Phenylenevinylene conjugated oligoelectrolytes as fluorescent dyes for mammalian cell imaging

Gwozdzinska, Paulina; Pawłowska, Róża; Milczarek, Justyna; Garner, Logan E.; Thomas, Alexander; Bazan, Guillermo C.; Chworoś, Arkadiusz

doi:10.1039/c4cc06478j

Cited by 30 publications

(30 citation statements)

References 38 publications

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“…Moreover, E. coli cells treated with DSBN+ are found to be more vulnerable to osmotic stress, whereas the presence of DSSN+ in membranes prevented cells from osmotic stress . When compared to DSBN+, COE1–5C did not exhibit as significant a toxicity toward mammalian cells within a concentration of 20 × 10 −6 m , indicating that a mismatch between a longer molecular length and the dimension of lipid bilayer is cell‐dependent and not the only factor to consider. These findings suggest that it is possible to tailor COE structures for different applications, including antimicrobial treatment and their role as benign membrane insertion molecules for more‐facile transmembrane movement of ions/substrates.…”

Section: Antimicrobial Properties Of Coesmentioning

confidence: 95%

Membrane‐Intercalating Conjugated Oligoelectrolytes: Impact on Bioelectrochemical Systems

2015

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Conjugated oligoelectrolytes (COEs), molecules that are defined by a π-delocalized backbone and terminal ionic pendant groups, have been previously demonstrated to effectively reduce charge-injection/extraction barriers at metal/organic interfaces in thin-film organic-electronic devices. Recent studies demonstrate a spontaneous affinity of certain COEs to intercalate into, and align within, lipid bilayers in an ordered orientation, thereby allowing modification of membrane properties and the functions of microbes in bioelectrochemical and photosynthetic systems. Several reports have provided evidence of enhanced current generation and bioproduction. Mechanistic approaches suggest that COEs influence microbial extracellular electron transport to abiotic electrode surfaces via more than one proposed pathway, including direct electron transfer and meditated electron transfer. Molecular dynamics simulations as a function of molecular structure suggest that insertion of cationic COEs results in membrane thinning as the lipid phosphate head groups are drawn toward the center of the bilayer. Since variations in molecular structures, especially the length of the conjugated backbone, distribution of ionic groups, and hydrophobic substitutions, show an effect on their antimicrobial properties, preferential cell localization, and microbial selection, it is promising to further design novel membrane-intercalating molecules based on COEs for practical applications, including energy generation, environmental remediation, and antimicrobial treatment.

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Section: Antimicrobial Properties Of Coesmentioning

confidence: 95%

Membrane‐Intercalating Conjugated Oligoelectrolytes: Impact on Bioelectrochemical Systems

2015

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“…[1] Certain MICOEs lead to increases in the current generation of bioelectrochemical systems, [2] serve as cell staining methods, [3] and provide the molecular basis for membrane permeation and antimicrobial function. [1] Certain MICOEs lead to increases in the current generation of bioelectrochemical systems, [2] serve as cell staining methods, [3] and provide the molecular basis for membrane permeation and antimicrobial function.…”

Section: Membrane-intercalating Conjugated Oligoelectrolytesmentioning

confidence: 99%

A Membrane‐Intercalating Conjugated Oligoelectrolyte with High‐Efficiency Photodynamic Antimicrobial Activity

et al. 2017

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A membrane-intercalating conjugated oligoelectrolyte (COE), PTTP, was designed and synthesized with the goal of providing red-shifted absorption spectra relative to previously synthesized COE analogs. Specifically, electron-rich and electron-poor subunits were introduced in the conjugated backbone to modulate the band gap. PTTP exhibits maxima of absorption at 507 nm and of emission at 725 nm. PTTP can also efficiently function to generate singlet oxygen in situ (Φ ≈20 %) and has appropriate topology and dimensions to interact with lipid membranes. The resulting rapid membrane insertion and sensitizing ability provide PTTP with a highly efficient antibacterial capability under a low light dose (0.6 J cm ) toward Gram-negative bacteria E. coli, making it a remarkably efficient optically mediated antimicrobial agent.

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“…Membrane‐intercalating conjugated oligoelectrolytes (MICOEs) typically consist of a linear π‐conjugated core and terminal side chains with functionalities capable of ionizing in aqueous media . Certain MICOEs lead to increases in the current generation of bioelectrochemical systems, serve as cell staining methods, and provide the molecular basis for membrane permeation and antimicrobial function . All these properties are known to be dependent on the specific chemical structure of the MICOE.…”

Section: Methodsmentioning

confidence: 99%

A Membrane‐Intercalating Conjugated Oligoelectrolyte with High‐Efficiency Photodynamic Antimicrobial Activity

Wang

Mikhailovsky

et al. 2017

Angewandte Chemie

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Phenylenevinylene conjugated oligoelectrolytes as fluorescent dyes for mammalian cell imaging

Cited by 30 publications

References 38 publications

Membrane‐Intercalating Conjugated Oligoelectrolytes: Impact on Bioelectrochemical Systems

Membrane‐Intercalating Conjugated Oligoelectrolytes: Impact on Bioelectrochemical Systems

A Membrane‐Intercalating Conjugated Oligoelectrolyte with High‐Efficiency Photodynamic Antimicrobial Activity

A Membrane‐Intercalating Conjugated Oligoelectrolyte with High‐Efficiency Photodynamic Antimicrobial Activity

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