- Synthesis and preliminary biological evaluation of O-2((2-[ 18F]fluoroethyl)methylamino)ethyltyrosine ([18F]FEMAET) as a potential cationic amino acid PET tracer for tumor imaging
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Amino acid transport is an attractive target for oncologic imaging. Despite a high demand of cancer cells for cationic amino acids, their potential as PET probes remains unexplored. Arginine, in particular, is involved in a number of biosynthetic pathways
- Chiotellis, Aristeidis,Mueller, Adrienne,Weyermann, Karin,Leutwiler, Dominique S.,Schibli, Roger,Ametamey, Simon M.,Kraemer, Stefanie D.,Mu, Linjing
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Read Online
- Development of a Photoactivatable Protein Phosphatase-1-Disrupting Peptide
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We describe here the development of a photoreleasable version of a protein phosphatase-1 (PP1)-disrupting peptide (PDP-Nal) that triggers protein phosphatase-1 activity. PDP-Nal is a 23 mer that binds to PP1 through several interactions. It was photocaged
- Henschke, Lars,K?hn, Maja,Makotta, Leslie,Trebacz, Malgorzata,Wang, Yansong
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- Facile synthesis of sulfotyrosine-containing α-conotoxins
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α-Conotoxins (Ctx) can selectively target distinct subtypes of nicotinic acetylcholine receptors (nAChRs), which are closely related to a number of neurological diseases, and they have been considered as ideal probes and model peptide drugs. Sulfotyrosine
- He, Chunmao,Li, Changpeng
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supporting information
p. 7559 - 7564
(2020/10/14)
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- DIMETHYLAMINOETHANOL SALT OF A GLP-1 RECEPTOR MODULATOR
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Crystalline 2-hydroxy-N,N-dimethylethanaminium 1 -(2-(5-(tert-butyl) -thiophene-2-carboxamido)-3-(4-(5-(4'-ethyl-[1,1'-bi(cyclohexan)]-3- en-4-yl)pyrimidin-2-yl)phenyl)propanoyl)azetidine-3-carboxylate salt, and methods related to synthesis and therapeuti
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Paragraph 125; 126; 127
(2018/04/17)
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- Base/Cryptand/Metal-Free Automated Nucleophilic Radiofluorination of [18F]FDOPA from Iodonium Salts: Importance of Hydrogen Carbonate Counterion
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As evidenced by the number of publications and patents published in the last years, the radiosynthesis of 6-[18F]fluoro-3,4-dihydroxy-L-phenylalanine ([18F]FDOPA) using the nucleophilic [18F]F- process remains currently a challenge for the radiochemists scientific community even if promising methods for the radiofluorination of electron-rich aromatic structures were recently developed from arylboronate, arylstannane or iodonium salt precursors. In such context, based on the use of an iodonium triflate salt precursor, we optimized a fast and efficient radiofluorination route fully automated and free from any base, cryptand or metal catalyst for the radiosynthesis of [18F]FDOPA. Using this method, this clinically relevant radiotracer was produced in 64 min, 27–38 % RCY d.c. (n = 5), >99 % RCP, >99 % ee., and high Am 170–230 GBq/μmol. In addition, this optimization study clearly highlighted the important role of a triflate-hydrogen carbonate counterion exchange during the radiolabeling process to achieve high fluorine-18 incorporation yields.
- Maisonial-Besset, Aurélie,Serre, Audrey,Ouadi, Ali,Schmitt, Sébastien,Canitrot, Damien,Léal, Fernand,Miot-Noirault, Elisabeth,Brasse, David,Marchand, Patrice,Chezal, Jean-Michel
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p. 7058 - 7065
(2019/01/04)
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- Development of a Kilogram-Scale Synthesis of a Novel Anti-HCV Agent, CH4930808
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Herein, we report the kilogram-scale synthesis of CH4930808 (1), a novel anti-hepatitis C virus agent. While pursuing improved productivity using many through-process strategies, we conducted scrupulous impurity control. Finally, we successfully developed
- Haneishi, Tsuyoshi,Kato, Yoshiaki,Fukuda, Hiroshi,Shimamura, Tomoyuki,Tanokura, Takemi,Hiraide, Akira,Koyama, Kaichiro,Fudesaka, Masato,Maeda, Kenji,Nakata, Nobuyuki,Nagase, Masahiro,Yabuzaki, Takahiko,Takao, Hiroaki,Kigawa, Masaharu,Shimizu, Hitoshi,Shimizu, Makoto
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p. 236 - 240
(2018/02/23)
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- NURR1:RXR ACTIVATING COMPOUNDS FOR SIMULTANEOUS TREATMENT OF SYMPTOMS AND PATHOLOGY OF PARKINSON'S DISEASE
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The invention provides a series of substituted aryl pyrimidine compounds and the use of these compounds as therapeutics to treat or prevent neurodegenerative disorders, including Parkinson's disease. Compounds of the invention are also able to treat the s
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Page/Page column 44
(2017/08/01)
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- THIAZOLIDINONE COMPOUNDS AND USE THEREOF
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A pharmaceutical composition containing a compound of Formula (I) for treating an opioid receptor-associated condition. Also disclosed is a method for treating an opioid receptor-associated condition using such a compound. Further disclosed are two sets of thiazolidinone compounds of formula (I): (i) compounds each having an enantiomeric excess greater than 90% and (ii) compounds each being substituted with deuterium.
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Paragraph 0708-0709
(2017/09/21)
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- COMPOSITIONS CONTAINING, METHODS INVOLVING, AND USES OF NON-NATURAL AMINO ACIDS AND POLYPEPTIDES
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Disclosed herein are non-natural amino acids and polypeptides that include at least one non-natural amino acid, and methods for making such non-natural amino acids and polypeptides. The non-natural amino acids, by themselves or as a part of a polypeptide, can include a wide range of possible functionalities, but typical have at least one oxime, carbonyl, dicarbonyl, and/or hydroxylamine group. Also disclosed herein are non-natural amino acid polypeptides that are further modified post-translationally, methods for effecting such modifications, and methods for purifying such polypeptides. Typically, the modified non-natural amino acid polypeptides include at least one oximine, carbonyl, dicarbonyl, and/or hydroxylamine group. Further disclosed are methods for using such non-natural amino acid polypeptides and modified non-natural amino acid polypeptides, including therapeutic, diagnostic, and other biotechnology uses.
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Page/Page column 197
(2016/07/27)
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- NOVEL GLP-1 RECEPTOR MODULATORS
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Compounds are provided that modulate the glucagon-like peptide 1 (GLP-1) receptor, as well as methods of their synthesis, and methods of their therapeutic and/or prophylactic use. Such compounds can act as modulators or potentiators of GLP-1 receptor on their own, or with incretin peptides such as GLP-1(7-36), GLP-1(9-36), and oxyntomodulin, or with peptide-based therapies, such as exenatide and liraglutide, and have the following general structure (where "?" represents either or both the R and S form of the compound): where A, B, C, R1, R2, R3, R4, R5, n, p and q are as defined herein.
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Paragraph 0384
(2016/02/09)
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- Synergistic Photobactericidal Activity Based on Ultraviolet-A Irradiation and Ferulic Acid Derivatives
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Ultraviolet-A (UV-A)-mediated bactericidal activity was enhanced by combined treatment with trans-ferulic acid (trans-FA, compound 1) or its derivatives. Derivative compounds 4 and 10 contain a phenyl group or an l-tyrosine HCl tert-butyl ester, respectiv
- Shirai, Akihiro,Kajiura, Masato,Omasa, Takeshi
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p. 1422 - 1428
(2015/11/10)
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- A novel SWCNT platform bearing DOTA and β-cyclodextrin units. "one shot" multidecoration under microwave irradiation
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The functionalization of single-walled carbon nanotubes (SWCNTs) via microwave-assisted grafting reactions enables efficient multidecoration in a single step. A novel water-soluble SWCNT platform was prepared via the simple 1,3-dipolar cycloaddition of azomethine ylides under dielectric heating. Thanks to a single grafting reaction the CNT surface binds in a 1:1 ratio an amino acidic β-cyclodextrin (β-CD) derivative and the DOTAMA moiety (1,4,7,10-tetraazacyclododecane-N,N′,N′′,N′′ ′-tetraacetic acid monoamide). This novel "one shot" synthesis, compared with multistep functionalizations, preserves the SWCNT's structural integrity (TEM images). Besides thermogravimetric analyses, the determination of the amount of β-CD and DOTA moieties grafting onto the SWCNT's surface was performed on the basis of phenolphthalein and gadolinium complexation, respectively. This journal is
- Calcio Gaudino,Tagliapietra,Martina,Barge,Lolli,Terreno,Lembo,Cravotto
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p. 4708 - 4715
(2014/06/24)
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- Study of the stability of the 5-aminolevulinic acid tyrosine ester in aqueous solution
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Photodynamic therapy based on photoactivable porphyrins (PAPs) can treat various dermatological conditions. The side-effects as well as the non-selective or insufficient accumulation of PAPs in the targeted tissues limit performances. We studied the stability in solution at different temperatures (21 °C; 4 °C), different pH values (7.5; 2.0), and as a function of time of 5-aminolevulinic acid's Tyrosine-ester, a molecule presenting interesting properties to selectively produce PAPs in blood vessels after topical application. Solutions of this precursor can be kept up to 24 h at refrigerated temperatures and under acidic pH. At room temperature or physiological pH, they must be prepared minutes before their use. ARKAT-USA, Inc.
- Gay, Sandrine,Martoccia, Carla,Zellweger, Matthieu,Wang, Qian,Wagnieres, Georges
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p. 228 - 238
(2014/06/09)
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- A resin-linker-vector approach to radiopharmaceuticals containing 18F: Application in the synthesis of O-(2-[18F]- Fluoroethyl)-L-tyrosine
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A Resin-linker-vector (RLV) strategy is described for the radiosynthesis of tracer molecules containing the radionuclide 18F, which releases the labelled vector into solution upon nucleophilic substitution of a polystyrene-bound arylsulfonate linker with [18F]-fluoride ion. Three model linker-vector molecules 7 a-c containing different alkyl spacer groups were assembled in solution from (4-chlorosulfonylphenyl)alkanoate esters, exploiting a lipase-catalysed chemoselective carboxylic ester hydrolysis in the presence of the sulfonate ester as a key step. The linker-vector systems were attached to aminomethyl polystyrene resin through amide bond formation to give RLVs 8 a-c with acetate, butyrate and hexanoate spacers, which were characterised by using magic-angle spinning (MAS) NMR spectroscopy. On fluoridolysis, the RLVs 8 a, b containing the longer spacers were shown to be more effective in the release of the fluorinated model vector (4-fluorobutyl)phenylcarbamic acid tert-butyl ester (9) in NMR kinetic studies and gave superior radiochemical yields (RCY≈60 %) of the 18F- labelled vector. The approach was applied to the synthesis of the radiopharmaceutical O-(2-[18F]-fluoroethyl)-L-tyrosine ([ 18F]-FET), delivering protected [18F]-FET in >90 % RCY. Acid deprotection gave [18F]-FET in an overall RCY of 41 % from the RLV. Copyright
- Topley, Amy C.,Isoni, Valerio,Logothetis, Thomas A.,Wynn, Duncan,Wadsworth, Harry,Gibson, Alex M. R.,Khan, Imtiaz,Wells, Neil J.,Perrio, Cécile,Brown, Richard C.D.
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supporting information
p. 1720 - 1725
(2013/02/25)
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- Divergent and site-selective solid-phase synthesis of sulfopeptides
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On solid ground: A solid-phase strategy for the efficient synthesis of sulfopeptides is described. Selective deprotection of orthogonally-protected tyrosine residues and solid-phase sulfation provided divergent access to differentially sulfated peptides in high yields. Copyright
- Taleski, Deni,Butler, Stephen J.,Stone, Martin J.,Payne, Richard J.
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supporting information
p. 1316 - 1320
(2013/01/11)
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- PRODRUGS OF OXAZOLIDINONE CETP INHIBITORS
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The compounds of Formula I are prodrugs of CETP inhibitors having a central oxazolidinone ring. The compounds cyclize by the elimination of HX to form an oxazolidinone ring after administration to a patient.
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Page/Page column 9
(2010/04/27)
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- Substituted ureas as cell adhesion inhibitors
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Compounds of Formula I are antagonists of VLA-4 and/or α4β7, and as such are useful in the inhibition or prevention of cell adhesion and cell-adhesion mediated pathologies. These compounds may be formulated into pharmaceutical compositions and are suitable for use in the treatment of AIDS-related dementia, allergic conjunctivitis, allergic rhinitis, Alzheimer's disease, asthma, atherosclerosis, autologous bone marrow transplantation, certain types of toxic and immune-based nephritis, contact dermal hypersensitivity, inflammatory bowel disease including ulcerative colitis and Crohn's disease, inflammatory lung diseases, inflammatory sequelae of viral infections, meningitis, multiple sclerosis, multiple myeloma, myocarditis, organ transplantation, psoriasis, pulmonary fibrosis, restenosis, retinitis, rheumatoid arthritis, septic arthritis, stroke, tumor metastasis, uveititis, and type I diabetes.
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Page column 28
(2010/02/05)
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- N-aryl 2,6-dimethoxybiphenylalanine analogues as VLA-4 antagonists
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A series of N-arylated phenylalanine derivatives has been synthesized and has been shown to be potent inhibitors of the integrin VLA-4. N-phenyl and N-heteroaryl derivatives with hydrogen bond acceptors in the meta position demonstrated low nanomolar acti
- Doherty, George A.,Kamenecka, Theodore,McCauley, Ermenegilda,Van Riper, Gail,Mumford, Richard A.,Tong, Sharon,Hagmann, William K.
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p. 729 - 731
(2007/10/03)
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- Design of new mononucleotide prodrugs: Aryl (SATE) phosphotriester derivatives
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Synthesis, biological activities and decomposition kinetics of novel phosphotriester derivatives of 3′-azido-2′,3′-dideoxythymidine (AZT) bearing a S-tButyl-2-thioethyl (tBuSATE) group and L-tyrosinyl residues are reported. All the derivatives appeared to
- Peyrottes,Schlienger,Beltran,Lefebvre,Pompon,Gosselin,Aubertin,Imbach,Perigaud
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p. 315 - 321
(2007/10/03)
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- S-acyl-2-thioethyl aryl phosphotriester derivatives as mononucleotide prodrugs
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The synthesis and biological activities of phosphotriester derivatives of 3′-azido-2′,3′-dideoxythymidine (AZT) bearing a phenyl group or L-tyrosinyl residues are reported. The target compounds were obtained via either PV or PIII che
- Schlienger,Peyrottes,Kassem,Imbach,Gosselin,Aubertin,Périgaud
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p. 4570 - 4574
(2007/10/03)
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- 2-Phenyl isopropyl and t-butyl trichloroacetimidates: Useful reagents for ester preparation of N-protected amino acids under neutral conditions
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2-Phenylisopropyl and t-butyl trichloroacetamidates 1 and 2 are useful reagents for the esterification of N-protected aminoacids under mild neutral conditions. In the case of hydroxyl-containing amino acids dialkylation occurs but no selectivity could be obtained.
- Thierry, Josiane,Yue, Chongwei,Potier, Pierre
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p. 1557 - 1560
(2007/10/03)
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