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1.  (E)-2,2′-[3-(4-Chloro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy-5,5-di­methyl­cyclo­hex-2-en-1-one) 
The title compound, C25H29ClO4, adopts a trans conformation about the C=C double bond and the di­methyl­cyclo­hexenone rings both show an envelope conformation with the dimethyl-substituted C atom as the flap. In the mol­ecule, the hy­droxy and carbonyl groups form two intra­molecular O—H⋯O hydrogen bonds typical for xanthene derivatives. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into chains running parallel to the a-axis direction.
doi:10.1107/S1600536813020357
PMCID: PMC3793826  PMID: 24109413
2.  (E)-N-(3,3-Di­phenyl­allyl­idene)naph­thal­en-1-amine 
The title compound, C25H19N, adopts an E conformation about the C=N bond. The naphthalene ring system and the phenyl rings form dihedral angles 38.1 (1), 46.9 (8) and 48.5 (1)°, respectively, with the mean plane of the central enimino fragment. The crystal packing exhibits no directional close contacts.
doi:10.1107/S1600536813014888
PMCID: PMC3772462  PMID: 24046605
3.  (E)-9-(4-Fluoro­styr­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-2H-xanthene-1,8-dione 
In the title compound, C25H27FO3, each of the cyclo­hexenone rings adopts a half-chair conformation, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating by 0.0769 (15) and 0.196 (2) Å, respectively, from the plane of the other four atoms (r.m.s. deviation = 0.004 Å). The C=C double bond adopts an E conformation. The dihedral angle between the benzene and pyran (all atoms) rings is 89.94 (10)°. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into chains running parallel to the b axis.
doi:10.1107/S1600536813014049
PMCID: PMC3685118  PMID: 23795137
4.  (E)-N-(3,3-Di­phenyl­allyl­idene)-2-(tri­fluoro­meth­yl)aniline 
In the title compound, C22H16F3N, the C=N bond of the central imine group adopts an E conformation. The dihedral angles between the 2-(tri­fluoro­meth­yl)phenyl ring and the benzene rings are 9.34 (1) and 68.8 (1)°. The imine group displays a C—C—N=C torsion angle of 41.6 (3)°. In the crystal, weak C—H⋯F hydrogen bonds link the mol­ecules into chains parallel to the b-axis direction.
doi:10.1107/S1600536813010283
PMCID: PMC3648283  PMID: 23723903
5.  (E)-N-[(E)-3-(4-Nitro­phen­yl)allyl­idene]naphthalen-1-amine 
In the title compound, C19H14N2O2, the dihedral angle between the mean planes of the 4-nitro­phenyl ring and the naphthalene ring system is 12.79 (2)°. The imine group displays a C—C—N=C torsion angle of 41.0 (2)° and the C=N group has an E conformation. In the crystal, weak C—H⋯O hydrogen bonds link molecules into layers parallel to the b axis.
doi:10.1107/S1600536813006417
PMCID: PMC3629600  PMID: 23634087
6.  (E)-2,2′-[3-(4-Fluoro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy-5,5-dimethyl­cyclo­hex-2-en-1-one) 
In the title compound, C25H29FO4, each cyclo­hexenone ring has an envelope conformation with the dimethyl-substituted atom as the flap. The hy­droxy and carbonyl groups form two intra­molecular O—H⋯O hydrogen bonds, as is typical for xanthene derivatives. In the crystal, very weak C—H⋯O hydrogen bonds link mol­ecules into dimers.
doi:10.1107/S1600536813004364
PMCID: PMC3588420  PMID: 23476580
7.  (E)-N-(3,3-Diphenyl­allyl­idene)-3-nitro­aniline 
In the title compound, C21H16N2O2, the 3-nitro­phenyl and two phenyl rings are twisted from the mean plane of the enimino fragment by 44.4 (1), 37.2 (1) and 74.1 (1)°, respectively. The crystal packing exhibits no classical inter­molecular contacts.
doi:10.1107/S1600536812040354
PMCID: PMC3470384  PMID: 23125797
8.  (E)-N-(3,3-Diphenyl­allyl­idene)-4-nitro­aniline 
In the title compound, C21H16N2O2, the dihedral angles between the mean planes of the 4-nitro­phenyl ring and the two phenyl rings are 57.3 (5) and 16.8 (6)°. The imine group displays a C—C—N—C torsion angle of −24.9 (3)°.
doi:10.1107/S1600536812040391
PMCID: PMC3470385  PMID: 23125798
9.  2,2′-[(E)-3-(4-Nitro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy-5,5-dimethyl­cyclo­hex-2-en-1-one) 
In the title compound, C25H29NO6, each of the cyclo­hexenone rings adopts a half-chair conformation. The hy­droxy and carbonyl O atoms face each other and are oriented to allow for the formation of two intra­molecular O—H⋯O hydrogen bonds. In the crystal, weak C—H⋯O hydrogen bonds are formed between molecules, generating a two-dimensional supramolecular structure.
doi:10.1107/S1600536812032242
PMCID: PMC3414961  PMID: 22904948
10.  (E)-3,3,6,6-Tetra­methyl-9-(2-nitro­styr­yl)-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione 
In the title compound, C25H27NO5, each of the cyclo­hexenone rings adopts a half-chair conformation, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating from the plane of the other four atoms. In the crystal, weak C—H⋯O hydrogen bonds link mol­ecules into chains parallel to the c axis.
doi:10.1107/S1600536812023495
PMCID: PMC3379499  PMID: 22719697
11.  (E)-9-(4-Chloro­styr­yl)-3,4,5,6,7,9-hexa­hydro-2H-xanthene-1,8-dione 
In the title compound, C21H19ClO3, the two cyclo­hexenone rings adopt half-chair conformations, whereas the pyran ring adopts a boat conformation. The 4-chloro­phenyl ring is almost perpendicular to the plane through the four C atoms of the pyran ring [dihedral angle = 87.97 (6)°]. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into a chain parallel to the a-axis.
doi:10.1107/S1600536812002139
PMCID: PMC3275246  PMID: 22347102
12.  9-[(E)-2-(2-Meth­oxy­phen­yl)ethen­yl]-3,4,5,6,7,9-hexa­hydro-2H-xanthene-1,8-dione 
In the title compound, C22H22O4, the two cyclo­hexenone rings adopt half-chair conformations, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating from the plane of the other four atoms by 0.142 (2) and 0.287 (2)Å, respectively. In the crystal, weak C—H⋯O hydrogen bonds link mol­ecules into chains running parallel to the a axis.
doi:10.1107/S1600536812001419
PMCID: PMC3275209  PMID: 22347065
13.  (E)-2,2′-[3-(2-Nitro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy­cyclo­hex-2-en-1-one) 
In the title compound, C21H21NO6, each of the cyclo­hexenone rings adopts a half-chair conformation. Each of the pairs of hy­droxy and carbonyl O atoms are oriented to allow for the formation of intra­molecular O—H⋯O hydrogen bonds, which are typical of xanthene derivatives.
doi:10.1107/S1600536811054730
PMCID: PMC3254576  PMID: 22259527
14.  [2-(4-Chloro­phen­yl)-5-phenyl­oxolan-3-yl](cyclo­penten­yl)methanone 
In the title compound, C22H21ClO2, the oxolane ring adopts a twisted conformation. The dihedral angles between the mean plane of the oxolane ring and the mean planes of the 4-chloro­phenyl, phenyl and cyclo­pentenyl rings are 71.81 (18), 76.9 (18) and 82.08 (18)°, respectively.
doi:10.1107/S1600536811051993
PMCID: PMC3254405  PMID: 22259548
15.  2,2-[(E)-3,3-Diphenyl­prop-2-ene-1,1-di­yl]bis­(3-hy­droxy­cyclo­hex-2-en-1-one) 
In the title compound, C27H26O4, each of the cyclo­hexenone rings adopts a half-chair conformation. The dihedral angle between the two phenyl rings is 89.53 (5)°. The hy­droxy and carbonyl O atoms face each other and are orientated to allow the formation of two intra­molecular O—H⋯O hydrogen bonds, which are typical of xanthene derivatives.
doi:10.1107/S1600536811048355
PMCID: PMC3239045  PMID: 22199893
16.  (E)-2,2′-[3-(2-Nitro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy-5,5-dimethyl­cyclo­hex-2-en-1-one) 
In the title compound, C25H29NO6, each of the cyclo­hexenone rings adopts a half-chair conformation. Each of the pairs of hy­droxy and carbonyl O atoms are oriented to allow for the formation of intra­molecular O—H⋯O hydrogen bonds, which are typical of xanthene derivatives. The nitro group is rotationally disordered over two orientations in a 0.544 (6):0.456 (6) ratio. In the crystal, weak inter­molecualr C—H⋯O hydrogen bonds link mol­ecules into layers parallel to the ab plane.
doi:10.1107/S1600536811043686
PMCID: PMC3238826  PMID: 22199679
17.  3-Hy­droxy-2-[(2E)-1-(2-hy­droxy-6-oxocyclo­hex-1-en-1-yl)-3-(2-meth­oxy­phen­yl)prop-2-en-1-yl]cyclo­hex-2-en-1-one 
In the title compound, C22H24O5, each of the cyclo­hexenone rings adopts a half-chair conformation. The hy­droxy and carbonyl O atoms face each other and are orientated to allow for the formation of the two intra­molecular O—H⋯O hydrogen bonds which are typical of xanthene derivatives. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link mol­ecules into layers parallel to the ab plane.
doi:10.1107/S1600536811038207
PMCID: PMC3201272  PMID: 22065620
18.  The N Terminus of Monoamine Transporters Is a Lever Required for the Action of Amphetamines* 
The Journal of Biological Chemistry  2010;285(14):10924-10938.
The serotonin transporter (SERT) terminates neurotransmission by removing serotonin from the synaptic cleft. In addition, it is the site of action of antidepressants (which block the transporter) and of amphetamines (which induce substrate efflux). We explored the functional importance of the N terminus in mediating the action of amphetamines by focusing initially on the highly conserved threonine residue at position 81, a candidate site for phosphorylation by protein kinase C. Molecular dynamics simulations of the wild type SERT, compared with its mutations SERTT81A and SERTT81D, suggested structural changes in the inner vestibule indicative of an opening of the inner vestibule. Predictions from this model (e.g. the preferential accumulation of SERTT81A in the inward conformation, its reduced turnover number, and a larger distance between its N and C termini) were verified. Most importantly, SERTT81A (and the homologous mutations in noradrenaline and dopamine) failed to support amphetamine-induced efflux, and this was not remedied by aspartate at this position. Amphetamine-induced currents through SERTT81A were comparable with those through the wild type transporter. Both abundant Na+ entry and accumulation of SERTT81A in the inward facing conformation ought to favor amphetamine-induced efflux. Thus, we surmised that the N terminus must play a direct role in driving the transporter into a state that supports amphetamine-induced efflux. This hypothesis was verified by truncating the first 64 amino acids and by tethering the N terminus to an additional transmembrane helix. Either modification abolished amphetamine-induced efflux. We therefore conclude that the N terminus of monoamine transporters acts as a lever that sustains reverse transport.
doi:10.1074/jbc.M109.083154
PMCID: PMC2856298  PMID: 20118234
Phosphorylation; Transport/Neurotransmitter; Oocyte; Transport Drugs; Zinc; Amphetamine; Carrier-mediated Efflux; Fluorescence Resonance Energy Transfer Microscopy; Serotonin
19.  Visualization of Dopamine Transporter Trafficking in Live Neurons by Use of Fluorescent Cocaine Analogs 
The Journal of Neuroscience  2009;29(21):6794-6808.
The dopamine transporter (DAT) mediates reuptake of dopamine from the synaptic cleft and is a target for widely abused psychostimulants such as cocaine and amphetamine. Nonetheless, little is known about the cellular distribution and trafficking of natively expressed DAT. Here we use novel fluorescently tagged cocaine analogs to visualize DAT and DAT trafficking in cultured live midbrain dopaminergic neurons. The fluorescent tags were extended from the tropane N-position of 2β-carbomethoxy-3β-(3,4-dichlorophenyl)tropane using an ethylamino-linker. The rhodamine-, OR Green-, or Cy3-labeled ligands had high binding affinity for DAT and enabled specific labeling of DAT in live neurons and visualization by confocal imaging. In the dopaminergic neurons, DAT was uniformly distributed in the plasma membrane of the soma, the neuronal extensions, and varicosities along these extensions. FRAP (fluorescence recovery after photobleaching) experiments demonstrated bidirectional movement of DAT in the extensions and indicated that DAT is highly mobile both in the extensions and in the varicosities (immobile fraction less than ∼30%). DAT was constitutively internalized into vesicular structures likely representing intracellular transporter pools. The internalization was blocked by lentiviral-mediated expression of dominant-negative dynamin and internalized DAT displayed partial colocalization with the early endosomal marker EGFP-Rab5 and with the transferrin receptor. DAT internalization and function was not affected by activation of protein kinase C (PKC) with phorbol-12-myristate-13-acetate (PMA) or by inhibition with staurosporine or GF109203X. These data are in contrast to findings for DAT in transfected heterologous cells and challenge the paradigm that trafficking and cellular distribution of endogenous DAT is subject to regulation by PKC.
doi:10.1523/JNEUROSCI.4177-08.2009
PMCID: PMC3849467  PMID: 19474307

Results 1-19 (19)