Browse
Submit Data
Databases
API
Help

Dataset Information

10 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Triptycene Walled Glycoluril Trimer: Synthesis and Recognition Properties.

ABSTRACT: We report the synthesis of a new acyclic CB[n]-type host (1) that features a central glycoluril trimer capped by triptycene sidewalls. Host 1 has good solubility in water (≈ 3 mM) and does not undergo strong self-association (K_s = 480 M^-1). We probed the geometry of the complexes by analyzing the complexation induced changes in the ¹H NMR spectra and measured the complexation thermodynamics by isothermal titration calorimetry. The conformation of 1 and its packing in the solid state was revealed by single crystal x-ray diffraction measurements.

SUBMITTER: Ndendjio SZ

PROVIDER: S-EPMC8049523 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Recognition of nucleic acid junctions using triptycene-based molecules.

Project description:The modulation of nucleic acids by small molecules is an essential process across the kingdoms of life. Targeting nucleic acids with small molecules represents a significant challenge at the forefront of chemical biology. Nucleic acid junctions are ubiquitous structural motifs in nature and in designed materials. Herein, we describe a new class of structure-specific nucleic acid junction stabilizers based on a triptycene scaffold. Triptycenes provide significant stabilization of DNA and RNA three-way junctions, providing a new scaffold for the development of nucleic acid junction binders with enhanced recognition properties. Additionally, we report cytotoxicity and cell uptake data in two human ovarian carcinoma cell lines.

| S-EPMC4265365 | biostudies-literature

Synthesis of Chiral Helic[1]triptycene[3]arenes and Their Enantioselective Recognition Towards Chiral Guests Containing Aminoindan Groups.

Project description:Starting from the enantiopure precursors, a pair of chiral macrocyclic arenes named helic[1]triptycene[3]arenes were conveniently synthesized. The circular dichroism (CD) spectra of the enantiomeric macrocyclic arenes exhibited mirror images, and the X-ray single crystal structures confirmed their absolute conformations as well. Moreover, the macrocyclic arenes showed strong complexation with secondary ammonium and primary ammonium salts containing aminoindan groups. In particular, the chiral macrocyclic arenes exhibited enantioselective recognition ability towards the chiral secondary ammonium salts containing aminoindan groups with an enantioselective ratio up to 3.89.

| S-EPMC7864338 | biostudies-literature

Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives.

Project description:A new class of molecules with a triptycene rigid core surrounded by six monosaccharide residues was synthesized. Hexakis(bromomethyl) substituted triptycene was converted into a six-armed triptycene azide (2,3,6,7,14,15-hexakis(azidomethyl)-9,10-dihydro-9,10-[1',2']benzenoanthracene). The key step of the synthesis was the cycloaddition of the azide to 2-propyn-1-yl ?-D-gluco- or galactopyranosides. All products were isolated in good yields and were fully characterized.

| S-EPMC3869296 | biostudies-literature

Synthesis, characterization and DNA interaction studies of new triptycene derivatives.

Project description:A facile and efficient synthesis of a new series of triptycene-based tripods is being reported. Using 2,6,14- or 2,7,14-triaminotriptycenes as synthons, the corresponding triazidotriptycenes were prepared in high yield. Additionally, we report the transformation of 2,6,14- or 2,7,14-triaminotriptycenes to the corresponding ethynyl-substituted triptycenes via their tribromo derivatives. Subsequently, derivatization of ethynyl-substituted triptycenes was studied to yield the respective propiolic acid and ethynylphosphine derivatives. Characterization of the newly functionalized triptycene derivatives and their regioisomers were carried out using FTIR and multinuclear NMR spectroscopy, mass spectrometry, and elemental analyses techniques. The study of the interaction of these trisubstituted triptycenes with various forms of DNA revealed interesting dependency on the functional groups of the triptycene core to initiate damage or conformational changes in DNA.

| S-EPMC4077457 | biostudies-literature

Antibody recognition of the Pneumovirus fusion protein trimer interface.

Project description:Human metapneumovirus (hMPV) is a leading cause of viral respiratory infection in children, and can cause severe lower respiratory tract infection in infants, the elderly, and immunocompromised patients. However, there remain no licensed vaccines or specific treatments for hMPV infection. Although the hMPV fusion (F) protein is the sole target of neutralizing antibodies, the immunological properties of hMPV F remain poorly understood. To further define the humoral immune response to the hMPV F protein, we isolated two new human monoclonal antibodies (mAbs), MPV458 and MPV465. Both mAbs are neutralizing in vitro and were determined to target a unique antigenic site using competitive biolayer interferometry. We determined both MPV458 and MPV465 have higher affinity for monomeric hMPV F than trimeric hMPV F. MPV458 was co-crystallized with hMPV F, and the mAb primarily interacts with an alpha helix on the F2 region of the hMPV F protein. Surprisingly, the major epitope for MPV458 lies within the trimeric interface of the hMPV F protein, suggesting significant breathing of the hMPV F protein must occur for host immune recognition of the novel epitope. In addition, significant glycan interactions were observed with a somatically mutated light chain framework residue. The data presented identifies a novel epitope on the hMPV F protein for epitope-based vaccine design, and illustrates a new mechanism for human antibody neutralization of viral glycoproteins.

| S-EPMC7598476 | biostudies-literature

Towards triptycene functionalization and triptycene-linked porphyrin arrays.

Project description:Herein, 9,10-diethynyltriptycene is investigated for its use as a rigid isolating unit in the synthesis of multichromophoric arrays. Sonogashira cross-coupling conditions are utilized to attach various porphyrins and boron dipyrromethenes (BODIPYs) to the triptycene scaffold. While there are previous examples of triptycene porphyrin complexes, this work reports the first example of a linearly connected porphyrin dimer, linked through the bridgehead carbons of triptycene. Symmetric and unsymmetric examples of these complexes are demonstrated and single crystal X-ray analysis of an unsymmetrically substituted porphyrin dimer highlights the evident linearity in these systems. Moreover, initial UV-vis and fluorescence studies show the promise of triptycene as a linker for electron transfer studies, showcasing its isolating nature.

| S-EPMC7176921 | biostudies-literature

A Triptycene-Based Enantiopure Bis(Diazadibenzoanthracene) by a Chirality-Assisted Synthesis Approach.

Project description:By applying a chirality-assisted synthesis (CAS) approach enantiopure diaminodibromotriptycenes were converted to rigid chiral helical diazadibenzoanthracenes, which show besides pronounced Cotton effects in circular dichroism spectra higher photoluminescence quantum yields as comparable carbacyclic analogues. For the enantiopure building blocks, a protocol was developed allowing the large scale synthesis without the necessity of separation via HPLC.

| S-EPMC7756852 | biostudies-literature

Synthesis of Bis-Terpyridine-Based Metallopolymers and the Thermoelectric Properties of Their Single Walled Carbon Nanotube Composites.

Project description:Although the organic and the conventional inorganic thermoelectric (TE) materials have been extensively developed in recent years, the number of cases involving conducting metallopolymers is still quite limited. In view of the versatile coordination capability of the terpyridine fraction and the electron-rich nature of the 3,4-ethylenedioxythiophene moiety, a bis-terpyridine-featured ligand was designed, and a series of metallopolymers were then synthesized. Upon the addition of single-walled carbon nanotube (SWCNT), the TE properties of the resulting metallopolymer-SWCNT composite films were investigated. It was found that metal centres played an important role in affecting the morphology of the thin films, which was a key factor that determined the TE performances of the composites. Additionally, the energy levels of the metallopolymers were feasibly tuned by selecting different metal centres. With the combined effects of a uniform and condensed surface and an optimized band structure, the highest power factor was achieved by the Cu(II)-containing metallopolymer-SWCNT composite at the doping ratio of 75%, which reached 38.3 μW·m-1·K-2.

| S-EPMC8124700 | biostudies-literature

Single-walled vs. Multi-walled Carbon Nanotubes: Influence of Physico-Chemical Properties on Toxicogenomics Responses in Mouse Lungs

Project description:Transcriptional profiling of mouse lung tissue comparing control vs exposure to different carbon nanotubes. The aim was to determine if the physico-chemical properties influence the genotoxic, inflammatory and pro-fibrotic responses.

2023-03-16 | GSE223520 | GEO

1-Iodo-triptycene.

Project description:The title compound, C(20)H(13)I, is a halogenated derivative of triptycene. The mol-ecule shows crystallographic as well as non-crystallographic C(3) symmetry. The asymmetric unit comprises one third of the mol-ecule. Dispersive I?I contacts [I?I = 3.6389?(3)?Å] connect the mol-ecules into dimers. The shortest centroid-centroid distance between two ?-systems is 3.8403?(12)?Å.

| S-EPMC3200641 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data