2-acetylfuranonaphthoquinone has been researched along with Psoriasis* in 2 studies
2 other study(ies) available for 2-acetylfuranonaphthoquinone and Psoriasis
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Synthesis and structure-activity relationships of lapacho analogues. 1. Suppression of human keratinocyte hyperproliferation by 2-substituted naphtho[2,3-b]furan-4,9-diones, activation by enzymatic one- and two-electron reduction, and intracellular genera
A series of linearly anellated lapacho quinone analogues substituted at the 2-position of the tricyclic naphtho[2,3-b]furan-4,9-dione system were synthesized and evaluated for their ability to suppress keratinocyte hyperproliferation using HaCaT cells as the primary test system. While very good in vitro potency with IC(50) values in the submicromolar range was attained with electron-withdrawing substituents, some compounds were found to induce plasma membrane damage, as evidenced by the release of LDH activity from cytoplasm of the keratinocytes. The most potent analogue against keratinocyte hyperproliferation was the 1,2,4-oxadiazole 18, the potency of which was combined with comparably low cytotoxic membrane damaging effects. Structure-activity relationship studies with either metabolically stable or labile analogues revealed that the quinone moiety was required for activity. Selected compounds were studied in detail for their capability to generate superoxide radicals both in isolated enzymatic one- and two-electron reduction assays as well as in a HaCaT cell-based assay. Topics: Cell Line; Cell Membrane; Cell Proliferation; Dermatologic Agents; Dicumarol; Furans; Humans; Keratinocytes; L-Lactate Dehydrogenase; NAD(P)H Dehydrogenase (Quinone); NADPH-Ferrihemoprotein Reductase; Naphthoquinones; Oxadiazoles; Psoriasis; Structure-Activity Relationship; Superoxides | 2012 |
Potential antipsoriatic agents: lapacho compounds as potent inhibitors of HaCaT cell growth.
A number of lapacho compounds, representing the most common constituents of the inner bark of Tabebuia impetiginosa, together with some synthetic analogues, were evaluated in vitro against the growth of the human keratinocyte cell line HaCaT. With an IC(50) value of 0.7 microM, beta-lapachone (4) displayed activity comparable to that of the antipsoriatic drug anthralin. 2-Acetyl-8-hydroxynaphtho[2,3-b]furan-4,9-dione (7), which was prepared in a four-step synthesis from 2,8-dihydroxy-1, 4-naphthoquinone, was the most potent inhibitor among the known lapacho-derived compounds and inhibited cell growth with an IC(50) value of 0.35 microM. Furthermore, other active constituents of lapacho inhibited keratinocyte growth, with IC(50) values in the range of 0.5-3.0 microM. However, as already observed with anthralin, treatment of HaCaT cells with these potent lapacho compounds also caused remarkable damage to the plasma membrane. This was documented by leakage of lactate dehydrogenase into the culture medium, which significantly exceeded that of the vehicle control. Because of their potent activity against the growth of human keratinocytes, some lapacho-derived compounds appear to be promising as effective antipsoriatic agents. Topics: Administration, Topical; Anthralin; Anti-Inflammatory Agents; Cell Division; Cell Line; Humans; Keratinocytes; Keratolytic Agents; L-Lactate Dehydrogenase; Naphthoquinones; Psoriasis; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet | 1999 |