Publications

Recent multidisciplinary research output generated through our projects can be found below.
2024

H. Stubb, J. Sevón, C. Schlegel, M. Viljanen, J. Moilanen, T. Viitaja, F. S. Ekholm, Decipher ‘Em All: A Profiling Study on the Effects of Acyl Groups in O‑Acyl-ω-hydroxy Fatty Acids, Langmuir 2024, 40, 21559–21572. 

J. Matović, J. Järvinen, I. K. Sokka, S. Imlimthan, O. Aitio, M. Sarparanta, J. Rautio, F. S. Ekholm, Towards New Delivery Agents for Boron Neutron Capture Therapy: Synthesis and In Vitro Evaluation of a Set of Fluorinated Carbohydrate Derivatives, Molecules 2024, 29, 4263. (Special issue in honor of Prof. David Crich's 65th Birthday and his outstanding contributions to carbohydrate chemistry). 

F. Ekholm, R. Paananen, T. Viitaja, J. Sevón, J.-E. Raitanen, T. Lajunen, M. Ruponen, J. Jäntti, Anti-evaporative lipid formulations, WO/2024/094759/A1.

Z. J. Leśnikowski, F. Ekholm, N. S. Hosmane, M. Kellert, E. Matsuura, H. Nakamura, A. B. Olejniczak, L. Panza, L. M. Rendina, W. A. G. Sauerwein, Early Stage In Vitro Bioprofiling of Potential Low-Molecular-Weight Organoboron Compounds for Boron Neutron Capture Therapy (BNCT) – Proposal for a Guide, Cells 2024, 13, 798.

H. Stubb, T. Viitaja, R. M. Trevorah, J.-E. Raitanen, J. Moilanen, K. J. Svedström, F. S. Ekholm, Another Brick in the Wall of Tear Film Insights Added Through the Total Synthesis and Biophysical Profiling of anteiso-Branched Wax and Cholesteryl Esters, J. Nat. Prod. 2024, 87, 954–965.

R. M. Trevorah, M. Viljanen, T. Viitaja, H. Stubb, J. Sevón, O. Konovalov, M. Jankowski, P. Fontaine, A. Hemmerle, J.-E. Raitanen, F. S. Ekholm, K. J. Svedström, New Insights into the Molecular Structure of Tear Film Lipids by Surface X-ray Scattering, J. Phys. Chem. Lett. 2024, 15, 316–322. 

2023

J. Jäntti, T. Viitaja, J. Sevón, T. Lajunen, J.-E. Raitanen, C. Schlegel, M. Viljanen, R. O. Paananen, J. Moilanen, M. Ruponen,  F. S. Ekholm, Early-Stage Development of an Anti-Evaporative Liposomal Formulation for the Potential Treatment of Dry Eyes, ACS Pharmacol. Transl. Sci. 20236, 1518-1530.

J. Matović, K. Bahrami, P. Stockmann, I. K. Sokka, Y. C. Khng, M. Sarparanta, E. Hey-Hawkins, J. Rautio, F. S. Ekholm, Sweet Battle of the Epimers - Continued Exploration of Monosaccharide-Derived Delivery Agents for Boron Neutron Capture Therapy, Mol. Pharmaceutics 2023, 20, 3127-3139.

T. Viitaja, J.-E. Raitanen, J. Moilanen, R. O. Paananen, F. S. Ekholm, Biophysical Profiling of Synthetic Ultra-Long Tear Film Lipids, Colloids Surf. B: Biointerfaces 2023, 223, 113145.

2022

J. Matović, J. Järvinen, I. K. Sokka, P. Stockmann, M. Kellert, S. Imlimthan, M. Sarparanta, M. P. Johansson, E. Hey-Hawkins, J. Rautio, F. S. Ekholm, Synthesis and In Vitro Evaluation of a Set of 6-Deoxy-6-thio-carboranyl D-Glucoconjugates Sheds Light on the Substrate Specificity of the GLUT1 Transporter, ACS Omega 2022, 7, 30376–30388.

T. Viitaja, J.-E. Raitanen, A. Hynynen, J. Moilanen, K. Svedström, R. O. Paananen, F. S. Ekholm, On the Importance of Chain Branching in Tear Film Lipid Layer Wax and Cholesteryl Esters, Colloids Surf. B: Biointerfaces 2022, 214, 112429.

H. Bland, J.-E. Raitanen, J. Moilanen, R. Paananen, T. Viitaja, F. Ekholm, A specific combination of lipids and methods and uses related thereto, WO/2022/229441/A2.

2021

T. Viitaja, J. Moilanen, K. J. Svedström, F. S. Ekholm, R. O. Paananen, Tear Film Lipid Layer Structure: Self-Assembly of O‑Acyl-ω-Hydroxy Fatty Acids and Wax Esters into Evaporation-Resistant Monolayers, Nano Lett. 2021, 18, 7676–7683.

I. K. Sokka, S. Imlimthan, M. Sarparanta, H. Maaheimo, M. P. Johansson, F. S. Ekholm, Halogenation at the Phenylalanine Residue of Monomethyl Auristatin F Leads to a Favorable cis/trans Equilibrium and Retained Cytotoxicity, Mol. Pharmaceutics 2021, 18, 3125–3131.

T. Viitaja, J.-E. Raitanen, J. Moilanen, R. O. Paananen, F. S. Ekholm, The Properties and Role of O-Acyl-ω-hydroxy Fatty Acids and Type I-St and Type II Diesters in the Tear Film Lipid Layer Revealed by a Combined Chemistry and Biophysics Approach, J. Org. Chem. 2021, 86, 4965–4976; and a correction notice; J. Org. Chem. 2021, 86, 17533.

J. Matović, J. Järvinen, I. K. Sokka, S. Imlimthan, J.-E. Raitanen, A. Montaser, K. M. Huttunen, H. Maaheimo, S. Peräniemi, A. J. Airaksinen, M. Sarparanta, M. P. Johansson, J. Rautio, F. S. Ekholm, Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and In Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates Mol. Pharmaceutics 2021, 18, 285–304.

2020

J. Matović, J. Järvinen, H. C. Bland, I. K. Sokka, S. Imlimthan, R. M. Ferrando, K. M. Huttunen, J. Timonen, S. Peräniemi, O. Aitio, A. J. Airaksinen, M. Sarparanta, M. P. Johansson, J. Rautio, F. S. Ekholm, Addressing the Biochemical Foundations of a Glucose-based “Trojan horse”–strategy to Boron Neutron Capture Therapy: From Chemical Synthesis to In Vitro Assessment, Mol. Pharmaceutics 2020, 17, 3885–3899.

A. A. Hettikankanamalage, R. Lassfolk, F. S. Ekholm, R. Leino, D. Crich, Mechanisms of stereodirecting participation and ester migration from near and far in glycosylation and related reactions, Chem. Rev. 2020, 120, 7104–7151.

R. O. Paananen, T. Viitaja, A. Olzynska, F. S. Ekholm, J. Moilanen, L. Cwiklik, Interactions of polar lipids with cholesteryl ester multilayers elucidate tear film lipid layer structure, Ocul. Surf. 2020, 18, 545–553.

J. Siirilä, S. Hietala, F. S. Ekholm, H. Tenhu, Glucose and maltose surface functionalized thermoresponsive poly(N-vinylcaprolactam) nanogels, Biomacromolecules 2020, 21, 955–965.

2019

I. K. Sokka, F. S. Ekholm, M. P. Johansson, Increasing the potential of the auristatin cancer-drug family by shifting the conformational equilibrium, Mol. Pharmaceutics 2019, 16, 3600–3608.

S.-K. Ruokonen, F. S. Ekholm, S. K. Wiedmer, Assessing interactions of auristatin derivatives with mixed phospholipid-sodium dodecyl sulfate aggregate dispersions, Langmuir 2019, 35, 5232–5240.

H. C. Bland, J. A. Moilanen, F. S. Ekholm, R. O. Paananen, Investigating the Role of Specific Tear Film Lipids Connected to Dry Eye Syndrome: A Study on O-acyl-ω-hydroxy-fatty acids and Diesters, Langmuir 2019, 35, 3545–3552 (ACS Editors' Choice article).

R. Lassfolk, J. Rahkila, M. P. Johansson, F. S. Ekholm, J. Wärnå, R. Leino, Acetyl group migration across saccharide units in oligomannoside model compounds, J. Am. Chem. Soc. 2019, 141, 1646–1654.

F. S. Ekholm, S.-K. Ruokonen, M. Redón, V. Pitkänen, A. Vilkman, J. Saarinen, J. Helin, T. Satomaa, S. K. Wiedmer, Hydrophilic Monomethyl Auristatin E derivatives as novel candidates for the design of antibody-drug conjugates, Separations 2019, 6, 1.

 J. Rahkila, F. S. Ekholm, A. Ardá, S. Delgado, J. Savolainen, J. Jiménez-Barbero, R. Leino, Novel Dextran-Supported Biological Probes Decorated with Disaccharide Entities for Probing the Carbohydrate – Protein Interactions of Gal-3, ChemBioChem 2019, 20, 203–209.

2018

 J. Rahkila, F. S. Ekholm, R. Leino, Cu(I) mediated degradation of polysaccharides leads to fragments with narrow polydispersities, Eur. J. Org. Chem. 2018, 1449–1454.

F. S. Ekholm, R. Leino, chapter 8: “Acyl migrations in carbohydrate chemistry” in the book; “Protective groups – Strategies and Applications in Carbohydrate Chemistry” (Ed. S. Vidal), Publisher: Wiley-VCH.

 

2017

M. P. Johansson, H. Maaheimo, F. S. Ekholm, New insights on the structural features of the cytotoxic auristatins MMAE and MMAF revealed by combined NMR spectroscopy and quantum chemical modelling, Sci. Rep. 2017, 7:15290.

K. Lagerblom, E. Lagerspets, J. Keskiväli, C. Cook, F. Ekholm, A. Parviainen, T. J. Repo, Practical aerobic oxidation of alcohols: ligand enhanced TEMPO/Mn(NO3)2 catalyst system, ChemCatChem 2017, 20, 3880–3887.

2016

F. S. Ekholm, H. Pynnönen, A. Vilkman, V. Pitkänen, J. Helin, J. Saarinen, T. Satomaa, Introducing glycolinkers for the functionalization of cytotoxic drugs and applications in antibody-drug conjugation chemistry, ChemMedChem 2016, 11, 2501–2505.

F. S. Ekholm, H. Pynnönen, A. Vilkman, J. Koponen, J. Helin, T. Satomaa, Synthesis of the copper chelator TGTA and evaluation of its ability to protect biomolecules from copper induced degradation during copper catalyzed azide-alkyne bioconjugation reactions, Org. Biomol. Chem. 2016, 14, 849–852.

J. Helin, J. Saarinen, T. Satomaa, F. S. Ekholm, Saccharide derivative of a toxic payload and antibody conjugates thereof, WO/2016/001485 (A1), Glykos Finland Ltd

A. Leppänen, F. S. Ekholm, J. Helin, H. Salo, A. Kanerva, Conjugate, JP/2016/020336 (A), US/2017/112931 (A1), Tenboron Ltd

 

2015

J. Helin, J. Saarinen, F. S. Ekholm, A. Leppänen, Payload-polymer-protein conjugates, WO/2015/15189478 (A1), US/2017/189549 (A1), Glykos Finland Ltd

 

2014

J. Rahkila, F. S. Ekholm, R. Panchadhayee, A. Ardá, F. J. Cañada, J. Jiménez Barbero, R. Leino, Synthesis and conformational analysis of phosphorylated β-(1→2)-linked mannosides, Carbohydrate Res. 2014, 383, 58–68.

T. Satomaa, J. Helin, F. S. Ekholm, Conjugates of a glycoprotein or a glycan with a toxic payload, WO/2014/177771 (A1); US/2016/106860 (A1), Glykos Finland Ltd

F. S. Ekholm, T. Satomaa, J. Helin, H. Pynnönen, Linker-payload molecule conjugates, WO/2014/096551 (A1); US/2015/314007 (A1), Glykos Finland Ltd

2012

F. S Ekholm, Á. Berényi, L. Lagerquist, T. Saloranta, I. Zupkó, G. Schneider, J. Wölfling, R. Leino, Cytotoxic activity of some glycoconjugates including saponins and anthracyclines, Carbohydrate Res. 2012, 356, 295–298.

K. Ranta, K. Nieminen, F. S. Ekholm, M. Poláková, M. U. Roslund, T. Saloranta, R. Leino, J. Savolainen, Evaluation of the immunostimulatory activities of synthetic mannose containing structures mimicking β-(1,2)-linked cell wall mannans of Candida albicans, Clin. Vaccine Immunol. 2012, 19, 1889–1893.

F. S. Ekholm, A. Ardá, P. Eklund, S. André, H.-J. Gabius, J. Jiménez-Barbero, R. Leino, Studies related to Norway spruce galactoglucomannans: chemical synthesis, conformational analysis, NMR spectroscopic characterization and molecular recognition of model compounds, Chem. Eur. J. 2012, 18, 14392–14405.

2011

F. S. Ekholm, G. Schneider, J. Wölfling, R. Leino, An Approach to the Synthesis and Attachment of Scillabiose to Steroids, Steroids 2011, 76, 588–595.

F. S. Ekholm, L. Lagerquist, R. Leino, Stereo- and regioselective glycosylation of 4-deoxy-e-rhodomycinone, Carbohydrate Res. 2011, 346, 858–862.

F. S. Ekholm, G. Schneider, J. Wölfling, R. Leino, Synthesis of a small library of estradiol based glycosteroid mimics containing a modified D-ring, Eur. J. Org. Chem. 2011, 1064–1077.

F. S. Ekholm, I. Mandity, F. Fülop, R. Leino, Rapid, simple and efficient deprotection of benzyl/benzylidene protected carbohydrates by utilization of flow chemistry, Tetrahedron Lett. 2011, 52, 1839–1841.

2010

F. S. Ekholm, J. Sinkkonen, R. Leino, Fully deprotected β-(1→2)-mannotetraose forms a contorted α-helix in solution: convergent synthesis and conformational characterization by NMR and DFT, New. J. Chem. 2010, 34, 667–675.

A. Hietanen, F. S. Ekholm, R. Leino, L. T. Kanerva, Applying biocatalysis to the synthesis of diastereomerically enriched cyanohydrin Mannosides, Eur. J. Org. Chem. 2010, 6974–6980.

F. S. Ekholm, P. Eklund, R. Leino, A short semi-synthesis and complete NMR-spectroscopic characterization of the naturally occurring lignan glycoside matairesinol 4,4'-di-O-β-D-glucoside, Carbohydrate Res. 2010, 345, 1963–1967.

2009

M. Poláková, M. U. Roslund, F. S. Ekholm, T. Saloranta, R. Leino, Synthesis of β-(1→2)-linked mannosides, Eur. J. Org. Chem. 2009, 870–888.  

F. S. Ekholm, M. Poláková, A. J. Pawłowicz, R. Leino, Synthesis of divalent 2,2'-linked mannose derivatives by homodimerization, Synthesis 2009, 567–576.