Article
Biochemistry & Molecular Biology
Patryk Niedbala, Kajetan Dabrowa, Agnieszka Cholewiak-Janusz, Janusz Jurczak
Summary: This study presents the synthesis and anion binding studies of a family of homologous molecular receptors based on a DITIPIRAM platform. The host-guest system offers multiple NH hydrogen bond donors to anions, forming stable complexes with carboxylates and chloride anions even in competitive solvent mixtures. Receptors 5 and 6 containing electron-withdrawing F- and -CF3 para-substituents were found to be the most effective derivatives in the series.
Article
Biochemistry & Molecular Biology
Krystyna Maslowska-Jarzyna, Maria L. Korczak, Jakub A. Wagner, Michal J. Chmielewski
Summary: The study describes the synthesis of 1,8-diaminocarbazoles with electron-withdrawing substituents, leading to enhanced anion affinities and acidities in the resulting receptors. The newly developed colorimetric anion sensor showed vivid color and fluorescence changes upon addition of basic anions, but exhibited poor selectivity due to the dominant proton transfer interaction with most anions. These highly acidic and strongly binding receptors may have potential applications in organocatalysis or pH-switchable anion transport through lipophilic membranes.
Article
Chemistry, Multidisciplinary
Oscar Francesconi, Francesco Milanesi, Cristina Nativi, Stefano Roelens
Summary: The study introduces a biomimetic receptor with unprecedented affinity for recognizing GlcNAc(2) in water, showing great selectivity among structurally related disaccharides and complete discrimination between mono- and disaccharides. Molecular modeling calculations supported by NOE data provided insights into the binding mode and origin of the affinities and selectivities exhibited by the receptor.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biochemistry & Molecular Biology
Patryk Niedbala, Kajetan Dabrowa, Sylwia Wasilek, Janusz Jurczak
Summary: Recognition of anionic species is crucial in various chemical, biological, and environmental processes. Despite progress in the molecular recognition of anions by synthetic receptors, design of receptors for chiral anions lags behind. Chiral recognition requires precise spatial organization and understanding this phenomenon may lead to more efficient receptor design.
Article
Biochemistry & Molecular Biology
Andrea Weisse, Wilhelm Seichter, Monika Mazik
Summary: In this study, a series of mono- and dicationic compounds containing pyridinium groups were synthesized and investigated, providing important insights into the development of new receptor molecules for anions and the selection of appropriate counterions through crystallographic analysis of their interactions with PF6- ions.
Review
Chemistry, Organic
Romain Plais, Gilles Clavier, Jean-Yves Salpin, Anne Gaucher, Damien Prim
Summary: Anion recognition is a prominent topic in supramolecular chemistry. Recent years have seen great progress in the design of new anion receptors, and the combination of experimental and theoretical studies has enhanced our understanding of anion complexation processes. This review highlights the use of anion-pi and hydrogen bonds and the concept of cooperativity in anion recognition, with specific examples from current literature.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Alex Iglesias-Reguant, Judyta Zielak-Milewska, Tomasz Misiaszek, Robert Zalesny, Josep M. Luis, Borys Osmialowski
Summary: This study investigates the halogen-bonding interactions between a pyridine-functionalized fluoroborate dye and perfluorohaloarenes using fluorescence spectroscopy. The results indicate that only the complex formed between C6F5I and the emissive dye is stable, and halogen-bonding interactions lead to significant Stokes shifts for the pi pi * band. Experimental evidence also shows that the emission of this complex is suppressed due to a simultaneous decrease in radiative decay rate constant and an increase in nonradiative decay rate constant.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Rebecca L. L. Spicer, Curtis C. C. Shearman, Nicholas H. H. Evans
Summary: This study presents the synthesis of two mechanically chiral rotaxanes with urea and squaramide motifs, with yields of 33% and 22% respectively. H-1 NMR spectroscopic titrations reveal the possibility of shuttling the macrocycle, detectable through modulation of mechanical chirality expression in the NMR spectrum, by the addition of achiral chloride anions, which can be reversed by the addition of sodium cations.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Canjia Zhai, Chengkai Xu, Yunpeng Cui, Lukasz Wojtas, Wenqi Liu
Summary: A biomimetic receptor with high affinity and selectivity for glucose has been synthesized using dynamic imine chemistry. The receptor features two durene panels and two pyridinium residues, which enhance solubility and provide polarized C-H bonds for substrate binding. These findings demonstrate the potential of dynamic covalent chemistry for creating molecular receptors and advancing carbohydrate recognition in water.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Oscar Francesconi, Francesco Milanesi, Cristina Nativi, Stefano Roelens
Summary: In designing new biomimetic receptors for carbohydrates, shape-persistent macrocyclic structures are commonly chosen for effective recognition of neutral saccharides in water. However, this study found that acyclic receptors, while less explored, provide advantages in terms of selectivity for recognizing important 1,4-disaccharides in biological contexts. NMR spectroscopic data and molecular modeling calculations were used to analyze the differences in binding mode and shed light on the origin of recognition efficacy and selectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biochemistry & Molecular Biology
Daniel Sebena, Kevin Rudolph, Bibhisan Roy, Christoph Woelper, Till Nitschke, Sarah Lampe, Michael Giese, Jens Voskuhl
Summary: This article presents fluorescent guanidiniocarbonyl-indoles as versatile oxo-anion binders, comparing their photophysical properties and binding behavior with the well-known guanidiniocarbonyl-pyrrole. The study found that the guanidiniocarbonyl-indoles efficiently bind carboxylates, phosphonates, and sulfonates, making them promising emissive oxo-anion binders. Additionally, the introduction of a methoxy-group successfully shifted the excitation and emission wavelength closer to the visible region, making them interesting for biological applications.
Article
Chemistry, Multidisciplinary
Bryce da Camara, Noa Bar Ziv, Veronica Carta, Gabriela A. Mota A. Orozco, Hoi-Ting Wu, Ryan R. Julian, Richard J. Hooley
Summary: Appending functional groups onto Zn4L4 cages can control anion binding by creating a doorstop that slows down guest exchange. The effects on anion exchange depend on factors such as anion size, nature of the leaving anion, and the properties of the pendant groups. The bulky external groups can selectively affect anion ingress and egress, resulting in significant variations in affinity even for similar anions within identically sized cavities.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Douglas H. Banning, Grace M. Kuhl, Madeline M. Howell, Darren W. Johnson
Summary: In this study, ChemFETs were used to evaluate the anion affinity of two different supramolecular scaffolds, showing that receptor modification can impact chemical selectivity. Slight changes in the steric bulk of the supramolecular scaffolds resulted in orders of magnitude differences in aqueous anion detection limits of ChemFET sensors.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Dharmendra Singh, Durga Lakshmi, Chhuttan L. Meena, Gamidi Rama Krishna, Gangadhar J. Sanjayan
Summary: This paper reports on the development of carbamate-protected 2-aminopyrimidinedione-based Janus G-C nucleobases as building blocks for smart polymers and self-healing materials. These nucleobases feature polymerizable groups and self-complementary triple H-bonding motifs, enabling the synthesis of smart polymers and eliminating solubility issues.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Bryce da Camara, Connor Z. Woods, Komal Sharma, Hoi-Ting Wu, Naira S. Farooqi, Changwei Chen, Ryan R. Julian, Douglas A. Vander Griend, Richard J. Hooley
Summary: Spacious M4L6 tetrahedra can act as catalytic inhibitors for base-mediated reactions by increasing the acidity of the reaction solvent, resulting in a reduced conversion rate of the conjugate addition reaction.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Ana Miljkovic, Sonia La Cognata, Greta Bergamaschi, Mauro Freccero, Antonio Poggi, Valeria Amendola
Review
Chemistry, Multidisciplinary
Sonia La Cognata, Ana Miljkovic, Riccardo Mobili, Greta Bergamaschi, Valeria Amendola
Article
Chemistry, Multidisciplinary
Marcia Dominguez, Juan F. Blandez, Beatriz Lozano-Torres, Cristina de la Torre, Maurizio Licchelli, Carlo Mangano, Valeria Amendola, Felix Sancenon, Ramon Martinez-Manez
Summary: Benzene is a highly toxic aromatic hydrocarbon with metabolization products causing various health issues, necessitating the development of reliable and rapid detection methods. This study reports a nanodevice for quantitative analysis of t,t-MA in urine using a simple fluorimeter for quick detection.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Sonia La Cognata, Riccardo Mobili, Francesca Merlo, Andrea Speltini, Massimo Boiocchi, Teresa Recca, Louis J. Maher, Valeria Amendola
Article
Biochemistry & Molecular Biology
Marcello Monteleone, Riccardo Mobili, Chiara Milanese, Elisa Esposito, Alessio Fuoco, Sonia La Cognata, Valeria Amendola, Johannes C. Jansen
Summary: Membrane-based processes are increasingly important for sustainable and energy-efficient gas separation applications. This study found that different organic cage fillers dispersed in poly(ether ether ketone) have varying effects on gas diffusion coefficients and selectivity. Specifically, furanyl imine cages significantly increased diffusion coefficients of bulkier gases, while m-xylyl imine cages improved size selectivity.
Article
Chemistry, Multidisciplinary
Riccardo Mobili, Giovanni Preda, Sonia La Cognata, Lucio Toma, Dario Pasini, Valeria Amendola
Summary: A chiral cage is proposed as an effective chiroptical sensor for detecting perrhenate in water, fruit juice, and artificial urine media. The key mechanism for chiroptical sensing involves changes in the dihedral angle of the binaphthyl unit and H-bonding with the guest, leading to significant changes in the CD signal.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Xuesong Li, Arthur H. G. David, Long Zhang, Bo Song, Yang Jiao, Damien Sluysmans, Yunyan Qiu, Yong Wu, Xingang Zhao, Yuanning Feng, Lorenzo Mosca, J. Fraser Stoddart
Summary: AMPs inspired by active cellular transport enable unidirectional cargo motion using molecular ratchet mechanisms. By utilizing radical interactions and Coulombic repulsive forces, significant progress has been made in creating working AMPs. This research demonstrates that the use of pumping cassettes can modify the photophysical properties of fluorophores in a [3]rotaxane structure, which cannot be achieved with a mixture of components in solution.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Sonia La Cognata, Riccardo Mobili, Chiara Milanese, Massimo Boiocchi, Mattia Gaboardi, Donatella Armentano, Johannes C. Jansen, Marcello Monteleone, Ariana R. Antonangelo, Mariolino Carta, Valeria Amendola
Summary: Two novel imide/imine-based organic cages were prepared and studied as materials for selective separation of CO2 from N-2 and CH4. The cages showed selectivity for CO2 over N-2 and CH4 in gas adsorption and membrane filling, leading to improved gas transport properties and CO2 selectivity in mixed-matrix membranes.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Biochemistry & Molecular Biology
Valentina Gazzola, Pietro Grisoli, Valeria Amendola, Giacomo Dacarro, Carlo Mangano, Piersandro Pallavicini, Antonio Poggi, Silvia Rossi, Barbara Vigani, Angelo Taglietti
Summary: This paper reports on the preparation of Imidazole-functionalized glass surfaces and demonstrates the use of a dinuclear Cu(II) complex to interact with deprotonated grafted imidazole moieties. This supramolecular approach leads to the development of an antimicrobial surface with a strong microbicidal effect using low amounts of the copper complex.
Article
Pharmacology & Pharmacy
Dalila Miele, Milena Sorrenti, Laura Catenacci, Paolo Minzioni, Giorgio Marrubini, Valeria Amendola, Marcello Maestri, Paolo Giunchedi, Maria Cristina Bonferoni
Summary: In this study, poly lactic-co-glycolic acid (PLGA) based nanoparticles (NPs) were proposed as carriers for indocyanine green (ICG), and fluorescence quenching experiments were conducted by studying the interaction between ICG and chitosan oleate (CS-OA). The results showed that associating ICG with NPs can reduce cell viability after laser irradiation, opening up new possibilities for utilizing PDT mechanism in cancer therapy.
Review
Chemistry, Multidisciplinary
Sonia La Cognata, Valeria Amendola
Summary: Organic cages have attracted great interest in the scientific community due to their unique features, such as simple synthesis, structural tunability, and high selectivity. In the past decade, organic cages have been extensively studied and applied as chemosensors, separation agents, and membrane materials.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Sonia La Cognata, Donatella Armentano, Nicoletta Marchesi, Pietro Grisoli, Alessia Pascale, Marion Kieffer, Angelo Taglietti, Anthony P. Davis, Valeria Amendola
Summary: This study reports a novel organic cage as a potential antimicrobial and antifungal agent. Experimental results demonstrate that the cage can bind and transport specific anions and exhibit antimicrobial activity against Staphylococcus aureus.
CHEMISTRY-SWITZERLAND
(2022)
Article
Chemistry, Inorganic & Nuclear
Alexiane Thevenet, Ana Miljkovic, Sonia La Cognata, Cecile Marie, Christelle Tamain, Nathalie Boubals, Carlo Mangano, Valeria Amendola, Philippe Guilbaud
Summary: The addition of complexing agents in nitric acid solutions improves the complexation strength towards pertechnetate anion and successfully retains it in the aqueous phase, showing potential for application in solvent extraction processes.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Multidisciplinary
Sara Sheykhi, Lorenzo Mosca, Mariia Pushina, Kaustav Dey, Pavel Anzenbacher
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Inorganic & Nuclear
Alexiane Thevenet, Cecile Marie, Christelle Tamain, Valeria Amendola, Ana Miljkovic, Dominique Guillaumont, Nathalie Boubals, Philippe Guilbaud
DALTON TRANSACTIONS
(2020)