NIR-II emissive donor-acceptor-donor fluorophores for dual fluorescence bioimaging and photothermal therapy applications

Fluorescence bioimaging with near-infrared II (NIR-II) emissive organic fluorophores has proven to be a viable noninvasive diagnostic technique. However, there is still the need for the development of fluorophores that possess increased stability as well as functionalities that impart stimuli respon...

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Published in:Journal of materials chemistry. C, Materials for optical and electronic devices Materials for optical and electronic devices, 2024-03, Vol.12 (12), p.4369-4383
Main Authors: Sparks, Nicholas E, Smith, Cameron, Stahl, Terrence, Amarasekara, Dhanush L, Hamadani, Christine, Lambert, Ethan, Tang, Sheng Wei, Kulkarni, Anuja, Derbigny, Blaine M, Dasanayake, Gaya S, Taylor, George, Ghazala, Maryam, Hammer, Nathan I, Sokolov, Alexander Y, Fitzkee, Nicholas C, Tanner, Eden E. L, Watkins, Davita L
Format: Article
Language:English
Subjects:
Biocompatibility
Biomedical materials
Chemical compounds
Chemistry
Emission analysis
Erythrocytes
Fluorescence
Heat generation
Irradiation
Medical imaging
Near infrared radiation
Pharmacology
Protonation
Reagents
Synthesis
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Summary:Fluorescence bioimaging with near-infrared II (NIR-II) emissive organic fluorophores has proven to be a viable noninvasive diagnostic technique. However, there is still the need for the development of fluorophores that possess increased stability as well as functionalities that impart stimuli responsiveness. Through strategic design, we can synthesize fluorophores that possess not only NIR-II optical profiles but also pH-sensitivity and the ability to generate heat upon irradiation. In this work, we employ a donor-acceptor-donor (D-A-D) design to synthesize a series of NIR-II fluorophores. Here we use thienothiadiazole (TTD) as the acceptor, 3-hexylthiophene (HexT) as the π-spacer and vary the alkyl amine donor units: N , N -dimethylaniline (DMA), phenylpiperidine (Pip), and phenylmorpholine (Morp). Spectroscopic analysis shows that all three derivatives exhibit emission in the NIR-II region with λ emi max ranging from 1030 to 1075 nm. Upon irradiation, the fluorophores exhibited noticeable heat generation through non-radiative processes. The ability to generate heat indicates that these fluorophores will act as theranostic (combination therapeutic and diagnostic) agents in which simultaneous visualization and treatment can be performed. Additionally, biosensing capabilities were supported by changes in the absorbance properties while under acidic conditions as a result of protonation of the alkyl amine donor units. The fluorophores also show minimal toxicity in a human mammary cell line and with murine red blood cells. Overall, initial results indicate viable NIR-II materials for multiple biomedical applications. Herein, we focus on the design, synthesis, and characterization of thienothiadiazole (TTD)-based near-infrared II (NIR-II) theranostic fluorophores and their nanoparticles.
ISSN:2050-7526
2050-7534
DOI:10.1039/d3tc04747d