Acetylated oligosaccharides are common in nature. While they involved several biochemical and biological processes, the role of acetyl groups complexity their migration has largely gone unnoticed. In this work, by combination organic synthesis, NMR spectroscopy quantum chemical modeling, we show that group is a much more complex phenomenon than previously known. By use synthetic oligomannoside model compounds, demonstrate, for first time, polysaccharides may not be limited to transfer within...

Dry eye syndrome (DES) is a prevalent disease in which the tear film homeostasis compromised. One of main causes DES thought to be an alteration composition outermost layer film, lipid (TFLL), resulting increased evaporation water from and subsequent drying ocular surface. Recent studies have suggested that specific TFLL lipids, namely, O-acyl-ω-hydroxy fatty acids (OAHFAs) diesters (DiEs), may play role development DES. However, their connection has remained largely unknown until now...

Soft nanoparticles are interesting materials due to their size, deformability, and ability host guest molecules. Surface properties play an essential role in determining the fate of particles biological medium, coating (and polymers) with carbohydrates has been found be efficient strategy for increasing biocompatibility fine-tuning other important such as aqueous solubility. In this work, soft nanogels poly(N-vinylcaprolactam), PNVCL, were surface-functionalized different glucose maltose...

The tear film lipid layer (TFLL) covers the film, stabilizing it and providing a protective barrier against environment. TFLL is divided into polar non-polar sublayers, but interplay between classes in these sublayers structure-function relationship of remains poorly characterized. This study aims to provide insight function by elucidating interactions lipids at molecular level.Mixed films O-acyl-ω-hydroxy fatty acids (OAHFA) or phospholipids cholesteryl esters (CE) were used as model TFLL....

Antibody-drug conjugates (ADCs) are emerging as a promising class of selective drug delivery systems in the battle against cancer and other diseases. The auristatins monomethyl auristatin E (MMAE) F (MMAF) appear cytotoxic almost half state-of-the-art ADCs on market or late stage clinical trials. Here, we present first complete NMR spectroscopic characterisation these challenging molecules, investigate their structural properties by combined quantum chemical modelling approach. We find that...

Abstract β‐(1→2)‐Linked oligomannosides constitute an important class of carbohydrate structures located on the cell surface several Candida species, including C. albicans . As a result immunostimulating properties such compounds, upscaling their synthesis is relevant. In this paper, highly stereoselective β‐(1→2)‐linked was performed by further development and modifications to methodologies described earlier in literature. addition fully deprotected mannobiose mannotriose, some preliminary...

Abstract Galactoglucomannan (GGM) is a polysaccharide mainly consisting of mannose, glucose, and galactose. GGM the most abundant hemicellulose in Norway spruce ( Picea abies ), but also found cell wall flax seeds, tobacco plants, kiwifruit. Although several applications for polysaccharides have been developed pulp paper manufacturing food medical industries, attempts to synthesize study distinct fragments this not reported previously. Herein, synthesis one core trisaccharide units together...

Boron neutron capture therapy (BNCT) for cancer is on the rise worldwide due to recent developments of in-hospital accelerators which are expected revolutionize patient treatments. There an urgent need improved boron delivery agents, and herein we have focused studying biochemical foundations upon a successful GLUT1-targeting strategy BNCT could be based. By combining synthesis molecular modeling with affinity cytotoxicity studies, unravel mechanisms behind considerable potential...

Antibody-drug conjugates (ADCs) are promising state-of-the-art biopharmaceutical drugs for selective drug-delivery applications and the treatment of diseases such as cancer. The idea behind ADC technology is remarkable it combines highly targeting capacity monoclonal antibodies with cancer-killing ability potent cytotoxic agents. continuous development improved ADCs requires systematic studies on nature effects warhead modification. Recently, we focused hydrophilic modification monomethyl...

Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers tumor-targeting selectivity that difficult match by other means, last obstacles preventing full harness this potential come in form suboptimal boron delivery strategies presently used clinics. To address these challenges, we have developed agents target glucose transporter GLUT1. Here, present chemical synthesis number ortho-carboranylmethyl-substituted...

ABSTRACT Immunostimulatory properties of synthetic structures mimicking the β-(1→2)-linked mannans Candida albicans were evaluated in vitro . Contrary to earlier observations, tumor necrosis factor (TNF) production was not detected after stimulation with mannotetraose mouse macrophages. Divalent disaccharide 1,4-bis(α- d -mannopyranosyloxy)butane induced TNF and some molecules low levels gamma interferon (IFN-γ) human peripheral blood mononuclear cells (PBMC).

In healthy eyes, the tear film lipid layer (TFLL) is considered to act as an evaporation resistant barrier, which prevents eyes from drying. Seeking understand mechanisms behind resistance of TFLL, we studied mixtures wax esters and O-acyl-ω-hydroxy fatty acids. Analyzing their self-assembly biophysical properties led new discoveries concerning structure function TFLL. We discovered how these lipids self-assemble at air–water interface form efficient antievaporative demonstrating for first...

Abstract A highly efficient, ligand‐enhanced 2,2,6,6‐tetramethylpiperidine‐1‐oxy (TEMPO)/Mn(NO 3 ) 2 catalyst system for the aerobic oxidation of alcohols is described. From series coordinating ligands studied herein, 2‐picolinic acid (PyCOOH) improves catalytic activity TEMPO/Mn(NO remarkably. Under ambient air at room temperature in acetic acid, converts aliphatic and benzylic primary that bear various functional groups into their respective aldehydes with near quantitative conversions....

Abstract Antibody–drug conjugates (ADCs) are promising alternatives to naked antibodies for selective drug‐delivery applications and treatment of diseases such as cancer. Construction ADCs relies upon site‐selective, efficient mild conjugation technologies. The choice a chemical linker is especially important, it affects the overall properties ADC. We envisioned that hydrophilic bifunctional linkers based on carbohydrates would be useful class derivatization agents construction linker–drug...

β-(1→2)-linked oligomannosides, found in the cell wall of Candida albicans, are promising structures for development C. albicans vaccines. Considerable effort recent years has been devoted to synthesis these carbohydrate structures. As a result, several successful synthetic methodologies based on linear approaches have emerged. Here, we demonstrate that fully deprotected mannotetrasaccharide can also be conveniently constructed by convergent direct coupling two appropriately protected...

The tear film lipid layer (TFLL) is a unique biological membrane that serves pivotal role in the maintenance of ocular surface health. Reaching an overarching understanding functional principle TFLL has been hampered by lack insights into structural and roles played individual classes. To bridge this knowledge gap, we herein focus on studying films formed principal classes scattering methods. Through grazing incidence X-ray diffraction reflectivity studies, reveal quantitative data about...

The tear film lipid layer (TFLL) plays a vital part in maintenance of ocular health and represents unique biological barrier comprising unusual specialized classes species. wax cholesteryl esters (WEs CEs) constitute roughly 80–90% the TFLL. majority species these are branched it is therefore surprising that synthesis properties second largest category species, i.e., anteiso-branched remain poorly characterized. In this study, we have developed total route completed detailed NMR...

Given the renewed interest in boron neutron capture therapy (BNCT) and intensified search for improved carriers, as well difficulties of coherently comparing carriers described so far, it seems necessary to define a basic set assays standardized methods be used early stages carrier development vitro. The selection corresponding is based on practical experience authors certainly not exhaustive, but open discussion. proposed tests/characteristics: Solubility, lipophilicity, stability,...

One of the most successful bioconjugation strategies to date is copper(I)-catalyzed cycloaddition reaction (CuAAC), however, typically applied conditions have been found degrade sensitive biomolecules. Herein, we present a water soluble copper chelator which can be utilized protect biomolecules from induced degradation.

The tear film lipid layer (TFLL) that covers the ocular surface contains several unique classes, including O-acyl-ω-hydroxy fatty acids, type I-St diesters, and II diesters. While TFLL represents a biological barrier plays central role in stabilizing entire film, little is known about properties roles of individual species. This because their isolation from samples sufficient quantities tedious task. To provide access to these species pure form, shed light on properties, we here report...

The tear film lipid layer (TFLL) is a unique biological membrane of importance to the maintenance ocular surface health. underlying factors at play, e.g. ability retard evaporation and offer protection from environment, are all closely connected properties individual components their interplay. TFLL contains ultra-long polar species such as O-acyl-ω-hydroxy fatty acids, type I-St diesters II diesters, which considered important for its proper function. Herein, we have synthesized model...

Abstract Glycosylated steroids, such as cardenolides and saponins, are widely distributed in nature have been shown to possess various types of biological activities. In the present study, carbohydrate donors were evaluated for glycosylation steroids; results show that benzoylated imidate superior terms efficiency operational simplicity. These then applied synthesis a limited library estradiol‐based glycosteroid mimics containing modified D‐ring. The deprotected molecules contained three...