Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

Abstract

Naphthoquinones are considered privileged structures for anticancer drug molecules. The Heck reaction of 2-hydroxy-1,4-naphthoquinone (lawsone) with 1-bromo-3-methyl-2-butene offered easy access to lapachol. Several naturally occurring linear and angular heterocyclic quinoids (α-lapachone, β-lapachone, dunnione, and related analogues) were prepared from lapachol. Furthermore, we demonstrated that the synthetic naphthoquinones inhibit cell proliferation in human leukemia HL-60 cells. In particular, angular-type derivatives were found to possess moderate cytotoxicity and to elevate the levels of intracellular glutathione disulfide (GSSG). Our work highlights the significant potential of naturally occurring angular-series naphthoquinones as antileukemic agents.

A common tattoo chemical for energy storage: henna plant-derived naphthoquinone dimer as a green and sustainable cathode material for Li-ion batteries

“…Lawsone (LS) is a pigment isolated from the leaves of the henna plant and has been utilized as a skin and hair dye since 1400 BC. [22][23][24] Lawsone has been reported to readily bind sodium atoms, 25 and has recently shown promising electrochemical activity. 26 However, the lithium binding capacity and electrochemical activity of bislawsone as a cathode material for LIB applications has not been previously reported.…”

Analysis of the Mechanisms of Action of Naphthoquinone-Based Anti-Acute Myeloid Leukemia Chemotherapeutics

“…Multi-substituted naphthoquinones, including shikonin [35,36,37,38,39] and its derivative SH-7 [40], and other dihydroxy or dimethoxy 1,4-naphthoquinones [41,42], compared with mono- or di-substituted naphthoquinones, demonstrated superior in vitro activity against AML cells with IC 50 s ranging 0.1–4 μM. Heterocyclic monomeric naphthoquinones included furanonaphthoquinones FNQ3 [43] and FN6-one [44], β-lapachone [45,46,47,48,49] and nor-β-lapachone [45,46,50,51], dunnione [47], and pterocarpanquinone LQB-118 [28,52]. FNQ3 was significantly more effective than low dose cytarabine in reducing cell viability ( p < 0.001) and combining the two drugs led to an even greater reduction in cell viability in NB4 and U937 cells ( p < 0.01) [43].…”

A Photoactivatable Probe for Super-Resolution Imaging of Enzymatic Activity in Live Cells

“…Compound 1 could be converted into compound 2 by recombinant human carboxylesterase II (hCEII) in solution. Irradiation of samples of 1 in the presence of hCEII gave a strong fluorescent signal, whereas a combination of compound 1, hCEII and β-lapachone (9, Figure 2D), which is a known inhibitor of carboxylesterases, 22 gave nearly no change in fluorescence ( Figure S19).…”