Water-soluble organic macrocycles based on dye chromophores and their applications.

Chem Commun (Camb)

Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Capital Normal University, Beijing 100048, China.

Published: November 2023

Traditional water-soluble organic macrocyclic receptors generally lack photofunctionality, thus monitoring the drug delivery and the phototheranostic applications of these host-guest macrocyclic systems has been greatly restricted. To address this issue, incorporating π-conjugated dye chromophores as building blocks into macrocyclic molecules is a straightforward and promising strategy. This approach not only imparts intrinsic optical features to the macrocycles themselves but also enhances the host-guest binding ability due to the large planar structures of the dyes. In this feature article, we focus on recent advances in water-soluble macrocyclic compounds based on organic dye chromophores, such as naphthalimide (NDI), perylene diimides (PDI), azobenzene (azo), tetraphenylethylene (TPE) and anthracene, and provide an overview of their various applications including molecular recognition, drug release, biological imaging, photothermal therapy, We hope that this article could be helpful and instructive for the design of water-soluble dye-based macrocycles and the further development of their biomedical applications, particularly in combination with drug therapy and phototheranostics.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d3cc04159jDOI Listing

Publication Analysis

Top Keywords

dye chromophores
12
water-soluble organic
8
water-soluble
4
organic macrocycles
4
macrocycles based
4
based dye
4
applications
4
chromophores applications
4
applications traditional
4
traditional water-soluble
4

Similar Publications

Cyanine dye-embedded fluorescent film for ratiometric pH measurement.

Photochem Photobiol Sci

January 2025

CNRS, Institut des Sciences Moléculaires d'Orsay, Université Paris-Saclay, 91405, Orsay, France.

The precise monitoring of pH is critical in various applications, particularly in biology-related areas. In this work, we report the synthesis and characterization of a novel cyanine-based fluorescent pH sensor with a pK around 6. This pH-sensitive dye features a cyanine chromophore coupled to a piperazine moiety, which modulates the protonation equilibrium and thus the optical response.

View Article and Find Full Text PDF

Photocurrent Generation by Plant Light-Harvesting Complexes is Enhanced by Lipid-Linked Chromophores in a Self-Assembled Lipid Membrane.

J Phys Chem B

January 2025

Department of Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan.

The light-harvesting pigment-protein complex II (LHCII) from plants can be used as a component for biohybrid photovoltaic devices, acting as a photosensitizer to increase the photocurrent generated when devices are illuminated with sunlight. LHCII is effective at photon absorption in the red and blue regions of the visible spectrum, however, it has low absorption in the green region (550-650 nm). Previous studies have shown that synthetic chromophores can be used to fill this spectral gap and transfer additional energy to LHCII, but it was uncertain whether this would translate into an improved performance for photovoltaics.

View Article and Find Full Text PDF

Enveloped viruses, such as flaviviruses and coronaviruses, are pathogens of significant medical concern that cause severe infections in humans. Some photosensitizers are known to possess virucidal activity against enveloped viruses, targeting their lipid bilayer. Here we report a series of halogenated difluoroboron-dipyrromethene (BODIPYs) photosensitizers with strong virus-inactivating activity.

View Article and Find Full Text PDF

Mechanisms of anthraquinone dye Vat Blue 4 biodegradation by Pseudomonas aeruginosa WYT and genotoxicity assessment of its transformation products.

Bioresour Technol

December 2024

School of Environment and Natural Resource, Zhejiang University of Science and Technology, Hangzhou 310018, China; National Supervision & Inspection Center of Environmental Protection Equipment Quality, Yixing, Jiangsu 214205, China. Electronic address:

Dye biodegradation products may cause genotoxicity, raising concerns about the safety of bioremediated water. The underlying biotransformation mechanism and related genotoxicity during anthraquinone degradation remain unclear. In this study, we employed Pseudomonas aeruginosa WYT (PaWYT) to investigate the biotransformation of Vat Blue 4 (VB4), a dye with a typical anthraquinone structure and low bioavailability.

View Article and Find Full Text PDF

Background: Photodynamic Therapy (PDT) is a therapeutic modality that combines the application of a photoactive compound (photosensitizer, PS) with low-power light to generate reactive oxygen species in the target tissue, resulting in cytotoxic damage and cell death, while sparing adjacent tissues. The objective of this study was to evaluate the phototoxicity of a cyanine dye with two chromophores (biscyanines, BCD) in systems with varying levels of cellular organization, and we used the Photogem® (a photosensitizer approved by the Brazilian ANVISA agency for clinical use in Photodynamic Therapy) as a positive control.

Materials And Methods: The cytotoxicity of the compounds was assessed in vitro in 2D monolayers, 3D spheroid cultures, and artificial skin models.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!