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4707-32-8

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4707-32-8 Usage

Description

β-Lapachone (4707-32-8) is a naturally occurring quinone found in the bark of the Lapacho tree (Tabebuia avellanedae). A novel DNA topoisomerase I inhibitor which unlike camptothecin does not stabilize the cleavable complex indicating a novel mode of action.1?Induces apoptosis in a number of cancer cell lines.2?In cancer cells over-expressing NAD(P)H:quinone oxidoreductase, reduction of β-lapachone leads to futile cycling between quinone and hydroquinone forms3?resulting in the production of reactive oxygen species4. Suppresses radiation-induced activation of NFκB.5

Chemical Properties

Orange Solid

Uses

Different sources of media describe the Uses of 4707-32-8 differently. You can refer to the following data:
1. β-Lapachone has been used:as an anticancer compound in catalase-inhibitable luminol/hydrogen peroxide (HRP)-dependent chemiluminometric?assay in Lewis lung carcinoma (LLC) cells and isolated mitochondriaas a naphthoquinone to study its effects on the growth and differentiation of mice granulocyte and macrophage progenitor cellsas a substrate to study the enzyme activity of human recombinant NAD(P)H dehydrogenase 1 (NQO1) protein
2. β-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae) with cancer chemopreventive properties. Induces apoptosis in HL-60 and human prostate cancer cells.

Definition

ChEBI: A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activi ies.

Biochem/physiol Actions

β-Lapachone acts as a DNA topoisomerase type I inhibitor. It exhibits anti-fungal, anti-bacterial, trypanocidal, and antiviral properties. β-Lapachone also inhibits nitric oxide?(NO) and inducible NO synthase (iNOS) in alveolar macrophages.

References

1) Li?et al.?(1993),?beta-Lapachone, a Novel DNA Topoisomerase I Inhibitor With a Mode of Action Different From Camptothecin; J. Biol. Chem.,?268?22463 2) Wuerzberger?et al.?(1998),?Induction of Apoptosis in MCF-7:WS8 Breast Cancer Cells by Beta-Lapachone; Cancer Res.,?58?1876 3) Pink?et al.?(2000),?NAD(P)H:Quinone Oxidoreductase Activity Is the Principal Determinant of Beta-Lapachone Cytotoxicity. J. Biol. Chem.,?275?5416 4) Siegel?et al. (2012),?NAD(P)H:quinone Oxidoreductase 1 (NQO1) in the Sensitivity and Resistance to Antitumor Quinones; Biochem. Pharmacol.,?83?1033 5) Dong?et al.?(2010), Beta-lapachone suppresses radiation-induced activation of nuclear factor-kappaB; Exp. Mol. Med.,?42?327

Check Digit Verification of cas no

The CAS Registry Mumber 4707-32-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,7,0 and 7 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 4707-32:
(6*4)+(5*7)+(4*0)+(3*7)+(2*3)+(1*2)=88
88 % 10 = 8
So 4707-32-8 is a valid CAS Registry Number.
InChI:InChI=1/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3

4707-32-8 Well-known Company Product Price

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  • (L2037)  β-Lapachone  ≥98% (TLC)

  • 4707-32-8

  • L2037-5MG

  • 1,531.53CNY

  • Detail

4707-32-8Relevant articles and documents

Redox Center Modification of Lapachones towards the Synthesis of Nitrogen Heterocycles as Selective Fluorescent Mitochondrial Imaging Probes

dos Santos, Fabíola S.,Dias, Gleiston G.,de Freitas, Rossimiriam P.,Santos, Lucas S.,de Lima, Guilherme F.,Duarte, Hélio A.,de Simone, Carlos A.,Rezende, Lidia M. S. L.,Vianna, Monique J. X.,Correa, José R.,Neto, Brenno A. D.,da Silva Júnior, Eufranio N.

, p. 3763 - 3773 (2017)

We describe herein a synthetic strategy for the synthesis of new fluorescent imidazole and phenazine derivatives synthesized from lapachol, a naturally occurring naphthoquinone isolated from Tabebuia species (ipê tree). The photophysical properties and computational details of these compounds have been studied, aiming at gaining a complete understanding of the potential of these derivatives as probes capable of staining mitochondria selectively. Cell imaging experiments proved the capacity of the imidazole derivatives as selective fluorescent mitochondrial imaging probes. These heterocycles present the same staining patterns as MitoTracker Red, corroborating the potential of these compounds as new mitochondria markers permeable to the cell membrane.

Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol

Bonifazi, Evelyn L.,Ríos-Luci, Carla,León, Leticia G.,Burton, Gerardo,Padrón, José M.,Misico, Rosana I.

, p. 2621 - 2630 (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)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 with GI50 values of 0.42-8.1 and 0.80-2.2 μM, respectively. The results provide insight into the correlation between some structural properties of 5-hydroxynaphthoquinones and their antiproliferative activity.

Electronic structure and gas-phase chemistry of protonated α- And β-quinonoid compounds: A mass spectrometry and computational study

Vessecchi, Ricardo,Emery, Flávio S.,Lopes, Norberto P.,Galembeck, Sérgio E.

, p. 816 - 824 (2013)

Rationale: The use of quinonoid compounds against tropical diseases and as antitumor agents has prompted the search for new naturally occurring and synthetic derivatives. Among these quinonoid compounds, lapachol and its isomers (α- and β-lapachone) serve as models for the synthesis of new compounds with biological activity, and the use of electrospray ionization tandem mass spectrometry (ESI-MS/MS) analysis as a tool to elucidate and characterize these products has furnished important information about these compounds. Methods: ESI-MS/MS analysis under collision-induced dissociation conditions was used to describe the fragmentation mechanisms for protonated 1,4-naphthoquinone, 1,2-naphthoquinone, α-lapachone, and β-lapachone. The B3LYP/6-31+G(d,p) model was used to obtain proton affinities, gas-phase basicities, and molecular electrostatic potential maps, thus indicating the probable protonation sites. Fragmentation pathways were suggested on the basis of the relative enthalpies of the product ions. Results: The ESI-MS signals of the cationized molecules of ortho quinonoid compounds were more intense than those of the protonated molecule. Formation of the major product ions with m/z 187 from protonated α- and β-lapachone has been attributed to a retro-Diels-Alder (RDA) reaction. Conclusions: MS/MS studies on lapachol isomers (α- and β-lapachone) will facilitate the interpretation of the liquid chromatography (LC)-MS/MS analysis of new metabolites. MS/MS data on the 1,4-naphthoquinone, 1,2-naphthoquinone, α-lapachone and β-lapachone core will help characterize new derivatives from in vitro/in vivo metabolism studies in complex matrices. The product ions revealed the major fragmentation mechanisms and these ions will serve as diagnostic ions to identify each studied compound. Copyright

Selective endocytic trafficking in live cells with fluorescent naphthoxazoles and their boron complexes

Dias, Gleiston G.,Rodrigues, Bernardo L.,Resende, Jarbas M.,Calado, Hállen D. R.,De Simone, Carlos A.,Silva, Valter H. C.,Neto, Brenno A. D.,Goulart, Marilia O. F.,Ferreira, Fabricia R.,Meira, Assuero S.,Pessoa, Claudia,Correa, José R.,Da Silva Júnior, Eufranio N.

, p. 9141 - 9144 (2015)

Fluorescent naphthoxazoles and their boron derivatives have been synthesized and applied as superior and selective probes for endocytic pathway tracking in live cancer cells. The best fluorophores were compared with the commercially available acridine orange (co-staining experiments), showing far better selectivity.

Synthesis of pharmacologically important naphthoquinones and anticancer activity of 2-benzyllawsone through DNA topoisomerase-II inhibition

Kumar, Balagani Sathish,Ravi, Kusumoori,Verma, Amit Kumar,Fatima, Kaneez,Hasanain, Mohammad,Singh, Arjun,Sarkar, Jayanta,Luqman, Suaib,Chanda, Debabrata,Negi, Arvind S.

, p. 1364 - 1373 (2017)

Naphthoquinones are naturally occurring biologically active entities. Practical de novo syntheses of three naphthoquinones i.e. lawsone (1), lapachol (2), and β-lapachone (3b) have been achieved from commercially available starting materials. The conversion of lapachol (2) to β-lapachone (3b) was achieved through p-TSA/Iodine/BF3-etherate mediated regioselective cyclisation. Further, 2-alkyl and 2-benzyllawsone derivatives have been prepared as possible anticancer agents. Four derivatives exhibited significant anticancer activity and the best analogue i.e. compound 21a exhibited potential anticancer activity (IC50?=?5.2?μM) against FaDu cell line. Compound 21a induced apoptosis through activation of caspase pathway and exerted cell cycle arrest at S phase in FaDU cells. It also exhibited significant topoisomerase-II inhibition activity. Compound 21a was found to be safe in Swiss albino mice up to 1000?mg/kg oral dose.

α- and β-Lapachone Isomerization in Acidic Media: Insights from Experimental and Implicit/Explicit Solvation Approaches

Delarmelina, Maicon,Nicoletti, Caroline D.,de Moraes, Marcela C.,Futuro, Debora O.,Bühl, Michael,de C. da Silva, Fernando,Ferreira, Vitor F.,de M. Carneiro, José W.

, p. 52 - 61 (2019)

Combined experimental and mixed implicit/explicit solvation approaches were employed to gain insights into the origin of switchable regioselectivity of acid-catalyzed lapachol cyclization and α-/β-lapachone isomerization. It was found that solvating species under distinct experimental conditions stabilized α- and β-lapachone differently, thus altering the identity of the thermodynamic product. The energy profile for lapachol cyclization revealed that this process can occur with low free-energy barriers (lower than 8.0 kcal mol?1). For α/β isomerization in a dilute medium, the computed enthalpic barriers are 15.1 kcal mol?1 (α→β) and 14.2 kcal mol?1 (β→α). These barriers are lowered in concentrated medium to 11.5 and 12.6 kcal mol?1, respectively. Experimental determination of isomers ratio was quantified by HPLC and NMR measurements. These findings provide insights into the chemical behavior of lapachol and lapachone derivatives in more complex environments.

Lewis acid mediated highly regioselective intramolecular cyclization for the synthesis of β-lapachone

Bian, Jinlei,Deng, Bang,Zhang, Xiaojin,Hu, Tianhan,Wang, Nan,Wang, Wei,Pei, Haixiang,Xu, Yu,Chu, Hongxi,Li, Xiang,Sun, Haopeng,You, Qidong

, p. 1475 - 1478 (2014)

A highly regioselective intramolecular cyclization of lapachol mediated by Lewis acids including NbCl5, AlCl3, and FeCl3 was developed for synthesizing β-lapachone in excellent yields without any formation of the isomer α-lapachone. This procedure was efficient, mild, and easily scalable that avoided using highly hazardous concd H 2SO4. In the case of ZrCl4 the cyclization was found to give α-lapachone as the main product. A possible mechanism for the Lewis acid mediated cyclization was also discussed.

Nanocomposite gels of poloxamine and Laponite for β-Lapachone release in anticancer therapy

Camara, Gabriel Bezerra Motta,Barbosa, Raquel de Melo,García-Villén, Fátima,Viseras, César,Almeida Júnior, Renato Ferreira de,Machado, Paula Renata Lima,Camara, Celso Amorim,Farias, Kleber Juvenal Silva,de Lima e Moura, Tulio Flavio Accioly,Dreiss, Cécile A.,Raffin, Fernanda Nervo

, (2021)

Nano-hybrid systems have been shown to be an attractive platform for drug delivery. Laponite RD (LAP), a biocompatible synthetic clay, has been exploited for its ability to establish of strong secondary interactions with guest compounds and hybridization with polymers or small molecules that improves, for instance, cell adhesion, proliferation, and differentiation or facilitates drug attachment to their surfaces through charge interaction. In this work, LAP was combined with Tetronics, X-shaped amphiphilic PPO-PEO (poly (propylene oxide)–poly (ethylene oxide) block copolymers. β-Lapachone (BLPC) was selected for its anticancer activity and its limited bioavailability due to very low aqueous solubility, with the aim to improve this by using LAP/Tetronic nano-hybrid systems. The nanocarriers were prepared over a range of Tetronic 1304 concentrations (1 to 20% w/w) and LAP (0 to 3% w/w). A combination of physicochemical methods was employed to characterize the hybrid systems, including rheology, particle size and shape (DLS, TEM), thermal analysis (TG and DSC), FTIR, solubility studies and drug release experiments. In vitro cytotoxicity assays were performed with BALB/3T3 and MCF-7 cell lines. In hybrid systems, a sol-gel transition can occur below physiological temperature. BLPC exhibits the most significant increase in solubility in formulations with a high concentration of T1304 (over 10% w/w) and 1.5% w/w LAP, or systems with only LAP (1.5%), with a 50 and 100-fold increase in solubilisation, respectively. TEM images showed spherical micelles of T1304, which elongated into wormlike micelles with concentration (20%) and in the presence of LAP, a finding that has not been reported before. A sustained release of BLPC over 140 hours was achieved in one of the formulations (10% T1304 with 1.5% laponite), which also showed the best selectivity index towards cancer cells (MCF-7) over BALB/3T3 cell lines. In conclusion, BLPC-loaded T1304/LAP nano-hybrid systems proved safe and highly effective and are thus a promising formulation for anticancer therapy.

-

Ettlinger

, p. 3085,3086 (1950)

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Naphthoquinone-based hydrazone hybrids: Synthesis and potent activity against cancer cell lines

Gonsalves, Arlan de Assis,Pessoa, Claudia,Silva, Maria Francilene Souza,Silva, Thaissa Lucio,Araújo, Cle?nia Roberta Melo,Araújo, Edigênia Cavalcante,Goulart, Marília Oliveira Fonseca,Guimar?es, Délis Galv?o,Rolim, Larissa Araújo,Santos, Danyelle Candido,Santos, Victória Laysna Dos Anjos,da Costa, Marcília Pinheiro,de Oliveira, Fátima de Cássia Evangelista

, p. 945 - 955 (2021/11/30)

Background: Natural naphthoquinones have shown diversified biological activities including antibacterial, antifungal, antimalarial, and cytotoxic activities. However, they are also compounds with acute cytotoxicity, immunotoxicity, carcinogenesis, and cardio-and hepatotoxicity, and the modification at their redox center is an interesting strategy to overcome such harmful activity. Objective: In this study, four novel semisynthetic hydrazones, derived from the isomers α-and βlapachones (α and β, respectively) and coupled with the drugs hydralazine (HDZ) and isoniazid (ACIL), were prepared, evaluated by electrochemical methods and assayed for anticancer activity. Methods: The semisynthetic hydrazones were obtained and had their molecular structures established by NMR, IR, and MS. Anticancer activity was evaluated by cell viability determined by reduction of 3-(4,5-dimethyl-2-thiazol)-2,5-diphenyl-2H-tetrazolium bromide (MTT). The electrochemical studies, mainly cyclic voltammetry, were performed, in aprotic and protic media. Results: The study showed that the compounds 2, 3, and 4 were active against at least one of the cancer cell lines evaluated, compounds 3 and 4 being the most cytotoxic. Toward HL-60 cells, compound 3 was 20x more active than β-lapachone, and 3x more cytotoxic than doxorubicin. Furthermore, 3 showed an SI value of 39.62 for HL-60 cells. Compound 4 was active against all cancer cells tested, with IC50 values in the range 2.90–12.40 μM. Electrochemical studies revealed a profile typical of self-protonation and reductive cleavage, dependent on the supporting electrolyte. Conclusion: These results therefore indicate that compounds 3 and 4 are strong candidates as prototypes of new antineoplastic drugs.

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