Article
Multidisciplinary Sciences
Zhihua Cheng, Matthew R. Jones
Summary: The study reports the self-assembly of 2D chiral superlattices from achiral tetrahedron-shaped building blocks, explains the formation mechanism, and lays the scientific foundation for the high-throughput assembly of planar chiral metamaterials.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Yongshen Zheng, Xiao Han, Puxin Cheng, Xiaodi Jia, Jialiang Xu, Xian-He Bu
Summary: Chiral hybrid organic-inorganic metal halides (HOMHs) with intrinsic noncentrosymmetry have great potential in various applications. This study successfully constructed a series of chiral HOMHs using an induction approach, resulting in products with superior optical properties. The use of this induction approach could facilitate the construction of chiral HOMH libraries from achiral precursors.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Chengxi Li, Yutao Sang, Xue Jin, Pengfei Duan, Minghua Liu
Summary: This study reveals a general process to generate chiral supramolecular polymers from achiral molecules by combining a physical vortex and chiral seeds. It also explores the effects of fragmentation and elongation on the chiral nuclei during the polymerization process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Hyong-Jin Rhee, Jala Ranjith, Huimyoung Byeon, Hyun-Joon Ha, Jung Woon Yang
Summary: In this study, chiral contiguous bisaziridines were prepared via aziridination of chiral 3-[1-(1-phenylethyl)aziridin-2-yl)]acrylaldehydes, using N-Boc-O-tosyl or N-Ts-O-tosyl hydroxylamine as a nitrogen source and (2R)- or (2S)-[diphenyl (trimethylsilyloxy)methyl]pyrrolidine as a chiral organocatalyst. The regioselective ring opening of bisaziridines yielded chiral nitrogen-rich molecules.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Biochemistry & Molecular Biology
Yu-Yu Hsieh, Jing-Jong Shyue, Yu-Chiang Chao, Ken-Tsung Wong, Dario M. Bassani
Summary: The incorporation of biuret hydrogen-bonding sites onto chiral binaphthalene-based chromophores was investigated for the synthesis of sub-micron-sized, vesicle-like aggregates with chiroptical properties. Luminescent chromophores were synthesized via Suzuki-Miyaura coupling of the corresponding chiral 4,4'-dibromo-1,1'-bis(2-naphthol), and their emission spectrum could be tuned through conjugation extension. Scanning electron microscopy confirmed the spontaneous formation of hollow spheres with a diameter of ca. 200-800 nm, along with strong asymmetry in the circularly polarized absorption spectra. Circular polarization of the emission, with values of g(lum) = ca. 10(-3), could be further enhanced upon aggregation.
Article
Chemistry, Inorganic & Nuclear
Montserrat Ferrer, Albert Gallen, Manuel Martinez, Merce Rocamora, Rakesh Puttreddy, Kari Rissanen
Summary: New chiral tetranuclear square-like homo- and hetero-metallamacrocycles containing allyl-palladium and optically pure moieties have been successfully synthesized. The structures have been characterized by multinuclear NMR spectroscopy and MS spectrometry. XRD analysis confirms the structural characteristics of the new metallamacrocycles. These architectures have shown catalytic activity in asymmetric allylic alkylation reaction.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Johal Ruiz, Philippe Oger, Laurent Soulere, Florence Popowycz
Summary: Starting from commercially available (R)- and (S)-beta-citronellol, two strategies were designed to synthesize all four stereoisomers of 2,6-dimethyloctane monoterpene chirons in four or five steps in 32-47% overall yield. Key Ru-catalyzed asymmetric olefin hydrogenation step under moderate conditions allowed the obtainment of desired fragments. DM-SEGPHOS was identified as a economically advantageous alternative to H8-BINAP for equal performances in catalyst screening, opening up new possibilities for versatile and scalable syntheses of these useful building blocks.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Irena Dokli, Nevena Milcic, Petra Marin, Marina Svetec Miklenic, Martina Sudar, Lixia Tang, Zvjezdana Findrik Blazevic, Maja Majeric Elenkov
Summary: The kinetic resolution of a series of fluorinated styrene oxide derivatives using halohydrin dehalogenase was studied. A mutant HheC-W249P showed excellent enantioselectivity in catalyzing nucleophilic ring-opening reactions with azide and cyanide ions, yielding various enantiopure beta-substituted alcohols and epoxides. The enzyme demonstrated tolerance to substrates at concentrations over 50 mM, but different side reactions were observed at elevated concentrations and prolonged reaction times. Bio-catalytic azidolysis and cyanolysis of racemic 4-trifluoromethylstyrene oxide on a preparative scale resulted in the production of specific enantiomers with high yields and enantiomeric excesses.
CATALYSIS COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yuan Zhang, Benjamin Ourri, Pierre-Thomas Skowron, Emeric Jeamet, Titouan Chetot, Christian Duchamp, Ana M. Belenguer, Nicolas Vanthuyne, Olivier Cala, Elise Dumont, Pradeep K. Mandal, Ivan Huc, Florent Perret, Laurent Vial, Julien Leclaire
Summary: By incorporating stereo-electronic information on synthetic organic building blocks and templates, and utilizing non-directional interactions, achiral constituents can be selectively assembled into complex covalent architectures with multiple stereogenic elements. This proof of concept has implications beyond supramolecular chemistry and could stimulate the on-demand production of highly structured polyfunctional architectures.
Article
Chemistry, Multidisciplinary
Niuniu Dong, Yishan Sun, Geng Sun, Lei Zhang, Sha Sun
Summary: This study systematically explores the independent and synergistic effects of bending and twisting deformations on the geometry of DNA nanotubes. Design rules enable the construction of DNA nanotubes with prescribed chirality and tailored diameters.
Article
Chemistry, Multidisciplinary
M. John Plater, William T. A. Harrison
Summary: Studies have been conducted to synthesize N-heteroacenes and assess their suitability through intermolecular interactions. The high reactivity of the resulting compounds has been explained.
Article
Chemistry, Multidisciplinary
Ming-Hao Du, Su-Hui Xu, Guan-Jun Li, Han Xu, Yang Lin, Wei-Dong Liu, La-Sheng Long, Lan-Sun Zheng, Xiang-Jian Kong
Summary: A modification procedure for a multi-component building block was reported to form new building blocks which can further assemble into chiral molecular rings. These molecular rings exhibit specific electronic adsorption and magneto-optic responses.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Ruth Suchsland, Bettina Appel, Pasi Virta, Sabine Muller
Summary: The preparation of fully protected trinucleotide phosphoramidites has attracted much attention in recent years, with this study focusing on the preparation of such synthons on a soluble support using a disulphide linker.
Article
Chemistry, Physical
Jojo P. Joseph, Shema R. Abraham, Avisek Dutta, Alexander Baev, Mark T. Swihart, Paras N. Prasad
Summary: This study introduces a new approach to enhance the optical activity of chiral polymer systems through conformational engineering by tuning the conjugation system in the polymer backbone.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Physical
Jojo P. Joseph, Shema R. Abraham, Avisek Dutta, Alexander Baev, Mark T. Swihart, Paras N. Prasad
Summary: This study enhances optical activity and successfully synthesizes chiral polymers that meet the predictions of quantum chemical calculations by tuning the conformation of the chiral polymer backbone. The rotational strength of the chiral polymer can be modulated by adjusting the number of functional units in the monomer components.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Pharmacology & Pharmacy
Patrick Froslev, Henrik Franzyk, Burak Ozgur, Birger Brodin, Mie Kristensen
Summary: The study investigated the potential of CPPs Tat(47-57), penetratin, apidaecin, and oncocin for interaction with and permeation of the BBB in vitro. The cationic and proline-rich cationic CPPs were taken up into brain capillary endothelial-like monolayers. T-Tat(47-57), T-apidaecin, and T-oncocin also permeated the monolayers, while T-penetratin did not.
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES
(2022)
Article
Pharmacology & Pharmacy
You Xu, Laure Harinck, Abhijeet G. Lokras, Per Gerde, Ewa Selg, Carl-Olof Sjoberg, Henrik Franzyk, Aneesh Thakur, Camilla Foged
Summary: The study demonstrates that a mixture of stabilizing excipients trehalose and dextran with the shell-forming dispersion enhancer leucine can stabilize TNF-alpha siRNA-loaded LPNs and result in DPI formulations with high aerosol performance. At optimal ratios, the formulations display suitable aerosol properties for inhalation and homogeneous deep lung deposition.
INTERNATIONAL JOURNAL OF PHARMACEUTICS
(2022)
Article
Immunology
Moa Viklund, Johanna Fredriksson, Andre Holdfeldt, Simon Lind, Henrik Franzyk, Claes Dahlgren, Martina Sundqvist, Huamei Forsman
Summary: This study investigated the recognition and signaling of phenol-soluble modulins (PSMs) produced by highly pathogenic Staphylococcus aureus strains on the formyl peptide receptors 1 (FPR1) and 2 (FPR2). The results showed that the N-terminal and C-terminal regions of PSMa2 play a critical role in the selectivity and signaling of FPR1 and FPR2.
JOURNAL OF IMMUNOLOGY
(2022)
Article
Infectious Diseases
Ida Kristine Lysgaard Andersen, Thomas T. Thomsen, Jasmina Rashid, Thomas Ronnemoes Bobak, Alberto Oddo, Henrik Franzyk, Anders Lobner-Olesen, Paul R. Hansen
Summary: The present study investigated the effect of C-terminus-to-side chain macrocyclization and fatty acid modification on the antimicrobial and hemolytic activity of BP214, an all-D antimicrobial peptide amide. The results showed that analog 13 exhibited the most promising antimicrobial activity against E. coli and low hemolytic activity.
Article
Pharmacology & Pharmacy
Abhijeet Lokras, Akash Chakravarty, Thomas Rades, Dennis Christensen, Henrik Franzyk, Aneesh Thakur, Camilla Foged
Summary: In this study, a new analytical method was developed for the simultaneous quantification of single-stranded and double-stranded RNA drug cargos. The extraction and separation of RNA cargos from nanoparticle carriers were achieved using ion-pair reversed-phase high-performance liquid chromatography combined with UV detection. The methods were sensitive, linear, and accurate, allowing for convenient quantification of multiple RNA cargos loaded into nanoparticle-based delivery systems.
INTERNATIONAL JOURNAL OF PHARMACEUTICS
(2022)
Article
Biochemistry & Molecular Biology
Ingvill Pedersen Saebo, Magnar Bjoras, Henrik Franzyk, Emily Helgesen, James Alexander Booth
Summary: In vitro determination of hemolytic properties is commonly used to evaluate the cytotoxicity of chemicals, drugs, or blood-contacting medical devices or materials. However, there is significant variation in the protocols used in different experimental setups, leading to difficulties in interpretation and comparison of results. This study examines the impact of different variables on the outcome of the assay and proposes an optimized protocol to standardize future hemolysis studies.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Review
Biochemistry & Molecular Biology
Aiva Plotniece, Arkadij Sobolev, Claudiu T. Supuran, Fabrizio Carta, Fredrik Bjoerkling, Henrik Franzyk, Jari Yli-Kauhaluoma, Koen Augustyns, Paul Cos, Linda De Vooght, Matthias Govaerts, Juliana Aizawa, Paeivi Tammela, Raivis Zalubovskis
Summary: Natural products and analogues are valuable sources for the discovery of antibacterial drugs. The identification of bacterial metalloenzymes and the synthesis of selective inhibitors are interesting for the development of antibacterial agents due to increasing drug resistance. Peptide nucleic acids represent a novel strategy for targeting pathogens through antisense inhibition and development of antisense peptide nucleic acids. The review also discusses alternative therapeutic options and optimized in vitro and in vivo models for studying biofilm-related infections along with an overview of drug delivery nanosystems.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Salvia Sajid, Lilia Hernandez Salas, Maria Rafiq, Torben Lund, Mikkel Girke Jorgensen, Bent Honore, Lars Porskaer Christensen, Paul Robert Hansen, Henrik Franzyk, Osman Mirza, Bala Krishna Prabhala
Summary: Membrane transport proteins play a crucial role in maintaining cellular homeostasis by facilitating the transport of various molecules across the cell membrane. Overexpression of these proteins has been shown to alter the metabolomic and proteomic profiles of host cells. In this study, we investigated the physiological consequences of overexpressing the membrane transport protein YdgR from E. coli in two different strains. We observed significant differences in the metabolomics and proteomics profiles between cells expressing functional YdgR and attenuated YdgR. The findings suggest a potential role of YdgR in the transport of proline-containing tripeptides.
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS
(2023)
Article
Microbiology
Salvia Sajid, Marcus M. K. Nielsen, Ruqaiya Khalil, Paul R. Hansen, Henrik Franzyk, Mikkel Girke Jorgensen, Lars P. Christensen, Osman Mirza, Bala Krishna Prabhala
Summary: In this study, peptides similar to Beta-ala-Lys and substrates from both plants and mammals were investigated to identify the substrate space of POTs. A substrate space sketch based on Tanimoto Index was mapped. It was found that carnosine was the only observed substrate for YdgR-mediated transport.
FEMS MICROBIOLOGY LETTERS
(2023)
Article
Chemistry, Physical
You Xu, Elisa Parra-Ortiz, Feng Wan, Olga Canadas, Begona Garcia-Alvarez, Aneesh Thakur, Henrik Franzyk, Jesus Perez-Gil, Martin Malmsten, Camilla Foged
Summary: Pulmonary delivery of siRNA using nanoparticle-based systems shows promise for treating respiratory diseases. We developed inhaler formulations of siRNA-loaded lipid-polymer hybrid nanoparticles and optimized them for inhalation therapy. The interaction between the nanoparticles and pulmonary surfactant was studied to understand the mechanisms involved. The results provide new insights into the design criteria for nanoparticle transport through the air-blood barrier.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2023)
Article
Chemistry, Physical
Anas Aljabbari, Abhijeet Girish Lokras, Jacob Judas Kain Kirkensgaard, Thomas Rades, Henrik Franzyk, Aneesh Thakur, Yibang Zhang, Camilla Foged
Summary: We investigated the structural and material properties of siRNA-loaded LPNs using various analytical techniques. The results revealed the self-assembly of lipidoid into lamellar structures, the lateral organization of siRNA between lipidoid bilayers, and the core-shell structure of siRNA-loaded LPNs. The interactions between lipidoid and siRNA were observed, and the inclusion of siRNA affected the phase behavior of lipidoid. These findings contribute to the understanding of siRNA-loaded LPNs and their applications.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2023)
Article
Pharmacology & Pharmacy
Ditlev Birch, Edward J. Sayers, Malene V. Christensen, Arwyn T. Jones, Henrik Franzyk, Hanne M. Nielsen
Summary: This study compared the membrane association, cellular uptake, and delivery capacity of all-l and all-d enantiomers of penetratin in different cell models and cargos. The results showed that d-PEN had tighter membrane binding and was superior in delivering hydrophilic peptide cargoes across the Caco-2 epithelium compared to l-PEN. However, there was no enhanced delivery of the hydrophobic cyclosporin, and both enantiomers had similar intracellular insulin uptake.
Article
Pharmacology & Pharmacy
Aneesh Thakur, Abishek Wadhwa, Abhijeet Lokras, Olivia Amanda Oest Mullertz, Dennis Christensen, Henrik Franzyk, Camilla Foged
Summary: The incorporation of ionizable lipid L5N12 in liposomal cationic adjuvant CAF (R) 09 maintains the adjuvant function and induces antigen-specific immune responses comparable to unmodified CAF (R) 09.
EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS
(2023)
Article
Chemistry, Applied
Laura Maria Duran Gleriani Primo, Cesar Augusto Roque-Borda, Christian Shleider Carnero Canales, Icaro Putinhon Caruso, Isabella Ottenio de Lourenco, Vitoria Maria Medalha Colturato, Rafael Miguel Sabio, Fernando Alves de Melo, Eduardo Festozo Vicente, Marlus Chorilli, Hernane da Silva Barud, Paula Aboud Barbugli, Henrik Franzyk, Paul Robert Hansen, Fernando Rogerio Pavan
Summary: This study investigates the use of antimicrobial peptide (AMP)-grafted antibiotic-loaded nanoparticles as a potential treatment for multidrug-resistant tuberculosis. The results show that the modified nanoparticles effectively inhibit the growth of drug-resistant tuberculosis strains, suggesting that this approach could be a powerful tool for revitalizing drugs against such strains.
CARBOHYDRATE POLYMERS
(2024)
Article
Biochemistry & Molecular Biology
Ashif Y. Shaikh, Fredrik Bjorkling, Dorota Zabicka, Magdalena Tomczak, Malgorzata Urbas, Ilona Domraceva, Agrita Kreicberga, Henrik Franzyk
Summary: In this study, oncocin analogues with different arginine modifications were synthesized using a synthetic method. A new reagent was found to be effective in converting peptides with natural arginine residues or N-terminal guanidinium groups. Further investigation revealed that the replacement of proline residues in oncocin had an impact on its antimicrobial activity, and the introduction of stabilizing modifications and bis-fluorinated proline further optimized the activity of AMPs.
BIOORGANIC CHEMISTRY
(2023)
