The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
2-Acetylpyridine Thiosemicarbazones are Potent Iron Chelators and Antiproliferative Agents: Redox Activity, Iron Complexation and Characterization of their Antitumor Activity
Abstract
Through systematic structure-activity studies of the 2-benzoylpyridine thiosemicarbazone (HBpT), 2-(3-nitrobenzoyl)pyridine thiosemicarbazone (HNBpT) and dipyridylketone thiosemicarbazone (HDpT) series of iron (Fe) chelators, we identified structural features necessary to form Fe complexes with potent anticancer activity (J. Med. Chem. 2007, 50, 3716-3729). In this investigation, we generated the related 2-acetylpyridine thiosemicarbazone (HApT) analogues to examine the influence of the methyl group at the imine carbon. Four of the six HApT chelators had potent antitumor activity (IC(50): 0.001-0.002 microM) and Fe chelation efficacy that was similar to the most effective HBpT and HDpT ligands. The HApT Fe complexes had the lowest Fe(III/II) redox potentials of any thiosemicarbazone series we have generated. This property, in combination with their ability to effectively chelate cellular Fe, make the HApT series one of the most potent antiproliferative agents developed by our group.
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Citations
Cites
The Evolution of Iron Chelators for the Treatment of Iron Overload Disease and Cancer
Kalinowski, D. S., & Richardson, D. R. (2005) · Pharmacological Reviews · doi:10.1124/pr.57.4.2 · Cited by 721
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Cited by
Targeting Free Radicals in Oxidative Stress-Related Human Diseases
Poprac, P., Jomova, K., Simunkova, M., Kollar, V., Rhodes, C. J., & Valko, M. (2017) · Trends in Pharmacological Sciences · doi:10.1016/j.tips.2017.04.005 · Cited by 1,107
Is resistance useless? Multidrug resistance and collateral sensitivity
Hall, M. D., Handley, M. D., & Gottesman, M. M. (2009) · Trends in Pharmacological Sciences · doi:10.1016/j.tips.2009.07.003 · Cited by 259
Bendova, P., Mackova, E., Haskova, P., Vavrova, A., Jirkovsky, E., Sterba, M., Popelova, O., Kalinowski, D. S., Kovarikova, P., Vavrova, K., et al. (2010) · Chemical Research in Toxicology · doi:10.1021/tx100125t · Cited by 73
Metadata
- Authors
- Richardson, D. R., Kalinowski, D. S., Richardson, V., Sharpe, P. C., Lovejoy, D. B., Islam, M., & Bernhardt, P. V.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-02-13
- Volume
- 52
- Issue
- 5
- Pages
- 1459-1470
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2047553979
- Cited by
- 200
- References
- 1
- FWCI
- 6.41
- Type
- journal article
- Language
- en
- Open access
- closed
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