Encapsulation and cellular internalization of cyanine dye using amphiphilic dendronized polymers

Kumar, Shiv; Achazi, Katharina; Böttcher, Christoph; Licha, Kai; Haag, Rainer; Sharma, Sunil K.

doi:10.1016/j.eurpolymj.2015.06.017

Cited by 11 publications

(10 citation statements)

References 43 publications

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“…The successful substitution was confirmed by elemental analysis with a 99.8% degree of sulfation. Linear PEG‐ and triglycerol‐based polymer P backbone 4 was synthesized according to a reported procedure with a degree of polymerization of 8.5 monomer units per polymer used to calculate the molecular weights (see polymer synthesis, Supporting Information). Subsequent alkylation of the secondary hydroxyl groups with stearic acid via a Steglich‐type esterification afforded grafted block copolymer P alkyl 5 in good yields.…”

Section: Resultsmentioning

confidence: 99%

Fluorescent Polymer—Single‐Walled Carbon Nanotube Complexes with Charged and Noncharged Dendronized Perylene Bisimides for Bioimaging Studies

Huth

Glaeske

Achazi

et al. 2018

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Fluorescent nanomaterials are expected to revolutionize medical diagnostic, imaging, and therapeutic tools due to their superior optical and structural properties. Their inefficient water solubility, cell permeability, biodistribution, and high toxicity, however, limit the full potential of their application. To overcome these obstacles, a water-soluble, fluorescent, cytocompatible polymer-single-walled carbon nanotube (SWNT) complex is introduced for bioimaging applications. The supramolecular complex consists of an alkylated polymer conjugated with neutral hydroxylated or charged sulfated dendronized perylene bisimides (PBIs) and SWNTs as a general immobilization platform. The polymer backbone solubilizes the SWNTs, decorates them with fluorescent PBIs, and strongly improves their cytocompatibility by wrapping around the SWNT scaffold. In photophysical measurements and biological in vitro studies, sulfated complexes exhibit superior optical properties, cellular uptake, and intracellular staining over their hydroxylated analogs. A toxicity assay confirms the highly improved cytocompatibility of the polymer-wrapped SWNTs toward surfactant-solubilized SWNTs. In microscopy studies the complexes allow for the direct imaging of the SWNTs' cellular uptake via the PBI and SWNT emission using the 1st and 2nd optical window for bioimaging. These findings render the polymer-SWNT complexes with nanometer size, dual fluorescence, multiple charges, and high cytocompatibility as valuable systems for a broad range of fluorescence bioimaging studies.

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Section: Resultsmentioning

confidence: 99%

Fluorescent Polymer—Single‐Walled Carbon Nanotube Complexes with Charged and Noncharged Dendronized Perylene Bisimides for Bioimaging Studies

Huth

Glaeske

Achazi

et al. 2018

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“…[31] The peak at δ 1.26 ppm in the 1 H NMR spectrum was assigned to the methyl of the ethyl end group and the corresponding carbon was observed at δ 14.27 ppm in 13 C NMR spectrum. The polymerization takes place selectively through the primary hydroxyl groups of azidotriglycerol.…”

Section: Synthesis Of Dendronized Polymersmentioning

confidence: 99%

Chemo‐enzymatic synthesis of dendronized polymers for cyanine dye encapsulation

et al. 2017

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Cyanine 3 is an amphiphilic fluorescent dye used in optical imaging, bioengineering, and for cellular internalization. However, the applications of the dye are limited due to its poor aqueous stability, aggregation tendency, and lack of selectivity. To address these issues, we have developed PEG and azidotriglycerol based dendronized polymers using Novozym 435 as a biocatalyst under solvent free conditions. The resulting polymer having azido and hydroxyl functionalities available in the backbone were further grafted with alkyl chains and polyglycerol dendrons using esterification and 'Click' chemistry approach. These polymers form stable micelles at micromolar concentration. All the polymers were characterized from their spectral data and their tendency to encapsulate cyanine 3 dye studied using UV-Vis and fluorescence spectroscopy. The cytotoxicity study of the polymers performed against A549 cell lines suggests them to be nontoxic up to a concentration of 500 μg/ml. K E Y W O R D Sazidotriglycerol, cyanine 3, cytotoxicity, nanoparticles, PEG, transport capacity

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“…The polymeric micelles fabricated from linear polymers are the promising candidates for many applications including catalysis and drug delivery, but these micelles are unstable and easily disassembled into free chains when the environmental parameters change, such as temperature, pH, concentration, and so on . Compared to linear polymers, dendronized polymers (DPs) with bulky branched dendrons can offer plentiful interior or peripheral functional groups to covalently fixate payload molecules or, depending on their core‐shell architecture, to segregate guest molecules . Therefore, DPs are potential candidates to create new polymeric carriers owing to their unique characteristics, namely, one‐dimensional conformation, nanoscale size, tremendous periphery groups, and versatile structural control .…”

Section: Introductionmentioning

confidence: 99%

“…Compared to linear polymers, dendronized polymers (DPs) with bulky branched dendrons can offer plentiful interior or peripheral functional groups to covalently fixate payload molecules or, depending on their core‐shell architecture, to segregate guest molecules . Therefore, DPs are potential candidates to create new polymeric carriers owing to their unique characteristics, namely, one‐dimensional conformation, nanoscale size, tremendous periphery groups, and versatile structural control . Although a linear‐dendritic amphiphilic block copolymer with a single ferrocenyl dendron has been reported for redox‐controlled reversible self‐assembly and oxidation‐triggered payload release, no side‐chain Fc‐containing DP has been reported for the fabrication of polymeric carriers as yet.…”

Section: Introductionmentioning

confidence: 99%

Controlled ROMP Synthesis of Ferrocene‐Containing Amphiphilic Dendronized Diblock Copolymers as Redox‐Controlled Polymer Carriers

Liu

Qiu

Zhang

et al. 2018

Macro Chemistry & Physics

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Novel well‐defined redox‐responsive Ferrocene (Fc)‐containing amphiphilic dendronized diblock copolymers are synthesized by the ring‐opening metathesis polymerization technique using Grubbs’ third‐generation olefin metathesis catalyst as the initiator. These dendronized block copolymers can self‐assemble into spherical micelles in aqueous solution. The size of self‐assembled micelles can be modulated by the composition (namely, the ratio of hydrophobic and hydrophilic segments) and concentration of the dendronized copolymers. The obtained micelles show reversible redox‐controlled self‐assembly behaviors using FeCl3 as oxidant and glutathione as reductant. Furthermore, the model molecule Rhodamine B is successfully loaded in these micelles, and the oxidation‐triggered controllable release is achieved by changing the type of oxidants (FeCl3 and H2O2) and their concentrations. This is the first example of redox‐responsive micelles self‐assembled by novel amphiphilic dendronized Fc‐containing block copolymers, and the present micelles are visualized to be potential candidates in many fields, especially in stimuli‐responsive drug delivery systems.

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Encapsulation and cellular internalization of cyanine dye using amphiphilic dendronized polymers

Cited by 11 publications

References 43 publications

Fluorescent Polymer—Single‐Walled Carbon Nanotube Complexes with Charged and Noncharged Dendronized Perylene Bisimides for Bioimaging Studies

Fluorescent Polymer—Single‐Walled Carbon Nanotube Complexes with Charged and Noncharged Dendronized Perylene Bisimides for Bioimaging Studies

Chemo‐enzymatic synthesis of dendronized polymers for cyanine dye encapsulation

Controlled ROMP Synthesis of Ferrocene‐Containing Amphiphilic Dendronized Diblock Copolymers as Redox‐Controlled Polymer Carriers

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