Ultrabright Fluorescent Polymeric Nanoparticles Made from a New Family of BODIPY Monomers

Grazon, Chloé; Rieger, Jutta; Méallet‐Renault, Rachel; Charleux, Bernadette; Clavier, Gilles

doi:10.1021/ma400590q

Cited by 57 publications

(71 citation statements)

References 37 publications

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“…The presence of rhodamine dyes on the surface may affect the cellular association of PISA nanoparticles and therefore, this approach is not suitable for this study. To label the core of PISA nanoparticles with fluorescent dyes, Clavier and co‐workres synthesized a family of boron‐dipyrromethene (BODIPY) monomers . This method can covalently attach fluorescent dyes in the core of PISA nanoparticles during emulsion polymerization.…”

Section: Resultsmentioning

confidence: 99%

Elucidating the Influences of Size, Surface Chemistry, and Dynamic Flow on Cellular Association of Nanoparticles Made by Polymerization‐Induced Self‐Assembly

Khor

Pilkington

et al. 2018

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The size and surface chemistry of nanoparticles dictate their interactions with biological systems. However, it remains unclear how these key physicochemical properties affect the cellular association of nanoparticles under dynamic flow conditions encountered in human vascular networks. Here, the facile synthesis of novel fluorescent nanoparticles with tunable sizes and surface chemistries and their association with primary human umbilical vein endothelial cells (HUVECs) is reported. First, a one-pot polymerization-induced self-assembly (PISA) methodology is developed to covalently incorporate a commercially available fluorescent dye into the nanoparticle core and tune nanoparticle size and surface chemistry. To characterize cellular association under flow, HUVECs are cultured onto the surface of a synthetic microvascular network embedded in a microfluidic device (SynVivo, INC). Interestingly, increasing the size of carboxylic acid-functionalized nanoparticles leads to higher cellular association under static conditions but lower cellular association under flow conditions, whereas increasing the size of tertiary amine-decorated nanoparticles results in a higher level of cellular association, under both static and flow conditions. These findings provide new insights into the interactions between polymeric nanomaterials and endothelial cells. Altogether, this work establishes innovative methods for the facile synthesis and biological characterization of polymeric nanomaterials for various potential applications.

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Section: Resultsmentioning

confidence: 99%

Elucidating the Influences of Size, Surface Chemistry, and Dynamic Flow on Cellular Association of Nanoparticles Made by Polymerization‐Induced Self‐Assembly

Khor

Pilkington

et al. 2018

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“…We have previously shown that BDPMA is consumed faster than styrene in the course of their copolymerization. 21 Hence, as explained in the introduction, the BODIPY fluorophores are predominantly incorporated early in the growing polymer chains; therefore, when their concentration in the NP is increased, some fluorophores could be close enough in the outer part of the NP to form nonfluorescent aggregates which act as quenchers or traps of the fluorescence.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Ultrabright BODIPY-Tagged Polystyrene Nanoparticles: Study of Concentration Effect on Photophysical Properties

et al. 2014

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Fluorescent nanomaterials are invaluable tools for bioimaging. Polymeric nanoparticles labeled with organic dyes are very promising for this purpose. It is thus very important to fully understand their photophysical properties. New fluorescent core−shell nanoparticles have been prepared. The outer part is a poly(ethylene glycol)-block-poly(acrylic acid) copolymer, and the core is a copolymer of styrene and methacrylic BODIPY fluorophore. The hydrophilic and hydrophobic parts are covalently linked, ensuring both stability and biocompatibility. We prepared nanoparticles with increasing amounts of BODIPY, from 500 to 5000 fluorophores per particles. Increasing the concentration of BODIPY lowers both the fluorescence quantum yield and the lifetime. However, the brightness of the individual particles increases up to 8 × 10 7 . To understand the loss of fluorescence efficiency, fluorescence decays have been recorded and fitted with a mathematical model using a stretched exponential function. This result gives an insight into the fluorophore arrangement within the hydrophobic core. ■ INTRODUCTIONOptical imaging is becoming increasingly attractive in medicine, biology, and biochemistry because it can achieve high spatial and temporal resolution and is noninvasive. 1 In addition, fluorescence imaging is a very sensitive technique which can be miniaturized into high sensitivity and cost-effective devices. 2 Usually, organic fluorophores are hydrophobic compounds and as such are not soluble in biological media. They can be modified with water-solubilizing groups; however, most of the time this results in a dramatic drop of the fluorescence quantum yield. 3 An appealing alternative is to incorporate them in organic or inorganic nanoparticles that can be dispersed in water. 1,4 The advantages are numerous because high local concentration of dye can be achieved, leading to lower total amount of material needed for detection of the fluorescence signal. Additionally, multiple fluorophores can be used to achieve bar-coding or multiplex analysis using energy transfer. 5 Furthermore, the nanocarrier itself can bring complementary properties such as protection toward photodegradation, water solubility, and, more importantly, biocompatibility while being small enough to penetrate cells.To this end, polymeric nanoparticles have received widespread interest because they benefit from a great variety of synthetic mode, available monomers, and compatibility with organic fluorophores. Two main doping techniques have been developed: physical trapping of dyes in polymeric particles 6 and covalent attachment. 7 One of the main problems of the first approach is that the fluorophores can leak out of the particles with time. Covalent linking of the fluorophore to the polymer backbone can be achieved either by postmodifying the polymer 8 with reactive fluorophores or by copolymerizing fluorescent monomers with a comonomer. As such, rhodamine, 9 fluorescein, 10 or BODIPY-derived monomers 11,12 have been successfully used to prepare fluorescent nan...

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“…As a known hydrophobic dye, BDPMA exhibited low absorption ( Figure 3A) and negligible fluorescence in water due to its low solubility ( Figure 3B). 12 However, it showed intense fluorescence intensity and ultrahigh brightness after it was encapsulated in polymeric nanoparticles. 12 Additionally, the maximum absorption wavelength for BDPMA in nanoparticles sample (NP-N3) and dichloromethane were identical, revealing that the fluorescent dye was located in the hydrophobic polymer matrix.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Amphiphilic BODIPY-Based Photoswitchable Fluorescent Polymeric Nanoparticles for Rewritable Patterning and Dual-Color Cell Imaging

et al. 2015

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Photoswitchable fluorescent polymeric nanoparticles (PFPNs) with controllable molecular weight, high contrast, biocompatibility, and prominent photostability are highly desirable but still scarce for rewritable printing, superresolution bioimaging, and rewritable data storage. In this study, novel amphiphilic BODIPY-based PFPNs with considerable merits are first synthesized by a facile onepot RAFT-mediated miniemulsion polymerization method. The polymerization is performed by adopting polymerizable BODIPY and spiropyran derivatives, together with MMA as monomer, and mediated by utilizing biocompatible PEO macro-RAFT agent as both control agent and reactive stabilizer. The amphiphilic BODIPY-based PFPNs not only exhibit reversibly photoswitchable fluorescence properties under the alternative UV and visible light illumination through induced intraparticle fluorescence resonance energy transfer (FRET) but also display controllable molecular weight with narrow polydispersity index (PDI), high contrast of fluorescence, tunable energy transfer efficiency, good biocompatibility, excellent photostability, favorable photoreversibility, etc. The as-prepared PFPNs are successfully demonstrated for rewritable fluorescence patterning and high-contrast dual-color fluorescence imaging of living cells, implying its potential for rewritable data storage and broad biological applications in cell biology and diagnostics.

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Ultrabright Fluorescent Polymeric Nanoparticles Made from a New Family of BODIPY Monomers

Cited by 57 publications

References 37 publications

Elucidating the Influences of Size, Surface Chemistry, and Dynamic Flow on Cellular Association of Nanoparticles Made by Polymerization‐Induced Self‐Assembly

Elucidating the Influences of Size, Surface Chemistry, and Dynamic Flow on Cellular Association of Nanoparticles Made by Polymerization‐Induced Self‐Assembly

Ultrabright BODIPY-Tagged Polystyrene Nanoparticles: Study of Concentration Effect on Photophysical Properties

Amphiphilic BODIPY-Based Photoswitchable Fluorescent Polymeric Nanoparticles for Rewritable Patterning and Dual-Color Cell Imaging

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