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  • 1.
    Abdelhamid, Hani Nasser
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Bermejo-Gómez, Antonio
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Zou, Xiaodong
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    A water-stable lanthanide metal-organic framework for fluorimetric detection of ferric ions and tryptophan2017Ingår i: Microchimica Acta, ISSN 0026-3672, E-ISSN 1436-5073, Vol. 184, nr 9, s. 3363-3371Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The preparation of a highly water stable and porous lanthanide metal-organic framework (MOF) nanoparticles (denoted SUMOF-7II; SU refers to Stockholm University) is described. SUMOF-7II was synthesized starting from the tritopic linker of 2,4,6-tri-p-carboxyphenyl pyridine (H3L2) and La(III) as metal clusters. SUMOF-7II forms a stable dispersion and displays high fluorescence emission with small variation over the pH range of 6 to 12. Its fluorescence is selectively quenched by Fe(III) ions compared to other metal ions. The intensity of the fluorescene emission drops drops linearly in 16.6–167 μM Fe(III) concentration range, and Stern-Volmer plots are linear. The limit of detection (LOD) is 16.6 μM (at an S/N ratio of >3). This indicator probe can also be used for selective detection of tryptophan among several amino acids. Compared to the free linker H3L2, SUMOF-7II offers improved sensitivity and selectivity of the investigated species.

  • 2.
    Abdelhamid, Hani
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Wilk-Kozubek, Magdalena
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Ahmed, M. El-Zohry
    Valiente, Alejandro
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bermejo-Gomez, Antonio
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Mudring, Anja-Verena
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Zou, Xiaodong
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Luminescence Properties for a Family of Highly Stable Lanthanide Metal-Organic FrameworksManuskript (preprint) (Övrigt vetenskapligt)
  • 3.
    Abdel-Magied, Ahmed F.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Arafa, Wael A. A.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Laine, Tanja M.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Shatskiy, Andrey
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kärkäs, Markus D.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Johnston, Eric V.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Substituent Effects in Molecular Ruthenium Water Oxidation Catalysts Based on Amide Ligands2017Ingår i: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 9, nr 9, s. 1583-1587Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The production of clean and sustainable energy is considered as one of the most urgent issues for our society. Mastering the oxidation of water to dioxygen is essential for the production of solar fuels. A study of the influence of the substituents on the catalytic activity of a series of mononuclear Ru complexes (2a-e) based on a tetradentate ligand framework is presented. At neutral pH, using [Ru(bpy)(3)](PF6)(3) (bpy=2,2'-bipyridine) as the terminal oxidant, a good correlation between the turnover frequency (TOF) and the Hammett sigma(meta) parameters was obtained. Additionally, a general pathway for the deactivation of Ru-based catalysts 2a-e during the catalytic oxidation of water through poisoning by carbon monoxide was demonstrated. These results highlight the importance of ligand design for fine-tuning the catalytic activity of water oxidation catalysts.

  • 4.
    Abdel-Magied, Ahmed F.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Shatskiy, Andrey
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Liao, Rong-Zhen
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Laine, Tanja M.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Arafa, Wael A. A.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. University Fayoum, Egypt.
    Siegbahn, Per E. M.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kärkäs, Markus D.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Bjorn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Johnston, Eric V.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Chemical and Photochemical Water Oxidation Mediated by an Efficient Single-Site Ruthenium Catalyst2016Ingår i: ChemSusChem, ISSN 1864-5631, E-ISSN 1864-564X, Vol. 9, nr 24, s. 3448-3456Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Water oxidation is a fundamental step in artificial photosynthesis for solar fuels production. In this study, we report a single-site Ru-based water oxidation catalyst, housing a dicarboxylate-benzimidazole ligand, that mediates both chemical and light-driven oxidation of water efficiently under neutral conditions. The importance of the incorporation of the negatively charged ligand framework is manifested in the low redox potentials of the developed complex, which allows water oxidation to be driven by the mild one-electron oxidant [Ru(bpy)(3)](3+) (bpy = 2,2'-bipyridine). Furthermore, combined experimental and DFT studies provide insight into the mechanistic details of the catalytic cycle.

  • 5. Abrahamsson, Maria
    et al.
    Lundqvist, Maria J.
    Wolpher, Henriette
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Johansson, Olof
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Eriksson, Lars
    Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi.
    Bergquist, Jonas
    Rasmussen, Torben
    Becker, Hans-Christian
    Hammarström, Leif
    Norrby, Per-Ola
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Persson, Petter
    Steric influence on the excited-state lifetimes of ruthenium complexes with bipyridyl-alkanylene-pyridyl ligands2008Ingår i: Inorganic Chemistry, ISSN 0020-1669, Vol. 47, nr 9, s. 3540-3548Artikel i tidskrift (Refereegranskat)
  • 6. Abrahamsson, Maria
    et al.
    Wolpher, Henriette
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Johansson, Olof
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Larsson, Jan
    Kritikos, Mikael
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi, Avdelningen för strukturkemi.
    Eriksson, Lars
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för fysikalisk kemi, oorganisk kemi och strukturkemi, Avdelningen för strukturkemi.
    Norrby, Per-Ola
    Bergquist, Jonas
    Sun, Licheng
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Hammarström, Leif
    A New Strategy for Improvement of Photophysical Properties in Ruthenium(II) Polypyridyl Complexes. Synthesis, Photophysical and Electrochemical characterisation of Six Mononuclear Ruthenium(II) Bisterpyridine Type Complexes2005Ingår i: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 44, nr 9, s. 3215-3225Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The synthesis and characterization of six ruthenium(II) bistridentate polypyridyl complexes is described. These were designed on the basis of a new approach to increase the excited-state lifetime of ruthenium(II) bisterpyridine-type complexes. By the use of a bipyridylpyridyl methane ligand in place of terpyridine, the coordination environment of the metal ion becomes nearly octahedral and the rate of deactivation via ligand-field (i.e., metal-centered) states was reduced as shown by temperature-dependent emission lifetime studies. Still, the possibility to make quasi-linear donor−ruthenium−acceptor triads is maintained in the complexes. The most promising complex shows an excited-state lifetime of τ = 15 ns in alcohol solutions at room temperature, which should be compared to a lifetime of τ = 0.25 ns for [Ru(tpy)2]2+. The X-ray structure of the new complex indeed shows a more octahedral geometry than that of [Ru(tpy)2]2+. Most importantly, the high excited-state energy was retained, and thus, so was the potential high reactivity of the excited complex, which has not been the case with previously published strategies based on bistridentate complexes.

  • 7.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Alkene and Imino Reductions by Organocatalysis2008Ingår i: Modern Reduction Methods, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim , 2008, s. 341-361Kapitel i bok, del av antologi (Refereegranskat)
  • 8.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Product Class 2: Epoxides (Oxiranes): Synthesis from Alkenes by Metal-Mediated Oxidation2008Ingår i: Houben-Weyl Methods of Molecular Transformations: Compounds with One Saturated Carbon-Heteroatom Bond, Georg Thieme Verlag KG, Stuttgart , 2008, s. 227-276Kapitel i bok, del av antologi (Refereegranskat)
  • 9.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Transition metal-catalyzed epoxidation of alkenes2010Ingår i: Modern Oxidation Methods / [ed] Jan-Erling Bäckvall, Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA , 2010, 2, s. 37-84Kapitel i bok, del av antologi (Övrigt vetenskapligt)
  • 10.
    Adrian Meredith, Jenny
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Design and Synthesis of Inhibitors Targeting the Aspartic Proteases HIV-1 PR and BACE-12009Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
    Abstract [en]

    This thesis describes the synthesis of molecules designed for inhibition of two aspartic proteases, viral HIV-1 PR and human BACE-1. It also reports on the structure activity relationships of the targeted enzyme inhibitors.

    It is estimated that currently 33 million people are infected with HIV, the causative agent of AIDS. The virus targets T-lymphocytes and macrophages of the human immune system. The HIV-1 PR plays an important role in the viral replication, and by inhibiting the enzyme the disease progression can be slowed down or even halted.

    Herein is reported the design and synthesis of a series of HIV-1 PR inhibitors with novel P2 substituents of which several inhibit the enzyme in the nanomolar range. The aim of the second work was to further develop the inhibitors by the introduction of fluorine. Several attempts were performed to fluorinate different P2-substituents.

    Alzheimer’s disease (AD) is neurodegenerative, progressive and fatal disorder of the brain. It is associated with accumulation of plaques and tangles that cause impairment and functional decline of brain tissue which result in loss of memory and cognition. The plaques are mainly constituted of amyloid-β peptides that are generated in two steps from the amyloid precursor protein (APP). The cleavage sequence is initiated by the aspartic protease BACE-1, which makes the enzyme a key target in the effort of finding a therapy that aim to slow down the progression of AD.

    Herein are enclosed the development of two series of potent BACE-1 inhibitors. In the first work a synthetic strategy was developed to truncate a previously reported hydroxyethylene core structure in order to generate more drug-like inhibitors. This generated a series of truncated inhibitors where two amide bonds have been replaced with an ether - or alternatively a secondary amine linkage. A number of these inhibitors show potency against BACE-1. In the second part of the work the aim was investigate the effect of alterations in the P1 position. Five scaffolds with new P1 substituents were designed, synthesized and coupled with two different P2-P3 substituents. This resulted in a series of potent inhibitors that inhibit BACE-1 in the nanomolar range.

  • 11.
    Adrian Meredith, Jenny
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Björklund, Catarina
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Edlund, Michael
    Jansson, Katarina
    Lindberg, Jimmy
    Vrang, Lotta
    Hallberg, Anders
    Institutionen för läkemedelskemi, Uppsala universitet.
    Rosenquist, Åsa
    Samuelsson, Bertil
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Design and Synthesis of BACE-1 Inhibitors Containing a New Hydroxyethylene (HE) Scaffold: Potent activities in a cellular assayManuskript (preprint) (Övrigt vetenskapligt)
    Abstract [en]

    In a preceding report from our group we disclosed the development of a novel HE transition state isostere with a difluorophenoxymethyl side chain in the P1 position and a methoxy group in the P1’ position furnishing highly potent inhibitors of BACE-1 (i.e. lead compound 1), which moreover exhibit very promising selectivity over cathepsin D. In a continuation of this work with the aim at improving on the cell-based activity and pharmacokinetic properties, we have further developed the SAR for the P1 side chain of inhibitor 1 whereby the P1 side chain oxygen has been substituted for an amine, a carbon or a bond. The chemistry developed for the previous HE inhibitor structure 1 has now been extended to readily accommodate the introduction of new P1 side chains into this new HE scaffold. These modifications have given rise to several highly potent inhibitors where the most potent displayed a BACE-1 Ki value of 0.2 nM and a cell-based Aβ40 IC50 value of 9 nM. Thus, regarding the enzyme inhibition in the cell assay a more than 600-fold improvement compared to compound 1 was achieved via minor structural alterations.

  • 12.
    Adrian Meredith, Jenny
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Björklund, Catarina
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Adolfsson, Hans
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Jansson, Katarina
    Hallberg, Anders
    Institutionen för läkemedelskemi, Uppsala universitet.
    Rosenquist, Åsa
    Samuelsson, Bertil
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    P2’-truncated BACE-1 inhibitors with a novel hydroxethylene-like core2010Ingår i: European Journal of Medicinal Chemistry, ISSN 0223-5234, E-ISSN 1768-3254, Vol. 45, nr 2, s. 542-554Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Highly potent BACE-1 protease inhibitors derived from a novel hydroxyethylene-like core structure were recently developed by our group using X-ray crystal structure data and molecular modelling. In a continuation of this work guided by molecular modelling we have explored a truncated core motif where the P2’ amide group is replaced by an ether linkage resulting in a set of alkoxy, aryloxy and alkylaryl groups, with the overall aim to reduce molecular weight and the number of amide bonds to increase permeability and bestow the inhibitors with drug-like features. The most potent of these inhibitors displayed a BACE-1 IC50 value of 140 nM. The synthesis of these BACE-1 inhibitors utilizes readily available starting materials, furnishing the target compounds in good overall yields.

  • 13.
    Adrian Meredith, Jenny
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Wallberg, Hans
    Vrang, Lotta
    Oscarson, Stefan
    Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
    Parkes, Kevin
    Hallberg, Anders
    Institutionen för läkemedelskemi, Uppsala universitet.
    Samuelsson, Bertil
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Design and Synthesis of Novel P2 Substituents in Diol-based HIV Protease Inhibitors2010Ingår i: European Journal of Medicinal Chemistry, ISSN 0223-5234, E-ISSN 1768-3254, Vol. 45, nr 1, s. 160-170Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The synthesis and SAR of HIV-1 protease inhibitors containing novel P2 structural elements are presented. The inhibitors were designed having hydrogen bond accepting P2 substituents to probe potential favorable interactions to Asp-29/Asp-30 of the HIV-1 protease backbone utilizing inhibitor 3 as a model template. Several inhibitors were synthesized from an L-Val-methylamide P2 motif by appending hydrogen bonding moieties from either the isopropyl side chain or from the methylamide portion. The most promising inhibitors 4a and 4e displayed Ki values of 1.0 nM and 0.7 nM respectively and EC50 values in the MT4 cell-based assay of 0.17 µM and 0.33 µM respectively, a slight loss in potency compared to lead inhibitor 3. These inhibitors were also tested against an HIV protease inhibitor resistant strain carrying the M46I, V82F, and I84V mutations. Inhibitors 4a and 4e displayed a 3 and 4 fold change respectively compared with HIV wild type, whereas lead inhibitor 3 showed a higher 9 fold change. This study further demonstrate the chemical tractability of the approach where various P2 substituents can be introduced in just one chemical step from lactone x enabling facile modifications of the overall properties in this inhibitor class.

  • 14. Afewerki, Samson
    et al.
    Breistein, Palle
    Deiana, Luca
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Dziedzic, Pawel
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Ibrahem, Ismail
    Córdova, Armando
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Catalytic enantioselective β -alkylation of α,β-unsaturated aldehydes by combination of transition-metal- and aminocatalysis: Total synthesis of bisabolane sesquiterpenes2011Ingår i: Chemistry: a European Journal, ISSN 0947-6539, Vol. 17, nr 32, s. 8784-8788Artikel i tidskrift (Refereegranskat)
  • 15. Afewerki, Samson
    et al.
    Ibrahem, Ismail
    Rydfjord, Jonas
    Breistein, Palle
    Córdova, Armando
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Direct Regiospecific and Highly Enantioselective Intermolecular α-Allylic Alkylation of Aldehydes by a Combination of Transition-Metal and Chiral Amine Catalysts2012Ingår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, nr 10, s. 2972-2977Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The first direct intermolecular regiospecific and highly enantioselective a-allylic alkylation of linear aldehydes by a combination of achiral bench-stable Pd0 complexes and simple chiral amines as co-catalysts is disclosed. The co-catalytic asymmetric chemoselective and regiospecific a-allylic alkylation reaction is linked in tandem with in situ reduction to give the corresponding 2-alkyl alcohols with high enantiomeric ratios (up to 98:2 e.r.; e.r.=enantiomeric ratio). It is also an expeditious entry to valuable 2-alkyl substituted hemiacetals, 2-alkyl-butane-1,4-diols, and amines. The concise co-catalytic asymmetric total syntheses of biologically active natural products (e.g., Arundic acid) are disclosed.

  • 16. Agasti, Soumitra
    et al.
    Maity, Soham
    Szabó, Kálmán J.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Maiti, Debabrata
    Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds2015Ingår i: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 357, nr 10, s. 2331-2338Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Palladium-catalyzed oxidative annulations between phenols and alkenylcarboxylic acids produced a library of benzofuran compounds. Depending on the nature of the substitution of the phenol precursor, either 2,3-dialkylbenzofurans or 2-alkyl-3-methylene-2,3-dihydrobenzofurans can be synthesized with excellent regioselectivity. Reactions between conjugated 5-phenylpenta-2,4-dienoic acids and phenol gave 3-alkylidenedihydrobenzofuran alkaloid motifs while biologically active 7-arylbenzofuran derivatives were prepared by starting from 2-phenylphenols. More interestingly, selective incorporation of deuterium from D2O has been discovered, which offers an attractive one-step method to access deuterated compounds.

  • 17.
    Aggarwal, Varinder K.
    et al.
    Bristol University.
    Olofsson, Berit
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. University of Bristol, Bristol, UK.
    Enantioselective α-arylation of cyclohexanones with diaryl iodonium salts: Application to the synthesis of (-)-epibatidine.2005Ingår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 44, nr 34, s. 5516-5519Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The direct asym. α-arylation of prochiral ketones has been effected using chiral lithium amide bases and diaryl iodonium salts. The methodol. has been employed in a short total synthesis of the alkaloid (-)-epibatidine. [on SciFinder(R)]