β-Lapachone - CAS 4707-32-8
Catalog number: 4707-32-8
Category: Inhibitor
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Molecular Formula:
C15H14O3
Molecular Weight:
242.27
COA:
Inquire
Targets:
IDO | Topoisomerase
Description:
β-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae), exhibiting anti-inflammatory properties by suppressing the NF-κB activation by blocking IκBα degradation and downregulating the ERK, p38 mitogen-activated protein kinase and Akt pathway.
Brife Description:
A naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae), exhibiting anti-inflammatory properties by suppressing the NF-κB activation by blocking IκBα degradation and downregulating the ERK, p38 mitogen-activated protein kinase and Akt pathway.
Purity:
> 98%
Appearance:
Orange Solid
Synonyms:
ARQ501, ARQ 501, ARQ-501, beta lapachone; BETA-LAPACHONE; 3,4-DIHYDRO-2,2-DIMETHYL-2H-NAPHTHO[1,2-B]PYRAN-5,6-DIONE; 3,4-DIHYDRO-2,2-DIMETHYL-2H-NAPHTHOL[1,2-B]PYRAN-5,6-DIONE; 2-b)pyran-5,6-dione,3,4-dihydro-2,2-dimethyl-2h-naphtho(; b-Lapachone; B-LAPACHONE,2,2-DIMETHYL-3,4-DIHYDRO-2H-BENZO[H]CHROME
Solubility:
Soluble in DMSO (>25 mg/ml) at 5° C, ethanol (20 mg/ml), chloroform, and DMF.
Storage:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
MSDS:
Inquire
Quality Standard:
In-house
Quantity:
Grams-Kilos
Boiling Point:
~381.4 C at 760 mmHg (Predicted)
Melting Point:
~151-153° C (dec.)
InChIKey:
QZPQTZZNNJUOLS-UHFFFAOYSA-N
InChI:
1S/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
Canonical SMILES:
CC1(CCC2=C(O1)C3=CC=CC=C3C(=O)C2=O)C
1.2-Phenyl-beta-lapachone can affect mitochondrial function by redox cycling mediated oxidation.
de Witte NV;Stoppani AO;Dubin M Arch Biochem Biophys. 2004 Dec 15;432(2):129-35.
2-Phenyl-beta-lapachone (3,4-dihydro-2-methyl-2-phenyl-2H-naphtho[1,2b]pyran-5,6-dione) (2PBL) is a o-naphthoquinone synthesized as a possible antitumoral agent. The addition of micromolar concentrations of 2PBL to rat liver mitochondria (in the presence of malate-glutamate or succinate, as respiratory substrates): (1) stimulated O(2) consumption in state 4 and inhibited O(2) consumption in state 3, thus decreasing respiratory control index (RCI); and (2) collapsed the mitochondrial membrane potential. The addition of 2PBL to rat liver submitochondrial particles: (1) stimulated NADH oxidation in the presence of rotenone, antimycin, myxothiazol or cyanide; (2) stimulated (.-)O(2)(-) production in the presence of NADH and antimycin; and (3) led to 2PBL semiquinone radical production. Control studies carried out with two p-naphthoquinones, menadione and atovaquone, did not produced equivalent effects. These findings support the hypothesis that 2PBL, undergoes redox cycling and affects mitochondrial function. The 2PBL effect is complex, involving inhibition of electron transfer, uncoupling of oxidative phosphorylation, collapse of mitochondrial membrane potential and (.-)O(2)(-) production by redox cycling.
2.Photosensitizing properties of triplet beta-lapachones in acetonitrile solution.
Netto-Ferreira JC;Lhiaubet-Vallet V;de Oliveira Bernardes B;Ferreira AB;Miranda MA Photochem Photobiol. 2009 Jan-Feb;85(1):153-9. doi: 10.1111/j.1751-1097.2008.00410.x. Epub 2008 Jul 30.
The photochemical reactivity of beta-lapachone (1), nor-beta-lapachone (2) and 1,2-naphthoquinone (3) towards amino acids and nucleobases or nucleosides has been examined employing the nanosecond laser flash photolysis technique. Excitation (lambda = 355 nm) of degassed solutions of 1-3, in acetonitrile, resulted in the formation of their corresponding triplet excited states. These transients were efficiently quenched by l-tryptophan, l-tryptophan methyl ester, l-tyrosine, l-tyrosine methyl ester and l-cysteine (k(q) approximately 10(9) L mol(-1) s(-1)). For l-tryptophan, l-tyrosine and their methyl esters new transients were formed in the quenching process, which were assigned to the corresponding radical pair resulting from an initial electron transfer from the amino acids or their esters to the excited quinone, followed by a fast proton transfer. No measurable quenching rate constants could be observed in the presence of thymine and thymidine. On the other hand, efficient rate constants were obtained when 1-3 were quenched by 2'-deoxyguanosine (k(q) approximately 10(9) L mol(-1) s(-1)). The quantum efficiency of singlet oxygen ((1)O(2)) formation from 1 to 3 was determined employing time-resolved near-IR emission studies upon laser excitation and showed considerably high values in all cases (Phi(Delta) = 0.
3.Nanotechnology-enabled delivery of NQO1 bioactivatable drugs.
Ma X;Moore ZR;Huang G;Huang X;Boothman DA;Gao J J Drug Target. 2015;23(7-8):672-80. doi: 10.3109/1061186X.2015.1073296.
Current cancer chemotherapy lacks specificity and is limited by undesirable toxic side-effects, as well as a high rate of recurrence. Nanotechnology has the potential to offer paradigm-shifting solutions to improve the outcome of cancer diagnosis and therapy. β-Lapachone (β-lap) is a novel anticancer agent whose mechanism of action is highly dependent on;NAD(P)H: ;quinone oxidoreductase 1 (NQO1), a phase II detoxifying enzyme overexpressed in solid tumors from a variety of cancer types. However, the poor water solubility of β-lap limits its clinical potential. A series of drug formulations were developed for systemic administration in preclinical evaluations. Encapsulation of β-lap into polymeric micelles showed less side-effects and higher maximum tolerated dose (MTD), prolonged blood circulation time and preferential accumulation in tumors with greatly improved safety and antitumor efficacy. The prodrug strategy of β-lap further decreases the crystallization of β-lap by introducing esterase degradable side chains to the rigid fused ring structure. β-Lap prodrugs considerably increased the stability, drug-loading content and delivery efficiency of nanoparticles. The optimized formulation of β-lap-dC3 prodrug micelles showed excellent antitumor efficacy in treating orthotopic non-small cell lung tumors that overexpress NQO1, with target validation using pharmacodynamic endpoints.
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CAS 4707-32-8 β-Lapachone

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