TY - JOUR
T1 - 1,2-Diaryl-3,4-dihydronaphthalenes
T2 - Photofluorogenic ligands for the estrogen receptor
AU - Bindal, Rajeshwar D.
AU - Katzenellenbogen, John A.
N1 - Funding Information:
Acknowledgemenfs-Supporot f this researcht hrough a grant from the N.I.H. (PHS5ROl AM-15556)i s gratefully acknowledgedH. igh-resolutionm asss pectraw ereo btained using instrumentsin the Universityo f Illinois Mass Spec-trometerC enter,s upportedb y NIH Grant GM 27029a nd high-resolutionN Gk spectra-weroeb tainedo n instruments in the Universityo f Illinois NSF RegionalI nstrumentation Facility (NSF CHE 79-16100W). e areg ratefutl o Drs David W. Robertsona nd David F. Heiman for preliminarys yn-thetic work on those compoundsa nd to Dr Paul W. O’Connell ^ (Upjohn Co.) for providing a supply of na-
PY - 1985/12
Y1 - 1985/12
N2 - 1,2-Diaryl-3,4-dihydronaphthalene systems related to the Upjohn antiestrogen nafoxidine (U11, 110A) (1) have high affinity for the estrogen receptor, but are essentially non-fluorescent. Upon u.v. irradiation, however, the cis-stilbene system within their structure undergo a photocyclization (2) followed by a spontaneous oxidation, forming a dihydrobenzochrysene system (3) that is highly fluorescent, but is only weakly bound by the estrogen receptor. This system can be oxidized further to the benzochrysene system, which exhibits similar fluorescence. The 1,2-diarylnaphthalene systems, obtained by direct oxidation of the dihydronaphthalenes, however, do not undergo photocyclization. The binding affinity of these derivatives for the estrogen receptor appears to be related to their degree of non-planarity and can be correlated with their molecular surface area. This facile photochemical conversion of a high-affinity ligand to a highly fluorescent species offers a new approach to the design of fluorescent estrogens.
AB - 1,2-Diaryl-3,4-dihydronaphthalene systems related to the Upjohn antiestrogen nafoxidine (U11, 110A) (1) have high affinity for the estrogen receptor, but are essentially non-fluorescent. Upon u.v. irradiation, however, the cis-stilbene system within their structure undergo a photocyclization (2) followed by a spontaneous oxidation, forming a dihydrobenzochrysene system (3) that is highly fluorescent, but is only weakly bound by the estrogen receptor. This system can be oxidized further to the benzochrysene system, which exhibits similar fluorescence. The 1,2-diarylnaphthalene systems, obtained by direct oxidation of the dihydronaphthalenes, however, do not undergo photocyclization. The binding affinity of these derivatives for the estrogen receptor appears to be related to their degree of non-planarity and can be correlated with their molecular surface area. This facile photochemical conversion of a high-affinity ligand to a highly fluorescent species offers a new approach to the design of fluorescent estrogens.
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U2 - 10.1016/0022-4731(85)90049-4
DO - 10.1016/0022-4731(85)90049-4
M3 - Article
C2 - 4094420
AN - SCOPUS:0022312813
SN - 0022-4731
VL - 23
SP - 929
EP - 937
JO - Journal of Steroid Biochemistry
JF - Journal of Steroid Biochemistry
IS - 6 PART 1
ER -