Synthesis of AX7593, a quinazoline-derived photoaffinity probe for EGFR.
[structure: see text] 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 (K(b) = 280 nM) was shown to have an efficiency of 34% and to be competitive with the EGFR inhibitors PP2 and AG1478.
ActivX Biosciences, Inc., 11025 North Torrey Pines Road, La Jolla, California 92037, USA. kevins@activx.com
Kevin R
KR
Shreder
Melissa S
MS
Wong
Tyzoon
T
Nomanbhoy
Phillip S
PS
Leventhal
Stacy R
SR
Fuller
D066246:ErbB Receptors / Q000737:chemistry*; D019920:Photoaffinity Labels / Q000138:chemical synthesis* / Q000737:chemistry; D011799:Quinazolines / Q000138:chemical synthesis / Q000737:chemistry*
C508460:AX7593; D019920:Photoaffinity Labels; D011799:Quinazolines; D066246:ErbB Receptors