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  • 1.
    Christensen, Gustav
    et al.
    University of Tübingen, Germany.
    Chen, Yiyi
    University of Tübingen, Germany.
    Urimi, Dileep
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development.
    Zizmare, Laimdota
    University Hospital Tübingen, Germany.
    Trautwein, Christoph
    University Hospital Tübingen, Germany.
    Schipper, Nicolaas
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development.
    Paquet-Durand, Francois
    University of Tübingen, Germany.
    Pyruvate-conjugation of PEGylated liposomes for targeted drug delivery to retinal photoreceptors2023In: Biomedicine and Pharmacotherapy, ISSN 0753-3322, E-ISSN 1950-6007, Vol. 163, article id 114717Article in journal (Refereed)
    Abstract [en]

    Despite several promising candidates, there is a paucity of drug treatments available for patients suffering from retinal diseases. An important reason for this is the lack of suitable delivery systems that can achieve sufficiently high drug uptake in the retina and its photoreceptors. A promising and versatile method for drug delivery to specific cell types involves transporter-targeted liposomes, i.e., liposomes surface-coated with substrates for transporter proteins highly expressed on the target cell. We identified strong lactate transporter (monocarboxylate transporter, MCT) expression on photoreceptors as a potential target for drug delivery vehicles. To evaluate MCT suitability for drug targeting, we used PEG-coated liposomes and conjugated these with different monocarboxylates, including lactate, pyruvate, and cysteine. Monocarboxylate-conjugated and dye-loaded liposomes were tested on both human-derived cell-lines and murine retinal explant cultures. We found that liposomes conjugated with pyruvate consistently displayed higher cell uptake than unconjugated liposomes or liposomes conjugated with lactate or cysteine. Pharmacological inhibition of MCT1 and MCT2 reduced internalization, suggesting an MCT-dependent uptake mechanism. Notably, pyruvate-conjugated liposomes loaded with the drug candidate CN04 reduced photoreceptor cell death in the murine rd1 retinal degeneration model while free drug solutions could not achieve the same therapeutic effect. Our study thus highlights pyruvate-conjugated liposomes as a promising system for drug delivery to retinal photoreceptors, as well as other neuronal cell types displaying high expression of MCT-type proteins. © 2023 The Authors

  • 2.
    Christensen, Gustav
    et al.
    University of Tübingen, Germany.
    Urimi, Dileep
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development. University of Iceland, Iceland.
    Lorenzo‐Soler, Laura
    University of Iceland, Iceland.
    Schipper, Nicolaas
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development.
    Paquet-Durand, François
    University of Tübingen, Germany.
    Ocular permeability, intraocular biodistribution of lipid nanocapsule formulation intended for retinal drug delivery2023In: European journal of pharmaceutics and biopharmaceutics, ISSN 0939-6411, E-ISSN 1873-3441, Vol. 187, p. 175-183Article in journal (Refereed)
    Abstract [en]

    Recently, cGMP analogues have been investigated for the treatment of inherited retinal degenerations (IRD) using intravitreal injections. However, higher vitreous elimination rates limit the possibility to treat the retina with small molecule drugs. Here, we investigated the potential of lipid nanocapsules (LNCs) as vehicles to reduce clearance and prolong the delivery of cGMP analogue, CN03 to the retinal photoreceptors. Initially LNCs were investigated for both topical/periocular and intravitreal administration routes. While LNC-mediated drug permeation through the cornea proved to be too low for clinical applications, intravitreal application showed significant promise. Intravitreally administered LNCs containing fluorescent tracer in ex vivo porcine eyes showed complete intravitreal dispersal within 24 h. Ocular bio-distribution on histological sections showed that around 10 % of the LNCs had reached the retina, and 40 % accumulated in the ciliary body. For comparison, we used fluorescently labeled liposomes and these showed a different intraocular distribution with 48 % accumulated in the retina, and almost none were in the ciliary body. LNCs were then tested in retinal explants prepared from wild-type (WT) and rd1 mouse. In WT retina LNCs showed no significant toxic effects up to a concentration of 5 mg/mL. In rd1 retina, the LNC/CN03 formulation protected rd1 photoreceptors with similar efficacy to that of free CN03, demonstrating the usefulness of LNC/CN03 formulation in the treatment of IRD. Overall, our results indicate the suitability of LNCs for intraocular administration and drug delivery to both the retina and the ciliary body. © 2023 The Author(s)

  • 3.
    Ghoreishi, Farzaneh S.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry. Tarbiat Modares Univ, Dept Nanotechnol Engn, Tehran 14115111, Iran.
    Ahmadi, Vahid
    Tarbiat Modares Univ, Dept Nanotechnol Engn, Tehran 14115111, Iran.;Tarbiat Modares Univ, Dept Elect & Comp Engn, Tehran 14115194, Iran..
    Alidaei, Maryam
    Tarbiat Modares Univ, Dept Elect & Comp Engn, Tehran 14115194, Iran..
    Arabpour Roghabadi, Farzaneh
    Tarbiat Modares Univ, Dept Elect & Comp Engn, Tehran 14115194, Iran.;Tarbiat Modares Univ, Dept Chem Engn, Tehran 14115114, Iran..
    Samadpour, Mahmoud
    KN Toosi Univ Technol, Dept Phys, Tehran 1541849611, Iran..
    Poursalehi, Reza
    Tarbiat Modares Univ, Dept Nanotechnol Engn, Tehran 14115111, Iran..
    Johansson, Erik M. J.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
    Enhancing the efficiency and stability of perovskite solar cells based on moisture-resistant dopant free hole transport materials by using a 2D-BA2PbI4 interfacial layer2022In: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 24, no 3, p. 1675-1684Article in journal (Refereed)
    Abstract [en]

    In this work, the photovoltaic performance and stability of perovskite solar cells (PSCs) based on a dopant-free hole transport layer (HTL) are efficiently improved by inserting a two-dimensional (2D) interfacial layer. The benzyl ammonium lead iodide (BA2PbI4) 2D perovskite is used as an interfacial layer between the 3D CH3NH3PbI3 perovskite and two moisture-resistant dopant-free HTLs including poly[[2,3-bis(3-octyloxyphenyl)-5,8-quinoxalinediyl]-2,5-thiophenediyl] (TQ1) and poly(3-hexylthiophene) (P3HT). TQ1 with a facile synthesis procedure has a higher moisture resistivity compared to P3HT which can improve the stability of PSCs. The 2D BA2PbI4 perovskite with a less-volatile bulkier organic cation efficiently passivates the defects at the perovskite/HTL interface, leading to 11.95% and 15.04% efficiency for the modified TQ1 and P3HT based cells, respectively. For a better understanding, the structural, optical, and electrical properties of PSCs comprising P3HT and TQ1 HTLs with and without interface modification are studied. The interface modified PSCs show slower open-circuit voltage decay and longer carrier lifetimes compared to unmodified cells. In addition, impedance spectroscopy reveals lower charge transport resistance and higher recombination resistance for the modified devices, which could be associated with the modification of the interface between the 3D CH3NH3PbI3 perovskite and HTL caused by the 2D interfacial layer. Also after aging under ambient conditions for about 800 hours, the modified PCSs retain more than 80% of their initial PCEs. These results give us the hope of achieving simpler, cheaper, and more stable PSCs with dopant-free HTLs through 2D interfacial layers, which have great potential for commercialization.

  • 4. Christensen, Gustav
    et al.
    Urimi, Dileep
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development.
    Schipper, Nicolaas
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development.
    Novel treatments for retinal degeneration: Ocular bio-distribution and treatment efficacy of lipid nanocapsules and liposomes2022Conference paper (Other academic)
  • 5.
    Urimi, Dileep
    et al.
    RISE Res Inst Sweden, Div Bioecon & Hlth Chem Proc & Pharmaceut Dev, S-15136 Södertälje, Sweden.;Univ Iceland, Fac Pharmaceut Sci, Sch Hlth Sci, IS-107 Reykjavik, Iceland..
    Hellsing, Maja
    RISE Res Inst Sweden, Div Bioecon & Hlth Chem Proc & Pharmaceut Dev, S-15136 Södertälje, Sweden.;Swedish Res Council, Dept Res Infrastruct, Vastra Jarnvagsgatan 3,Box 1035, S-10138 Stockholm, Sweden..
    Mahmoudi, Najet
    Rutherford Appleton Lab, ISIS Pulsed Neutron & Muon Source, Didcot OX11 0QX, Oxon, England..
    Soderberg, Christopher
    RISE Res Inst Sweden, Div Bioecon & Hlth Chem Proc & Pharmaceut Dev, S-15136 Södertälje, Sweden..
    Widenbring, Ronja
    RISE Res Inst Sweden, Div Bioecon & Hlth Chem Proc & Pharmaceut Dev, S-15136 Södertälje, Sweden..
    Gedda, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
    Edwards, Katarina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
    Loftsson, Thorsteinn
    Univ Iceland, Fac Pharmaceut Sci, Sch Hlth Sci, IS-107 Reykjavik, Iceland..
    Schipper, Nicolaas
    RISE Res Inst Sweden, Div Bioecon & Hlth Chem Proc & Pharmaceut Dev, S-15136 Södertälje, Sweden..
    Structural Characterization Study of a Lipid Nanocapsule Formulation Intended for Drug Delivery Applications Using Small-Angle Scattering Techniques2022In: Molecular Pharmaceutics, ISSN 1543-8384, E-ISSN 1543-8392, Vol. 19, no 4, p. 1068-1077Article in journal (Refereed)
    Abstract [en]

    Lipid nanocapsules (LNCs) are increasingly being used for various drug delivery applications due to their versatile nature and ability to carry a wide variety of therapeutic drug molecules. In the present investigation, small-angle X-ray (SAXS) and neutron scattering (SANS) techniques were used to elucidate the structure of LNCs. Overall, size measurements obtained from SAXS and SANS techniques were complemented with dynamic light scattering, zeta potential, and cryogenic transmission electron microscopy measurements. The structural aspects of LNCs can be affected by drug loading and the properties of the drug. Here, the impact of drug loading on the overall structure was evaluated using DF003 as a model drug molecule. LNCs with varying compositions were prepared using a phase inversion method. Combined analysis of SAXS and SANS measurements indicated the presence of a core-shell structure in the LNCs. Further, the drug loading did not alter the overall core-shell structure of the LNCs. SANS data revealed that the core size remained unchanged with a radius of 20.0 +/- 0.9 nm for unloaded LNCs and 20.2 +/- 0.6 nm for drug-loaded LNCs. Furthermore, interestingly, the shell becomes thicker in an order of similar to 1 nm in presence of the drug compared to the shell thickness of unloaded LNCs as demonstrated by SAXS data. This can be correlated with the strong association of hydrophilic DF003 with Kolliphor HS 15, a polyethylene glycol-based surfactant that predominantly makes up the shell, resulting in a drug-rich hydrated shell.

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  • 6.
    Urimi, Dileep
    et al.
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development. University of Iceland, Iceland.
    Hellsing, Maja
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development. Swedish Research Council, Sweden.
    Mahmoudi, Najet
    Rutherford Appleton Laboratory, Uk.
    Söderberg, Christopher
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development.
    Widenbring, Ronja
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development.
    Gedda, Lars
    Uppsala University, Sweden.
    Edwards, Katarina
    Uppsala University, Sweden.
    Loftsson, Thorsteinn
    University of Iceland, Iceland.
    Schipper, Nicolaas
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development.
    Structural Characterization Study of a Lipid Nanocapsule Formulation Intended for Drug Delivery Applications Using Small-Angle Scattering Techniques2022In: Molecular Pharmaceutics, ISSN 1543-8384, E-ISSN 1543-8392, Vol. 19, no 4, p. 1068-1077Article in journal (Refereed)
    Abstract [en]

    Lipid nanocapsules (LNCs) are increasingly being used for various drug delivery applications due to their versatile nature and ability to carry a wide variety of therapeutic drug molecules. In the present investigation, small-angle X-ray (SAXS) and neutron scattering (SANS) techniques were used to elucidate the structure of LNCs. Overall, size measurements obtained from SAXS and SANS techniques were complemented with dynamic light scattering, zeta potential, and cryogenic transmission electron microscopy measurements. The structural aspects of LNCs can be affected by drug loading and the properties of the drug. Here, the impact of drug loading on the overall structure was evaluated using DF003 as a model drug molecule. LNCs with varying compositions were prepared using a phase inversion method. Combined analysis of SAXS and SANS measurements indicated the presence of a core–shell structure in the LNCs. Further, the drug loading did not alter the overall core–shell structure of the LNCs. SANS data revealed that the core size remained unchanged with a radius of 20.0 ± 0.9 nm for unloaded LNCs and 20.2 ± 0.6 nm for drug-loaded LNCs. Furthermore, interestingly, the shell becomes thicker in an order of ∼1 nm in presence of the drug compared to the shell thickness of unloaded LNCs as demonstrated by SAXS data. This can be correlated with the strong association of hydrophilic DF003 with Kolliphor HS 15, a polyethylene glycol-based surfactant that predominantly makes up the shell, resulting in a drug-rich hydrated shell.

  • 7.
    Urimi, Dileep
    et al.
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development. University of Iceland, Iceland.
    Widenbring, Ronja
    RISE Research Institutes of Sweden.
    Perez, Oswaldo
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development. University of Iceland, Iceland.
    Gedda, Lars
    Uppsala University, Uppsala.
    Edwards, Katarina
    Uppsala University, Uppsala.
    Loftsson, Thorsteinn
    University of Iceland, Iceland.
    Schipper, Nicolaas
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development.
    Formulation development and upscaling of lipid nanocapsules as a drug delivery system for a novel cyclic GMP analogue intended for retinal drug delivery2021In: International Journal of Pharmaceutics, ISSN 0378-5173, E-ISSN 1873-3476, Vol. 602, article id 120640Article in journal (Refereed)
    Abstract [en]

    Lipid nanocapsules (LNCs) were prepared with a novel cyclic GMP analogue, DF003, intended for the treatment of neurodegenerative retinal degenerations. LNCs loaded with DF003 were prepared by a phase inversion method and characterized for particle size, polydispersity index, drug loading, entrapment efficiency, stability, and in vitro drug release. Particle size, PdI and zeta potential of selected optimized formulation were 76 ± 1.2 nm, 0.16 ± 0.02, and −11.6 ± 0.4 mV, respectively, with an entrapment efficiency of 69 ± 0.5%. The selected formulation showed a sustained drug release for up to 6 days in phosphate buffer as well as in vitreous components. Stability evaluation of LNCs in presence of vitreous components demonstrated structural stability and compatibility. Further, the nanoparticle preparation process was upscaled to 1000 times (10 L) of the typical lab scale (0.01 L). Product parameters were observed to be unaffected by the upscaling, demonstrating that the LNCs were of the same quality as those prepared at lab scale. Additionally, the manufacturing process was adapted and assessed for a continuous production of LNCs to leverage it for industrial viability. Overall, these findings reveal the remarkable potential of LNCs as drug delivery vehicles and their possibility for clinical translation.

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  • 8.
    Christensen, Gustav
    et al.
    University of Tübingen, Germany.
    Barut, Leon
    University of Tübingen, Germany.
    Urimi, Dileep
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development.
    Schipper, Nicolaas
    RISE Research Institutes of Sweden, Bioeconomy and Health, Chemical Process and Pharmaceutical Development.
    Paquet-Durand, François
    University of Tübingen, Germany.
    Investigating Ex Vivo Animal Models to Test the Performance of Intravitreal Liposomal Drug Delivery Systems2021In: Pharmaceutics, E-ISSN 1999-4923, Vol. 13, no 7, article id 1013Article in journal (Refereed)
    Abstract [en]

    There is a strong need for innovative and efficient drug delivery systems for ocular therapy development. However, testing intravitreal drug delivery systems without using live animals is challenging. Ex vivo animal models offer an interesting alternative. We analyzed the potential of using fresh porcine eyes obtained from the local slaughterhouse as a model for testing the intravitreal biodistribution and retention of liposomes with or without polyethylene glycol (PEG) conjugation and with different surface charges. The histology of the eyes was analyzed to localize the liposomes, and it was found that liposomes with PEG absorbed rapidly on the retina (within 1 h), with positively charged and PEG-coated liposomes being retained for at least 24 h. In parallel, fluorophotometry was employed on intact eyes, to determine the pharmacokinetics of the fluorophore calcein, as a substitute for a small hydrophilic therapeutic compound. We found a 4.5-fold increase in the vitreous half-life of calcein loaded in liposomes, compared with the free solution. Retinal toxicity was addressed using murine-derived retinal explant cultures. Liposomes were non-toxic up to 500 µg/mL. Toxicity was observed at 5 mg/mL for anionic and cationic liposomes, with 2-fold and 2.5-fold increased photoreceptor cell death, respectively. Overall, we could show that important ocular drug delivery considerations such as pharmacokinetics and biodistribution can be estimated in ex vivo porcine eyes, and may guide subsequent in vivo experiments.

  • 9.
    Oko, Asaf
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Surface and Corrosion Science. SP Technical Research Institute of Sweden, Sweden.
    Martinez, D.Mark
    Swerin, Agne
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Surface and Corrosion Science. SP Technical Research Institute of Sweden, Sweden.
    Infiltration and dimensional scaling of inkjet droplets on thick isotropic porous materials2014In: Microfluidics and Nanofluidics, ISSN 1613-4982, E-ISSN 1613-4990, Vol. 17, no 2, p. 413-422Article in journal (Refereed)
    Abstract [en]

    We study the imbibition of picoliter (pL)-sized inkjet droplets on controlled pore glass membranes (CPG), as a suitable model for isotropic three-dimensional porous materials. We do so using a variety of liquids, i.e., water, formamide and diiodomethane, and measure the evolution of the imbibition process using high-speed digital imaging. Here, experiments were conducted on 2-280 nm CPG membranes with drops with initial volumes ranging from 100 to 600 pL. We derive scaling laws for imbibition through dimensional analysis and advance the argument that the rate of absorption is related to two-dimensionless groups where v(t) is the imbibed volume, as determined from experiments, t is the time, v (tot) the total liquid volume, the porosity, mu the liquid viscosity, k the permeability, and p (c) the Laplace capillary pressure. We show this scaling to well describe the system at intermediate T values and report that V alpha T-0.8.

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