Lapachol
Lapachol structure
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Common Name | Lapachol | ||
|---|---|---|---|---|
| CAS Number | 84-79-7 | Molecular Weight | 242.270 | |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 390.1±42.0 °C at 760 mmHg | |
| Molecular Formula | C15H14O3 | Melting Point | 141-143ºC(lit.) | |
| MSDS | Chinese USA | Flash Point | 203.9±24.4 °C | |
| Symbol |
GHS07 |
Signal Word | Warning | |
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Quinones derived from plant secondary metabolites as anti-cancer agents.
Anticancer Agents Med. Chem. 13(3) , 456-63, (2013) 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-emodi... |
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Organometallic anticancer complexes of lapachol: metal centre-dependent formation of reactive oxygen species and correlation with cytotoxicity.
Chem. Commun. (Camb.) 49(32) , 3348-50, (2013) 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. |
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Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
Bioorg. Med. Chem. 18 , 2621-30, (2010) 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)naphtha... |
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Determination of lapachol in the presence of other naphthoquinones using 3MPA-CdTe quantum dots fluorescent probe.
Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 100 , 155-60, (2013) 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 aq... |
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Biomimetic in vitro oxidation of lapachol: a model to predict and analyse the in vivo phase I metabolism of bioactive compounds.
Eur. J. Med. Chem. 54 , 804-12, (2012) 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 postu... |
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The hydroxy-naphthoquinone lapachol arrests mycobacterial growth and immunomodulates host macrophages
Int. Immunopharmacol. 10(11) , 1463-73, (2010) 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. My... |
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Screening for small molecule modulators of Hsp70 chaperone activity using protein aggregation suppression assays: inhibition of the plasmodial chaperone PfHsp70-1.
Biol. Chem. 392(5) , 431-8, (2011) 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 a... |
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Coordination of lapachol to bismuth(III) improves its anti-inflammatory and anti-angiogenic activities.
Biometals 25(1) , 55-62, (2012) 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 polyethe... |
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Potential gastroprotective effect of novel cyperenoic acid/quinone derivatives in human cell cultures.
Planta Med. 78(17) , 1807-12, (2012) 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... |
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Acanthamoeba castellanii Neff: In vitro activity against the trophozoite stage of a natural sesquiterpene and a synthetic cobalt(II)-lapachol complex.
Exp. Parasitol. 126(1) , 106-8, (2010) 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 trophozoi... |