74654-06-1Relevant academic research and scientific papers
Enhancing the efficacy of photodynamic therapy (PDT) via water-soluble pillar[5]arene-based supramolecular complexes
Wu, Jian,Tian, Jia,Rui, Leilei,Zhang, Weian
, p. 7629 - 7632 (2018)
A supramolecular nanovesicle was constructed by complexation between pyrophaeophorbide A (PPhA) and water-soluble pillar[5]arene, and then a biotin-pyridinium targeting agent was introduced to its surface. This nanovesicle exhibited reduced aggregation of PPhA photosensitizers and high targeting ability towards cancer cells, thereby leading to excellent therapeutic efficacy under red light.
Simultaneous copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) and living radical polymerization
Geng, Jin,Lindqvist, Josefina,Mantovani, Giuseppe,Haddleton, David M.
, p. 4180 - 4183 (2008)
(Chemical Equation Presented) All in one: CuBr/iminopyridine systems can catalyze simultaneously both copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC, "click") and living radical polymerization (LRP) processes (see scheme). The relative rate of the two processes can be tailored by a judicious choice of the reaction conditions (solvent, temperature, [CuBr] 0) leading to the development of a potentially very efficient synthetic route to well-defined functional polymers.
[2 × 2] metallo-supramolecular grids based on 4,6-bis((1H-1,2,3-triazol-4-yl)-pyridin-2-yl)-2-phenylpyrimidine ligands: From discrete [2 × 2] grid structures to star-shaped supramolecular polymeric architectures
Hoogenboom, Richard,Jana, Somdeb,Jerca, Valentin Victor,Lenaerts, Ruben,Ryskulova, Kanykei,Seiffert, Anne K.,Van Hecke, Kristof,Xu, Xiaowen
, p. 8746 - 8751 (2021)
The self-assembly of bis-tridentate ligands leads to the spontaneous formation of [2 × 2] grid-like metal complexes. However, the synthesis of such ligands is rather cumbersome. In the work, we demonstrate a straightforward synthesis route to prepare bis-tridentate 4,6-bis((1H-1,2,3-triazol-4-yl)-pyridin-2-yl)-2-phenylpyrimidine ligands through double CuAAC click chemistry with 4,6-bis(6-ethynylpyridin-2-yl)-2-phenylpyrimidine as well as their self-assembly into [2 × 2] grid-like metal complexes. In addition, four macromolecular ligands were synthesized starting from azido-end-functionalized poly(2-ethyl-2-oxazoline) (PEtOx) or poly(ethylene glycol) (PEG). These macromolecular ligands were used in the construction of star-shaped supramolecular polymers through complexation with transition metal ions (e.g., Fe2+or Zn2+). The successful fabrication of complexes and star-shaped polymers was confirmed by UV-vis titration measurements and MALDI-TOF mass spectrometry. However, the chemical structure of the polymer was found to have a strong influence on the [2 × 2] grid formation, which was successful with the PEG-ligands but not with the PEtOx-ligands, while the molecular weight of the PEG did not interfere with grid formation.
A Molecular Strategy to Lock-in the Conformation of a Perylene Bisimide-Derived Supramolecular Polymer
Ashcraft, Adam,Bernard, Brianna,Husainy, Dalia,Liu, Chuan,Liu, Kaixuan,Mukhopadhyay, Arindam,Olivier, Jean-Hubert,Paulino, Victor,Phan, Tina
, p. 7487 - 7493 (2020/03/13)
Locking-in the conformation of supramolecular assemblies provides a new avenue to regulate the (opto)electronic properties of robust nanoscale objects. In the present contribution, we show that the covalent tethering of a perylene bisimide (PBI)-derived s
Targeting G Protein-Coupled Receptors with Magnetic Carbon Nanotubes: The Case of the A3 Adenosine Receptor
Pineux, Florent,Federico, Stephanie,Klotz, Karl-Norbert,Kachler, Sonja,Michiels, Carine,Sturlese, Mattia,Prato, Maurizio,Spalluto, Giampiero,Moro, Stefano,Bonifazi, Davide
, p. 1909 - 1920 (2020/09/11)
The A3 adenosine receptor (AR) is a G protein-coupled receptor (GPCR) overexpressed in the membrane of specific cancer cells. Thus, the development of nanosystems targeting this receptor could be a strategy to both treat and diagnose cancer. Iron-filled carbon nanotubes (CNTs) are an optimal platform for theranostic purposes, and the use of a magnetic field can be exploited for cancer magnetic cell sorting and thermal therapy. In this work, we have conjugated an A3AR ligand on the surface of iron-filled CNTs with the aim of targeting cells overexpressing A3ARs. In particular, two conjugates bearing PEG linkers of different length were designed. A docking analysis of A3AR showed that neither CNT nor linker interferes with ligand binding to the receptor; this was confirmed by in vitro preliminary radioligand competition assays on A3AR. Encouraged by this result, magnetic cell sorting was applied to a mixture of cells overexpressing or not the A3AR in which our compound displayed indiscriminate binding to all cells. Despite this, it is the first time that a GPCR ligand has been anchored to a magnetic nanosystem, thus it opens the door to new applications for cancer treatment.
Selective sensing of sulfate anions in water with cyclopeptide-decorated gold nanoparticles
Bartl, Julia,Koch, Marcus,Kubik, Stefan,Reinke, Lena
, p. 10457 - 10460 (2020/10/02)
The interaction of cyclopeptides bound to the surface of mixed monolayer-protected gold nanoparticles with sulfate anions causes the crosslinking and concomitant precipitation of the nanoparticles from aqueous solutions even in presence of an excess of competing anions, thus allowing the naked eye detection of sulfate in water.
Optical detection of di- And triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)-dipicolylamine complexes
Reinke, Lena,Bartl, Julia,Koch, Marcus,Kubik, Stefan
, p. 2687 - 2700 (2020/12/01)
Gold nanoparticles covered with a mixture of ligands of which one type contains solubilizing triethylene glycol residues and the other peripheral zinc(II)-dipicolylamine (DPA) complexes allowed the optical detection of hydrogenphosphate, diphosphate, and triphosphate anions in water/methanol 1:2 (v/v). These anions caused the bright red solutions of the nanoparticles to change their color because of nanoparticle aggregation followed by precipitation, whereas halides or oxoanions such as sulfate, nitrate, or carbonate produced no effect. The sensitivity of phosphate sensing depended on the nature of the anion, with diphosphate and triphosphate inducing visual changes at significantly lower concentrations than hydrogenphosphate. In addition, the sensing sensitivity was also affected by the ratio of the ligands on the nanoparticle surface, decreasing as the number of immobilized zinc(II)-dipicolylamine groups increased. A nanoparticle containing a 9:1 ratio of the solubilizing and the anion-binding ligand showed a color change at diphosphate and triphosphate concentrations as low as 10 μmol/L, for example, and precipitated at slightly higher concentrations. Hydrogenphosphate induced a nanoparticle precipitation only at a concentration of ca. 400 μmol/L, at which the precipitates formed in the presence of diphosphates and triphosphates redissolved. A nanoparticle containing fewer binding sites was more sensitive, while increasing the relative number of zinc(II)-dipicolylamine complexes beyond 25% had a negative impact on the limit of detection and the optical response. Transmission electron microscopy provided evidence that the changes of the nanoparticle properties observed in the presence of the phosphates were due to a nanoparticle crosslinking, consistent with the preferred binding mode of zinc(II)-dipicolylamine complexes with phosphate anions which involves binding of the anion between two metal centers. This work thus provided information on how the behavior of mixed monolayer-protected gold nanoparticles is affected by multivalent interactions, at the same time introducing a method to assess whether certain biologically relevant anions are present in an aqueous solution within a specific concentration range.
Anion Recognition in Water by Charge-Neutral Halogen and Chalcogen Bonding Foldamer Receptors
Borissov, Arseni,Marques, Igor,Lim, Jason Y.C.,Félix, Vítor,Smith, Martin D.,Beer, Paul D.
, p. 4119 - 4129 (2019/03/07)
A novel strategy for the recognition of anions in water using charge-neutral σ-hole halogen and chalcogen bonding acyclic hosts is demonstrated for the first time. Exploiting the intrinsic hydrophobicity of halogen and chalcogen bond donor atoms integrated into a foldamer structural molecular framework containing hydrophilic functionalities, a series of water-soluble receptors was constructed for an anion recognition investigation. Isothermal titration calorimetry (ITC) binding studies with a range of anions revealed the receptors to display very strong and selective binding of large, weakly hydrated anions such as I- and ReO4-. This is achieved through the formation of 2:1 host-guest stoichiometric complex assemblies, resulting in an encapsulated anion stabilized by cooperative, multidentate, convergent σ-hole donors, as shown by molecular dynamics simulations carried out in water. Importantly, the combination of multiple σ-hole-anion interactions and hydrophobic collapse results in I- affinities in water that exceed all known σ-hole receptors, including cationic systems (β2 up to 1.68 × 1011 M-2). Furthermore, the anion binding affinities and selectivity trends of the first example of an all-chalcogen bonding anion receptor in pure water are compared with halogen bonding and hydrogen bonding receptor analogues. These results further advance and establish halogen and chalcogen bond donor functions as new tools for overcoming the challenging goal of anion recognition in pure water.
A halogen-bonding foldamer molecular film for selective reagentless anion sensing in water
Hein, Robert,Borissov, Arseni,Smith, Martin D.,Beer, Paul D.,Davis, Jason J.
, p. 4849 - 4852 (2019/05/02)
We describe self-assembled monolayers of novel halogen-bonding and hydrogen-bonding foldamer receptors capable of selectively recruiting perrhenate, iodide and thiocyanate in water. Unprecedented anion sensing via impedance-derived capacitance spectroscopy enables subsequent sensitive and selective anion detection without the need for a redox probe. Importantly, the sensing of any anion should be possible using this novel electrochemical approach.
LANTHANIDE COMPLEXES COMPRISING DENDRIMERS
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, (2019/12/01)
The present invention relates to a complex comprising at least one dendrimer and at least one lanthanide, wherein the dendrimer comprises a unit of formula (I) below: in which: C1 is a valence group 4 of formula >N—CH2—CH2—N1, A2 and A3 are groups of formula —(CH2)2—C(O)—NH—(CH2)2—; the unit of formula (I) being connected covalently to at least one antenna which absorbs at a wavelength ranging from 500 nm to 900 nm.
