Topic
Lapachol
About: Lapachol is a research topic. Over the lifetime, 360 publications have been published within this topic receiving 8227 citations.
Papers published on a yearly basis
1 / 2
Papers
Journal Article•
TL;DR: It is proposed that the intracellular activation of these quinone anticancer drugs to a free radical state may be primary to their cytotoxic activity.
Abstract: The highly active, quinone-containing anticancer drugs, Adriamycin, daunorubicin, carminomycin, rubidazone, nogalamycin, aclacinomycin A, and steffimycin (benzanthraquinones); mitomycin C and streptonigrin (N-heterocyclic quinones); and lapachol (naphthoquinone) interact with mammalian microsomes and function as free radical carriers. These quinone drugs augment the flow of electrons from reduced nicotinamide adenine dinucleotide phosphate to molecular oxygen as measured by enhanced reduced nicotinamide adenine dinucleotide phosphate oxidation and oxygen consumption. This reaction is catalyzed by microsomal protein and produces a free radical intermediate form of the drugs as determined by electron paramagnetic resonance spectroscopy. Microsomes from mouse and rat liver, heart, lung, and spleen and mouse L1210 and P388 tumors all catalyze the augmented oxygen consumption. Apparent Km values determined with normal rat liver microsomes range from 0.49 × 10-4m for steffimycin to 13.4 × 10-4m for lapachol. Since SKF 525A and carbon monoxide have little effect on this reaction, cytochrome P-450 is probably not involved. Several nonquinone anticancer agents were tested and were found inactive in the system. Since quinone anticancer drugs are associated with chromosomal damage that appears to be dependent on metabolic activation of these drugs, we propose that the intracellular activation of these drugs to a free radical state may be primary to their cytotoxic activity. As free radicals, these drugs, because of their high affinity and selective binding to nucleic acids, have the potential to be “site-specific free radicals” that bind to DNA or RNA and either react directly or generate oxygen-dependent free radicals such as superoxide radical or hydroxyl radical to cause the damage associated with their cytotoxic actions.
685 citations
TL;DR: These simple phenazines, containing polar (-Br,-I) and ionizable (-SO(3)H, -OH) groups, easily synthesized from cheap, natural or synthetic precursors (lapachol and beta-lapachone), at rather low cost, provide prototypes for development of new antimalarials aiming the chloroquine resistant parasites.
302 citations
TL;DR: The interesting and most usefull knowledge on lapachol, which is reviewed in this paper, can be used as a starting point in future research endeavors.
Abstract: Lapachol is a naphthoquinone that was first isolated by E. Paterno from Tabebuia avellanedae (Bignoniaceae) in 1882. A wide spectrum of therapeutic activities have been attributed to lapachol or its derivatives viz., anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, anti- edemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, bactericidal, fungicidal, insectifugal, pesticidal, protisticidal, respiradepressant, schistosomicidal, termiticidal, and viricidal. Originally isolated from species of the Bignoniaceae family, lapachol can also be found in other families such as Verbenaceae, Proteaceae, Leguminosae, Sapotaceae, Scrophulariaceae, and Malvaceae. The interesting and most usefull knowledge on lapachol, which is reviewed in this paper, can be used as a starting point in future research endeavors.
234 citations
TL;DR: Results of the literature indicating that b-Lapachone may take part in quinone-elicited apoptosis despite the fact that its mechanism of action in vivo and its targets are still unknown are summarized.
Abstract: Naphthoquinones have been extensively studied due to their activity as topoisomerase inhibitors. These enzymes are critical to DNA replication in cells. In addition, naphthoquinones have been shown to induce what are known as "reactive oxygen species" that can cause damage to cells. b-Lapachone is a very important pyranaphthoquinone obtained from the heartwood of the lapacho tree, Tabebuia avellanedae Lorentz ex. Griseb. (Bignoniaceae), and other Tabebuia trees native to Central and South America and chemically from lapachol. b-Lapachone has a diversity of useful biological activities against various cancer cell lines such as human ovarian and prostate tumors and, at lower doses is a radiosensitizer of several human cancer cell lines. It gives rise to a variety of effects in vitro including the inhibition or activation of topoisomerase I an II in a distinct manner from that of other topoisomerase inhibitors. This review intend to discuss some details of the mechanisms of quinone-induced cell damage and death, and we also summarize results of the literature indicating that b-Lapachone may take part in quinone-elicited apoptosis despite the fact that its mechanism of action in vivo and its targets are still unknown.
160 citations
TL;DR: In this paper, the in vitro antiplasmodial activity of 26 naphthoquinone derivatives related to the natural lapachol and beta-lapachone was tested.
Abstract: The in vitro antiplasmodial activity of 26 naphthoquinone derivatives related to the natural lapachol (1) and beta-lapachone (2) was tested. Ten of these derivatives are reported for the first time. The evaluation was performed on cultures of F32 strain of Plasmodium falciparum, and some derivatives displayed attractive in vitro activities (IC50 < 10 microM). Based on these results, some structure-activity relationships have been determined.
154 citations
Related Topics (5)
Performance Metrics
| Year | Papers |
|---|---|
| 2021 | 11 |
| 2020 | 15 |
| 2019 | 9 |
| 2018 | 11 |
| 2017 | 13 |
| 2016 | 7 |