Showing 1-30 of 32 results for "142905"
Kenneth O Eyong et al.
Bioorganic & medicinal chemistry letters, 18(20), 5387-5390 (2008-10-03)
Ozonolysis of lapachol (1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone (3) along with the expected aldehyde 6, is described. The reaction of lapachol (1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is...
Marcele Neves Rocha et al.
Bioinorganic chemistry and applications, 2013, 961783-961783 (2013-06-20)
Leishmania amazonensis is the etiologic agent of the cutaneous and diffuse leishmaniasis often associated with drug resistance. Lapachol [2-hydroxy-3-(3'-methyl-2-butenyl)-1,4-naphthoquinone] displays a wide range of antimicrobial properties against many pathogens. In this study, using the classic microscopic in vitro model, we...
Xueyin Zu et al.
Phytotherapy research : PTR, 33(9), 2337-2346 (2019-06-22)
Lapachol is a 1,4-naphthoquinone that is isolated from the Bignoniaceae family. It has been reported to exert anti-inflammatory, antibacterial, and anticancer activities. However, the anticancer activity of lapachol and its molecular mechanisms against esophageal squamous cell carcinoma (ESCC) cells have...
Camila Raquel Paludo et al.
European journal of drug metabolism and pharmacokinetics, 42(2), 213-220 (2016-04-10)
β-Lapachone is a drug candidate in phase II clinical trials for treatment of solid tumors. The therapeutic efficacy of β-lapachone is closely related to its metabolism, since this o-naphthoquinone produces cytotoxic effect after intracellular bioreduction by reactive oxygen species formation....
Ingrid L Cockburn et al.
Biological chemistry, 392(5), 431-438 (2011-03-24)
Plasmodium falciparum heat shock protein 70 (PfHsp70-1) is thought to play an essential role in parasite survival and virulence in the human host, making it a potential antimalarial drug target. A malate dehydrogenase based aggregation suppression assay was adapted for...
Fabiana de A Cavalcante et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 65(9-10), 627-636 (2010-12-09)
The present study was designed to further evaluate a possible spasmolytic activity of synthetic lapachol derivatives, norlapachol, alpha-norlapachone, beta-norlapachone and hydro-hydroxy-norlapachol (HH-norlapachol), on guinea-pig ileum. In guinea-pig ileum, except for norlapachol, all naphthoquinones inhibited the phasic contractions induced by carbachol...
Ricardo Vessecchi et al.
Rapid communications in mass spectrometry : RCM, 24(14), 2101-2108 (2010-06-17)
Electrospray ionization mass spectrometric analysis of lapachol (2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone) was accomplished in order to elucidate the gas-phase dissociation reactions of this important biologically active natural product. The occurrence of protonated and cationized species in the positive mode and of deprotonated species...
Ricardo Q Aucélio et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 100, 155-160 (2012-05-18)
3MPA-CdTe QDs in aqueous dispersion was used as a fluorescent probe for the determination of lapachol, a natural naphthoquinone found in plants of the Bignoniaceae family genus Tabebuia. Working QDs dispersions (4.5×10(-8) mol L(-1) of QDs) was prepared in aqueous...
Cristina Theoduloz et al.
Planta medica, 78(17), 1807-1812 (2012-10-11)
The stem bark of Tabebuia species and the rhizomes of Jatropha isabelii are used in Paraguayan traditional medicine to treat gastric lesions and as anti-inflammatory agents. The sesquiterpene cyperenoic acid obtained from J. isabelii has been shown to display a...
Masayo Maeda et al.
Toxicology and applied pharmacology, 229(2), 232-238 (2008-02-26)
Lapachol [2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone] is a vitamin K antagonist with antitumor activity. The effect of lapachol on the experimental metastasis of murine B16BL6 melanoma cells was examined. A single oral administration of a high toxic dose of lapachol (80-100 mg/kg) 6 h...
Lucas Bonfim Marques et al.
Toxicology in vitro : an international journal published in association with BIBRA, 65, 104772-104772 (2020-01-15)
Lapachol is a plant-derived naphthoquinone that kills several types of cancer cells. Derivatives of this molecule may therefore prove to be useful chemotherapeutic agents. In this study, we explored whether glycosylation increases the cytotoxic potency of lapachol towards HL-60 human...
Gabrieli L Parrilha et al.
Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine, 25(1), 55-62 (2011-08-09)
Complex [Bi(Lp)(2)]Cl was obtained with 4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione, "lapachol" (HLp). Lapachol, [Bi(Lp)(2)]Cl and BiCl(3) were evaluated in a murine model of inflammatory angiogenesis induced by subcutaneous implantation of polyether polyurethane sponge discs. Intraperitoneal (i.p.) administration of lapachol or [Bi(Lp)(2)]Cl reduced the hemoglobin...
Ludmila G de Oliveira et al.
Molecules (Basel, Switzerland), 16(12), 10314-10323 (2011-12-14)
Antimony(V) and bismuth(V) complexes of lapachol have been synthesized by the reaction of Ph₃SbCl₂ or Ph₃BiCl₂ with lapachol (Lp) and characterized by several physicochemical techniques such as IR, and NMR spectroscopy and X-ray crystallography. The compounds contain six-coordinated antimony and...
Renato A S Oliveira et al.
International immunopharmacology, 10(11), 1463-1473 (2010-09-15)
The present study reports the anti-mycobacterial activity of 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (lapachol) as well as its influence on macrophage functions. Lapachol (L) did not induce apoptosis/necrosis of THP-1 macrophages at ≤32 μg/mL. Mycobacterium avium liquid growth was arrested by ≥32 μg/mL and...
Edson Luis Maistro et al.
Planta medica, 76(9), 858-862 (2010-01-30)
Lapachol is a naturally occurring naphthoquinone derivative found in the heartwood of several plants, particularly those of the genus Tabebuia (Bignoneaceae). Despite its use as a therapeutic product with anti-inflammatory, analgesic, antipsoriatic, trypanocidal effects, among others, its in vivo mutagenic...
Antônio Wilton Cavalcante Fernandes et al.
Current microbiology, 77(2), 204-209 (2019-12-01)
Antimicrobial resistance in bacteria, such as Staphylococcus aureus, has been the subject of many assistance studies of alternatives for the treatment of infections. These studies aim to solve this problem for bacteria, such as biofilm formation. Aiming to control the...
Evelyn L Bonifazi et al.
Bioorganic & medicinal chemistry, 18(7), 2621-2630 (2010-03-23)
A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-(prop-1-en-2-yl)naphtho[2,3-b]furan-4,9-dione (27) were the most potent antiproliferative agents...
Sanjay Gurule et al.
Biomedical chromatography : BMC, 24(5), 497-505 (2009-08-28)
A newly developed LC-APCI mass spectrometric method is described for human plasma determination of atovaquone using lapachol internal standard. A single-step protein precipitation technique for plasma extraction of atovaquone achieving mean recovery of 94.17% (CV 8%) without compromising sensitivity (limit...
Beatrice Nyanchama Kiage-Mokua et al.
Phytotherapy research : PTR, 26(12), 1878-1883 (2012-03-21)
Earlier work in our laboratory indicated that ethanolic extracts of Tabebuia impetiginosa, Arctium lappa L., Calendula officinalis, Helianthus annuus, Linum usitatissimum and L. propolis, inhibit pancreatic lipase in vitro. In a follow-up study we assessed their effects on plasma triglycerides...
Renato A S Oliveira et al.
International immunopharmacology, 14(1), 54-65 (2012-06-19)
We report the effect of an immunomodulatory and anti-mycobacterial naphthoquinone, lapachol, on the bi-dimensional patterns of protein expression of toll-like receptor 2 (TLR2)-agonised and IFN-γ-treated THP-1 macrophages. This non-hypothesis driven proteomic analysis intends to shed light on the cellular functions...
Wolfgang Kandioller et al.
Chemical communications (Cambridge, England), 49(32), 3348-3350 (2013-03-19)
Organometallic Ru(II), Os(II) and Rh(III) complexes of lapachol induce apoptosis in human tumour cell lines in the low μM range by a mode of action involving oxidative stress, especially in the case of the ruthenium compound.
Eduardo J S Salustiano et al.
Investigational new drugs, 28(2), 139-144 (2009-03-04)
The pentacyclic 1,4-naphthoquinones 1a-d were cytotoxic (IC(50) approximately 2-7 microM) to human leukemic cell lines K562 (oxidative stress-resistant), Lucena-1 (MDR phenotype) and Daudi. Fresh leukemic cells obtained from patients, some with the MDR phenotype, were also sensitive to these compounds....
Takuya Matsui et al.
The Journal of pharmacy and pharmacology, 63(7), 960-966 (2011-06-04)
The pathogenesis and therapy of hypertrophic scar have not yet been established. Our aim was to investigate the antiproliferative and antisecretory effects of lapachol, isolated from the stem bark of Avicennia rumphiana Hall. f., on hypertrophic scar fibroblasts. The effects...
Michael Niehues et al.
European journal of medicinal chemistry, 54, 804-812 (2012-07-17)
The bioactive naphtoquinone lapachol was studied in vitro by a biomimetic model with Jacobsen catalyst (manganese(III) salen) and iodosylbenzene as oxidizing agent. Eleven oxidation derivatives were thus identified and two competitive oxidation pathways postulated. Similar to Mn(III) porphyrins, Jacobsen catalyst...
Ricardo Vessecchi et al.
Journal of mass spectrometry : JMS, 47(12), 1648-1659 (2013-01-03)
In order to understand the influence of alkyl side chains on the gas-phase reactivity of 1,4-naphthoquinone derivatives, some 2-hydroxy-1,4-naphthoquinone derivatives have been prepared and studied by electrospray ionization tandem mass spectrometry in combination with computational quantum chemistry calculations. Protonation and...
Carmen M Martín-Navarro et al.
Experimental parasitology, 126(1), 106-108 (2010-01-05)
In this study, the in vitro activities of a natural sesquiterpene, alpha-cyperotundone, isolated from the root bark of Maytenus retusa and a cobalt(II)-complex of a natural occurring prenyl hydroxynaphthoquinone (lapachol) were evaluated against the trophozoite stage of Acanthamoeba castellanii Neff...
Mariano Walter Pertino et al.
Molecules (Basel, Switzerland), 16(10), 8614-8628 (2011-10-15)
New diterpenylquinones, combining a diterpene diacid and a naphthoquinone, were prepared from junicedric acid and lapachol. The new derivatives were assessed as gastroprotective agents by the HCl-EtOH-induced gastric lesions model in mice as well as for basal cytotoxicity on the...
Lu Bai et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 944, 128-135 (2013-12-10)
Lapachol is a natural naphthoquinone compound derived from Bignoniaceae (Tabebuia sp.) that possesses a range of significant biological activities. Nine phase I and four phase II metabolites of lapachol in rat bile were firstly elucidated and identified using a sensitive...
Ana Amélia M Lira et al.
AAPS PharmSciTech, 9(1), 163-168 (2008-05-01)
This study aimed at developing a topical formulation of lapachol, a compound isolated from various Bignoniaceae species and at evaluating its topical anti-inflammatory activity. The influence of the pharmaceutical form and different types of emulsifiers was evaluated by in-vitro release...
Jin-Jian Lu et al.
Anti-cancer agents in medicinal chemistry, 13(3), 456-463 (2012-08-31)
Quinones are plant-derived secondary metabolites that present some anti-proliferation and anti-metastasis effects in various cancer types both in vitro and in vivo. This review focuses on the anti-cancer prospects of plant-derived quinones, namely, aloe-emodin, juglone, β-lapachol, plumbagin, shikonin, and thymoquinone....

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