Abstract
C4-[18F]Fluorocyclofenil ([18F]FCF, 6) and C3-[18F]fluoroethylcyclofenil ([18F]FECF, 9), two high-affinity nonsteroidal estrogens, were prepared and investigated as potential agents for imaging estrogen receptors (ERs) in breast tumors. Both of these compounds could be prepared conveniently from alkyl methanesulfonate precursors (5,8) by fluoride displacement reactions, and they were obtained in high radiochemical purity and radiochemical yields, with effective specific activities sufficient for in vivo biodistribution studies. While the biodistribution of [18F]FCF (6) in immature female rats showed no selective target tissue uptake, the biodistribution of [18F]FECF (9) showed selective uptake by the uterus, but this uptake could not be blocked by excess estradiol. The poor in vivo biodistribution of these otherwise high-affinity ligands arouses curiosity, and together with recent results on the biodistribution of other nonsteroidal ligands suggests that factors other than receptor binding affinity are important for in vivo imaging of estrogen target tissues and ER-positive breast tumors.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 383-390 |
| Number of pages | 8 |
| Journal | Nuclear Medicine and Biology |
| Volume | 34 |
| Issue number | 4 |
| DOIs | |
| State | Published - May 1 2007 |
| Externally published | Yes |
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Keywords
- Cyclofenil
- Estrogen receptor
- Estrogen receptor imaging
- Fluorine-18
ASJC Scopus subject areas
- Molecular Medicine
- Radiology Nuclear Medicine and imaging
- Cancer Research
Cite this
Synthesis and biodistribution of fluorine-18-labeled fluorocyclofenils for imaging the estrogen receptor. / Seo, Jai; Chi, Dae Yoon; Dence, Carmen S.; Welch, Michael J.; Katzenellenbogen, John A.
In: Nuclear Medicine and Biology, Vol. 34, No. 4, 01.05.2007, p. 383-390.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and biodistribution of fluorine-18-labeled fluorocyclofenils for imaging the estrogen receptor
AU - Seo, Jai
AU - Chi, Dae Yoon
AU - Dence, Carmen S.
AU - Welch, Michael J.
AU - Katzenellenbogen, John A.
PY - 2007/5/1
Y1 - 2007/5/1
N2 - C4-[18F]Fluorocyclofenil ([18F]FCF, 6) and C3-[18F]fluoroethylcyclofenil ([18F]FECF, 9), two high-affinity nonsteroidal estrogens, were prepared and investigated as potential agents for imaging estrogen receptors (ERs) in breast tumors. Both of these compounds could be prepared conveniently from alkyl methanesulfonate precursors (5,8) by fluoride displacement reactions, and they were obtained in high radiochemical purity and radiochemical yields, with effective specific activities sufficient for in vivo biodistribution studies. While the biodistribution of [18F]FCF (6) in immature female rats showed no selective target tissue uptake, the biodistribution of [18F]FECF (9) showed selective uptake by the uterus, but this uptake could not be blocked by excess estradiol. The poor in vivo biodistribution of these otherwise high-affinity ligands arouses curiosity, and together with recent results on the biodistribution of other nonsteroidal ligands suggests that factors other than receptor binding affinity are important for in vivo imaging of estrogen target tissues and ER-positive breast tumors.
AB - C4-[18F]Fluorocyclofenil ([18F]FCF, 6) and C3-[18F]fluoroethylcyclofenil ([18F]FECF, 9), two high-affinity nonsteroidal estrogens, were prepared and investigated as potential agents for imaging estrogen receptors (ERs) in breast tumors. Both of these compounds could be prepared conveniently from alkyl methanesulfonate precursors (5,8) by fluoride displacement reactions, and they were obtained in high radiochemical purity and radiochemical yields, with effective specific activities sufficient for in vivo biodistribution studies. While the biodistribution of [18F]FCF (6) in immature female rats showed no selective target tissue uptake, the biodistribution of [18F]FECF (9) showed selective uptake by the uterus, but this uptake could not be blocked by excess estradiol. The poor in vivo biodistribution of these otherwise high-affinity ligands arouses curiosity, and together with recent results on the biodistribution of other nonsteroidal ligands suggests that factors other than receptor binding affinity are important for in vivo imaging of estrogen target tissues and ER-positive breast tumors.
KW - Cyclofenil
KW - Estrogen receptor
KW - Estrogen receptor imaging
KW - Fluorine-18
UR - http://www.scopus.com/inward/record.url?scp=34248149419&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34248149419&partnerID=8YFLogxK
U2 - 10.1016/j.nucmedbio.2007.01.010
DO - 10.1016/j.nucmedbio.2007.01.010
M3 - Article
C2 - 17499727
AN - SCOPUS:34248149419
VL - 34
SP - 383
EP - 390
JO - Nuclear Medicine and Biology
JF - Nuclear Medicine and Biology
SN - 0969-8051
IS - 4
ER -