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

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.

doi:10.1039/d3tc04747d

Cited by 4 publications

(1 citation statement)

References 91 publications

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“…Further validation of our proposed molecular descriptors was performed based on 50 non-MAP NIR-II dyes reported by other groups. − ,− These non-MAP NIR-II dyes could be classified into five types, including 14 BBT dyes, ,,,− ,,− 10 BODIPY dyes, ,− 12 xanthene dyes, ,− 12 polymethine dyes, ,,,, and 2 tetra-benzannulated xanthene dyes; , these basically covered most of the NIR-II dyes reported in previous works (Table S7). The absorption/emission wavelengths in the experiments and the corresponding values of the calculated Δ E gs and μ gs for these NIR-II dyes are summarized in Table S7.…”

Section: Resultsmentioning

confidence: 78%

Two Key Descriptors for Designing Second Near-Infrared Dyes and Experimental Validation

Zeng,

Qu,

et al. 2024

J. Am. Chem. Soc.

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Second near-infrared (NIR-II) optical imaging technology has emerged as a powerful tool for diagnostic and image-guided surgery due to its higher imaging contrast. However, a general strategy for efficiently designing NIR-II organic molecules is still lacking, because NIR-II dyes are usually difficult to synthesize, which has impeded the rapid development of NIR-II bioprobes. Herein, based on the theoretical calculations on 62 multiaryl-pyrrole (MAP) systems with spectra ranging from the visible to the NIR-II region, a continuous red shift of the spectra toward the NIR-II region could be achieved by adjusting the type and site of substituents on the MAPs. Two descriptors (ΔE gs and μ gs ) were identified as exhibiting strong correlations with the maximum absorption/ emission wavelengths, and the descriptors could be used to predict the emission spectrum in the NIR-II region only if ΔE gs ≤ 2.5 eV and μ gs ≤ 22.55 D. The experimental absorption and emission spectra of ten MAPs fully confirmed the theoretical predictions, and biological imaging in vivo of newly designed MAP23-BBT showed high spatial resolution in the NIR-II region in deep tissue angiography. More importantly, both descriptors of ΔE gs and μ gs have shown general applicability to most of the reported donor−acceptor−donor-type non-MAP NIR-II dyes. These results have broad implications for the efficient design of NIR-II dyes.

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Section: Resultsmentioning

confidence: 78%

Two Key Descriptors for Designing Second Near-Infrared Dyes and Experimental Validation

Zeng,

Qu,

et al. 2024

J. Am. Chem. Soc.

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Optical Transparency Windows in Near‐Infrared and Short‐Wave Infrared for the Skin, Skull, and Brain: Fluorescence Bioimaging Using PbS Quantum Dots

Qu,

Golovynska,

Liu

et al. 2024

Journal of Biophotonics

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Fluorescence imaging (FI) employing near‐infrared (NIR) light within the range of ~750–1350 nm enables biomedical imaging several millimeters beneath the tissue surface. More recent investigations into the short‐wave IR (SWIR) transparency windows between ~1550–1870 and 2100–2300 nm highlight their superior capabilities. This research presents a comparison of IR‐FI of PbS quantum dots, emitting at 990, 1310, and 1580 nm, through the mouse scalp skin, skull, and brain. The SWIR fluorescence is the most effectively transmitted signal, showing particularly significant enhancement when passing through the skull, which causes high light scattering. For the analysis of the imaging results and light propagation through the organs, their spectra of attenuation, absorption, and scattering coefficients are measured. In view of biomedical imaging, attenuation due to light scattering is a more destructive factor. Hence, the spatial resolution and imaging contrast can be improved by operating in SWIR due to decreased light scattering.

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Uptake of Self-Assembling Amphiphilic Tryptophan-Based Polymer Nanoparticles in Three-Dimensional Cell Culture Models

Mukherjee,

Kulkarni,

Holbrook

et al. 2024

ACS Appl. Nano Mater.

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Synthetic polymeric nanoparticles (NPs) have been proven to be essential drug delivery systems and cancer therapy tools. However, NPs derived from traditional linear polymers often fail to provide the stability, biocompatibility, and loading efficiencies needed for clinical application. The present work explores strategically designed amino acid-based NPs formed from self-assembling amphiphilic Y and H-shaped polymers consisting of a tryptophan-based hydrophobic segment coupled to a hydrophilic block of polyethylene glycol (PEG). This study employs tryptophan due to its natural availability and abilities as a cancer immunotherapeutic agent. These amphiphilic polymers (SM_Trp2P and SM_Trp4P) were synthesized via a combination of Steglich esterification and "click" chemistry (azide−alkyne cycloaddition). Their resulting NPs were characterized using electron microscopy and dynamic light scattering (DLS), by which the morphologies of the NPs were confirmed. Spherical NPs possessing a tryptophan core enabled the loading of hydrophobic cargo, such as drug molecules and near-infrared dyes, demonstrating the potential for dual imaging and delivery applications. Cytotoxicity and spectroscopic analysis of the NPs supported comparative studies between the two polymers and the biological relevancy of the nanomaterials. Employing matrix-assisted laser desorption/ionization-imaging mass spectrometry (MALDI-MSI), full penetration and metabolism of irinotecan-loaded NPs were observed in three-dimensional cell cultures. Results indicate that these strategically designed polymer frameworks and their resulting NPs are exceptional candidates for biomedical applications.

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

Abstract: 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...

Cited by 4 publications

References 91 publications

Two Key Descriptors for Designing Second Near-Infrared Dyes and Experimental Validation

Two Key Descriptors for Designing Second Near-Infrared Dyes and Experimental Validation

Optical Transparency Windows in Near‐Infrared and Short‐Wave Infrared for the Skin, Skull, and Brain: Fluorescence Bioimaging Using PbS Quantum Dots

Uptake of Self-Assembling Amphiphilic Tryptophan-Based Polymer Nanoparticles in Three-Dimensional Cell Culture Models

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