Photophysical and Photoacoustic Properties of <i>π</i>‐Extended Curcumin Dyes. Effects of the Terminal Dimethylamino Electron‐donor and the Bridging Aryl Ring

Borg, Raymond E; Hatamimoslehabadi, Maryam; Bellinger, Stephanie; La, Jeffrey; Mithila, Farha; Yelleswarapu, Chandra S.; Rochford, Jonathan

doi:10.1111/php.12980

Cited by 7 publications

(4 citation statements)

References 57 publications

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“…The UV–vis absorption spectrum of curcumin has a band centered at 466 nm, corresponding to the charge‐transfer involved in the lowest energy transition of quadrupolar donor‐ π ‐acceptor‐ π ‐donor curcuminoids (Figure 1D). [ 30 ] In comparison, the absorption spectrum of CCM‐CPDs displays a band at 285 nm with a broad shoulder at 320−360 nm, attributed to π → π * (conjugated C═C) and n → π * (C═O) transitions, respectively, further revealing the presence of oxygen‐rich functional groups in the CCM‐CPDs. [ 31 ] The CCM‐CPDs, upon excitation at 365 nm, exhibit a fluorescence spectrum with a maximum emission at 450 nm (Figure 1E).…”

Section: Resultsmentioning

confidence: 99%

Augmenting Neutrophil Extracellular Traps with Carbonized Polymer Dots: A Potential Treatment for Bacterial Sepsis

Lin,

Hwang,

Wang

et al. 2024

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Sepsis is a life‐threatening condition that can progress to septic shock as the body's extreme response to pathogenesis damages its own vital organs. Staphylococcus aureus (S. aureus) accounts for 50% of nosocomial infections, which are clinically treated with antibiotics. However, methicillin‐resistant strains (MRSA) have emerged and can withstand harsh antibiotic treatment. To address this problem, curcumin (CCM) is employed to prepare carbonized polymer dots (CPDs) through mild pyrolysis. Contrary to curcumin, the as‐formed CCM‐CPDs are highly biocompatible and soluble in aqueous solution. Most importantly, the CCM‐CPDs induce the release of neutrophil extracellular traps (NETs) from the neutrophils, which entrap and eliminate microbes. In an MRSA‐induced septic mouse model, it is observed that CCM‐CPDs efficiently suppress bacterial colonization. Moreover, the intrinsic antioxidative, anti‐inflammatory, and anticoagulation activities resulting from the preserved functional groups of the precursor molecule on the CCM‐CPDs prevent progression to severe sepsis. As a result, infected mice treated with CCM‐CPDs show a significant decrease in mortality even through oral administration. Histological staining indicates negligible organ damage in the MRSA‐infected mice treated with CCM‐CPDs. It is believed that the in vivo studies presented herein demonstrate that multifunctional therapeutic CPDs hold great potential against life‐threatening infectious diseases.

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Section: Resultsmentioning

confidence: 99%

Augmenting Neutrophil Extracellular Traps with Carbonized Polymer Dots: A Potential Treatment for Bacterial Sepsis

Lin,

Hwang,

Wang

et al. 2024

Small

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“…20 However, further excitation depends non-linearly on (high) laser fluence; and within biologically-allowed energy limits, RSAs are outperformed by ordinary PA emitters that simply absorb light more strongly. 29,30 We also argue that cycling RSAs between S1/Sn states may cause photoreactive damage to the chromophore or to biological tissues.…”

Section: Introductionmentioning

confidence: 88%

Merged molecular switches excel as optoacoustic dyes: azobenzene-cyanines are loud and photostable NIR imaging agents

Müller

Liu

Gujrati

et al. 2023

Preprint

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Optoacoustic imaging, also known as photoacoustic imaging, promises micron-resolution noninvasive imaging in biology at much deeper penetration (>cm) depths than e.g. fluorescence. However, the loud, photostable, NIR-absorbing molecular contrast agents which would be needed for optoacoustic imaging of enzyme activity remain unknown: most organic molecular contrast agents are simply repurposed fluorophores, with severe shortcomings of photoinstability or phototoxicity under optoacoustic imaging conditions, which are consequences of their slow S1→S0 electronic relaxation rates. We now disclose that known fluorophores can be rationally modified to reach ultrafast S1→S0 rates, without much extra molecular complexity, simply by merging them with molecular switches. Here, we merge azobenzene switches to cyanine dyes to give ultrafast relaxation (<10 ps, >100-fold faster). Even without adapting instrument settings, these azohemicyanine optoacoustic imaging agents deliver outstanding improvements in signal longevity (>1000-fold increase of photostability) and signal loudness (here: >3-fold even at time zero). We show why this still-unexplored design strategy can offer even stronger performance in the future, as a simple method that will also increase the spatial resolution and the quantitative linearity of photoacoustic response even over extended longitudinal imaging. By bringing the world of molecular switches and rotors to bear on unsolved problems that have faced optoacoustic agents, this practical strategy may be a crucial step towards unleashing the full potential, in fundamental studies and in translational uses, of optoacoustic imaging.

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“…Biologically allowed energy limits dictate such low fluence in deep tissue that in practice, RSAs are outperformed by ordinary PA emitters that simply absorb light more strongly. [33,34] We also argue that cycling RSAs between S 1 /S n states may cause photoreactive damage to the chromophore or to biological tissues.…”

Section: Introductionmentioning

confidence: 89%

Merged Molecular Switches Excel as Optoacoustic Dyes: Azobenzene–Cyanines Are Loud and Photostable NIR Imaging Agents

Müller,

Liu,

Gujrati

et al. 2024

Angewandte Chemie

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Optoacoustic (or photoacoustic) imaging promises micron‐resolution noninvasive bioimaging with much deeper penetration (>cm) than fluorescence. However, optoacoustic imaging of enzyme activity would require loud, photostable, NIR‐absorbing molecular contrast agents: which remain unknown. Most organic molecular contrast agents are repurposed fluorophores, with severe shortcomings of photoinstability or phototoxicity under optoacoustic imaging, as consequences of their slow S1→S0 electronic relaxation. We now report that known fluorophores can be rationally modified to reach ultrafast S1→S0 rates, without much extra molecular complexity, simply by merging them with molecular switches. Here, we merge azobenzene switches to cyanine dyes to give ultrafast relaxation (<10 ps, >100‐fold faster). Without even adapting instrument settings, these azohemicyanines display outstanding improvements in signal longevity (>1000‐fold increase of photostability) and signal loudness (here: >3‐fold even at time zero). We show why this simple but unexplored design strategy can still offer stronger performance in the future, and can also increase the spatial resolution and the quantitative linearity of photoacoustic response over extended longitudinal imaging. By bringing the world of molecular switches and rotors to bear on problems facing optoacoustic agents, this practical strategy will help to unleash the full potential of optoacoustic imaging in fundamental studies and translational uses.

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Photophysical and Photoacoustic Properties of π‐Extended Curcumin Dyes. Effects of the Terminal Dimethylamino Electron‐donor and the Bridging Aryl Ring

Cited by 7 publications

References 57 publications

Augmenting Neutrophil Extracellular Traps with Carbonized Polymer Dots: A Potential Treatment for Bacterial Sepsis

Augmenting Neutrophil Extracellular Traps with Carbonized Polymer Dots: A Potential Treatment for Bacterial Sepsis

Merged molecular switches excel as optoacoustic dyes: azobenzene-cyanines are loud and photostable NIR imaging agents

Merged Molecular Switches Excel as Optoacoustic Dyes: Azobenzene–Cyanines Are Loud and Photostable NIR Imaging Agents

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