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alpha-Lapachone
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Product Name alpha-Lapachone
Price:
CAS No.: 4707-33-9
Catalog No.: CFN98702
Molecular Formula: C15H14O3
Molecular Weight: 242.3 g/mol
Purity: >=98%
Type of Compound: Quinones
Physical Desc.: Yellow powder
Source: The barks of Catalpa ovata.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
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Similar structural: Comparison (Web)  (SDF)
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Related Screening Libraries
Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries
Biological Activity
Description: alpha-Lapachone has antineoplastic activity, it shows an approximately trypanocidal activity against Trypanosoma cruzi. alpha-Lapachone is an "irreversible" inhibitor of topoisomerase II, it can inhibit initial non-covalent binding of topoisomerase II to DNA and, and can induce religation of DNA breaks (even in pre-established ternary complexes) before dissociating the enzyme from DNA.
Targets: Topoisomerase | Antifection
In vitro:
J Org Chem. 2015 Aug 7;80(15):7340-50.
Photoconversion of β-Lapachone to α-Lapachone via a Protonation-Assisted Singlet Excited State Pathway in Aqueous Solution: A Time-Resolved Spectroscopic Study.[Pubmed: 26133974 ]

METHODS AND RESULTS:
The photophysical and photochemical reactions of β-lapachone were studied using femtosecond transient absorption, nanosecond transient absorption, and nanosecond time-resolved resonance Raman spectroscopy techniques and density functional theory calculations. In acetonitrile, β-lapachone underwent an efficient intersystem crossing to form the triplet state of β-lapachone. However, in water-rich solutions, the singlet state of β-lapachone was predominantly quenched by the photoinduced protonation of the carbonyl group at the β position (O9). After protonation, a series of fast reaction steps occurred to eventually generate the triplet state α-lapachone intermediate. This triplet state of α-lapachone then underwent intersystem crossing to produce the ground singlet state of α-lapachone as the final product. 1,2-Naphthoquinone is examined in acetonitrile and water solutions in order to elucidate the important roles that water and the pyran ring play during the photoconversion from β-lapachone to α-lapachone. β-Lapachone can also be converted to α-lapachone in the ground state when a strong acid is added to an aqueous solution.
CONCLUSIONS:
Our investigation indicates that β-lapachone can be converted to α-lapachone by photoconversion in aqueous solutions by a protonation-assisted singlet excited state reaction or by an acid-assisted ground state reaction.
Invest New Drugs. 2010 Apr;28(2):139-44.
Comparison of the cytotoxic effect of lapachol, alpha-lapachone and pentacyclic 1,4-naphthoquinones on human leukemic cells.[Pubmed: 19255723]

METHODS AND RESULTS:
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. The pentacyclic 1,4-naphthoquinones 1a and 1c induced apoptotic cell death in cells from leukemic patients as determined by flow cytometry. Conversely, the cell lines were highly insensitive to lapachol (2) and alpha-Lapachone (3). Mitomycin-C inhibited cell proliferation at concentrations as low as 0.5 microM. The low toxicity against lymphocytes activated by phytohemagglutinin shows that these compounds are selective for the cancer cells studied.
CONCLUSIONS:
Previous data suggest that these compounds (1a-d) can be bioactivated in situ by reduction followed by rearrangement leading to enones, which are powerful alkylating agents. In contrast, lapachol (2) and beta-lapachone (3), which cannot be bioactivated by reduction, showed little activity against the same cell lines.
Parasitol Res. 2006 Sep;99(4):429-33.
Oxyrane derivative of alpha-lapachone is potent growth inhibitor of Trypanosoma cruzi epimastigote forms.[Pubmed: 16596415 ]

METHODS AND RESULTS:
The investigation of trypanocidal effects against Trypanosoma cruzi and cytotoxicity in VERO cell line of several oxyranes structurally related to beta-lapachone, nor-beta-lapachone, alpha-Lapachone, and 4-methoxy-1,2-naphthoquinone is described.
CONCLUSIONS:
It was found that the oxyranes 10 derived from alpha-Lapachone showed an approximately the same trypanocidal activity of beta-lapachone. In addition, all the oxyranes showed less cytotoxicity than the corresponding naphthoquinones.
alpha-Lapachone Description
Source: The barks of Catalpa ovata.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

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After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

Cell. 2018 Jan 11;172(1-2):249-261.e12.
doi: 10.1016/j.cell.2017.12.019.
IF=36.216(2019)

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Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.1271 mL 20.6356 mL 41.2712 mL 82.5423 mL 103.1779 mL
5 mM 0.8254 mL 4.1271 mL 8.2542 mL 16.5085 mL 20.6356 mL
10 mM 0.4127 mL 2.0636 mL 4.1271 mL 8.2542 mL 10.3178 mL
50 mM 0.0825 mL 0.4127 mL 0.8254 mL 1.6508 mL 2.0636 mL
100 mM 0.0413 mL 0.2064 mL 0.4127 mL 0.8254 mL 1.0318 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Kinase Assay:
Biochem Pharmacol. 2000 Nov 1;60(9):1367-79.
Novel mechanisms of DNA topoisomerase II inhibition by pyranonaphthoquinone derivatives-eleutherin, alpha lapachone, and beta lapachone.[Pubmed: 11008131]
Pyranonaphthoquinones have diverse biological activities against Gram-positive bacteria, fungi, and mycoplasms, and, recently, there has also been an increasing interest in their anti-cancer activity.
METHODS AND RESULTS:
This study includes three derivatives: eleutherin (compound 1), beta lapachone (compound 2), and its structural isomer, alpha-Lapachone (compound 3). The mechanism of topoisomerase II inhibition by the three derivatives was examined systematically with respect to the steps of the catalytic cycle of the enzyme. Etoposide, the prototypical enzyme poison, was used as a control and in combination with compounds 1-3 to localize their mechanism of action. The study revealed that eleutherin (1) and beta lapachone (2) inhibited topoisomerase II by inducing religation and dissociation of the enzyme from DNA in the presence of ATP. Whereas compound 2 was an "irreversible" inhibitor of topoisomerase II, compound 1 merely slowed the catalytic cycle of the enzyme. alpha Lapachone (3), on the other hand, inhibited initial non-covalent binding of topoisomerase II to DNA and, in addition, induced religation of DNA breaks (even in pre-established ternary complexes) before dissociating the enzyme from DNA.
CONCLUSIONS:
Compound 3 was an "irreversible" inhibitor of topoisomerase II. The diverse and unique mechanisms of topoisomerase II inhibition by pyranonaphthoquinone derivatives reveal novel ways to target the enzyme with potential for anti-cancer drug design.
Structure Identification:
Pharmazie. 2003 Oct;58(10):690-5.
Monoarylhydrazones of alpha-lapachone: synthesis, chemical properties and antineoplastic activity.[Pubmed: 14609278]
The biological activities of the naphthoquinones lapachol, extracted from trees of the genus Tabebuia and its cyclization products alpha and beta-lapachone, have been intensively studied.
METHODS AND RESULTS:
Giving continuity to the research about new derivatives obtained from the reaction of these naphthoquinones with amino-containing reagents, a series of arylhydrazones of alpha-Lapachone was synthesized and their antineoplastic activity was evaluated. This new structure is based on the great electrophilicity of 1,4-quinoidal carbonyl groups towards reagents containing nitrogen as nucleophilic centers, such as arylhydrazines.
CONCLUSIONS:
The products were assayed by the National Cancer Institute (NCI, USA) and their binding to DNA, redox properties and QSAR studies were also determined.
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