220040-48-2Relevant articles and documents
Monopicolinate cyclen and cyclam derivatives for stable copper(II) complexation
Lima, Luis M. P.,Esteban-Gomez, David,Delgado, Rita,Platas-Iglesias, Carlos,Tripier, Raphael
, p. 6916 - 6927 (2012)
The syntheses of a new 1,4,7,10-tetraazacyclododecane (cyclen) derivative bearing a picolinate pendant arm (HL1), and its 1,4,8,11- tetraazacyclotetradecane (cyclam) analogue HL2, were achieved by using two different selective-protection methods involving the preparation of cyclen-bisaminal or phosphoryl cyclam derivatives. The acid-base properties of both compounds were investigated as well as their coordination chemistry, especially with Cu2+, in aqueous solution and in solid state. The copper(II) complexes were synthesized, and the single crystal X-ray diffraction structures of compounds of formula [Cu(HL)](ClO4)2· H2O (L = L1 or L2), [CuL1](ClO4) and [CuL2] Cl·2H2O, were determined. These studies revealed that protonation of the complexes occurs on the carboxylate group of the picolinate moiety. Stability constants of the complexes were determined at 25.0 °C and ionic strength 0.10 M in KNO3 using potentiometric titrations. Both ligands form complexes with Cu2+ that are thermodynamically very stable. Additionally, both HL1 and HL2 exhibit an important selectivity for Cu2+ over Zn2+. The kinetic inertness in acidic medium of both complexes of Cu2+ was evaluated by spectrophotometry revealing that [CuL2]+ is much more inert than [CuL1]+. The determined half-life values also demonstrate the very high kinetic inertness of [CuL2]+ when compared to a list of copper(II) complexes of other macrocyclic ligands. The coordination geometry of the copper center in the complexes was established in aqueous solution from UV-visible and electron paramagnetic resonance (EPR) spectroscopy, showing that the solution structures of both complexes are in excellent agreement with those of crystallographic data. Cyclic voltammetry experiments point to a good stability of the complexes with respect to metal ion dissociation upon reduction of the metal ion to Cu+ at about neutral pH. Our results revealed that the cyclam-based ligand HL2 is a very attractive receptor for copper(II), presenting a fast complexation process, a high kinetic inertness, and important thermodynamic and electrochemical stability.
MODULATORS OF MAS-RELATED G-PROTEIN RECEPTOR X4 AND RELATED PRODUCTS AND METHODS
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Page/Page column 168-170, (2020/10/18)
Methods are provided for modulating MRGPR X4 generally, or for treating a MRGPR X4 dependent condition more specifically, by contacting the MRGPR X4 or administering to a subject in need thereof, respectively, an effective amount of a compound having the structure of Formula (I): (I) or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein n, x, A, Q1, Q2, Z, R, R1, R2, R3, R4 and R5 are as defined herein. Pharmaceutical compositions containing such compounds, as well as to compounds themselves, are also provided.
OXOPYRIDINE DERIVATIVES USEFUL AS AMINOCARBOXYMUCONATE SEMIALDEHYDE DECARBOXYLASE (ACMSD) INHIBITORS
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Page/Page column 63, (2018/07/29)
The present invention is related to a compound represented by the following structural formula: The present invention is also related a method of treating a subject with a disease which can be ameliorated by inhibition of aminocarboxymuconate semialdehyde decarboxylase (ACMSD).
Optimizing the readout of lanthanide-DOTA complexes for the detection of ligand-bound copper(I)
Hanna, Jill R.,Allan, Christopher,Lawrence, Charlotte,Meyer, Odile,Wilson, Neil D.,Hulme, Alison N.
supporting information, (2017/06/08)
The CuAAC 'click' reaction was used to couple alkyne-functionalized lanthanide-DOTA complexes to a range of fluorescent antennae. Screening of the antenna components was aided by comparison of the luminescent output of the resultant sensors using data normalized to account for reaction conversion as assessed by IR. A maximum 82-fold enhanced signal:background luminescence output was achieved using a Eu(III)-DOTA complex coupled to a coumarin-azide, in a reaction which is specific to the presence of copper(I). This optimized complex provides a new lead design for lanthanide-DOTA complexes which can act as irreversible 'turn-on' catalytic sensors for the detection of ligand-bound copper(I).
SUBSTITUTED BICYCLIC AZA-HETEROCYCLES AND ANALOGUES AS SIRTUIN MODULATORS
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Paragraph 0720; 0721, (2017/04/04)
Provided herein are novel substituted bicyclic aza-heterocycle sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.
Novel optimization of valmerins (tetrahydropyrido[1,2- a ]isoindolones) as potent dual CDK5/GSK3 inhibitors
Ouach, Aziz,Boulahjar, Rajaa,Vala, Christine,Bourg, Stéphane,Bonnet, Pascal,Guguen-Guillouzo, Christiane,Ravache, Myriam,Le Guevel, Rémy,Lozach, Olivier,Lazar, Sa?d,Troin, Yves,Meijer, Laurent,Ruchaud, Sandrine,Akssira, Mohamed,Guillaumet, Gérald,Routier, Sylvain
, p. 311 - 325 (2016/04/05)
An efficient synthetic strategy able to modulate the structure of the tetrahydropyridine isoindolone (Valmerin) skeleton was developed. A library of more than 30 novel final structures was generated. Biological activities on CDK5 and GSK3 as well as cellular effects on cancer cell lines were measured for each novel compound. Additionally to support the SAR, a docking study was performed. A potent GSK3/CDK5 dual inhibitor (37, IC50 CDK5/GSK3 35/7 nM) was obtained. Best antiproliferative effects were obtained on lung and prostate cell lines with IC50 Combining double low line 20 nM.
Separation of Am (III) by solvent extraction using water-soluble H4tpaen derivatives
Gracia, Stéphanie,Arrachart, Guilhem,Marie, Cécile,Chapron, Simon,Miguirditchian, Manuel,Pellet-Rostaing, Stéphane
, p. 5321 - 5336 (2015/07/15)
The water-soluble ligand N,N,N′,N′-tetrakis[(6-carboxypyridin-2-yl)methyl]ethylenediamine (H4tpaen) and its derivatives were synthesized and evaluated for Am/Cm separation by solvent extraction. In this context, different ligands were studied for their possible use as selective back-extraction agents of actinides, especially americium, from an organic TPH phase. The solvent consisted of different extractants mixtures (DMDOHEMA/HDEHP or TODGA/TBP systems) and was preliminarily loaded with trivalent lanthanide and actinide cations. The aim of these new water-soluble agents was to strip americium or curium in an aqueous acidic phase in order to perform their mutual separation while maintaining other cations in the organic phase. A specific ligand bearing n-alkoxy groups connected to the pyridyl rings of H4tpaen showed water solubility slightly enhanced associated with efficient back-extraction properties with the possibility to perform simultaneously inter-group separation of Am (III) from Eu (III), and intra-group separation of Am(III) from Cm(III).
Cation-Transporting Peptides: Scaffolds for Functionalized Pores?
Behera, Harekrushna,Ramkumar, Venkatachalam,Madhavan, Nandita
supporting information, p. 10179 - 10184 (2015/07/07)
Protein pores that selectively transport ions across membranes are among nature's most efficient machines. The selectivity of these pores can be exploited for ion sensing and water purification. Since it is difficult to reconstitute membrane proteins in their active form for practical applications it is desirable to develop robust synthetic compounds that selectively transport ions across cell membranes. One can envision tuning the selectivity of pores by incorporating functional groups inside the pore. Readily accessible octapeptides containing (aminomethyl)benzoic acid and alanine are reported here that preferentially transport cations over halides across the lipid bilayer. Ion transport is hypothesized through pores formed by stable assemblies of the peptides. The aromatic ring(s) appear to be proximal to the pore and could be potentially utilized for functionalizing the pore interior.
SUBSTITUTED BICYCLIC AZA-HETEROCYCLES AND ANALOGUES AS SIRTUIN MODULATORS
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Page/Page column 186; 187; 194, (2013/05/09)
Provided herein are novel substituted bicyclic aza-heterocycle sirtuin- modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin- modulating compound in combination with another therapeutic agent.
Two-way linkage photoisomerization of [Ru(2,2':6',2''-terpyridine)(6- {(methylsulfinyl)methyl}picolinate)]BF4
Suzuki, Shoko,Sakamoto, Ryota,Nishihara, Hiroshi
supporting information, p. 17 - 18 (2013/03/14)
[Ru(tpy)(picSO)]BF4 (tpy: 2,2':6',2''-terpyridine, picSO: 6- [(methylsulfinyl)methyl]picolinate) undergoes profound linkage isomerization behavior between stable S-bound and metastable O-bound isomers. S-[RuII(tpy)(picSO)]BF4 experiences photoisomerization to O-[RuII(tpy)(picSO)] BF4 upon irradiation with 436nm light, whereas the back reaction is triggered with 546nm light. Electrochemical linkage isomerization also takes place.
