AI Article Synopsis
- Protoapigenone is a new, low-toxicity anticancer agent derived from apigenin, with a one-step economical synthesis developed for gram-scale production.
- The study synthesized 13 new 1'-O-alkylflavone analogs and tested their cytotoxic effects on six human cancer cell lines.
- Among the derivatives, 1'-O-butyl ether of protoapigenone showed significantly improved activity against specific cancer cell lines compared to the non-substituted protoapigenone, while β-naphthoflavone derivatives displayed decreased activity with O-alkyl substitutions.
Article Abstract
Protoapigenone, a natural flavonoid possessing an unusual p-quinol moiety on its B-ring, is a novel prospective anticancer agent with low toxicity that is currently in development. The first economical, one-step synthesis of protoapigenone from apigenin is described on up to gram scale. 13 new 1'-O-alkylflavone analogs were also synthesized, either from apigenin or β-naphthoflavone. The in vitro cytotoxic activity of each compound was tested on six human cancer cell lines (HepG2, Hep3B, Ca9-22, A549, MCF-7 and MDA-MB-231). In the case of 1'-O-alkyl-protoapigenone derivatives, structure-activity relationships were found depending on the side-chain, and protoapigenone 1'-O-butyl ether was found to exert significantly stronger activity against three of the cell lines (Hep3B, MCF-7 and MDA-MB-231) than its non-substituted analog, protoapigenone itself. In contrast to this, all β-naphthoflavone derivatives bearing the same pharmacophore on their B-ring showed decreased cytotoxic activities when substituted with an O-alkyl side-chain at position 1', comparing to that of the non-substituted compound.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3166065 | PMC |
| http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0023922 | PLOS |
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Article Synopsis
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- The study synthesized 13 new 1'-O-alkylflavone analogs and tested their cytotoxic effects on six human cancer cell lines.
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