4722 J ournal of Medicinal Chemistry, 2002, Vol. 45, No. 21
Oya et al.
(23) J agust, W. J .; Eberling, J . L.; Biegon, A.; Taylor, S. E.; Van-
Brocklin, H. F.; J ordan, S.; Hanrahan, S. M.; Roberts, J . A.;
Brennan, K. M.; Mathis, C. A. Iodine-123-5-iodo-6-nitroqui-
pazine: SPECT radiotracer to image the serotonin transporter.
J . Nucl. Med. 1996, 37, 1207-1214.
(24) Fujita, M.; Takatoku, K.; Matoba, Y.; Nishiura, M.; Kobayashi,
K.; Inoue, O.; Nishimura, T. Differential kinetics of [123I]beta-
CIT binding to dopamine and serotonin transporters. Eur. J .
Nucl. Med. 1996, 23, 431-436.
(25) Kuikka, J . T.; Bergstrom, K. A.; Ahonen, A.; Hiltunen, J .;
Haukka, J .; Lansimies, E.; Wang, S.; Neumeyer, J . L. Compari-
son of iodine-123 labeled 2 beta-carbomethoxy-3 beta-(4-iodo-
phenyl)tropane and 2 beta-carbomethoxy-3 beta-(4-iodophenyl)-
N-(3-fluoropropyl)nortropane for imaging of the dopamine trans-
porter in the living human brain. Eur. J . Nucl. Med. 1995, 22,
356-360.
(26) Tiihonen, J .; Kuikka, J . T.; Bergstrom, K. A.; Karhu, J .;
Viinamaki, H.; Lehtonen, J .; Hallikainen, T.; Yang, J .; Hakola,
P. Single-photon emission tomography imaging of monoamine
transporters in impulsive violent behaviour. Eur. J . Nucl. Med.
1997, 24, 1253-1260.
(27) Laruelle, M.; Baldwin, R. M.; Malison, R. T.; Zea-Ponce, Y.;
Zoghbi, S. S.; al-Tikriti, M. S.; Sybirska, E. H.; Zimmermann,
R. C.; Wisniewski, G.; Neumeyer, J . L.; et al. SPECT imaging
of dopamine and serotonin transporters with [123I]â-CIT: phar-
macological characterization of brain uptake in nonhuman
primates. Synapse 1993, 13, 295-309.
(28) Pirker, W.; Asenbaum, S.; Kasper, S.; Walter, H.; Angelberger,
P.; Koch, G.; Pozzera, A.; Deecke, L.; Podreka, I.; Brucke, T.
â-CIT SPECT demonstrates blockade of 5HT-uptake sites by
citalopram in the human brain in vivo. J . Neural. Transm. Gen.
Sect. 1995, 100, 247-256.
(29) Tauscher, J .; Pirker, W.; de Zwaan, M.; Asenbaum, S.; Brucke,
T.; Kasper, S. In vivo visualization of serotonin transporters in
the human brain during fluoxetine treatment. Eur. Neuropsy-
chopharmacol. 1999, 9, 177-179.
(30) Malison, R. T.; Price, L. H.; Berman, R.; van Dyck, C. H.; Pelton,
G. H.; Carpenter, L.; Sanacora, G.; Owens, M. J .; Nemeroff, C.
B.; Rajeevan, N.; Baldwin, R. M.; Seibyl, J . P.; Innis, R. B.;
Charney, D. S. Reduced brain serotonin transporter availability
in major depression as measured by [123I]-2â-carbomethoxy-3â-
(4-iodophenyl)tropane and single photon emission computed
tomography. Biol. Psychiatry 1998, 44, 1090-1098.
Refer en ces
(1) Owens, M. J .; Nemeroff, C. B. Role of serotonin in the patho-
physiology of depression: focus on the serotonin transporter.
Clin. Chem. 1994, 40, 288-295.
(2) Harvey, B. H. The neurobiology and pharmacology of depression.
A comparative overview of serotonin selective antidepressants.
S. Afr. Med. J . 1997, 87, 540-550.
(3) Hyttel, J . Pharmacological characterization of selective serotonin
reuptake inhibitors (SSRIs). Int. Clin. Psychopharmacol. 1994,
1, 19-26.
(4) Frazer, A. Antidepressants. J . Clin. Psychiatry 1997, 6, 9-25.
(5) Staley, J . K.; Malison, R. T.; Innis, R. B. Imaging of the
serotonergic system: interactions of neuroanatomical and func-
tional abnormalities of depression. Biol. Psychiatry 1998, 44,
534-549.
(6) Szabo, Z.; Kao, P. F.; Scheffel, U.; Suehiro, M.; Mathews, W. B.;
Ravert, H. T.; Musachio, J . L.; Marenco, S.; Kim, S. E.; Ricaurte,
G. A.; Wong, D. F.; Wagner, H. N., J r.; Dannals, R. F. Positron
emission tomography imaging of serotonin transporters in the
human brain using [11C](+)McN5652. Synapse 1995, 20, 37-
43.
(7) Suehiro, M.; Musachio, J . L.; Dannals, R. F.; Mathews, W. B.;
Ravert, H. T.; Scheffel, U.; Wagner, H. N. An improved method
for the synthesis of radiolabeled McN5652 via thioester precur-
sors. Nucl. Med. Biol. 1995, 22, 543-545.
(8) Suehiro, M.; Scheffel, U.; Dannals, R. F.; Ravert, H. T.; Ricaurte,
G. A.; Wagner, H. N. A PET radiotracer for studying serotonin
uptake sites: carbon-11-McN-5652Z. J . Nucl. Med. 1993, 34,
120-127.
(9) Elfving, B.; Bjornholm, B.; Ebert, B.; Knudsen, G. M. Binding
characteristics of selective serotonin reuptake inhibitors with
relation to emission tomography studies. Synapse 2001, 41, 203-
211.
(10) Maryanoff, E. M.; Vaught, J . L.; Shank, R. P.; McComsey, D.
F.; Costanzo, M. J .; Nortey, S. O. Pyrroloisoquinoleines anti-
depressants. 3. A focus on serotonin. J . Med. Chem. 1990, 33,
2793-2797.
(11) Szabo, Z.; Scheffel, U.; Mathews, W. B.; Ravert, H. T.; Szabo,
K.; Kraut, M.; Palmon, S.; Ricaurte, G. A.; Dannals, R. F. Kinetic
analysis of [11C]McN5652: a serotonin transporter radioligand.
J . Cereb. Blood Flow Metab. 1999, 19, 967-981.
(12) Szabo, Z.; Mohamadiyeh, M.; Scheffel, U.; Matthews, W. B.;
Ravert, H. T.; Szabo, K.; Palmon, S.; Dannals, R. F. Impulse-
response function and kinetic-model of C-11-labeled (+)McN5652.
J . Nucl. Med. 1996, 37, 125.
(13) Parsey, R. V.; Kegeles, L. S.; Hwang, D. R.; Simpson, N.; Abi-
Dargham, A.; Mawlawi, O.; Slifstein, M.; Van Heertum, R. L.;
Mann, J . J .; Laruelle, M. In vivo quantification of brain serotonin
transporters in humans using [11C]McN 5652. J . Nucl. Med.
2000, 41, 1465-1477.
(14) Ricaurte, G. A.; McCann, U. D.; Szabo, Z.; Scheffel, U. Toxico-
dynamics and long-term toxicity of the recreational drug, 3,4-
methylenedioxymethamphetamine (MDMA, “Ecstasy”). Toxicol.
Lett. 2000, 112-113, 143-146.
(15) McCann, U. D.; Szabo, Z.; Scheffel, U.; Dannals, R. F.; Ricaurte,
G. A. Positron emission tomographic evidence of toxic effect of
MDMA (“Ecstasy”) on brain serotonin neurons in human beings.
Lancet 1998, 352, 1433-1437.
(16) Chumpradit, S.; Kung, M.-P.; Panyachotipun, C.; Prapansiri, V.;
Foulon, C.; Brooks, B. P.; Szabo, S. A.; Tejani-Butt, S.; Frazer,
A.; Kung, H. F. Iodinated tomoxetine derivatives as selective
ligands for serotonin and norepinephrine uptake sites. J . Med.
Chem. 1992, 35, 4492-4497.
(17) Soudijn, W.; van Wijngaarden, I. 5-HT Transporter. Serotonin
Receptors and Their Ligands; Elsevier Science: New York, 1997;
pp 327-361.
(31) Meltzer, C. C.; Smith, G.; DeKosky, S. T.; Pollock, B. G.; Mathis,
C. A.; Moore, R. Y.; Kupfer, D. J .; Reynolds, C. F., III. Serotonin
in aging, late-life depression, and Alzheimer’s disease: the
emerging role of functional imaging. Neuropsychopharmacology
1998, 18, 407-430.
(32) Willeit, M.; Praschak-Rieder, N.; Neumeister, A.; Pirker, W.;
Asenbaum, S.; Vitouch, O.; Tauscher, J .; Hilger, E.; Stastny, J .;
Brucke, T.; Kasper, S.
[
123I]-â-CIT SPECT imaging shows
reduced brain serotonin transporter availability in drug-free
depressed patients with seasonal affective disorder. Biol. Psy-
chiatry 2000, 47, 482-489.
(33) Laruelle, M.; Abi-Dargham, A.; van Dyck, C.; Gil, R.; D’Souza,
D. C.; Krystal, J .; Seibyl, J .; Baldwin, R.; Innis, R. Dopamine
and serotonin transporters in patients with schizophrenia: an
imaging study with [123I]â-CIT. Biol. Psychiatry 2000, 47, 371-
379.
(34) Bergstrom, K. A.; Halldin, C.; Hall, H.; Lundkvist, C.; Ginovart,
N.; Swahn, C. G.; Farde, L. In vitro and in vivo characterisation
of nor-beta-CIT: a potential radioligand for visualisation of the
serotonin transporter in the brain. Eur. J . Nucl. Med. 1997, 24,
596-601.
(35) Blough, B. E.; Abraham, P.; Mills, A. C.; Lewin, A. H.; Boja, J .
W.; Scheffel, U.; Kuhar, M. J .; Carroll, F. I. 3-â-(4-ethyl-3-
iodophenyl)nortropane-2-â-carboxylic acid methyl ester as a
high-affinity selective ligand for the serotonin transporter. J .
Med. Chem. 1997, 40, 3861-3864.
(36) Hiltunen, J .; Akerman, K. K.; Kuikka, J . T.; Bergstrom, K. A.;
Halldin, C.; Nikula, T.; Rasanen, P.; Tiihonen, J .; Vauhkonen,
M.; Karhu, J .; Kupila, J .; Lansimies, E.; Farde, L. Iodine-123
labeled nor-beta-CIT as a potential tracer for serotonin trans-
porter imaging in the human brain with single-photon emission
tomography. Eur. J . Nucl. Med. 1998, 25, 19-23.
(37) Ferris, R. M.; Brieaddy, L.; Mehta, N.; Hollingsworth, E.; Rigdon,
G.; Wang, C.; Soroko, F.; Wastila, W.; Cooper, B. Pharmacologi-
cal properties of 403U76, a new chemical class of 5-hydroxy-
tryptamine- and noradrenaline-reuptake inhibitor. J . Pharm.
Pharmacol. 1995, 47, 775-781.
(38) Brieaddy, L. E. Substituted diphenylsulfides as serotonin uptake
inhibitors. WO 93/12080, 1993.
(39) Mehta, N. B.; Hollingsworth, C. E.; Brieaddy, L. E.; Cooper, B.
R. Halogen substituted diphenylsulfides. EP 0 402 097 A1,
Europe, 1990.
(18) Suehiro, M.; Scheffel, U. A.; Ravert, H. T.; Ricaurte, G. A.;
Hatzidimitriou, G.; Dannals, R. F.; Bogeso, K. P.; Wagner, H.
N. Highly potent indanamine serotonin uptake blockers as
radiotracers for imaging serotonin uptake sites. Nucl. Med. Biol.
1994, 21, 1083-1091.
(19) Kung, M.-P.; Chumpradit, S.; Billings, J . J .; Kung, H. F.
4-Iodotomoxetine: a novel ligand for serotonin uptake sites. Life
Sci. 1992, 51, 95-106.
(20) Biegon, A.; Mathis, C. A.; Hanrahan, S. M.; J agust, W. J . [125I]5-
Iodo-6-nitroquipazine: a potent and selective ligand for the
5-hydroxytryptamine uptake complex II in vivo studies in rats.
Brain Res. 1993, 619, 236-246.
(21) Mathis, C. A.; Taylor, S. E.; Biegon, A.; Enas, J . D. [125I]5-Iodo-
6-nitroquipazine: a potent and selective ligand for the 5-hy-
droxytryptamine uptake complex I in vitro studies. Brain Res.
1993, 619, 229-235.
(22) Mathis, C. A.; Biegon, A.; Taylor, S. E.; Enas, J . D.; Hanrahan,
S. M. [I-125]5-Iodo-6-nitro-2-piperazinylquinoline: a potent and
selective ligand for the serotonin uptake complex. Eur. J .
Pharmacol. 1992, 210, 103-104.