• A novel series of carbohydrate -based 1,2-naphthoquinones 13a-c and their substituted phenylhydrazono derivatives 14a-l were synthesized and evaluated for cytotoxicity against HL-60, MDA-MB435, HCT-116 and SF-295 cancer cell lines. (rsc.org)
  • Thus, we evaluated the potential antimycobacterial activity of six 1,4-naphthoquinones derivatives. (frontiersin.org)
  • Moreover, two naphthoquinones derivatives 5 and 6 probably do not exhibit cross resistance with isoniazid and rifampicin, respectively, and regarding ADME analysis, no compound violated the Lipinski's rule-of-five. (frontiersin.org)
  • Naphthoquinone derivatives exert their antitrypanosomal activity via a multi-target mechanism. (sigmaaldrich.com)
  • Recently, we reported on a new class of naphthoquinone derivatives showing a promising anti-trypanosomatid profile in cell-based experiments. (sigmaaldrich.com)
  • This investigation deals with the synthesis of 2-alkylpyridine and 2-alkylpyrazine derivatives of 2,3-dichloro-1,4-naphthoquinone. (unt.edu)
  • Three isomers are normally discussed: ⁕1,2-Naphthoquinone ⁕1,4-Naphthoquinone, of which the Vitamin K group compounds are derivatives ⁕2,6-Naphthoquinone Naphthoquinones are also a class of natural phenolic compounds formed on a C6-C4 skeleton. (definitions.net)
  • The 1,4-naphthoquinone derivatives are inactive against the serine protease, porcine pancreatic elastase. (open.ac.uk)
  • 1,4-naphthoquinone derivatives have vitamin K activity (for example, menaquinone). (thefreedictionary.com)
  • By using the optimized separation method described above, ShD can be detected in herbals or formulations prepared from Boraginaceae family plants, which are rich in naphthoquinone derivatives. (thefreedictionary.com)
  • The structure activity relationship of the isolated naphthoquinones, and commercially available derivatives were also studied. (up.ac.za)
  • The antitrypanosomal activities, cytotoxicity, and selectivity indices of eleven imido-substituted 1,4-naphthoquinone derivatives and nifurtimox have been studied. (elsevier.com)
  • Recently, naphthoquinone derivatives have shown promising results as antiparasitic lead compounds [28]. (sorafenib.us)
  • Synthesis and SAR study of novel anticancer and antimicrobial naphthoquinone amide derivatives. (thefreedictionary.com)
  • Bioactive naphthoquinone derivatives form Diospyros maritime blume. (thefreedictionary.com)
  • Effects of quinone derivatives, such as 1,4-naphthoquinone , on DNA polymerase inhibition and anti-inflammatory action. (freethesaurus.com)
  • Our synthetic scheme started with naphthoquinone derivatives, such as menadione and 2,3-dichloro-1,4-naphthoquinone. (elsevier.com)
  • In conclusion, we successfully synthesized naphthoquinone derivatives that act as LXRα/β agonists and selective LXRα agonists. (elsevier.com)
  • Using Saccharomyces cerevisiae, we evaluated the main mechanisms of toxicity of two naphthoquinones, menadione and plumbagin, by determining tolerance and oxidative stress biomarkers such as GSH and GSSG, lipid peroxidation levels, as well as aconitase activity. (unboundmedicine.com)
  • Cross-tolerance experiments confirmed distinct cytotoxicity mechanisms for these naphthoquinones since only a pre-treatment with menadione was able to induce acquisition of tolerance against stress with plumbagin. (unboundmedicine.com)
  • TY - JOUR T1 - Cytotoxicity mechanism of two naphthoquinones (menadione and plumbagin) in Saccharomyces cerevisiae. (unboundmedicine.com)
  • Plumbagin, a medicinal plant-derived naphthoquinone, is a novel inhibitor of the growth and invasion of hormone-refractory prostate cancer. (semanticscholar.org)
  • The objective of this study was to examine the potential of silver nanoparticles (AgNPs) to enhance the antimicrobial activity of selected naphthoquinones (NQs): plumbagin (PL), ramentaceone (RAM), droserone (DR), and 3-chloroplumbagin (3ChPL). (frontiersin.org)
  • The root cultures likewise produced the known alkaloids dioncophylline A (8) 5-O-demethyldioncophylline A (9) dioncopeltine A (10) habropetaline A (11) and 5-O-methyldioncophylline D (12a/b) the naphthalene glucoside plumbaside A (2) and the naphthoquinones plumbagin (13) droserone (14) and 8-hydroxydroserone (15). (lianaecologyproject.com)
  • It has been shown that plumbagin, a bioactive naphthoquinone isolated from three major plant families viz. (bireme.br)
  • Naphthoquinone is a class of organic compounds structurally related to naphthalene. (wikipedia.org)
  • Naphthoquinones are compounds present in several families of higher plants. (mdpi.com)
  • Naphthoquinones are wide-spread phenolic compounds in nature. (semanticscholar.org)
  • Interleukin 6 production by lipopolysaccharide-stimulated human fibroblasts is potently inhibited by naphthoquinone (vitamin K) compounds. (semanticscholar.org)
  • Quinones are compounds found in natural sources and among them, the naphthoquinones show antifungal, antiparasitic, and antimycobacterial activity. (frontiersin.org)
  • All evaluated naphthoquinones were active against the three strains with MIC between 206.6 and 12.5 μM, and the compounds with lower MIC values have also showed low cytotoxicity. (frontiersin.org)
  • Dimeric naphthoquinones (BiQs) with the ability to undergo redox cycling and to generate reactive oxygen species (ROS) in cancer cells are a novel class of compounds with unique characteristics that make them excellent candidates to be tested against AML cells. (mdpi.com)
  • Naphthoquinone is a class of organic compounds derived from naphthalene. (definitions.net)
  • Five unknown compounds, morindaparvins C-G, consisting of naphthohydroquinones, a naphthoquinone, an anthraquinone, and a naphthohydroquinone dimer, together with three known quinones and seven other known compounds, were isolated from the aerial parts of Morinda parvifolia. (unboundmedicine.com)
  • Compounds of 2-methoxy-1,4-naphthoquinone (MeONQ) and stigmasta-7,22-diene-3 β -ol (spinasterol) were isolated from the pods and roots/stems/leaves of I. balsamina L., respectively. (hindawi.com)
  • The chemical reactivity of the compounds towards cysteine as a model thiol is dependent on the naphthoquinone LUMO energy, whereas papain inactivation is not. (open.ac.uk)
  • 2. A class of compounds containing the naphthoquinone (1) structure. (thefreedictionary.com)
  • Vitamin K is a generic name for a group of quinone compounds with methylated naphthoquinone structure. (thefreedictionary.com)
  • The isolation and antimycobacterial activity of several naphthoquinones from Euclea natalensis were previously reported and initiated this study into the occurrence, chemistry and biological activity of this class of compounds. (up.ac.za)
  • The mode of action of some of the naphthoquinones was investigated and it was established that the compounds might interfere with the mycobacterial electron transport chain. (up.ac.za)
  • Interestingly, the compounds reported in this paper also possess a 1,4-naphthoquinone moiety, similarly to atovaquone, as well as a large hydrophobic substituent attached at position 3. (sorafenib.us)
  • A new fungal naphthoquinone which stimulates the production of antifungal compounds in alfalfa callus. (thefreedictionary.com)
  • 7. The pharmaceutical composition according to claim 1, wherein the naphthoquinone-based compound is selected from the compounds below: ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## or a pharmaceutically acceptable salt, solvate or isomer thereof. (patentsencyclopedia.com)
  • Out of 11 naphthoquinone compounds evaluated, 2-aziridinyl-5-hydroxy-1,4-naphthoquinone (compound 2), 2,3-bis(aziridinyl)-5-hydroxy-1,4-naphthoquinone (compound 3), and 2-aziridinyl-6-hydroxymethyl-1,4-naphthoquinone (compound 11) were selected for further evaluation based on good substrate specificity for NQO1 and selectivity towards NQO1-rich cells in vitro. (hud.ac.uk)
  • WB-F344 rat liver epithelial cells were exposed to synthetic and natural naphthoquinones. (ualberta.ca)
  • The synergistic effect of natural naphthoquinones and other anti-cancer therapies was reviewed and toxicity of natural naphthoquinones and plant extracts was discussed. (eurekaselect.com)
  • For further research , 69 new natural naphthoquinones reported in the last five years (2013-2017) were reviewed. (bvsalud.org)
  • Cytotoxic naphthoquinones and plumbagic acid glucosides from Plumbago zeylanica. (semanticscholar.org)
  • Three naphthoquinones had moderate cytotoxic effects with IC50 values ranging from 1.51 to 9.56 μM, through up-regulation of p53 transcriptional activity. (unboundmedicine.com)
  • Comparison of the cytotoxic effect of lapachol, alpha-lapachone and pentacyclic 1,4-naphthoquinones on human leukemic cells. (sigmaaldrich.com)
  • 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. (sigmaaldrich.com)
  • Satish Rao, "Juglone, a naphthoquinone from walnut, exerts cytotoxic and genotoxic effects against cultured melanoma tumor cells," Cell Biology International, vol. (thefreedictionary.com)
  • Lawsone, a naphthoquinone derivative isolated from the plant has been shown to possess cytotoxic activity (Sauriasari, R. (thefreedictionary.com)
  • Previous studies on the anticancer activities of this 1,4-naphthoquinone derivative are mostly focused on its cytotoxic properties via the induction of apoptosis and necrosis (Ding et al. (freethesaurus.com)
  • Cytotoxic lactam and naphthoquinone alkaloids from roots of Goniothalamus lanceolatus Miq. (unimas.my)
  • They were divided into five major types simple 1,4- naphthoquinones , furan and pyran naphthoquinones , 1,2- naphthoquinones , naphthohydroquinones and naphthoquinone polymers , which showed cytotoxic, antioxidative, anti-inflammatory and antibacterial biological activities, et al. (bvsalud.org)
  • In vitro activity of Brazilian medicinal plants, naturally occurring naphthoquinones and their analogues, against methicillin-resistant Staphylococcus aureus. (semanticscholar.org)
  • We evaluated the effect of two BiQ analogues and one monomeric naphthoquinone in AML cell lines and primary cells from patients. (mdpi.com)
  • Substituted naphthoquinones and their analogues, such as streptonigrin, are involved in various important biochemical processes. (oxy.edu)
  • The application of this method to the synthesis of a series of simpler and less lipophilic trimeric naphthoquinone simple analogues of conocurvone is also reported together with their anti-HIV activity. (monash.edu)
  • OBJECTIVES The aim of this work was to perform molecular modelling studies of 2-hydroxy-1,4- naphthoquinones analogues of atovaquone on the Qo site of P. falciparum cytochrome bc1 complex (Pfbc1) to suggest structural modifications that could improve their antimalarial activity. (bvsalud.org)
  • We previously reported that J78 (2-chloro-3-[2′-bromo, 4′-fluoro-phenyl]-amino-8-hydroxy-1,4-naphthoquinone), a newly synthesized 1,4-naphthoquinone derivative, exhibited a potent antithrombotic effect, which might be due to antiplatelet rather than anticoagulation activity. (aspetjournals.org)
  • In the present study, the effects of CM363, a novel naphthoquinone (NPQ) derivative, were evaluated on human CML-derived K562 cells. (oncotarget.com)
  • CB533 is an unexplored 1,4-naphthoquinone (NQ) derivative which unlike 1,4-NQ, induced rapid cell death without generating reactive oxygen species (ROS). (biomedcentral.com)
  • Due to its commercial unavailability, the chemical synthesis of two of these naphthoquinones, 7-methyljuglone and diospyrin, was attempted with varying degrees of success. (up.ac.za)
  • Thus, synthesis of complicated naphthoquinone structures by applying the substitution reactions starting with 1,4-naphthoquinones is one endeavor that could prove to have beneficial applications for the medical field in particular. (oxy.edu)
  • A general and convenient synthesis of trimeric naphthoquinones using the condensation of 2-hydroxynaphthoquinones and 2,3-dihaloquinones is described. (monash.edu)
  • Background: Recent years have brought the dynamic development in studies of naphthoquinones obtained from plants, in vitro cultures and semi- or total synthesis. (eurekaselect.com)
  • Experiments of protein synthesis analysis to investigate the naphthoquinones action were assessed. (biomedcentral.com)
  • abstract = "The manganese(III) acetate initiated oxidative free radical reaction between 2-phenyl-1,4-naphthoquinones and dimethyl malonate is described. (ncku.edu.tw)
  • Photochemical acylations of 2-substituted-1,4-naphthoquinones with various aldehydes furnished acylated hydroquinones and acylated quinones in moderate to good combined yields. (edu.au)
  • Diesel exhaust particles contain redox-active quinones, such as 9,10-phenanthraquinone (9,10-PQ) and 1,2-naphthoquinone (1,2-NQ), which act as potent electron acceptors, thereby altering electron transfer on proteins. (ovid.com)
  • From this, it was hypothesised that the toxicity of 1-naphthol, previously reported in isolated hepatocytes (5), may be mediated by naphthoquinone metabolites of l-naphthol. (springer.com)
  • While metabolic activation of naphthalene, yielding 1,2-naphthoquinone (1,2-NQ) and 1,4-NQ that can covalently bind to cellular proteins, has been recognized to be associated with its toxicity, the current consensus is that such electrophile-mediated covalent modification of sensor proteins with thiolate ions is also involved in activation of cellular signal transduction pathways for cellular protection against reactive materials. (go.jp)
  • The stability of some of the naphthoquinones was tested in various carriers in an attempt to explain the influence this will have on the obtained antituberculosis and toxicity data. (up.ac.za)
  • The antituberculosis activity and/or toxicity of 7-methyljuglone was investigated with three bioassays, to broaden our knowledge on the mechanism of action of naphthoquinones. (up.ac.za)
  • Naphthoquinone toxicity profiles were established using neutral red uptake for assessment of cell viability. (ualberta.ca)
  • Involvement of Akt in mitochondria-dependent apoptosis induced by a cdc25 phosphatase inhibitor naphthoquinone analog. (curehunter.com)
  • 2009, 1,4-Naphthoquinone is a potent inhibitor of human cancer cell growth and angiogenesis. (freethesaurus.com)
  • Of the naphthoquinones tested, menadione (2-methyl-1,4-naphthoquinone, MQ), 2-methoxy-1,4-naphthoquinone (MNQ) and 2,3-dimethoxy-1,4-naphthoquinone (DMNQ) caused a significant phosphorylation of connexin-43 at different concentrations. (ualberta.ca)
  • To date, the presence of some bioactive substances such as terpenes, sulfated sterols, carotenoid sulfate, phenylpropanoid and naphthoquinone in brittle stars has been proved which may have important role in anticancer therapy (11). (thefreedictionary.com)
  • vivax [7], numerous publications reported on the antiplasmodial activity of naphthoquinones leading to the development of atovaquone (3, Figure 1), a totally synthetic hydroxy-1,4-naphthoquinone [4]. (thefreedictionary.com)
  • Later, a lapachol modified structure led to development of the antimalarial atovaquone, a synthetic chloride naphthoquinone [40]. (sorafenib.us)
  • It has been crystallographically proven that the 1,4-naphthoquinone substructure of atovaquone binds into the H-bond pocket, while its large hydrophobic substituent resides in the hydrophobic pocket. (sorafenib.us)
  • A novel naphthoquinone glycoside from Rubia peregrina L. (tubitak.gov.tr)
  • Half-sandwich organometallic complexes featuring Ru(II), Os(II) and Rh(III) metal centers and naturally occurring bidentate 2-hydroxy-[1,4]-naphthoquinone ligands (lawsone and phthiocol) have been synthesized and characterized in both solid state and solution phase by analytical, spectroscopic, electrochemical and single crystal X-ray diffraction techniques. (ac.rs)
  • Antiplasmodial activity of naphthoquinones and one anthraquinone from Stereospermum kunthianum. (semanticscholar.org)
  • METHODS We have built the homology model of the cytochrome b (CYB) and Rieske iron - sulfur protein (ISP) subunits from Pfbc1 and performed the molecular docking of 41 2-hydroxy-1,4- naphthoquinones with known in vitro antimalarial activity and predicted to act on this target. (bvsalud.org)
  • Bignoniaceae), was the strategy aimed to prepare potentially more potent antimalarial naphthoquinones. (sorafenib.us)
  • the various vitamers of vitamin K can be referred to as substituted naphthoquinones. (oup.com)
  • Caspase-3-mediated cleavage of the NF-kappa B subunit p65 at the NH2 terminus potentiates naphthoquinone analog-induced apoptosis. (thefreedictionary.com)
  • Considering the set of findings in this study, we conclude that these naphthoquinones could be promising scaffolds to develop new therapeutic strategies to TB. (frontiersin.org)
  • Dimeric, but not monomeric, naphthoquinones demonstrated significant anti-AML activity in the cell lines and primary cells from patients with favorable therapeutic index compared to normal hematopoietic cells. (mdpi.com)
  • Naphthoquinones (e.g. diospyrin and 7-methyljuglone) have been shown to have therapeutic potential, particularly against Mycobacterium tuberculosis. (up.ac.za)
  • 1969). Preparation of Some Sulfonamide and Diaminodiphenyl Sulfone Analogs of 1,4-Naphthoquinone. (rti.org)
  • The lead of this series (B6, 2-phenoxy-1,4-naphthoquinone) showed an ED(50) of 80 nM against Trypanosoma brucei rhodesiense, and a selectivity index of 74 with respect to mammalian cells. (sigmaaldrich.com)
  • The naphthoquinone β-lapachone, for example, seems to increase the generation of superoxide anion and hydrogen peroxide in Trypanosoma cruzi [ 14 ]. (biomedcentral.com)
  • Antimicrobial activities of Marcgraviaceae species and isolation of a naphthoquinone from Marcgravia nervosa (Marcgraviaceae). (gc.ca)
  • Miller M.G., Powell J., Cohen G.M. (1986) Formation and Identification of Naphthoquinone Glutathione Conjugates Following Microsomal Metabolism of 1-Naphthol. (springer.com)
  • This study was conducted to investigate the effect of 2-methoxy-1, 4-naphthoquinone (MNQ), compound extracted from Impatiens balsamina on glycolytic activities in human breast adenocarcinoma, MDA-MB-231 cells. (waocp.org)
  • The bioassay-guided fractionation of aerial parts of a plant, Impatiens balsamina, led to the isolation of 2-methoxy-1,4-naphthoquinone (1) as an active compound. (elsevier.com)
  • Ramentaceone, a Naphthoquinone Derived from Drosera sp. (plos.org)
  • Expression of Concern: Ramentaceone, a Naphthoquinone Derived from Drosera sp . (plos.org)
  • The medicinal and chemical aspects of naphthoquinones isolated from Euclea natalensis A. DC. (up.ac.za)
  • Conversion of l-naphthol to naphthoquinone metabolites by rat liver microsomes: Demonstration by high performance liquid chromatography with reductive electrochemical detection. (springer.com)
  • Naphthoquinones are one of the groups of secondary metabolites widespread innature, where they mostly appear as chromatic pigments. (mdpi.com)
  • One- and two-electron reduction of 2-methyl-1,4-naphthoquinone bioreductive alkylating agents: kinetic studies, free-radical production, thiol oxidation and DNA-strand-break formation. (semanticscholar.org)
  • 1,2-Naphthoquinone or ortho-naphthoquinone is a polycyclic aromatic organic compound with formula C 10H 6O 2. (wikipedia.org)
  • It is said to contain a naphthoquinone that reacts with keratin, forming a "sclerojuglonic" compound. (thefreedictionary.com)
  • Provided is a pharmaceutical composition having excellent in vivo absorption properties by increasing solubility and absorption rate of a sparingly-soluble naphthoquinone-based compound via incorporation of micronized particles of a certain naphthoquinone-based compound. (patentsencyclopedia.com)
  • 8. The pharmaceutical composition according to claim 1, wherein the size of micronized particles of the naphthoquinone-based compound is that 90% of the particle sizes (X90) is within the range of 1 nm to 30 μm. (patentsencyclopedia.com)
  • 1 to 50% by weight based on the total weight of micronized particles of naphthoquinone-based compound and the surfactant. (patentsencyclopedia.com)
  • For the 2-methyl-1,4-naphthoquinone/butyraldehyde pair, a novel tri-keto compound has been additionally isolated. (edu.au)
  • Juglone is a naphthoquinone that induces superoxide anion radicals overproduction (24). (thefreedictionary.com)
  • Quantification of p- phenylenediamine and 2-hydroxy-1, 4- naphthoquinone in henna tattoos. (thefreedictionary.com)
  • Two new naphthoquinones with antiviral activity from Rhinacanthus nasutus. (semanticscholar.org)
  • Furthermore, naphthoquinones (-)-5-hydroxy2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione and their positional isomer (-)-8-hydroxy-2-(1'hydroxyethyl)naphtho[2,3-b]furan-4,9-dione (stereoselectively synthesized) exhibited a moderate antifungal activity against Candida albicans, Cryptococcus albidus and Aspergillus fumigatus, with MIC values of 25, 1. (thefreedictionary.com)
  • Moreover, the most recent anti-cancer activity studies on naphthoquinones which could be produced in hairy root cultures were outlined. (eurekaselect.com)
  • Forty papers outlined the anti-cancer activity of targeted naphthoquinones including the type of cancer and bioassays description. (eurekaselect.com)
  • Several naphthoquinones are found in the nature showing activity against aerobic and anaerobic bacterial species. (biomedcentral.com)
  • Molecular dynamics simulation of PHF6 oligomers and fibrils with the Naphthoquinone-Tryptophan hybrids provides a possible structure-function based mechanism-of-action, highlighting the role of hydrophobic interaction and hydrogen bond formation during fibril disassembly. (nature.com)
  • In conclusion, Redox-cycling naphthoquinones (with exclusive redox-cyclers, such as DMNQ, and alkylating/redox-cycling naphthoquinones, such as MQ and MNQ) stimulate connexin phosphorylation and a loss of GJIC. (ualberta.ca)
  • In more recent studies, 1,4-naphthoquinone formed from 1-naphthol has been directly measured with both rat liver microsomes (2,3) and a reconstituted cytochrome P-450 enzyme system (4). (springer.com)
  • Metabolic activation of l-naphthol by rat liver microsomes to 1,4-naphthoquinone and covalent binding species. (springer.com)
  • At ibuychemikals we offer 2,3 Dichloro 1,4-Naphthoquinone (Dichlone) at best price and also several other chemicals pertaining to categories fine chemical, Iso Paraffins, Paints and coatings etc. (ibuychemikals.com)
  • Buy 2,3 Dichloro 1,4-Naphthoquinone (Dichlone) @ ibuychemikals, we are backed by our parent company Pon Pure Chemicals who has 37 years of experience and stand for quality and trust. (ibuychemikals.com)
  • A role for glutathione disulfide as a scavenger of oxygen radicals produced by 2,3-dichloro-1,4-naphthoquinone. (biomedsearch.com)
  • The addition of 2,3-dichloro-1,4-naphthoquinone (CNQ) to isolated mitochondria supplemented with GSSG resulted in a respiratory burst with the production of O2- and H2O2, and a decrease in the level of measurable disulfide. (biomedsearch.com)
  • Cytochrome P-450 dependent metabolic activation of 1-naphthol to naphthoquinones and covalent binding species. (springer.com)
  • Bioassay-guided fractionation of this plant resulted in the isolation and identification of 2-methoxy-1,4-naphthoquinone (1) as the active principle with a minimum inhibitory concentration (MIC) of 85-100 μmol·L -1 against Saccharomyces cerevisiae BY4741 (haploid) and BY4743 (diploid). (gc.ca)
  • Vero cells were employed to determine the inhibitory concentration (IC50) of most of the naphthoquinones. (up.ac.za)
  • Methods: For databases survey two selection criteria were used: (i) naphthoquinone could be produced in hairy roots, and (ii) it exhibits anti-cancer properties. (eurekaselect.com)