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Ultralarge Stokes Shift Phosphorescence Artificial Harvesting Supramolecular System with Near-Infrared Emission.

ABSTRACT: A two-step sequential phosphorescence harvesting system with ultralarge Stokes shift and near-infrared (NIR) emission at 825 nm is successfully constructed by racemic 1,2-diaminocyclohexan-derived 6-bromoisoquinoline (BQ), cucurbit[8]uril (CB[8]), and amphipathic sulfonatocalix[4]arene (SC4AD) via cascaded assembly strategy in aqueous solution. In virtue of the confinement effect of CB[8] with rigid cavity, BQ can generate an emerging phosphorescent emission at 555 nm. Subsequently, the binary BQ⊂CB[8] further assemblies with SC4AD to form close-packed spherical aggregate, which contributes to the dramatic enhancement of phosphorescence emission intensity ≈30 times with prolonged lifetime from 21.3 µs to 0.364 ms. Notably, the BQ⊂CB[8]@SC4AD assembly can serve as an energy donor to conduct stepwise phosphorescence harvesting process through successive introduction of primary acceptors, cyanine 5 (Cy5) or nile blue (NiB), and secondary acceptor, heptamethine cyanine (IR780). The final aggregate with remarkable ultralarge Stokes shift (≈525 nm) and long-lived NIR photoluminescence (PL) emission at 825 nm is further employed as imaging agent for NIR cell labeling.

SUBMITTER: Huo M

PROVIDER: S-EPMC9353443 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Ultralarge Stokes Shift Phosphorescence Artificial Harvesting Supramolecular System with Near-Infrared Emission.

Huo Man M Dai Xian-Yin XY Liu Yu Y

Advanced science (Weinheim, Baden-Wurttemberg, Germany) 20220602 22

A two-step sequential phosphorescence harvesting system with ultralarge Stokes shift and near-infrared (NIR) emission at 825 nm is successfully constructed by racemic 1,2-diaminocyclohexan-derived 6-bromoisoquinoline (BQ), cucurbit[8]uril (CB[8]), and amphipathic sulfonatocalix[4]arene (SC4AD) via cascaded assembly strategy in aqueous solution. In virtue of the confinement effect of CB[8] with rigid cavity, BQ can generate an emerging phosphorescent emission at 555 nm. Subsequently, the binary B ...[more]

PMID: 35652258

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Project description:PurposeIntraoperative molecular imaging (IMI) utilizes optical dyes that accumulate within tumors to assist with detection during a cancer operation. IMI can detect disease not visualized preoperatively, as well as positive margins. However, these dyes are limited by autofluorescence, signal reflection, and photon-scatter. We hypothesize that a novel dye with a wide separation between excitation and emission spectra, SS180, would help overcome these obstacles.ProceduresTwo targeted molecular contrast agents, OTL38 and SS180, were selected for this study. Both dyes had the same targeting ligand to folate receptor alpha (FRα). OTL38, a well-annotated IMI agent in human trials, has a Stokes shift of 22 nm, whereas SS180, the new dye, has a Stokes shift of 129 nm. Cell lines were tested for FRα expression and incubated with dyes to demonstrate receptor-dependent binding. Cells were incubated in various concentrations of the dyes to compare dose- and time-dependent binding. Finally, cells tagged with the dyes were injected subcutaneously in a murine model to estimate tumor burden necessary to generate fluorescent signal.ResultsCellular studies demonstrated that SS180 binds cells in a dose-, receptor-, and time-dependent manner and exhibits higher mean fluorescence intensities by flow cytometry when compared with OTL38 for each time point and concentration. In an in vivo flank tumor model, SS180 had a higher tumor-to-background ratio (TBR) than OTL38, though not statistically significant (p = 0.08). Ex vivo, OTL38 had a higher TBR than SS180 (p = 0.02). The subcutaneous model revealed that SS180 had a higher TBR at 5 × 106 cells than OTL38 (p = 0.05). No toxicity was observed in the animals.ConclusionsSS180 exhibits greater TBRs in vivo, but not ex vivo. These findings suggest that SS180 may have weaker fluorescence, but superior contrast. Studies in large animal models and clinical trials may better elucidate the clinical value of a long Stokes shift.

Dataset Information

Ultralarge Stokes Shift Phosphorescence Artificial Harvesting Supramolecular System with Near-Infrared Emission.

Publications

Ultralarge Stokes Shift Phosphorescence Artificial Harvesting Supramolecular System with Near-Infrared Emission.

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