Disease relevance of Tecomin

• A lapachol derivative active against mouse lymphocytic leukemia P-388 [1].
• Lapachol [2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone] and its analogs [2-(3,7-dimethyl-2,6-octadienyl)-3-hydroxy-1,4-naphthoquinone and 2-(3,3-dibromo-2-propenyl)-3-hydroxy-1,4-naphthoquinone] have been described, among almost a hundred synthesized analogs, as active against rat tumor Walker 256 carcinosarcoma [1].
• We have used two hydroxylated naphthoquinol menaquinol analogues, reduced plumbagin (PBH2, 5-hydroxy-2-methyl-1,4-naphthoquinol) and reduced lapachol [LPCH2, 2-hydroxy-3-(3-methyl-2-butenyl)-1, 4-naphthoquinol], as substrates for Escherichia coli anaerobic reductases [2].
• Despite the piscicidal toxicity, the use of the salt of lapachol can be recommended for field tests in Schistosomiasis, with caution [3].
• Inhibitory effects of lapachol derivatives on epstein-barr virus activation [4].

High impact information on Tecomin

• Oxidative ring fission of the naphthoquinones lapachol and dichloroallyl lawsone by Penicillium notatum [5].
• Oxidized plumbagin and oxidized lapachol have well resolved absorbances at 419 nm (epsilon=3.95 mM-1. cm-1) and 481 nm (epsilon=2.66 mM-1.cm-1) respectively (in Mops/KOH buffer, pH 7.0) [2].
• In marked contrast, sensitivity to lapachol was similar amongst the five cell lines [6].
• These results provide a probably orientation in the binding site in relation to that for warfarin and lapachol [7].
• Lapachol inhibition of DT-diaphorase (NAD(P)H:quinone dehydrogenase) [8].

Chemical compound and disease context of Tecomin

• Sixteen derivatives (2-17) synthesized from the naphthoquinone lapachol (1), were tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA), as a test for potential cancer chemopreventive agents [4].
• Anthraquinone-2-carboxylic acid exhibited very strong growth inhibition of Clostridium paraputrificum at 1 microg/disk while 100 microg/disk of lapachol was needed for moderate growth inhibition of the same organism [9].
• The toxicity of soluble derivatives (potassium salt) of lapachol and isolapachol in different stages of the life cycle of Schistosoma mansoni is evaluated [3].
• To evaluate the effect of lapachol during fetogenesis, 20 pregnant Wistar rats were randomly divided into two groups: vehicle (10 mL of a 50% aqueous ethanol solution/kg body weight) and treated (100 mg of lapachol/kg body weight) [10].

Biological context of Tecomin

• Fetal growth in rats treated with lapachol [10].
• Previous studies have shown that lapachol does not interfere with embryonic development during the pre-implantation period [10].
• Microwave-assisted rapid cyclization of lapachol, a main constituent of Heterophragma adenophyllum [11].

Anatomical context of Tecomin

• HeLa cells were exposed to different concentrations of lapachol, and the resulting alterations on cellular protein profile, morphology and invasiveness property were studied [12].
• The observation that lapachol exerts leishmanicidal activity in vitro without offering significant protection against LVb-infected lesions in hamsters suggests that lapachol in vivo might possibly inhibit the microbicidal functioning of macrophages [13].

Associations of Tecomin with other chemical compounds

• DT-Diaphorase has been used to test a lapachol affinity chromatography column designed for purification of another coumarin anticoagulant and lapachol sensitive enzyme, vitamin K epoxide reductase [8].
• The activity in the pau d'arco extracts and of lapachol was inhibited by vitamin K1 [14].
• The toxic effect of lapachol, beta-lapachone and several 1,2-naphthoquinone derivatives on the growth, viability and infectivity of Trypanosoma cruzi were compared. beta-lapachone was the most active compound in vitro [15].
• The in vitro antiplasmodial activity of 26 naphthoquinone derivatives related to the natural lapachol (1) and beta-lapachone (2) was tested [16].
• The biological activity of the main compound lapachol and the related alpha-lapachone as well as the lignans cycloolivil and secoisolariciresinol can explain, at least in part, the effect atributed to the crude drug in Paraguayan folk medicine [17].

Gene context of Tecomin

• As a vitamin K antagonist, lapachol might target such vitamin K-dependent reactions as the activation of a ligand for the Axl receptor tyrosine kinase [14].

Analytical, diagnostic and therapeutic context of Tecomin

• Dichloroallyl lawsone (DCL, NSC-126771), a synthetic analogue of the antimalarial lapachol, is potentially useful in cancer chemotherapy [18].
• Purification of the activity in aqueous extracts by solvent partition and thin layer chromatography (TLC) indicated the presence of two activities, one of which was identified as lapachol [14].
• To study the reproductive toxicity potential of Lapachol, pregnant Wistar rats were treated with 0.5 mL of distilled water (control group), 0.5 mL of hydroalcoholic solution (vehicle group), or 20 mg of Lapachol in 0.5 mL of hydroalcoholic solution (treated group) by oral gavage from the 8th to the 12th day of pregnancy [19].

References