Publication: Exerting dna damaging effects of the ilimaquinones through the active hydroquinone species
Issued Date
2021-06-01
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ISSN
22180532
00368709
00368709
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2-s2.0-85108237795
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Mahidol University
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SCOPUS
Bibliographic Citation
Scientia Pharmaceutica. Vol.89, No.2 (2021)
Suggested Citation
Apisada Jiso, Laphatrada Yurasakpong, Sirorat Janta, Kulathida Chaithirayanon, Anuchit Plubrukarn Exerting dna damaging effects of the ilimaquinones through the active hydroquinone species. Scientia Pharmaceutica. Vol.89, No.2 (2021). doi:10.3390/scipharm89020026 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/78955
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Exerting dna damaging effects of the ilimaquinones through the active hydroquinone species
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Abstract
Possessing the quinone moiety, ilimaquinone (1), a sponge–derived sesquiterpene quinone, has been hypothesised to express its cytotoxicity through a redox cycling process, yielding active product(s) that can cause DNA damage. To determine the DNA damaging effects of 1 and examine whether a redox transformation may participate in its functions, the DNA damaging properties of 1, the corresponding hydroquinone (2) and hydroquinone triacetates (3) and their 5-epimeric counterparts (4–6) were tested and compared. When incubated directly with plasmid DNA, the hydroquinones were the only active species capable of cleaving the DNA. In cell-based assays, however, the quinones and hydroquinone triacetates were active in the same range as that of the corresponding hydroquinones, and all damaged the cellular DNA in a similar manner. The in situ reduction of 1 and 4 were supported by the decreases in the cytotoxicity when cells were pre-exposed to dicoumarol, an NAD(P)H:quinone oxidoreductase 1 (NQO1) inhibitor. The results confirmed the DNA damaging activities of the ilimaquinones 1 and 4, and indicated the necessity to undergo an in-situ transformation into the active hydroquinones, thereby exerting the DNA damaging properties as parts of the cytotoxic mechanisms.