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Prooxidant toxicity of polyphenolic antioxidants to HL‐60 cells: description of quantitative structure‐activity relationships
Open accessAbstract
Polyphenolic antioxidants exhibited a dose‐dependent toxicity against human promyelocytic leukemia cells (HL‐60). Their action was accompanied by malondialdehyde formation, and was partly prevented by desferrioxamine and the antioxidant N,N′‐diphenyl‐p‐phenylene diamine. This points to a prooxidant character of their cytotoxicity. A quantitative structure‐activity relationship (QSAR) has been obtained to describe the cytotoxicity of 13 polyphenolic antioxidants belonging to three different groups (flavonoids, derivatives of gallic and caffeic acid): log cL 50 (μM)=(2.7829±0.2339)+(1.2734±0.4715) E p/2 (V)−(0.3438±0.0582) log P (r 2=0.8129), where cL 50 represents the concentration for 50% cell survival, E p/2 represents the voltammetric midpoint potential, and P represents the octanol/water partition coefficient. Analogous QSARs were obtained using enthalpies of single‐electron oxidation of these compounds, obtained by quantum‐mechanical calculations. These findings clearly point to two important characteristics determining polyphenol cytotoxicity, namely their ease of oxidation and their lipophilicity.
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Cites
Structure-antioxidant activity relationships of flavonoids and phenolic acids
Rice-Evans, C. A., Miller, N. J., & Paganga, G. (1996) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(95)02227-9 · Cited by 9,085
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Bouayed, J., & Bohn, T. (2010) · Oxidative Medicine and Cellular Longevity · doi:10.4161/oxim.3.4.12858 · Cited by 1,095
Unravelling the conundrum of tannins in animal nutrition and health
Mueller‐Harvey, I. (2006) · Journal of the Science of Food and Agriculture · doi:10.1002/jsfa.2577 · Cited by 965
Saleem, A., Husheem, M., Härkönen, P., & Pihlaja, K. (2002) · Journal of Ethnopharmacology · doi:10.1016/s0378-8741(02)00099-5 · Cited by 462
Long, L. H., Clement, M. V., & Halliwell, B. (2000) · Biochemical and Biophysical Research Communications · doi:10.1006/bbrc.2000.2895 · Cited by 390
Hou, D.-X., Yanagita, T., Uto, T., Masuzaki, S., & Fujii, M. (2005) · Biochemical Pharmacology · doi:10.1016/j.bcp.2005.05.003 · Cited by 231
Metadata
- Authors
- Sergedien≐, E., Jönsson, K., Szymusiak, H., Tyrakowska, B., Rietjens, I. M. C. M., & Č≐nas, N.
- Venue
- FEBS Letters
- Publisher
- Wiley
- Published
- 1999-11-30
- Volume
- 462
- Issue
- 3
- Pages
- 392-396
- ISSN
- 0014-5793 (ISSN-L)
- 1873-3468
- OpenAlex
- W1979182110
- Cited by
- 234
- References
- 1
- FWCI
- 4.91
- Type
- journal article
- Language
- en
- Open access
- green
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- Sergedien≐, E., Jönsson, K., Szymusiak, H., Tyrakowska, B., Rietjens, I. M. C. M., & Č≐nas, N. (1999). Prooxidant toxicity of polyphenolic antioxidants to HL‐60 cells: description of quantitative structure‐activity relationships. FEBS Letters. https://doi.org/10.1016/s0014-5793(99)01561-6
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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