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Trisubstituted Isoalloxazines as a New Class of G-Quadruplex Binding Ligands: Small Molecule Regulation of c-kit Oncogene Expression
Open accessAbstract
Herein, we report the design, synthesis, biophysical evaluation with primary biological data of 3,8,10-trisubstituted isoalloxazines as a new class of G-quadruplex binding ligands. We have developed a short and robust synthesis for trisubstituted isoalloxazines in good yields. The G-quadruplex binding and stabilization potential of isoalloxazines was assessed by surface plasmon resonance and fluorescence resonance energy transfer assay. The data revealed that these isoalloxazines bind and stabilize G-quadruplex DNA, but not duplex DNA, and exhibit potential for discriminating between DNA quadruplexes. Cell-based experiments using cell lines that express the proto-oncogene c-kit (MCF-7 and HGC-27) showed that such isoalloxazines can inhibit the expression of c-kit.
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Citations
Cited by
DNA secondary structures: stability and function of G-quadruplex structures
Bochman, M. L., Paeschke, K., & Zakian, V. A. (2012) · Nature Reviews Genetics · doi:10.1038/nrg3296 · Cited by 1,446
A hitchhiker's guide to G-quadruplex ligands
Monchaud, D., & Teulade-Fichou, M.-P. (2008) · Org. Biomol. Chem. · doi:10.1039/b714772b · Cited by 788
G-quadruplex nucleic acids as therapeutic targets
Balasubramanian, S., & Neidle, S. (2009) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2009.04.637 · Cited by 586
Self-citationRodriguez, R., Müller, S., Yeoman, J. A., Trentesaux, C., Riou, J.-F., & Balasubramanian, S. (2008) · Journal of the American Chemical Society · doi:10.1021/ja805615w · Cited by 517
Self-citationMaking sense of G‐quadruplex and i‐motif functions in oncogene promoters
Brooks, T. A., Kendrick, S., & Hurley, L. (2010) · The FEBS Journal · doi:10.1111/j.1742-4658.2010.07759.x · Cited by 477
Metadata
- Authors
- Bejugam, M., Sewitz, S., Shirude, P. S., Rodriguez, R., Shahid, R., & Balasubramanian, S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-10-01
- Volume
- 129
- Issue
- 43
- Pages
- 12926-12927
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1991797965
- Cited by
- 248
- References
- 0
- FWCI
- 8.74
- Type
- journal article
- Language
- en
- Open access
- green
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- Bejugam, M., Sewitz, S., Shirude, P. S., Rodriguez, R., Shahid, R., & Balasubramanian, S. (2007). Trisubstituted Isoalloxazines as a New Class of G-Quadruplex Binding Ligands: Small Molecule Regulation of c-kit Oncogene Expression. Journal of the American Chemical Society. https://doi.org/10.1021/ja075881p
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