- Self-Assembly of Spherical Organic Molecules to Form Hollow Vesicular Structures in Water for Encapsulation of an Anticancer Drug and Its Release
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Developing hierarchical supramolecular structures is important for better understanding of various biological functions and possibly generating new materials for biomedical applications. Herein, we report the first examples of functional vesicles derived from cationic spherical organic molecules (C1-C3) which were readily synthesized by reacting a C3-symmetric tris-benzimmidazole derivative (possessing a 1,3,5-ethyl substituted aromatic core) with 1,3,5-substituted tris-bromomethyl benzene derivatives. Vesicle formation by C1-C3 was probed by high-resolution microscopy (TEM and AFM), dynamic light scattering (DLS) and fluorescence microscopic imaging of calcein-loaded vesicles. One of the vesicles [Vesicle(C3)] displayed the ability to load the anticancer drug doxorubicin (DOX). The drug was subsequently released from DOX@Vesicle(C3) in a stimuli-responsive manner in presence of the well-known vesicle destroyer Triton X-100, as revealed by in vitro cell migration assay carried out on a highly aggressive human breast cancer cell line (MDA-MB-231).
- Sarkar, Koushik,Ahmed, Sabir,Dastidar, Parthasarathi
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Read Online
- Synthesis of a novel tripodal receptor based on 1,8-naphthyridine derivatives
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A novel tripodal receptor, 1,3,5-tri((5,7-dimethyl-1,8-naphthyridin-2-yl-amino)methyl)-2,4,6-triethylbenzene (1) was synthesized from starting materials 2,6-diamino-pyridine (2) and 1,3,5-triethylbenzene (4) by three steps with an overall yield of 25%, and characterized by ESI-MS, FT-IR and 1H NMR spectra. Additionally, its absorption and emission spectra were investigated.
- Li, Hui Fang Jie,Fu, Wen Fu
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Read Online
- From transient sulfenic acids toward peculiar sulfurated molecules
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Sulfenic acids (R-SOH) frequently act as reactive intermediates in biological and synthetic chemistry. Among the numerous examples that Nature offers to our knowledge, cysteine-derived sulfenic acids are recognized as key intermediates in signal transduct
- Barattucci, Anna,Bonaccorsi, Paola
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Read Online
- A tricatecholic receptor for carbohydrate recognition: Synthesis and binding studies
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(Chemical Equation Presented) A new tripodal receptor bearing three catechol subunits on a benzene platform has been synthesized in four steps from 1,3,5-triethylbenzene and pyrogallol. The binding ability of the tricatecholic receptor was investigated to
- Cacciarmi, Martina,Cordiano, Elisa,Nativi, Cristina,Rodens, Stefano
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Read Online
- A Dichotomy in Cross-Coupling Site Selectivity in a Dihalogenated Heteroarene: Influence of Mononuclear Pd, Pd Clusters, and Pd Nanoparticles-The Case for Exploiting Pd Catalyst Speciation
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Site-selective dihalogenated heteroarene cross-coupling with organometallic reagents usually occurs at the halogen proximal to the heteroatom, enabled by intrinsic relative electrophilicity, particularly in strongly polarized systems. An archetypical exam
- Eyles, Anthony,Fairlamb, Ian J. S.,Ford, Mark J.,Jeddi, Neda,Scott, Neil W. J.,Simon, Lauriane,Tanner, Theo,Whitwood, Adrian C.,Willans, Charlotte E.
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supporting information
p. 9682 - 9693
(2021/07/19)
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- HEXASUBSTITUTED BENZENES, SURFACES MODIFIED THEREWITH, AND ASSOCIATED METHODS
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Phenyl rings provide a robust scaffold for molecular design, given the limited number of ring carbon atoms and the fixed geometry in between. However, it can be difficult to form highly substituted phenyl rings suitable for covalent attachment of multiple
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Paragraph 0028; 0154
(2021/03/19)
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- Covalent organic cage compound material with acid stimulation response function and preparation method and application thereof
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The invention belongs to the field of preparation of organic materials, and discloses synthesis and application of a covalent organic cage compound material with an acid stimulation response function. The preparation method is characterized by comprising
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Paragraph 0024
(2021/04/07)
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- Supramolecular Alloys from Fluorinated Hybrid Tri4Di6 Imine Cages
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To create innovative materials, efficient control and engineering of pore sizes and their characteristics, crystallinity and stability is required. Eight hybrid Tri4Di6 imine cages with a tunable degree of fluorination and one fully fluorinated Tri4Di6 imine cage are investigated. Although the fluorinated and the non-fluorinated building blocks used herein differ vastly in reactivity, it was possible to gain control over the outcome of the self-assembly process, by carefully controlling the feed ratio. This represents the first hybrid material based on fluorinated/hydrogenated porous organic cages (POCs). These cages with unlimited miscibility in the solid state were obtained as highly crystalline samples after recrystallization and even showed retention of the crystal lattice, forming alloys. All mixtures and the fully fluorinated Tri4Di6 imine cage were analyzed by MALDI-MS, single-crystal XRD, powder XRD and in regard to thermal stability (TGA).
- Kunde, Tom,Pausch, Tobias,Schmidt, Bernd M.
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supporting information
p. 8457 - 8460
(2021/05/24)
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- Photo-thermal platinum nanoparticle with mannose targeting as well as preparation method and application thereof
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The invention discloses a photo-thermal platinum nanoparticle with mannose targeting as well as a preparation method and application thereof. The photo-thermal platinum nanoparticle with mannose targeting is formed by self-assembling a polymer carrier, tw
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Paragraph 0028-0034
(2020/04/29)
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- Electroactive anion receptor with high affinity for arsenate
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Herein, we present the synthesis and characterization of a macrocyclic polyamide cage that incorporates redox-active 1,4-dithiin units. UV/vis titration experiments with eight anions in acetonitrile revealed high affinity for H2AsO4
- Etkind, Samuel I.,Vander Griend, Douglas A.,Swager, Timothy M.
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supporting information
p. 10050 - 10061
(2020/10/02)
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- Transformation of Imine Cages into Hydrocarbon Cages
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In contrast to organic cages which are formed by exploiting dynamic covalent chemistry, such as boronic ester cages, imine cages, or disulfide cages, those with a fully carbonaceous backbone are rarer. With the exception of alkyne metathesis based approac
- Schick, Tobias H. G.,Lauer, Jochen C.,Rominger, Frank,Mastalerz, Michael
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supporting information
p. 1768 - 1773
(2019/01/22)
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- Shape-Persistent [4+4] Imine Cages with a Truncated Tetrahedral Geometry
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The synthesis of shape-persistent organic cage compounds is often based on the usage of multiple dynamic covalent bond formation (such as imines) of readily available precursors. By careful choice of the precursors geometry, the geometry and size of the resulting cage can be accurately designed and indeed a number of different geometries and sizes have been realized to date. Despite of this fact, little is known about the precursors conformational rigidity and steric preorganization of reacting functional groups on the outcome of the reaction. Herein, the influence of conformational rigidity in the precursors on the formation of a [4+4] imine cage with truncated tetrahedral geometry is discussed.
- Lauer, Jochen C.,Zhang, Wen-Shan,Rominger, Frank,Schr?der, Rasmus R.,Mastalerz, Michael
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supporting information
p. 1816 - 1820
(2018/01/22)
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- Tripodal pyrrolotetrathiafulvalene receptors for recognition of electron-deficient molecular guests
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We report the synthesis of tripodal receptors with monopyrrolo- tetrathiafulvalene arms 1a,b, based on 1,3,5-substituted 2,4,6-triethylbenzene scaffold. The three converging pyrrolotetrathiafulvalene groups form an electron rich cone-shaped binding site. Molecular hosts 1a,b are capable of binding neutral electron deficient guests in solution, as well as positively charged pyridinium species in the gas phase.
- Watat, Michèle-Laure Lieunang,Dülcks, Thomas,Kemken, Dorit,Azov, Vladimir A.
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supporting information
p. 741 - 744
(2014/01/23)
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- Synthesis and coordination chemistry of a tris(benzene-o-dithiolato)- functionalized ligand as a siderophore analog
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As a siderophore analog, the tripodal tris(benzene-o-dithiol)- functionalized ligand H6-5, has been synthesized in four steps including the reaction of 1,3,5-(triaminomethyl)-2,4,6-triethylbenzene and 2,3-bis(isopropylmercapto)benzoyl chloride followed by removal of the S-protecting groups. Reaction of compound H6-5 with [Ti(OPr) 4] in the presence of (NEt4)Cl leads to the formation of complex (NEt4)2[Ti(5)] featuring three bidentate benzene-o-dithiolato donors from one ligand coordinated to the metal center. An X-ray diffraction structure analysis with crystals of (NEt4) 2[Ti(5)]·DMF has shown that the coordination geometry at the metal center is best described as distorted trigonal-prismatic with a twist angle of φav = 18:5°.
- Ruppel, Susanne,Schulte To Brinke, Christian,Hahn, F. Ekkehardt
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p. 551 - 556
(2013/07/26)
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- Differential recognition of mannose-based polysaccharides by tripodal receptors based on a triethylbenzene scaffold substituted with trihydroxybenzoyl moieties
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The tripodal receptors 1 and 2 based on a triethylbenzene scaffold substituted with trihydroxybenzoyl groups have been synthesised. The conformational preferences and carbohydrate-binding ability of 1 and 2 have been examined by NMR spectroscopy and model
- Carrero, Paula,Arda, Ana,Alvarez, Monica,Doyagueez, Elisa G.,Rivero-Buceta, Eva,Quesada, Ernesto,Prieto, Alicia,Solis, Dolores,Camarasa, Maria Jose,Perez-Perez, Maria Jesus,Jimenez-Barbero, Jesus,San-Felix, Ana
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- Mono- and trinuclear tripodal platinum(II) chelated complexes containing a pyridine/sulfoxide based anchoring framework
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New tripodal ligands 2,4,6-triethyl-1,3,5-tris{[1-(2-pyridinyl)ethenyl] sulfinylmethyl}benzenes 6, characterized by three pendant chains each containing both sulfoxide and pyridine moieties, were synthesized from the corresponding sulfenic acid and 2-ethy
- Barattucci, Anna,Plutino, M. Rosaria,Faggi, Cristina,Bonaccorsi, Paola,Monsu Scolaro, Luigi,Aversa, Maria Chiara
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p. 3412 - 3420
(2013/07/26)
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- Synthesis of a new tripodal chemosensor based on 2,4,6-triethyl-1,3,5- trimethylbencene scaffolding bearing thiourea and fluorescein for the chromo-fluorogenic detection of anions
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A tripodal receptor containing thiourea as binding site and fluorescein as signalling subunit has been designed, synthesized and used for the colorimetric detection of basic anions in DMSO solutions.
- Moragues, María E.,Santos-Figueroa, Luis E.,ábalos, Tatiana,Sancenón, Félix,Martínez-Má?ez, Ramón
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experimental part
p. 5110 - 5113
(2012/09/25)
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- From transient sulfenic acids to disulfide-functionalized tripodal structures
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The condensation of transient polysulfenic acids with thiols, some of which containing privileged structures, has been applied to the synthesis of tripodal disulfides. The easy access to this new kind of conformationally constrained polyfunctionalized com
- Aversa, Maria Chiara,Barattucci, Anna,Bonaccorsi, Paola
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scheme or table
p. 254 - 258
(2011/03/21)
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- Synthesis and supramolecular assemblies of tripodal 1,3,5- tris(phenoxymethyl)-2,4,6-triethylbenzene analogues
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Tripodal 1,3,5-tris(phenoxymethyl)-2,4,6-triethylbenzene analogues have been synthesized and structurally characterized by IR, 1H NMR and 13C NMR spectroscopy and HRMS, and additionally, the single crystal structures of compounds bea
- Ma, Mingliang,Kong, Lingwei,Li, Xiaoyan,Jin, Haishan,Zhao, Xiaoli,Wen, Ke
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scheme or table
p. 1503 - 1510
(2011/11/01)
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- Isopropylamino and isobutylamino groups as recognition sites for carbohydrates: Acyclic receptors with enhanced binding affinity toward β-galactosides
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Binding motifs observed in the crystal structures of protein-carbohydrate complexes, in particular the participation of the isopropyl/isobutyl side chain of valine/leucine in the formation of van der Waals contacts, have inspired the design of new artificial carbohydrate receptors. The new compounds, containing a trisubstituted triethylbenzene core, were expected to recognize sugar molecules through a combination of NH→O and OH→N hydrogen bonds, CH→π interactions, and numerous van der Waals contacts. 1H NMR spectroscopic titrations in competitive and noncompetitive media, as well as binding studies in two-phase systems, such as dissolution of solid carbohydrates in apolar media and phase transfer of sugars from aqueous into organic solvents, revealed effective recognition of neutral carbohydrates and β- vs α-anomer binding preferences in the recognition o' glycosides as well as significantly increased binding affinity of the receptors toward β-galactoside in comparison with the previously described receptors.
- Mazik, Monika,Sonnenberg, Claudia
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scheme or table
p. 6416 - 6423
(2010/12/20)
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- C3-symmetric proline-functionalized organocatalysts: Enantioselective michael addition reactions
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C3-Symmetric, tripodal catalyst 4 based on 1,3,5- triethylbenzene, which incorporates the features of a molecular receptor, is shown to catalyze Michael addition reactions ofcarbonyl compounds to β-nitrostyrenes in a high stereoselectivity (up to 99:1a dr and up to 98%ee). Copyright
- Moorthy, Jarugu Narasimha,Saha, Satyajit
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supporting information; experimental part
p. 6359 - 6365
(2011/03/17)
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- COMPOUNDS AND METHODS FOR CHELATING METALS IN AQUEOUS SOLUTIONS
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The present invention relates to a new class of organic compounds and their use, for example, to sequester metal ions, including actinides (such as uranium and plutonium), precious metals (such as gold, silver and platinum) and all other metals (such as transition metals), from aqueous solutions, such as bodies of water (including but not limited to ocean water, seawater, river water) and all other aqueous solutions. Specifically, the present invention relates to a new class of polydentate organic chelating agents and methods for their use to recover metals from aqueous solutions, such as uranium from seawater.
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Page/Page column 17-19
(2010/12/26)
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- Selective recognition and extraction of the uranyl ion
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A tripodal receptor capable of extracting uranyl ion from aqueous solutions has been developed. At a uranyl concentration of 400 ppm, the developed ligand extracts ～59% of the uranyl ion into the organic phase. The new receptor features three carboxylates
- Sather, Aaron C.,Berryman, Orion B.,Rebek Jr., Julius
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supporting information; experimental part
p. 13572 - 13574
(2010/12/18)
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- The advantage of covalent capture in the combinatorial screening of a dynamic library for the detection of weak interactions
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In this paper we address the advantage of screening a dynamic library by covalent capture in comparison with an approach in which the target is not covalently bound to the molecular receptor. The aim is the selection of recognition units for the binding of an anion (or polyanion) by relatively weak binding interactions, a situation typically found in supramolecular chemistry. To compare the two approaches, two model systems have been studied both based on the functionalization of a molecular platform, by reversible imine formation. In the case of the noncovalently bound substrate, the platform P1 is a trisubstituted benzene unit, 2,4,6-trimethylbenzene-1,3,5-tricarbaldehyde, to select: three recognition arms for the binding of the trisodium salt of benzene-1,3,5tricarboxylate. For the covalent-capture-based approach the platforms P2 and P4 are benzene derivatives with a tethered phosphonate target (tetrabutylammonium 2-formylphenyl ethylphosphonate) for the selection of a single recognition unit. The library of recognition elements comprises phenyl and ammonium-functionalized amines. We show that the selection of recognition units for the binding of the substrate with weak to medium, binding constants may encounter, by using a noncovalently bound substrate, serious problems. This is because the best conditions for the amplification of the library, that is, a large excess of variable recognition elements and target, lead also to competitive binding of the elements not bound to the platform, with the target. This may result in negligible amplification of the best-fit members of the library. In contrast, upon tethering the target to the platform and using the covalent-capture strategy for the selection of the recognition elements, significant amplification is observed, even for systems with much lower binding constants. Although competition with excess recognition units may also become an issue in the case of the tethered target, there is a way to overcome the problem by working at low concentrations.
- Martin, Marco,Gasparini, Giulio,Graziani, Matteo,Prins, Leonard J.,Scrimin, Paolo
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experimental part
p. 3858 - 3866
(2010/09/05)
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- Solution phase measurement of both weak σ and C-H...X - hydrogen bonding interactions in synthetic anion receptors
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A series of tripodal receptors preorganize electron-deficient aromatic rings to bind halides in organic solvents using weak σ anion-to-arene interactions or C-H...X- hydrogen bonds. 1H NMR spectroscopy proves to be a powerful techniq
- Berryman, Orion B.,Sather, Aaron C.,Hay, Benjamin P.,Meisner, Jeffrey S.,Johnson, Darren W.
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supporting information; experimental part
p. 10895 - 10897
(2009/02/05)
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- The pH controlled uptake/release of citrate by a tri-copper(II) complex
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The pH controlled movement of three copper ions inside a carefully designed receptor allows the recognition and uptake/release of citrate in aqueous solution in a manner that can be followed visually. The Royal Society of Chemistry and the Centre National
- Dacarro, Giacomo,Pallavicini, Piersandro,Taglietti, Angelo
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supporting information; experimental part
p. 1839 - 1842
(2009/02/07)
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- A combined experimental and theoretical study on the conformation of multiarmed chiral aryl ethers
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(Graph Presented) Four series of multiarmed chiral aryl ethers carrying two, three, five, or eight side-chains on a variety of aromatic core molecules (2-5) were prepared. The structure and conformation of 2 and 3 (in the solid state) were determined by the X-ray crystallographic analyses. While a pair of alternated (anti) conformers (i.e, up-down and down-up) were found in the crystal of 2, three side-arms in 3 were aligned in the same direction to give a C3-symmetric syn-conformation. Examinations by dispersion-corrected density functional (DFT-D) calculations revealed that two out of six anti- and two out of four syn-conformers of 2 are energetically most important. Two calculated structures of anti-conformers are in good agreement with those found in the solid state by X-ray analysis. Similarly, relevant conformations of syn-3, fully alternated 4, and C5-symmetric 5 were optimized at the DFT-D-B-LYP/TZVP level. The structure and conformation of the side-arms in 2-5 in solution were further studied by temperature dependent 1H NMR and UV-vis spectroscopy. In addition, comparative experimental and theoretical CD spectral studies were carried out in order to elucidate the contribution of the thermodynamically less-stable minor isomers in solution. The CD spectral changes observed for 2 and 3 at varying temperatures were quite different, while the parent chiral arene 1, as well as 4 and 5, only showed an increased intensity of the negative Cotton effect for the 1Lb band. The latter behavior is readily accounted for in terms of the conformational freezing of the chiral groups at low temperatures. The unusual CD spectral behavior observed for 2 and 3 was rationalized by the conformational alteration of the side-arms. Because of attractive van der Waals interactions between the aromatic units of the arms in nonpolar solvents, the syn-conformations become gradually more important for 2 at low temperatures, which eventually results in a weak positive Cotton effect for the 1Lb band. This was also supported by the SCS-MP2/TZVPP single-point energy calculations for the relevant conformers of 2. For 3, the contribution of the C3-symmetrical conformer becomes more important than the less-symmetrical isomers at low temperatures. The conformations of 2 and 3 in their excited states as well as in the oxidized states were also examined.
- Mori, Tadashi,Grimme, Stefan,Inoue, Yoshihisa
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p. 6998 - 7010
(2008/02/11)
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- Solvent-induced amphiphilic molecular baskets: Unimolecular reversed micelles with different size, shape, and flexibility
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Amphiphilic molecular baskets were obtained by attaching facially amphiphilic cholate groups to a covalent scaffold (calix[4]arene or 1,3,5-2,4,6-hexasubstituted benzene). In a solvent mixture consisting of mostly a nonpolar solvent (i.e., CCl4
- Ryu, Eui-Hyun,Yan, Jie,Zhong, Zhenqi,Zhao, Yan
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p. 7205 - 7213
(2008/02/01)
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- Preparation of 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene from two versatile 1,3,5-tri(halosubstituted) 2,4,6-triethylbenzene derivatives
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The use of 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene and the intermediates 1,3,5-tris(halomethyl)-2,4,6-triethylbenzene (halo = bromo and chloro) compounds, have been utilized as scaffolds for many molecular receptors. We report here for the first time a detailed practical synthetic procedure, starting from benzene, and in four straightforward steps, to prepare 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene, a very versatile molecular scaffold. The added advantage is the limited chromatography in the purification procedure. Georg Thieme Verlag Stuttgart.
- Wallace, Karl J.,Hanes, Robert,Anslyn, Eric,Morey, Jeroni,Kilway, Kathleen V.,Siegel, Jay
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p. 2080 - 2083
(2007/10/03)
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- Disposable receptor-based optical sensor for nitrate
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A new optical absorption-based disposable sensor for nitrate is described. The nitrate-sensitive element is a bicyclic cyclophane receptor next to a suitable pH-sensitive lipophilic dye immobilized in a plasticized polymeric membrane. The rigid amide-base
- Capitan-Vallvey, Luis Fermin,Arroyo-Guerrero, Eduardo,Fernandez-Ramos, Maria Dolores,Santoyo-Gonzalez
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p. 4459 - 4466
(2008/02/02)
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- A new tripodal receptor for molecular recognition of monosaccharides. A paradigm for assessing glycoside binding affinities and selectivities by 1H NMR spectroscopy
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A new tripodal receptor for the recognition of monosaccharides is described. The prototypical host 1 features a 1,3,5-substituted 2,4,6-triethylbenzene scaffold bearing three convergent H-bonding units. The binding ability of the t-octyl derivative 1a tow
- Vacca, Alberto,Nativi, Cristina,Cacciarini, Martina,Pergoli, Roberto,Roelens, Stefano
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p. 16456 - 16465
(2007/10/03)
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- "Flexiball" toolkit: A modular approach to self-assembling capsules
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We report the synthesis and characterization of new, self-assembling molecular capsules. The modular strategy makes use of glycoluril building blocks available in multigram amounts combined with aromatic spacer elements. The lengthy syntheses encountered with earlier generations of capsules are avoided, and several capsules of nanometer dimensions are now accessible. Single bond attachments between spacers and glycoluril modules result in monomers as dimeric capsules that are less rigid than their earlier counterparts. The host-guest properties of the homo- and heterodimeric capsules were studied using a combination of NMR and ESI-mass spectrometry. They show a less pronounced selectivity for guests of different sizes, and their increased flexibility prevents self-assembly when no rigidifying elements are present on the central spacer unit. Some of the new capsules bear inwardly directed, secondary amide N-H protons. These can be further functionalized, as shown by their methylation to give tertiary analogues. The structures hold broader implications for the placement of functional groups on concave molecular surfaces.
- O'Leary,Szabo,Svenstrup,Schalley,Luetzen,Schaefer,Rebek Jr.
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p. 11519 - 11533
(2007/10/03)
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- Metal triggered fluorescence sensing of citrate using a synthetic receptor
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A metal containing fluorescent chemosensor was designed, synthesized, and studied for the quantification of citrate in common beverages. The sensor consists of Cu(II) bound by a 1,10-phenanthroline ligand which is attached to a bis(aminoimidazolium) recep
- Cabell, Larry A.
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p. 315 - 323
(2007/10/03)
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- Synthesis, characterization and reactivity of copper(I) imidazole complexes based on a cavitand ligand design
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Two new cavitand-based imidazolyl ligands and their corresponding copper(I) complexes are reported; the tris(imidazole) complex is substitutionally inert while the bis(imidazole) complex readily reacts with CO, PMe3, N3- a
- Voo,Lam,Rheingold,Riordan
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p. 1803 - 1805
(2007/10/03)
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- A synthetic receptor selective for citrate
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Applied molecular recognition strong and selective binding of citrate in highly competitive media such as water and orange juice is reported. Five steps are enough to synthesize receptor 1 that is complementary in charge and shape to citrate. Electrostati
- Metzger,Lynch,Anslyn
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p. 862 - 865
(2007/10/03)
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- Synthesis of 1,3,5-Tris(bromomethyl)-2,4,6-triethylbenzene - a Versatile Precursor To Predisposed Ligand
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The previously unknown title compound was prepared by means of exhaustive bromomethylation of 1,3,5-triethylbenzene.It was used as a starting molecule in the synthesis of ligands carrying three thiourea groups.A predisposition of such ligands in an ababab-manner referring to the orientation of the substituents was confirmed by X-structure determination.
- Waladorff, Christian,Saak, Wolfgang,Pohl, Siegfrid
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p. 1601 - 1618
(2007/10/03)
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