Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 11, Pages 4940-4947Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo500520x
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Funding
- National Cancer Institute Innovative Molecular Analysis Technologies Program [CA182341-01]
- Bankhead-Coley New Investigator Research Program [3BN08]
- National Cancer Institute [CA98881-05]
- Braman Family Breast Cancer Institute
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Fluorescent N-phenyl-4-aminoquinazoline probes targeting the ATP-binding pocket of the ERBB family of receptor tyrosine kinases are reported. Extension of the aromatic quinazoline core with fluorophore arms through substitution at the 6- position of the quinazoline core with phenyl, styryl, and phenylbutadienyl moieties was predicted by means of TD-DFT calculations to produce probes with tunable photoexcitation energies and excited states possessing charge-transfer character. Optical spectroscopy identified several synthesized probes that are nonemissive in aqueous solutions and exhibit emission enhancements in solvents of low polarity, suggesting good performance as turn-on fluorophores. Ligand-induced ERBB2 phosphorylation assays demonstrate that despite chemical modification to the quinazoline core these probes still function as ERBB2 inhibitors in MCF7 cells. Two probes were found to exhibit ERBB2-induced fluorescence, demonstrating the utility of these probes as turn-on, fluoroescent kinase inhibitors.
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