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  • 1.
    Lind, Tania K.
    et al.
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
    Nilsson, Emelie J.
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
    Wyler, Benjamin
    LONZA AG, Switzerland.
    Scherer, Dieter
    LONZA AG, Switzerland.
    Skansberger, Tatyana
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
    Morin, Maxim
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
    Kocherbitov, Vitaly
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
    Engblom, Johan
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
    Effects of ethylene oxide chain length on crystallization of polysorbate 80 and its related compounds2021In: Journal of Colloid and Interface Science, ISSN 0021-9797, E-ISSN 1095-7103, Vol. 592, p. 468-484, article id S0021-9797(21)00078-3Article in journal (Refereed)
    Abstract [en]

    As a result of the synthesis protocol polyoxyethylene sorbitan monooleate (polysorbate 80, PS80) is a highly complex mixture of compounds. PS80 was therefore separated into its main constituents, e.g. polyoxyethylene isosorbide esters and polyoxyethylene esters, as well as mono- di- and polyesters using preparative high-performance liquid chromatography. In this comprehensive study the individual components and their ethoxylation level were verified by matrix assisted laser desorption/ionization time-of-flight and their thermotropic behavior was analyzed using differential scanning calorimetry and X-ray diffraction. A distinct correlation was found between the average length of the ethylene oxide (EO) chains in the headgroup and the individual compounds' ability to crystallize. Importantly, a critical number of EO units required for crystallization of the headgroup was determined (6 EO units per chain or 24 per molecule). The investigation also revealed that the hydrocarbon tails only crystallize for polyoxyethylene sorbitan esters if saturated. PS80 is synthesized by reacting with approximately 20 mol of EO per mole of sorbitol, however, the number of EO units in the sorbitan ester in commercial PS80 products is higher than the expected 20 (5 EO units per chain). The complex behavior of all tested compounds revealed that if the amount of several of the linear by-products is reduced, the number of EO units in the chains will stay below the critical number and the product will not be able to crystallize by the EO chains.

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  • 2.
    Nilsson, Emelie J.
    et al.
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
    Lind, Tania Kjellerup
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV).
    Scherer, Dieter
    LONZA AG, Basel, CH-4002, Switzerland.
    Skansberger, Tatyana
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV).
    Mortensen, Kell
    Niels Bohr Institute, University of Copenhagen, Copenhagen, DK-2100, Denmark.
    Engblom, Johan
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
    Kocherbitov, Vitaly
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
    Mechanisms of crystallisation in polysorbates and sorbitan esters2020In: CrystEngComm, ISSN 1466-8033, E-ISSN 1466-8033, Vol. 22, no 22, p. 3840-3853Article in journal (Refereed)
    Abstract [en]

    Polysorbates (PS), commonly known as Tween (TM), are some of the most extensively used excipients and protein stabilisers in biopharmaceutical products worldwide. It is stipulated in the pharmacopoeia specifications that these ethoxylated surfactants are complex mixtures comprised of a wealth of molecular species. While little is known about the propensity of PSs to crystallise, they are used in applications ranging from food products, cosmetics, different types of drug dosage forms like creams and oral products to parenteral applications. However, in recent years a range of issues and safety concerns have appeared when using them for stabilising biopharmaceutical products including precipitation, particle formation, and adverse biological effects. Therefore, the aim of this study was to thoroughly characterise the thermotropic behaviour and mechanism of crystallisation of polysorbates with different hydrocarbon tails and their non-ethoxylated sorbitan ester equivalents for comparison. A systematic and comprehensive product characterisation was carried out, taking advantage of a combination of complementary techniques such as differential scanning calorimetry, matrix assisted laser desorption ionisation time-of-flight and small- and wide-angle X-ray diffraction. We show that polysorbate 80, having an unsaturated hydrocarbon tail, crystallises by the ethylene oxide chains in the headgroup. Polysorbate 20, 40, and 60, containing saturated hydrocarbon esters tails, crystallise not only by the ethylene oxide chains but also by their hydrocarbon tails. An analogous behaviour was observed for the PS non-ethoxylated equivalents, the sorbitan esters. Sorbitan esters with saturated hydrocarbon tails displayed a crystallisation of the tail upon cooling, whereas the sorbitan ester with unsaturated hydrocarbon tail displayed no crystallisation.

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  • 3.
    Skansberger, Tatyana
    et al.
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
    Kocherbitov, Vitaly
    Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
    The Reversible and Irreversible Phenomena in Potato Starch Gelatinization2019In: Starke (Weinheim), ISSN 0038-9056, E-ISSN 1521-379X, Vol. 71, no 5-6, article id 1800233Article in journal (Refereed)
    Abstract [en]

    Gelatinization of starch is a complex process and can be considered using two different approaches. In a kinetic approach it is considered as an irreversible process and described using the formalism of chemical kinetics with activation energy as the main parameter. Alternatively, in a thermodynamic approach it can be viewed as a reversible process with van't Hoff enthalpy as the main parameter. The experimental DSC data on gelatinization of native and physically modified potato starches presented in this study support the equilibrium approach. The van't Hoff enthalpy of gelatinization of native potato starch is measured to be 737 ± 13 kJ mol−1, and it is more sensitive to physical modifications of starch than the calorimetric enthalpy. Moreover, van't Hoff enthalpy has a clear correlation with the granule size, while neither gelatinization temperature, nor calorimetric enthalpy are sensitive to the size. To explain the nonequilibrium nature of starch gelatinization, the authors propose a three‐step mechanism, which includes reversible and irreversible steps.

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