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  • 1.
    Bernlind, Alexandra
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas.
    Imaging agent of a TRPA1 inhibitor2013In: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 56, no 9-10, p. 536-537Article in journal (Refereed)
  • 2.
    Boge, Lukas
    et al.
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Kemi Material och Ytor, Life Science. Chalmers University of Technology, Sweden.
    Bysell, Helena
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Kemi Material och Ytor, Life Science.
    Ringstad, Lovisa
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Kemi Material och Ytor, Life Science.
    Wennman, David
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas.
    Umerska, Anita
    University of Angers, France.
    Cassisa, Viviane
    CHU Angers, France.
    Eriksson, Jonny
    Uppsala University, Sweden.
    Joly-Guillou, Marie-Laure
    CHU Angers, France.
    Edwards, Katarina
    Uppsala University, Sweden.
    Andersson, Martin
    Chalmers University of Technology, Sweden.
    Lipid-based liquid crystals as carriers for antimicrobial peptides: Phase behavior and antimicrobial effect2016In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 32, no 17, p. 4217-4228Article in journal (Refereed)
    Abstract [en]

    The number of antibiotic-resistant bacteria is increasing worldwide, and the demand for novel antimicrobials is constantly growing. Antimicrobial peptides (AMPs) could be an important part of future treatment strategies of various bacterial infection diseases. However, AMPs have relatively low stability, because of proteolytic and chemical degradation. As a consequence, carrier systems protecting the AMPs are greatly needed, to achieve efficient treatments. In addition, the carrier system also must administrate the peptide in a controlled manner to match the therapeutic dose window. In this work, lyotropic liquid crystalline (LC) structures consisting of cubic glycerol monooleate/water and hexagonal glycerol monooleate/oleic acid/water have been examined as carriers for AMPs. These LC structures have the capability of solubilizing both hydrophilic and hydrophobic substances, as well as being biocompatible and biodegradable. Both bulk gels and discrete dispersed structures (i.e., cubosomes and hexosomes) have been studied. Three AMPs have been investigated with respect to phase stability of the LC structures and antimicrobial effect: AP114, DPK-060, and LL-37. Characterization of the LC structures was performed using small-angle X-ray scattering (SAXS), dynamic light scattering, ζ-potential, and cryogenic transmission electron microscopy (Cryo-TEM) and peptide loading efficacy by ultra performance liquid chromatography. The antimicrobial effect of the LCNPs was investigated in vitro using minimum inhibitory concentration (MIC) and time-kill assay. The most hydrophobic peptide (AP114) was shown to induce an increase in negative curvature of the cubic LC system. The most polar peptide (DPK-060) induced a decrease in negative curvature while LL-37 did not change the LC phase at all. The hexagonal LC phase was not affected by any of the AMPs. Moreover, cubosomes loaded with peptides AP114 and DPK-060 showed preserved antimicrobial activity, whereas particles loaded with peptide LL-37 displayed a loss in its broad-spectrum bactericidal properties. AMP-loaded hexosomes showed a reduction in antimicrobial activity.

  • 3.
    Briggner, Lars-Erik
    et al.
    Adroit Science AB, Sweden.
    Kloo, Lars
    KTH Royal Institute of Technology, Sweden.
    Rosdahl, Jan
    KTH Royal Institute of Technology, Sweden.
    Svensson, Per H.
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas. KTH Royal Institute of Technology, Sweden.
    In silico solid state perturbation for solubility improvement2015In: ChemMedChem, ISSN 1860-7179, E-ISSN 1860-7187, Vol. 9, no 4, p. 724-726Article in journal (Refereed)
    Abstract [en]

    Solubility is a frequently recurring issue within pharmaceutical industry, and new methods to proactively resolve this are of fundamental importance. Here, a novel methodology is reported for intrinsic solubility improvement, using in silico prediction of crystal structures, by perturbing key interactions in the crystalline solid state. The methodology was evaluated with a set of benzodiazepine molecules, using the two‐dimensional molecular structure as the only a priori input. The overall trend in intrinsic solubility was correctly predicted for the entire set of benzodiazepines molecules. The results also indicate that, in drug compound series where the melting point is relatively high (i.e., “brick dust” compounds), the reported methodology should be very suitable for identifying strategically important molecular substitutions to improve solubility. As such, this approach could be a useful predictive tool for rational compound design in the early stages of drug development.

  • 4.
    Cong, Jiayan
    et al.
    KTH Royal Institute of Technology, Sweden.
    Kinschel, Dominik
    KTH Royal Institute of Technology, Sweden; Dyenamo AB, Sweden.
    Daniel, Quentin
    KTH Royal Institute of Technology, Sweden.
    Safdari, Majid
    KTH Royal Institute of Technology, Sweden.
    Gabrielsson, Erik
    Dyenamo AB, Sweden.
    Chen, Hong
    KTH Royal Institute of Technology, Sweden.
    Svensson, Per H.
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas. KTH Royal Institute of Technology, Sweden.
    Sun, Licheng
    KTH Royal Institute of Technology, Sweden; DUT Dalian University of Technology, China.
    Kloo, Lars
    KTH Royal Institute of Technology, Sweden.
    Bis(1,1-bis(2-pyridyl)ethane)copper(I/II) as an efficient redox couple for liquid dye-sensitized solar cells2016In: Journal of Materials Chemistry, ISSN 0959-9428, E-ISSN 1364-5501, Vol. 4, no 38, p. 14550-14554Article in journal (Refereed)
    Abstract [en]

    A new redox couple, [Cu(bpye)2]+/2+, has been synthesized, and applied in dye-sensitized solar cells (DSSCs). Overall efficiencies of 9.0% at 1 sun and 9.9% at 0.5 sun were obtained, which are considerably higher than those obtained for cells containing the reference redox couple, [Co(bpy)3]2+/3+. These results represent a record for copper-based complex redox systems in liquid DSSCs. Fast dye regeneration, sluggish recombination loss processes, faster electron self-exchange reactions and suitable redox potentials are the main reasons for the observed increase in efficiency. In particular, the main disadvantage of cobalt complex-based redox couples, charge-transport problems, appears to be resolved by a change to copper complex redox couples. The results make copper complex-based redox couples very promising for further development of highly efficient DSSCs.

  • 5.
    Gu, Chungang
    et al.
    AstraZeneca, US.
    Lewis, Richard J.
    AstraZeneca, Sweden; AstraZeneca, UK.
    Wells, Andrew S.
    AstraZeneca, UK.
    Svensson, Per H.
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas. AstraZeneca, Sweden; KTH Royal Institute of Technology, Sweden.
    Hosagrahara, Vinayak P.
    AstraZeneca, US.
    Johnsson, Eskil
    AstraZeneca, Sweden.
    Hallström, Gösta
    AstraZeneca, US; AstraZeneca, Sweden.
    Lipid Peroxide-Mediated Oxidative Rearrangement of the Pyrazinone Carboxamide Core of Neutrophil Elastase Inhibitor AZD9819 in Blood Plasma Samples2015In: Drug Metabolism And Disposition, ISSN 0090-9556, E-ISSN 1521-009X, Vol. 43, no 10, p. 1441-1449Article in journal (Refereed)
    Abstract [en]

    This study focused on the mechanistic interpretation of ex vivo oxidation of a candidate drug in blood plasma samples. An unexpected lipid peroxide-mediated epoxidation followed by a dramatic rearrangement led to production of a five-membered oxazole derivative from the original six-membered pyrazinone-carboxamide core of a human neutrophil elastase inhibitor, 6-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-N-ethyl-5-methyl-3-oxo-4-(3-(trifluoromethyl)phenyl)-3,4-dihydropyrazine-2-carboxamide (AZD9819). The rearranged oxidation product 2-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-5-(N-ethylacetamido)-N-(3-(trifluoromethyl)phenyl)oxazole-4-carboxamide was characterized by accurate-mass tandem mass spectrometry fragmentations, by two-dimensional NMR and X-ray crystallography of an authentic standard, and by incorporation of an (18)O atom from molecular (18)O2 to the location predicted by our proposed mechanism. The lipid peroxide-mediated oxidation was demonstrated by using human low-density lipoprotein (LDL) in pH 7.4 phosphate buffer and by inhibiting the oxidation with ascorbic acid or l-glutathione, two antioxidants effective in both plasma and the LDL incubation. A nucleophilic mechanism for the epoxidation of AZD9819 by lipid hydroperoxides explains the prevention of its ex vivo oxidation by acidification of the plasma samples. The discovery of the lipid peroxide-dependent oxidation of an analyte and the means of prevention could provide valuable information for biotransformation and bioanalysis.

  • 6.
    Hammarström, Lars G. J.
    et al.
    Science for Life Laboratory, Sweden; Glionova Therapeutics, Sweden.
    Harmel, Robert K.
    Science for Life Laboratory, Sweden; FMP Leibniz-Forschungsinstitut für Molekulare Pharmakologie, Germany.
    Granath, Mikael
    OnTargetChemistry AB, Sweden.
    Ringom, Rune
    OnTargetChemistry AB, Sweden.
    Gravenfors, Ylva
    Stockholm University, Sweden.
    Färnegårdh, Katarina
    Stockholm University, Sweden.
    Svensson, Per H.
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas.
    Wennman, David
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas.
    Lundin, Göran
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas.
    Roddis, Ylva
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas.
    Kitambi, Satish
    Karolinska Institute, Sweden.
    Bernlind, Alexandra
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas.
    Lehmann, Fredrik
    OnTargetChemistry AB, Sweden.
    Ernfors, Patrik
    Karolinska Institute, Sweden.
    The Oncolytic Efficacy and in Vivo Pharmacokinetics of [2-(4-Chlorophenyl)quinolin-4-yl](piperidine-2-yl)methanol (Vacquinol-1) Are Governed by Distinct Stereochemical Features2016In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 59, no 18, p. 8577-8592Article in journal (Refereed)
    Abstract [en]

    Glioblastoma remains an incurable brain cancer. Drugs developed in the past 20 years have not improved the prognosis for patients, necessitating the development of new treatments. We have previously reported the therapeutic potential of the quinoline methanol Vacquinol-1 (1) that targets glioblastoma cells and induces cell death by catastrophic vacuolization. Compound 1 is a mixture of four stereoisomers due to the two adjacent stereogenic centers in the molecule, complicating further development in the preclinical setting. This work describes the isolation and characterization of the individual isomers of 1 and shows that these display stereospecific pharmacokinetic and pharmacodynamic features. In addition, we present a stereoselective synthesis of the active isomers, providing a basis for further development of this compound series into a novel experimental therapeutic for glioblastoma.

  • 7.
    Koch, Daniel
    et al.
    Rönninge College, Sweden.
    Koch, Eva
    Karo Bio, Sweden.
    Desarbre, Eric
    Basilea Pharmaceutica Ltd, Switzerland.
    Stensland, Birgitta
    AstraZeneca, Sweden.
    Svensson, Per H.
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas. Novum, Sweden.
    Bergman, Jan
    Novum, Sweden.
    2,2′-Biindolyl Reactions with Aldehydes2016In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2016, no 7, p. 1389-1396Article in journal (Refereed)
    Abstract [en]

    2,2′-Biindolyl has been condensed with aromatic and aliphatic aldehydes and products featuring 10-membered rings have been obtained. Thus, benzaldehyde gave compound 24a as the primary product, which readily underwent transannular oxidative coupling to 25a. The structures of both compounds were confirmed by X-ray crystallography. The product from 2,2′-biindolyl and formaldehyde under strongly acidic conditions was slightly different leading to compound 11, whose structure also was confirmed by X-ray crystallography. In this case, two molecules of 2,2′-biindolyl reacted with six molecules of formaldehyde.

  • 8.
    Safdari, Majid
    et al.
    KTH Royal Institute of Technology, Sweden.
    Svensson, Per H.
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas. KTH Royal Institute of Technology, Sweden.
    Tam Hoang, Minh
    Kumoh National Institute of Technology, South Korea.
    Oh, Ilwhan
    Kumoh National Institute of Technology, South Korea.
    Kloo, Lars
    KTH Royal Institute of Technology, Sweden.
    Gardner, James M.
    KTH Royal Institute of Technology, Sweden.
    Layered 2D alkyldiammonium lead iodide perovskites: synthesis, characterization, and use in solar cells2016In: Journal of Materials Chemistry, ISSN 0959-9428, E-ISSN 1364-5501, Vol. 8, no 4, p. 1627-1640Article in journal (Refereed)
    Abstract [en]

    The synthetic route and properties of three 2D hybrid organic/inorganic lead iodide perovskite materials are reported. The 2D perovskites were synthesized from the reaction between PbI2and the di-cations of 1,4-diaminobutane, 1,6-diaminohexane, and 1,8-diaminooctane. The resulting products were [NH3(CH2)4NH3]PbI4 (BdAPbI4), [NH3(CH2)6NH3]PbI4 (HdAPbI4), and [NH3(CH2)8NH3]PbI4 (OdAPbI4). Structural characterization shows that two dimensional perovskite structures were formed with inorganic structural planes separated by organic layers. Absorption spectra show band gaps of 2.37 eV (BdAPbI4), 2.44 eV (HdAPbI4), and 2.55 eV (OdAPbI4). The 2D perovskite materials were investigated as light absorbing materials in solid state solar cells. The best performing material under moist, ambient conditions was BdAPbI4(1.08% efficiency), which was comparable to methylammonium Pb(II) iodide (MAPbI3) solar cells (2.1% efficiency) manufactured and studied under analogous conditions. When compared to MAPbI3, the 2D materials have larger band gaps and lower photoconductivity, while BdAPbI4based solar cells shows a comparable absorbed photon-to-current efficiency as compared toMAPbI3 based ones.

  • 9.
    Svensson, Per H
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas.
    De novo determination of the crystal structure of a large drug molecule by crystal structure prediction-based powder NMR crystallography2013In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 135, no 46, p. 17501-17507Article in journal (Refereed)
    Abstract [en]

    The crystal structure of form 4 of the drug 4-[4-(2-adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]benzoic acid is determined using a protocol for NMR powder crystallography at natural isotopic abundance combining solid-state (1)H NMR spectroscopy, crystal structure prediction, and density functional theory chemical shift calculations. This is the first example of NMR crystal structure determination for a molecular compound of previously unknown structure, and at 422 g/mol this is the largest compound to which this method has been applied so far.

  • 10.
    Svensson, Per H
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Analys och fastfas.
    Oxidative ring expansion of spirocyclic oxindole derivatives2014In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 79, no 19, p. 9065-9073Article in journal (Refereed)
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