Small molecular cyanine dyes for phototheranostics

Coordination Chemistry Reviews, Год журнала: 2024, Номер 516, С. 215986 - 215986

Опубликована: Июнь 2, 2024

Язык: Английский

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Mitochondria-targeted fluorophore: State of the art and future trends

Coordination Chemistry Reviews, Год журнала: 2024, Номер 508, С. 215772 - 215772

Опубликована: Март 13, 2024

Язык: Английский

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Near-infrared photocatalysis with cyanines: synthesis, applications and perspectives

Chemical Science, Год журнала: 2024, Номер 15(23), С. 8639 - 8650

Опубликована: Янв. 1, 2024

Cyanines are organic dyes bearing two aza-heterocycles linked by a polymethine chain.

Язык: Английский

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Pyridine-based strategies towards nitrogen isotope exchange and multiple isotope incorporation

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Июль 18, 2024

Abstract Isotopic labeling is at the core of health and life science applications such as nuclear imaging, metabolomics plays a central role in drug development. The rapid access to isotopically labeled organic molecules sine qua non condition support these societally vital areas research. Based on rationally driven approach, this study presents an innovative solution pyridines by nitrogen isotope exchange reaction based Zincke activation strategy. technology conceptualizes opportunity field labeling. 15 N-labeling other relevant heterocycles pyrimidines isoquinolines showcases large set derivatives, including pharmaceuticals. Finally, we explore nitrogen-to-carbon strategy order 13 C-labeled phenyl derivatives deuterium mono-substituted benzene from pyridine- 2 H 5 . These results open alternative avenues for multiple aromatic cores.

Язык: Английский

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Minimized background tumor imaging through self-assembled disulfide dicyanine nanoparticles

Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy, Год журнала: 2025, Номер 334, С. 125908 - 125908

Опубликована: Фев. 16, 2025

Язык: Английский

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Mechanistic Insight into the Thermal “Blueing” of Cyanine Dyes

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(29), С. 19756 - 19767

Опубликована: Июль 11, 2024

In recent work to develop cyanine dyes with especially large Stokes shifts, we encountered a "blueing" reaction, in which the heptamethine dye Cy7 (IUPAC: 1,3,3-trimethyl-2-((1E,3E,5E)-7-((E)-1,3,3-trimethylindolin-2-ylidene)hepta-1,3,5-trien-1-yl)-3H-indol-1-ium) undergoes shortening two-carbon steps form pentamethine (Cy5) and trimethine (Cy3) analogs. Each step blue-shifts resulting absorbance wavelength by ca. 100 nm. Though photochemical oxidative chain-shortening reactions had been noted previously, it is simple heating alone or amine bases that effects this unexpected net C2H2 excision. Explicit acetylene loss would be too endothermic merit consideration. Our mechanistic studies using 2H labeling, mass spectrometric NMR spectroscopic analyses, quantum chemical modeling point instead electrocyclic closure aromatization of chain forming Fischer's base FB (1,3,3-trimethyl-2-methyleneindoline), reactive carbon nucleophile initiates attack on their polymethine backbones. The byproduct cationic indolium species TMP 1,3,3 trimethyl-2-phenyl indolium).

Язык: Английский

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Engineering cyanine cyclizations for new fluorogenic probes

Nature Chemistry, Год журнала: 2023, Номер 16(1), С. 3 - 5

Опубликована: Дек. 18, 2023

Язык: Английский

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Design of Bright Chemogenetic Reporters Based on the Combined Engineering of Fluorogenic Molecular Rotors and of the HaloTag Protein

Chemistry - A European Journal, Год журнала: 2024, Номер 30(32)

Опубликована: Апрель 4, 2024

Abstract The combination of fluorogenic probes (fluorogens) and self‐labeling protein tags represent a promising tool for imaging biological processes with high specificity but it requires the adequation between fluorogen its target to ensure good activation fluorescence. In this work, we report strategy develop molecular rotors that specifically HaloTag strong enhancement their divergent design facilitates diversification structures tune photophysical cellular properties. Four bright fluorogens emissions ranging from green red were identified applied in wash‐free live cell experiments contrast selectivity. A mutant adapted previous literature reports was also tested shown further improve brightness reaction rate most series both vitro cells. This work opens new possibilities chemogenetic reporters diverse properties by exploring potentially large chemical space simple dipolar fluorophores engineering.

Язык: Английский

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Tracking the Fate of Therapeutic Proteins Using Ratiometric Imaging of Responsive Shortwave Infrared Probes

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Март 2, 2025

Monoclonal antibodies (mAbs) are essential agents for cancer treatment and diagnosis. Advanced optical imaging strategies have the potential to address specific questions regarding their complex in vivo life cycle. This study presents responsive shortwave infrared (SWIR) probes an associated scheme assess mAb biodistribution, cellular uptake, proteolysis. Specifically, we identify a Pegylated benzo-fused norcyanine derivative (Benz-NorCy7) that is activated acidic environments can be appended mAbs without significant changes properties. As conjugate, this agent shows high tumor specificity longitudinal murine model. To enable independent tracking of uptake lysosomal retention, two-color ratiometric strategy was employed using "always-ON" heptamethine cyanine dye (λex = 785 nm) pH-responsive Benz-NorCy7 890 nm). proteolytic catabolism, append cleavable carbamate create turn-ON probes. These facilitate comparison two common peptide linkers provide insights into Overall, these studies fate protein-based therapeutics imaging.

Язык: Английский

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Recent Advances for Synthesis and Bioapplications of Polymethine Cyanines

Asian Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 11, 2025

Abstract Polymethine cyanine dyes have witnessed significant advancements in bioimaging and phototherapy due to their optical properties ease of modification. This review categorizes introduces typical synthesis Cy3, Cy5, Cy7 longer polymethine dyes, highlights organic‐specific in‐cell cyanines via the newly‐established pseudo‐trimerization method using a single exogenous precursor activatable by visible light, free radicals or reactive oxygen species. Further discussions delve into functionalization strategies structure‐activity relationships summarizes bioapplications fluorescence imaging, multimodal assisted diagnosis treatments, aiming unlock full potential scientific research clinical translation.

Язык: Английский

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