- Synthesis, radiolabeling, and preliminary in vivo evaluation of [68ga] ipcat-nota as an imaging agent for dopamine transporter
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Introduction: Novel radiotracer development for imaging dopamine transporters is a subject of interest because although [99mTc]TRODAT-1, [123I]β-CIT, and [123I]FP-CIT are commercially available;99Mo/99mTc generator is in short supply and123I production is highly dependent on compact cyclotron. Therefore, we designed a novel positron emission tomography (PET) tracer based on a tropane derivative through C-2 modification to conjugate NOTA for chelating68Ga, a radioisotope derived from a68Ge/68Ga generator. Methods: IPCAT-NOTA 22 was synthesized and labeled with [68Ga]GaCl4 ? at room tem-perature. Biological studies on serum stability, LogP, and in vitro autoradiography (binding assay and competitive assay) were performed. Furthermore, ex vivo autoradiography, biodis-tribution, and dynamic PET imaging studies were performed in Sprague Dawley rats. Results: [68Ga]IPCAT-NOTA 24 obtained had a radiochemical yield of ≥90% and a specific activity of 4.25 MBq/nmol. [68Ga]IPCAT-NOTA 24 of 85% radiochemical purity (RCP%) was stable at 37°C for up to 60 minutes in serum with a lipophilicity of 0.88. The specific binding ratio (SBR%) reached 15.8 ± 6.7 at 60 minutes, and the 85% specific uptake could be blocked through co-injection at 100-and 1000-fold of the cold precursor in in vitro binding studies. Tissue regional distribution studies in rats with [68Ga]IPCAT-NOTA 24 showed striatal uptake (0.02% at 5 minutes and 0.007% at 60 minutes) with SBR% of 6%, 25%, and 62% at 5–15, 30–40, and 60–70 minutes, respectively, in NanoPET studies. The RCP% of [68Ga]IPCAT-NOTA 24 at 30 minutes in vivo remained 67.65%. Conclusion: Data described here provide new information on the design of PET probe of conjugate/pendent approach for DAT imaging. Another chelator or another direct method of intracranial injection must be used to prove the relation between [68Ga]IPCAT-NOTA 24 uptake and transporter localization.
- Farn, Shiou-Shiow,Chang, Kang-Wei,Lin, Wan-Chi,Yu, Hung-Man,Lin, Kun-Liang,Tseng, Yu-Chin,Chang, Yu,Yu, Chung-Shan,Lin, Wuu-Jyh
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p. 2577 - 2591
(2021/07/06)
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- Diastereo- and Enantioselective Cross-Couplings of Secondary Alkylcopper Reagents with 3-Halogeno-Unsaturated Carbonyl Derivatives
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Chiral secondary alkylcopper reagents were prepared from the corresponding alkyl iodides with retention of configuration by an I/Li-exchange using tBuLi (?100 °C, 1 min) followed by a transmetalation with CuBr?P(OEt)3 (?100 °C, 20 s). These ste
- Kremsmair, Alexander,Skotnitzki, Juri,Knochel, Paul
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supporting information
p. 11971 - 11973
(2020/09/07)
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- Tetra-substituted pyridinylimidazoles as dual inhibitors of p38α mitogen-activated protein kinase and c-jun N-terminal kinase 3 for potential treatment of neurodegenerative diseases
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Tetra-substituted imidazoles were designed as dual inhibitors of c-Jun N-terminal kinase (JNK) 3 and p38α mitogen-activated protein (MAP) kinase. A library of 45 derivatives was prepared and evaluated in a kinase activity assay for their ability to inhibi
- Muth, Felix,Günther, Marcel,Bauer, Silke M.,D?ring, Eva,Fischer, Sabine,Maier, Julia,Drückes, Peter,K?ppler, Jürgen,Trappe, J?rg,Rothbauer, Ulrich,Koch, Pierre,Laufer, Stefan A.
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supporting information
p. 443 - 456
(2015/07/27)
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- A convergent approach to (-)-callystatin a based on local symmetry
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The key is symmetry! A convergent synthetic approach of the highly cytotoxic natural product (-)-callystatin A was developed assembling three fragments through Julia-Kocienski olefination and Stille cross-coupling. The new strategy relies on a pivotal local symmetry of the target molecule. In this preliminary study, particular attention was devoted to facilitate the catalytic enantiocontrol of strategic stereogenic centers present in each of the fragments (see scheme). Copyright
- Candy, Mathieu,Tomas, Lo?c,Parat, Sabrina,Heran, Virginie,Bienaymé, Hugues,Pons, Jean-Marc,Bressy, Cyril
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supporting information
p. 14267 - 14271
(2013/01/15)
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- Synthesis and properties of seleno-analog MK-organic dye for photovoltaic cells prepared by CH functionalization reactions of selenophene derivatives
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C-H arylation and homocoupling reactions of 2-formylselenophene were carried out with a palladium catalyst. By using these coupling reactions a seleno-analog of MK dye MK-49, which is an organic dye molecule of a dye-sensitized solar cell (DSSC), was synt
- Tamba, Shunsuke,Fujii, Ryosuke,Mori, Atsunori,Hara, Kohjiro,Koumura, Nagatoshi
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supporting information; experimental part
p. 978 - 979
(2012/01/30)
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- The vinyl moiety as a handle for regiocontrol in the preparation of unsymmetrical 2,3-aliphatic-substituted indoles and pyrroles
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Rho-Rho-Rho your boat: A rhodium catalyst effects the regioselective oxidative coupling of enynes with N-aryl ureas (X=NR2) and N-vinylacetamides (X=C(O)Me), affording the corresponding 2-alkenylindoles and 2-alkenylpyrroles in good yield. Simple hydrogenation delivers the C2/C3-aliphatic-substituted indole or pyrrole (see scheme).
- Huestis, Malcolm P.,Chan, Lina,Stuart, David R.,Fagnou, Keith
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supporting information; scheme or table
p. 1338 - 1341
(2011/04/21)
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- Applying asymmetric dihydroxylation to the synthesis of difluorinated carbohydrate analogues: A 1,1-difluoro-1-deoxy-d-xylulose
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Readily available difluoroenol iodides and stannanes undergo palladium-catalysed coupling reactions with alkenylstannanes and iodides, respectively, to afford a trial set of difluorinated 1,3- and 1,4-dienes, which were then exposed to AD conditions. A nu
- Cox, Liam R.,Deboos, Gareth A.,Fullbrook, Jeremy J.,Percy, Jonathan M.,Spencer, Neil
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p. 347 - 359
(2007/10/03)
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- Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P
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A coordinatively unsaturated ruthenium complex catalyzed the formation of a carbon-carbon bond between two judiciously chosen alkene and alkyne partners in good yield, and in a chemo- and regioselective fashion, despite the significant degree of unsaturation of the substrates. The resulting 1,4-diene forms the backbone of the cytotoxic marine natural product amphidinolide P. The alkene partner was rapidly assembled from (R)-glycidyl tosylate, which served as a linchpin in a one-flask, sequential three-components coupling process using vinyllithium and a vinyl cyanocuprate. The synthesis of the alkyne partner made use of an unusual anti-selective addition under chelation-control conditions of an allyltin reagent derived from tiglic acid. In addition, a remarkably E-selective E2 process using the azodicarboxylate-triphenylphosphine system is featured. Also featured is the first example of the use of a β-lactone as a thermodynamic spring to effect macrolactonization. The oxetanone ring was thus used as a productive protecting group that increased the overall efficiency of this total synthesis. This work was also an opportunity to further probe the scope of the ruthenium-catalyzed alkene-alkyne coupling, in particular using enynes, and studies using various functionalized substrates are described.
- Trost, Barry M.,Papillon, Julien P. N.,Nussbaumer, Thomas
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p. 17921 - 17937
(2007/10/03)
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- Synthesis of 2E,4E,6E,11Z-octadecatetraenoic acid of the Rhizobium leguminosarum biovar viciae Nod factor
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2E,4E,6E,11Z-Octadecatetraenoic acid was synthesized in a good yield and in a stereospecific manner by coupling a vinylborane compound and ethyl trans-3-iodoacrylate. The trienic system (E,E,E) was obtained by successive use of metal-catalyzed coupling and hydro-metallation reactions.
- Ghomsi, Joseph-Nathan Téné,Goureau, Olivine,Treilhou, Michel
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p. 1537 - 1539
(2007/10/03)
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- Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose.
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[reaction: see text] A new route, of potential strategic importance, to a difluorosugar analogue has been developed. Key steps included a Stille coupling and a highly regio- and enantioselective dihydroxylation of a highly substituted diene. Protecting gr
- Cox, Liam R,DeBoos, Gareth A,Fullbrook, Jeremy J,Percy, Jonathan M,Spencer, Neil S,Tolley, Malcolm
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p. 337 - 339
(2007/10/03)
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- A simple and versatile method for the hydroiodination of alkenes and alkynes using I2 and Et3SiH in the presence of copper(II)
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The reagent system CuO·HBF4/I2/Et3SiH generates in situ hydrogen iodide which regioselectively adds to alkenes and alkynes. The mild nature of this system tolerates the presence of different groups on the unsaturated compound.
- Campos, Pedro J.,García, Bárbara,Rodríguez, Miguel A.
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p. 6111 - 6112
(2007/10/03)
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- Substituent Effects in the Intramolecular Diels-Alder Reaction of 6-Furylhexenoates
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The series of furyl enone esters, 4a-c, were synthesized from furan or furfural by straightforward routes. Their thermal intramolecular Diels-Alder reactions to give the tricyclic ketones 5a-c were studied in acetonitrile and toluene at two temperatures and the kinetics of the reactions determined. A comparison of these data with that obtained for the corresponding esters 2 to give the lactones 3 indicates that the rate enhancements seen for the esters (rate of dimethyl 310 times that of monomethyl) are much larger than those seen for the ketones (rate of dimethyl 6.8 times that of monomethyl). Thus, this is additional evidence for the earlier hypothesis that the presence of the oxygen atom in the tether is a factor responsible for the larger than normal rate enhancements.
- Jung, Michael E.,Kiankarimi, Mehrak
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p. 2968 - 2974
(2007/10/03)
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- STEREOCONTROLLED SYNTHESIS OF NATURALLY-OCCURRING POLYACETYLENES CHARACTERIZED BY (E)-1-EN-3-YNE, (E)-1-EN-3,5-DIYNE, (1E,5E)-1,5-DIEN-3-YNE, AND (1E,7E)-1,7-DIEN-3,5-DIYNE MOIETIES
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A stereocontrolled synthesis of five naturally-occurring polyacetylenes, i.e. methyl (E)-5-(2-thienyl)-2-penten-4-ynoate, 9, (E)-N-methyl-N-(2-methylpropyl)-2-decen-4,6-diynamide, 10, (E)-1-(3-methyl-2-butenoyloxy)-2-decen-4,6-diyne, 11, (2E,6E)-1-acetoxy-2,6-decadien-4-yne, 12, and (2E,8E)-1-acetoxy-2,8-decadien-4,6-diyne, 13, is reported.The flexible strategy involves palladium(0)-copper(I) catalyzed coupling reactions to construct the carbon skeleton of the target molecules and to prepare an important C5 building block, i.e. (E)-2-penten-4-yn-1-ol, 21.This compound is also an useful intermediate to lipoxins A and B.A highly diastereoselective palladium-catalyzed carbon-carbon bond forming reaction, recently developed in our laboratory, has been used in a key synthetic step to compound 12.
- Carpita, Adriano,Neri, Dario,Rossi, Renzo
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p. 481 - 490
(2007/10/02)
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