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  • 1.
    Martin-Serrano Ortiz, Angela
    et al.
    IBIMA Reg Univ Hosp Malaga UMA, Hosp Civil, Res Lab, Plaza Hosp Civil, Malaga 29009, Spain.;IBIMA Reg Univ Hosp Malaga UMA, Hosp Civil, Allergy Unit, Plaza Hosp Civil, Malaga 29009, Spain.;BIONAND Andalusian Ctr Nanomed & Biotechnol, Parque Tecnol Andalucia, Malaga 29590, Spain..
    Stenström, Patrik
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Antunez, Pablo Mesa
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Andrén, Oliver C. J.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Torres, Maria J.
    IBIMA Reg Univ Hosp Malaga UMA, Hosp Civil, Res Lab, Plaza Hosp Civil, Malaga 29009, Spain.;IBIMA Reg Univ Hosp Malaga UMA, Hosp Civil, Allergy Unit, Plaza Hosp Civil, Malaga 29009, Spain.;BIONAND Andalusian Ctr Nanomed & Biotechnol, Parque Tecnol Andalucia, Malaga 29590, Spain..
    Montanez, Maria I.
    IBIMA Reg Univ Hosp Malaga UMA, Hosp Civil, Res Lab, Plaza Hosp Civil, Malaga 29009, Spain.;IBIMA Reg Univ Hosp Malaga UMA, Hosp Civil, Allergy Unit, Plaza Hosp Civil, Malaga 29009, Spain.;BIONAND Andalusian Ctr Nanomed & Biotechnol, Parque Tecnol Andalucia, Malaga 29590, Spain..
    Malkoch, Michael
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
    Design of multivalent fluorescent dendritic probes for site-specific labeling of biomolecules2018In: Journal of Polymer Science Part A: Polymer Chemistry, ISSN 0887-624X, E-ISSN 1099-0518, Vol. 56, no 15, p. 1609-1616Article in journal (Refereed)
    Abstract [en]

    Herein, the synthesis and characterization of orthogonal dendrons decorated with multiple units of fluorescent and a chemoselective group at a focal point, followed by specific antibody labeling, is presented. Fluorescence results confirm the applicability of the fluorescent probes for biomolecule labeling and fluorescent signal amplification.

  • 2.
    Stenström, Patrik
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Andrén, Oliver C. J.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Malkoch, Michael
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Fluoride-promoted esterification (FPE) chemistry: A robust route to Bis-MPA dendrons and their postfunctionalization2016In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 21, no 3, article id 366Article in journal (Refereed)
    Abstract [en]

    Bifunctional dendrons based on 2,2-bis(methylol)propionic acid (bis-MPA) are highly desirable scaffolds for biomedical applications. This is due to their flawless nature and large and exact number of functional groups as well as being biodegradable and biocompatible. Herein, we describe a facile divergent growth approach to their synthesis from monobenzylated tetraethylene glycol and post functionalization utilizing fluoride-promoted esterification (FPE) chemistry protocols. The scaffolds, presenting selectively deprotectable hydroxyls in the periphery and at the focal point, were isolated on a multigram scale with excellent purity up to the fourth generation dendron with a molecular weight of 2346 Da in seven reactions with a total yield of 50%. The third generation dendron was used as a model compound to demonstrate its functionalizability. Selective deprotection of the dendron's focal point was achieved with an outstanding yield of 94%, and biotin as well as azido functionalities were introduced to its focal point and periphery, respectively, through FPE chemistry. Bulky disperse red dyes were clicked through CuAAC to the dendron's azido groups, giving a biotinylated dendron with multivalent dyes with a molecular weight of 6252 Da in a total yield of 37% in five reactions with an average yield of 82% starting from the third generation focally and peripherally protected dendron. FPE chemistry proved to be a superb improvement over previous protocols towards bis-MPA dendrons as high purity and yields were obtained with less toxic solvents and greatly improved monomer utilization.

  • 3.
    Stenström, Patrik
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Hjorth, Erik
    Zhang, Yuning
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Andrén, Oliver C. J.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
    Guette-Marquet, Simon
    Schultzberg, Marianne
    Malkoch, Michael
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Synthesis and in Vitro Evaluation of Monodisperse Amino-Functional Polyester Dendrimers with Rapid Degradability and Antibacterial Properties2017In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 18, no 12, p. 4323-4330Article in journal (Refereed)
    Abstract [en]

    Amine functional polymers, especially cationically charged, are interesting biomacromolecules for several reasons, including easy cell membrane entrance, their ability to escape endosomes through the proton sponge effect, spontaneous complexation and delivery of drugs and siRNA, and simple functionalization in aqueous solutions. Dendrimers, a subclass of precision polymers, are monodisperse and exhibit a large and exact number of peripheral end groups in relation to their size and have shown promise in drug delivery, biomedical imaging and as antiviral agents. In this work, hydroxyl functional dendrimers of generation 1 to 5 based on 2,2-bis(methylol)propionic acid (bis-MPA) were modified to bear 6 to 96 peripheral amino groups through esterification reactions with beta-alanine. All dendrimers were isolated in high yields and with remarkable monodispersity. This was successfully accomplished utilizing the present advantages of fluoride-promoted esterification (FPE) with imidazole-activated monomers. Straightforward postfunctionalization was conducted on a second generation amino functional dendrimer with tetraethylene glycol through NHS-amidation and carbonyl diimidazole (CDI) activation to full conversion with short reaction times. Fast biodegradation of the dendrimers through loss of peripheral beta-alanine groups was observed and generational- and dose-dependent cytotoxicity was evaluated with a set of cell lines. An increase. in neurotoxicity compared to hydroxyl-functional dendrimers was shown in neuronal cells, however, the dendrimers were slightly less neurotoxic than commercially available poly(amidoamine) dendrimers (PAMAMs). Additionally, their effect on bacteria was evaluated and the second generation dendrimer was found unique inhibiting the growth of Escherichia coli at physiological conditions while being nontoxic toward human cells. Finally, these results cement a robust and sustainable synthetic route to amino-functional polyester dendrimers with interesting chemical and biological properties.

  • 4.
    Stenström, Patrik
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Manzanares, D.
    Zhang, Yuning
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Ceña, V.
    Malkoch, Michael
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
    Evaluation of amino-functional polyester dendrimers based on Bis-MPA as nonviral vectors for siRNA delivery2018In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 23, no 8, article id 2028Article in journal (Refereed)
    Abstract [en]

    Herein, we present the first evaluation of cationic dendrimers based on 2,2-bis(methylol)propionic acid (bis-MPA) as nonviral vectors for transfection of short interfering RNA (siRNA) in cell cultures. The study encompassed dendrimers of generation one to four (G1-G4), modified to bear 6-48 amino end-groups, where the G2-G4 proved to be capable of siRNA complexation and protection against RNase-mediated degradation. The dendrimers were nontoxic to astrocytes, glioma (C6), and glioblastoma (U87), while G3 and G4 exhibited concentration dependent toxicity towards primary neurons. The G2 showed no toxicity to primary neurons at any of the tested concentrations. Fluorescence microscopy experiments suggested that the dendrimers are highly efficient at endo-lysosomal escape since fluorescently labeled dendrimers were localized specifically in mitochondria, and diffuse cytosolic distribution of fluorescent siRNA complexed by dendrimers was observed. This is a desired feature for intracellular drug delivery, since the endocytic pathway otherwise transfers the drugs into lysosomes where they can be degraded without reaching their intended target. siRNA-transfection was successful in C6 and U87 cell lines using the G3 and G4 dendrimers followed by a decrease of approximately 20% of target protein p42-MAPK expression.

1 - 4 of 4
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