Membrane-intercalating conjugated oligoelectrolytes

Zhou, Cheng; Chia, Geraldine W. N.; Yong, Ken‐Tye

doi:10.1039/d2cs00014h

Cited by 15 publications

(15 citation statements)

References 99 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Conjugated oligoelectrolytes (COEs) are a class of molecules comprising a hydrophobic conjugated backbone decorated by pendant ionic functional groups (1)(2)(3). Membrane-intercalating COEs are based on a linear topology and mimic the general spatial distribution of hydrophilic and hydrophobic domains of lipid bilayers (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Department of Chemistry, National University of Singapore, Singapore 117543, Singapore 2. Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, PR China 3. Institute for Functional Intelligent Materials, National University of Singapore, Singapore 117544, Singapore 4.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Water-soluble extracellular vesicle probes based on conjugated oligoelectrolytes

et al. 2023

Self Cite

View full text Add to dashboard Cite

We developed a series of transmembrane conjugated oligoelectrolytes (COEs) with tunable optical emissions from the UV to the near IR to address the false-positive problem when detecting nanometer-sized extracellular vesicles (EVs) by flow cytometry. The amphiphilic molecular framework of COEs is defined by a linear conjugated structure and cationic charged groups at each terminal site. Consequently, COEs have excellent water solubility and the absence of nanoaggregates at concentrations up to 50 μM, and unbound COE dyes can be readily removed through ultrafiltration. These properties enable unambiguous and simple detection of COE-labeled small EVs using flow cytometry with negligible background signals. We also demonstrated the time-lapsed tracking of small EV uptake into mammalian cells and the endogenous small EV labeling using COEs. Briefly, COEs provide a class of membrane-targeting dyes that behave as biomimetics of the lipid bilayer and a general and practical labeling strategy for nanosized EVs.

show abstract

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

Water-soluble extracellular vesicle probes based on conjugated oligoelectrolytes

et al. 2023

Self Cite

View full text Add to dashboard Cite

show abstract

“…Among them, the inorganic contrast agents still require substantial efforts to achieve practical clinical use, due to their biodegradability difficulties and potential chronic toxicity issues deriving from the long-term retention in vivo, and the biocompatibility problems (e.g., potential immunoreactions). By comparison, organic contrast agents, allowing not only good biocompatibility but also flexibility in the structure modification, ,− are promising alternatives to address the challenges encountered in their inorganic counterparts. While among the organic contrast agents, the SPs demonstrate higher photostability than small molecules .…”

Section: Introductionmentioning

confidence: 99%

“…These issues drive the researchers to develop cost-effective polymers for large-scale production. Alternatively, the thiophene-based polymers, which have the advantages of abundant raw materials, simple chemical structure and synthesis, and easy realization of large-scale production, , are more competitive and promising for commercialization. Moreover, it has been reported that the oligo(ethylene glycol) chains, when used as the side chains, endow the resulting SPs with good biocompatibility in tissues and high processability in polar solvents due to their polarity and hydrophilicity .…”

Section: Introductionmentioning

confidence: 99%

A Cost-Effective Semiconducting Polymer with an Ether Chain-Substituted Bithiophene as the Donor Unit Enabling Effective NIR-II Photoacoustic Imaging

Jiang

Lan

Zhou

et al. 2023

ACS Appl. Polym. Mater.

View full text Add to dashboard Cite

Due to their tunability in the chemical structure and light absorption, semiconducting polymers (SPs) have proven their promising potential for photoacoustic (PA) imaging within the second near-infrared (NIR-II) window. However, the syntheses of these polymers are generally lengthy and costly, limiting their potential applications. Herein, inspired by the commonly cost-effective thiophene-based compounds, we report a semiconducting polymer PTT-ATQ based on the non-fused ether chain-substituted donor unit 3,3′-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2,2′-bithiophene (TT). With the side chain substituted by the biocompatible ether chains, the TT unit possesses an even stronger electron-donating ability and thus, a strong intramolecular charge-transfer (ICT) effect in the polymer backbone; hence, an absorption band (peaked at ca. 1370 nm) within the NIR-II window for PTT-ATQ is realized. Meanwhile, the long and bulky side chains of the donor and acceptor units lead to a non-coplanarity in the polymer backbone, resulting in a twisted ICT effect that can induce high PA signals. Further results show that the PTT-ATQ has good biocompatibility and high in vivo PA imaging performance within the NIR-II window. This work highlights the effective strategy to realize high-performance NIR-II in vivo PA imaging SP contrast agents by using the cost-effective thiophene-based building blocks.

show abstract

“…[7] Of particular relevance is a class of watersoluble and membrane-intercalating molecules called conjugated oligoelectrolytes (COEs), which are characterized by a conjugated core with ionic pendant groups. [8] Previous reports primarily employ oligo p-phenylenevinylene (OPV)-based COEs to amplify transmembrane electron transport. [9] Initial studies suggested that OPV-COEs act as "molecular wires" by facilitating electron tunneling or hopping through their conjugated backbones.…”

mentioning

confidence: 99%

An n‐Type Conjugated Oligoelectrolyte Mimics Transmembrane Electron Transport Proteins for Enhanced Microbial Electrosynthesis

et al. 2023

View full text Add to dashboard Cite

Interfacing bacteria as biocatalysts with an electrode provides the basis for emerging bioelectrochemical systems that enable sustainable energy interconversion between electrical and chemical energy. Electron transfer rates at the abiotic‐biotic interface are, however, often limited by poor electrical contacts and the intrinsically insulating cell membranes. Herein, we report the first example of an n‐type redox‐active conjugated oligoelectrolyte, namely COE‐NDI, which spontaneously intercalates into cell membranes and mimics the function of endogenous transmembrane electron transport proteins. The incorporation of COE‐NDI into Shewanella oneidensis MR‐1 cells amplifies current uptake from the electrode by 4‐fold, resulting in the enhanced bio‐electroreduction of fumarate to succinate. Moreover, COE‐NDI can serve as a “protein prosthetic” to rescue current uptake in non‐electrogenic knockout mutants.

show abstract

Membrane-intercalating conjugated oligoelectrolytes

Abstract: Membrane-intercalating conjugated oligoelectrolytes are emerging as versatile tools to modify or functionalize lipid bilayers. Through modular chemical design, this new molecular platform has applications in a range of biological fields.

Cited by 15 publications

References 99 publications

Water-soluble extracellular vesicle probes based on conjugated oligoelectrolytes

Water-soluble extracellular vesicle probes based on conjugated oligoelectrolytes

A Cost-Effective Semiconducting Polymer with an Ether Chain-Substituted Bithiophene as the Donor Unit Enabling Effective NIR-II Photoacoustic Imaging

An n‐Type Conjugated Oligoelectrolyte Mimics Transmembrane Electron Transport Proteins for Enhanced Microbial Electrosynthesis

Contact Info

Product

Resources

About