition, naphthoquinoneshave been shown to induce what are known as "reactive oxygen species" that cancause damage to cells. b-Lapachone is a very importantpyranaphthoquinone obtained from the heartwood of the lapacho tree, Tabebuiaavellanedae Lorentz ex. Griseb. (Bignoniaceae), and other Tabebuiatrees native to Central and South America and chemically from lapachol. b-Lapachonehas a diversity of useful biological activities against various cancer celllines such as human ovarian and prostate tumors and, at lower doses is a radiosensitizerof several human cancer cell lines. It gives rise to a variety of effects invitro including the inhibition or activation of topoisomerase I an II ina distinct manner from that of other topoisomerase inhibitors. This review intendto discuss some details of the mechanisms of quinone-induced cell damage anddeath, and we also summarize results of the literature indicating that b-Lapachonemay take part in quinone-elicited apoptosis despite the fact that its mechanismof action in vivo and its targets are still unknown.

【 授权许可】

CC BY