α-Lapachone

SKU: orb1297467

Description

α-Lapachone is a small molecule with documented antineoplastic and trypanocidal properties, demonstrating activity against Trypanosoma cruzi. Research applications include studying its mechanisms in cancer cell lines and in vivo models, focusing on NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated pathways.

Research Area

Infectious Disease & Virology, Molecular Biology

Key Properties

• CAS Number: 4707-33-9
• MW: 242.27
• Purity: 99.17% (May vary between batches)
• Formula: C₁₅H₁₄O₃
• SMILES: CC1(C)CCC2=C(O1)C(=O)c1ccccc1C2=O
• Target: Topoisomerase|||Antifection
• Solubility: DMSO:50 mg/mL (206.38 mM)

Bioactivity

• In Vitro:
  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
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Storage & Handling

• Storage: -20°C
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Antifection, a-Lapachone, alpha-Lapachone, inhibit, Inhibitor, α Lapachone, αLapachone, α-Lapachone, Topoisomerase

Compound Identifiers

PubChem CID

72732