The rate and evenness of the substitutions on hyaluronan grafted by dodecanoic acid influenced by the mixed-solvent composition

Kutálková, Eva; Hrnčiřík, Josef; Witasek, Roman; Ingr, Marek; Huerta-Ángeles, Gloria; Hermannová, Martina; Velebný, Vladimı́r

doi:10.1016/j.ijbiomac.2021.08.137

Cited by 8 publications

(7 citation statements)

References 41 publications

(45 reference statements)

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“…Atomic-resolution explicit-solvent molecular dynamics simulations have also been used to rationalize the efficiency of the synthesis of conjugates of hyaluronan with a hydrophobic functional group as a function of solvent conditions containing a mixture of water plus an organic solvent. Specifically, having tert-butanol vs. 1,4-dioxane as the organic component of the mixed water-organic solvent results in substantial differences in the solvation shell surrounding hyaluronan, including much more enrichment of the solvation shell by water molecules in the case of tert-butanol [ 199 ].…”

Section: Atomic-resolution Molecular Dynamics Simulations Of Hyaluron...mentioning

confidence: 99%

Atomic-Resolution Experimental Structural Biology and Molecular Dynamics Simulations of Hyaluronan and Its Complexes

Guvench

2022

Molecules

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This review summarizes the atomic-resolution structural biology of hyaluronan and its complexes available in the Protein Data Bank, as well as published studies of atomic-resolution explicit-solvent molecular dynamics simulations on these and other hyaluronan and hyaluronan-containing systems. Advances in accurate molecular mechanics force fields, simulation methods and software, and computer hardware have supported a recent flourish in such simulations, such that the simulation publications now outnumber the structural biology publications by an order of magnitude. In addition to supplementing the experimental structural biology with computed dynamic and thermodynamic information, the molecular dynamics studies provide a wealth of atomic-resolution information on hyaluronan-containing systems for which there is no atomic-resolution structural biology either available or possible. Examples of these summarized in this review include hyaluronan pairing with other hyaluronan molecules and glycosaminoglycans, with ions, with proteins and peptides, with lipids, and with drugs and drug-like molecules. Despite limitations imposed by present-day computing resources on system size and simulation timescale, atomic-resolution explicit-solvent molecular dynamics simulations have been able to contribute significant insight into hyaluronan’s flexibility and capacity for intra- and intermolecular non-covalent interactions.

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Section: Atomic-resolution Molecular Dynamics Simulations Of Hyaluron...mentioning

confidence: 99%

Atomic-Resolution Experimental Structural Biology and Molecular Dynamics Simulations of Hyaluronan and Its Complexes

Guvench

2022

Molecules

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“…The derivatives tested in this work were prepared by acylation of sodium hyaluronate in a mixed water/THF solvent. The chemical modification of HA grafted by dodecanoyl fatty acid moieties was reported elsewhere [16,17].…”

Section: Synthesis Of Sodium Dodecanoyl Hyaluronate (Ha-c12)mentioning

confidence: 99%

“…As the solvent mixture drastically influences the selectivity of the reaction towards selected substitution at the primary and/or secondary hydroxyl moieties in HA [16]. The even substitution drastically changes the conjugate's solubility.…”

Section: Synthesis and Characterization Of Amphiphilic Hyaluronan (Ha-c12)mentioning

confidence: 99%

Insight into the Lubrication and Adhesion Properties of Hyaluronan for Ocular Drug Delivery

et al. 2021

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Hyaluronan (HA) is widely used for eye drops as lubricant to counteract dry eye disease. High and low molecular weight HA are currently used in ophthalmology. However, a large portion of the current literature on friction and lubrication addresses articular (joint) cartilage. Therefore, eye drops compositions based on HA and its derivatized forms are extensively characterized providing data on the tribological and mucoadhesive properties. The physiochemical properties are investigated in buffers used commonly in eye drops formulations. The tribological investigation reveals that amphiphilic HA-C12 decreases the friction coefficient. At the same time, the combination of trehalose/HA or HAC12 enhances up to eighty-fold the mucoadhesiveness. Thus, it is predicted a prolonged residence time on the surface of the eye. The incorporation of trehalose enhances the protection of human keratinocytes (HaCaT) cells, as demonstrated in an in-vitro cell-desiccation model. The presence of trehalose increases the friction coefficient. Medium molecular weight HA shows significantly lower friction coefficient than high molecular weight HA. This research represents a first, wide array of features of diverse HA forms for eye drops contributing to increase the knowledge of these preparations. The results here presented also provide valuable information for the design of highly performing HA-formulations addressing specific needs before preclinic.

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“…It is routine nowadays to read papers reporting simulations of complex molecular mixtures, involving mixtures of aqueous and organic solvents, together with ions, co-ions, and with much larger molecules, such as enzymes, and in the perspective of simulating realistic liquids, such as those involved in biological or pharmaceutical systems. , The recent interest in the structure of the solvation shell of hyaluronan oligosaccharides in aqueous organic solvent mixtures is among such modern simulation topics. − On the opposite side of the spectrum in terms of complexity, there are still studies of liquids such as alcohols or binary aqueous mixtures, with a particular focus on their microstructure. The computer simulations of these latter systems reveal appreciable model dependence, which often focuses on minute studies in molecular details.…”

Section: Introductionmentioning

confidence: 99%

“…In the present paper, we would like to examine closer binary mixtures of aqueous dioxane, which has been used lately as an aqueous organic solvent in the study of more complex mixtures involving hyaluronan and ions. − In particular, we are interested in why these works choose the TIP3P model for water, rather than more modern water models, such as SPC/E, TIP4P, TIP4P-2005, or TIP4P-ew . This question will be answered in the Discussion section below.…”

Section: Introductionmentioning

confidence: 99%

Concentration Fluctuation/Microheterogeneity Duality Illustrated with Aqueous 1,4-Dioxane Mixtures

Kolaříková,

Perera

2024

J. Chem. Theory Comput.

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The structural properties of aqueous 1-4 dioxane mixtures are studied by computer simulations of different water and dioxane force field models, from the perspective of illustrating the link between structural properties at the molecular level and measurable properties such as radiation scattering intensities and Kirkwood−Buff integrals (KBIs). A strategy to consistently correct the KBI obtained from simulations is proposed, which allows us to obtain the genuine KBI corresponding to a given pair of molecular species, in the entire concentration range, and without necessitating excessively large system sizes. The application of this method to the aqueous dioxane mixtures, with an all-atom CHARMM dioxane model and 2 water models, namely, SPC/E and TIP3P, allows one to understand the differences in the structure of the corresponding mixtures at the molecular level, particularly concerning the role of the water aggregates and its model dependence. This study allows us to characterize the dual role played by the concentration fluctuations and the domain segregation, particularly in what concerns the calculated X-ray spectra.

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The rate and evenness of the substitutions on hyaluronan grafted by dodecanoic acid influenced by the mixed-solvent composition

Cited by 8 publications

References 41 publications

Atomic-Resolution Experimental Structural Biology and Molecular Dynamics Simulations of Hyaluronan and Its Complexes

Atomic-Resolution Experimental Structural Biology and Molecular Dynamics Simulations of Hyaluronan and Its Complexes

Insight into the Lubrication and Adhesion Properties of Hyaluronan for Ocular Drug Delivery

Concentration Fluctuation/Microheterogeneity Duality Illustrated with Aqueous 1,4-Dioxane Mixtures

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