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Synthesis of AX7593, a Quinazoline-Derived Photoaffinity Probe for EGFR

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journal contribution
posted on 14.10.2004, 00:00 by Kevin R. Shreder, Melissa S. Wong, Tyzoon Nomanbhoy, Phillip S. Leventhal, Stacy R. Fuller
The synthesis of a photoaffinity probe for EGFR is described. O-Alkylation of 4-(meta-azidoanilino)-6-methoxy-7-hydroxy-quinazoline with a protected tetraethyleneglycol linker followed by the attachment of tetramethylrhodamine yielded the fluorescent probe AX7593. Photoaffinity labeling of EGFR by AX7593 (Kb = 280 nM) was shown to have an efficiency of 34% and to be competitive with the EGFR inhibitors PP2 and AG1478.