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  • 1.
    Huynh, Chau Minh
    et al.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Arribas Díez, Ignacio
    Department of Biochemistry & Molecular Biology, VILLUM Center for Bioanalytical Sciences, University of Southern Denmark, Campusvej 55, Odense M, Denmark.
    Thi, Hien Kim Le
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Jensen, Ole N.
    Department of Biochemistry & Molecular Biology, VILLUM Center for Bioanalytical Sciences, University of Southern Denmark, Campusvej 55, Odense M, Denmark.
    Sellergren, Börje
    Faculty of Health and Society, Department of Biomedical Science, Malmö University, Malmö, Sweden.
    Irgum, Knut
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Terminally phosphorylated triblock polyethers acting both as templates and pore-forming agents for surface molecular imprinting of monoliths targeting phosphopeptides2023Ingår i: ACS Omega, E-ISSN 2470-1343, Vol. 8, nr 9, s. 8791-8803Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The novel process reported here described the manufacture of monolithic molecularly imprinted polymers (MIPs) using a terminally functionalized block copolymer as the imprinting template and pore-forming agent. The MIPs were prepared through a step-growth polymerization process using a melamine-formaldehyde precondensate in a biphasic solvent system. Despite having a relatively low imprinting factor, the use of MIP monolith in liquid chromatography demonstrated the ability to selectively target desired analytes. An MIP capillary column was able to separate monophosphorylated peptides from a tryptic digest of bovine serum albumin. Multivariate data analysis and modeling of the phosphorylated and nonphosphorylated peptide retention times revealed that the number of phosphorylations was the strongest retention contributor for peptide retention on the monolithic MIP capillary column.

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  • 2.
    Huynh, Chau Minh
    et al.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Mavliutova, Liliia
    Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, Malmö, Sweden.
    Sparrman, Tobias
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Sellergren, Börje
    Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, Malmö, Sweden.
    Irgum, Knut
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Elucidation of the binding orientation in α2,3- and α2,6-linked neu5ac-gal epitopes toward a hydrophilic molecularly imprinted monolith2023Ingår i: ACS Omega, E-ISSN 2470-1343, Vol. 8, nr 46, s. 44238-44249Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    N-Acetylneuraminic acid and its α2,3/α2,6-glycosidic linkages with galactose (Neu5Ac-Gal) are major carbohydrate antigen epitopes expressed in various pathological processes, such as cancer, influenza, and SARS-CoV-2. We here report a strategy for the synthesis and binding investigation of molecularly imprinted polymers (MIPs) toward α2,3 and α2,6 conformations of Neu5Ac-Gal antigens. Hydrophilic imprinted monoliths were synthesized from melamine monomer in the presence of four different templates, namely, N-acetylneuraminic acid (Neu5Ac), N-acetylneuraminic acid methyl ester (Neu5Ac-M), 3′-sialyllactose (3SL), and 6′-sialyllactose (6SL), in a tertiary solvent mixture at temperatures varying from −20 to +80 °C. The MIPs prepared at cryotemperatures showed a preferential affinity for the α2,6 linkage sequence of 6SL, with an imprinting factor of 2.21, whereas the α2,3 linkage sequence of 3SL resulted in nonspecific binding to the polymer scaffold. The preferable affinity for the α2,6 conformation of Neu5Ac-Gal was evident also when challenged by a mixture of other mono- and disaccharides in an aqueous test mixture. The use of saturation transfer difference nuclear magnetic resonance (STD-NMR) on suspensions of crushed monoliths allowed for directional interactions between the α2,3/α2,6 linkage sequences on their corresponding MIPs to be revealed. The Neu5Ac epitope, containing acetyl and polyalcohol moieties, was the major contributor to the sequence recognition for Neu5Ac(α2,6)Gal(β1,4)Glc, whereas contributions from the Gal and Glc segments were substantially lower.

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  • 3. Liepuoniute, Ieva
    et al.
    Huynh, Chau Minh
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen. Department of Chemistry and Biochemistry, University of California, Los Angeles, USA.
    Perez-Estrada, Salvador
    Wang, Yangyang
    Khan, Saeed
    Houk, K. N.
    Garcia-Garibay, Miguel A.
    Enhanced Rotation by Ground State Destabilization in Amphidynamic Crystals of a Dipolar 2,3-Difluorophenylene Rotator as Established by Solid State 2H NMR and Dielectric Spectroscopy2020Ingår i: The Journal of Physical Chemistry C, ISSN 1932-7447, E-ISSN 1932-7455, Vol. 124, nr 28, s. 15391-15398Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    We report the synthesis and rotational dynamics of the pillared metal–organic framework Zn2(F2BDC)2(DABCO) where F2BDC = 2,3-difluorobenzene-1,4-dicarboxylate acts as a rotating dipolar linker and DABCO = 1,4-diazabicyclo[2.2.2]octane acts as a spacer (F2MOF 1). The pillared structure of F2MOF 1 was confirmed by X-ray diffraction and CP-MAS 13C NMR analyses. Using variable temperature solid state 2H NMR and broadband dielectric spectroscopy, we characterized the rotational dynamics of the dipolar F2BDC linker in the solid state. Variable temperature (VT) quadrupolar echo 2H NMR measurements revealed a rotational activation energy of Ea = 6.8 ± 0.1 kcal/mol, which agreed well with temperature- and frequency-dependent dielectric measurements, indicating a barrier of Ea = 7.1 ± 0.5 kcal/mol. Structural data from single crystal X-ray diffraction and quantum mechanical calculations (DFT) suggest that the rotational potential is determined by steric interactions between the dipolar rotator and the stator linkers such that fluorine atoms in the F2BDC linker reduce the activation energy by destabilization of the coplanar BDC ground state.

  • 4.
    Mavliutova, Liliia
    et al.
    Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, SE-20506 Malmö, Sweden.
    Munoz Aldeguer, Bruna
    Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, SE-20506 Malmö, Sweden.
    Wiklander, Jesper
    Bioorganic and Biophysical Chemistry Laboratory, Linnaeus University Centre for Biomaterials Chemistry, Department of Chemistry and Biomedical Sciences, Linnaeus University, Kalmar, Sweden.
    Wierzbicka, Celina
    Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, SE-20506 Malmö, Sweden.
    Huynh, Chau Minh
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Nicholls, Ian A.
    Bioorganic and Biophysical Chemistry Laboratory, Linnaeus University Centre for Biomaterials Chemistry, Department of Chemistry and Biomedical Sciences, Linnaeus University, Kalmar, Sweden.
    Irgum, Knut
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Sellergren, Börje
    Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, SE-20506 Malmö, Sweden.
    Discrimination between sialic acid linkage modes using sialyllactose-imprinted polymers2021Ingår i: RSC Advances, E-ISSN 2046-2069, Vol. 11, nr 36, s. 22409-22418Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Glycosylation plays an important role in various pathological processes such as cancer. One key alteration in the glycosylation pattern correlated with cancer progression is an increased level as well as changes in the type of sialylation. Developing molecularly-imprinted polymers (MIPs) with high affinity for sialic acid able to distinguish different glycoforms such as sialic acid linkages is an important task which can help in early cancer diagnosis. Sialyllactose with α2,6′vs.α2,3′ sialic acid linkage served as a model trisaccharide template. Boronate chemistry was employed in combination with a library of imidazolium-based monomers targeting the carboxylate group of sialic acid. The influence of counterions of the cationic monomers and template on their interactions was investigated by means of1H NMR titration studies. The highest affinities were afforded using a combination of Br−and Na+counterions of the monomers and template, respectively. The boronate ester formation was confirmed by MS and1H/11B NMR, indicating 1 : 2 stoichiometries between sialyllactoses and boronic acid monomer. Polymers were synthesized in the form of microparticles using boronate and imidazolium monomers. This combinatorial approach afforded MIPs selective for the sialic acid linkages and compatible with an aqueous environment. The molecular recognition properties with respect to saccharide templates and glycosylated targets were reported.

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