Cell organelle targeting of near-infrared croconaine dye controls photothermal outcome.
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ABSTRACT:
SUBMITTER: Wen Y
PROVIDER: S-EPMC7319869 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:In this work, we report the first example of a calamitic mesogenic near-infrared (NIR) absorbing organic dye, made by functionalizing a thiophene-croconaine chromophore rigid core with two symmetric long flexible alkyl chains. The liquid crystal (LC) NIR dye YHD796 exhibits a sharp and intense NIR absorption band with a maximum absorption peak at 796 nm. Taking advantage of the improved solubility of YHD796 dispersed in mesogenic molecules, a homogeneously-aligned mono-domain liquid crystalline elastomer (LCE)/YHD796 composite film is successfully prepared by applying the classical LC-cell-alignment method and in situ photo-polymerization of photocurable LC monomer mixtures. This LCE/YHD796 composite film performs a fully reversible contraction/expansion response towards NIR light stimulus due to the photo-thermal heating effect induced by the YHD796 dye well-dispersed in the LCE matrix.
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Project description:Croconaine dyes have narrow and intense absorption bands at ∼800 nm, very weak fluorescence, and high photostabilities, which combine to make them very attractive chromophores for absorption-based imaging or laser heating technologies. The physical supramolecular properties of croconaine dyes have rarely been investigated, especially in water. This study focuses on a molecular threading process that encapsulates a croconaine dye inside a tetralactam macrocycle in organic or aqueous solvent. Macrocycle association and rate constant data are reported for a series of croconaine structures with different substituents attached to the ends of the dye. The association constants were highest in water (Ka ∼ 10(9) M(-1)), and the threading rate constants (kon) increased in the solvent order H2O > MeOH > CHCl3. Systematic variation of croconaine substituents located just outside the croconaine/macrocycle complexation interface hardly changed Ka but had a strong influence on kon. A croconaine dye with N-propyl groups at each end of the structure exhibited a desirable mixture of macrocycle threading properties; that is, there was rapid and quantitative croconaine/macrocycle complexation at relatively high concentrations in water, and no dissociation of the preassembled complex when it was diluted into a solution of fetal bovine serum, even after laser-induced photothermal heating of the solution. The combination of favorable near-infrared absorption properties and tunable mechanical stability makes threaded croconaine/macrocycle complexes very attractive as molecular probes or as supramolecular composites for various applications in absorption-based imaging or photothermal therapy.
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Project description:Croconaines are an emerging class of near-infrared dyes that are useful for various sensing, photothermal, optoelectronic, and photoacoustic applications. Previous work encapsulated a dumbbell-shaped croconaine dye whose structure contains two thiophene flanking units inside a tetralactam macrocycle and produced a croconaine rotaxane 1 with a narrow 824 nm absorption band. Herein, a new rotaxane 2 is reported that encapsulates a croconaine dye with two thienothiophene flanking units. The new croconaine rotaxane 2 exhibits a narrow 984 nm absorption band that is distinct from the 824 nm absorption of rotaxane 1. Photothermal heating experiments showed that an 830 nm diode laser selectively heats a solution containing rotaxane 1, with no heating of a solution containing rotaxane 2. Conversely, a 980 nm diode laser selectively heats a solution containing rotaxane 2, with no heating of a solution containing rotaxane 1. The new croconaine rotaxane 2 shows no fatigue after four cycles of laser heating and cooling.
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Project description:The photothermal heating and release properties of biocompatible organic nanoparticles, doped with a near-infrared croconaine (Croc) dye, were compared with analogous nanoparticles doped with the common near-infrared dyes ICG and IR780. Separate formulations of lipid-polymer hybrid nanoparticles and liposomes, each containing Croc dye, absorbed strongly at 808 nm and generated clean laser-induced heating (no production of (1)O2 and no photobleaching of the dye). In contrast, laser-induced heating of nanoparticles containing ICG or IR780 produced reactive (1)O2, leading to bleaching of the dye and also decomposition of coencapsulated payload such as the drug doxorubicin. Croc dye was especially useful as a photothermal agent for laser-controlled release of chemically sensitive payload from nanoparticles. Solution state experiments demonstrated repetitive fractional release of water-soluble fluorescent dye from the interior of thermosensitive liposomes. Additional experiments used a focused laser beam to control leakage from immobilized liposomes with very high spatial and temporal precision. The results indicate that fractional photothermal leakage from nanoparticles doped with Croc dye is a promising method for a range of controlled release applications.
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Project description:To meet the criteria of effective theranostics, biocompatible nanomedicine endowing intrinsic therapeutic and imaging properties have gained extraordinary momentum. In this study, an ultra-stable near-infrared (NIR) dye croconaine (CR780) was engineered with arginine-glycine-aspartic acid (RGD) peptide and polyethylene glycol (PEG), which was then self-assembled into uniform nanoparticles (NPs). These RGD-CR780-PEG5K assemblies were radiolabeled with 125I through a facile standard Iodo-Gen method. The resulting [125I]RGD-CR780-PEG5K NPs showed effective accumulation in ?v?3 integrin expressing glioblastoma, as evidenced by single photon emission computed tomography (SPECT)/CT and NIR fluorescence imaging. More importantly, high-resolution photoacoustic imaging revealed that these NPs selectively targeted to angiogenic tumor vessels. With the favorable tumor selective accumulation and high photothermal conversion efficiency, the [125I]RGD-CR780-PEG5K NPs allowed thorough tumor ablation and inhibition of tumor relapse at a relatively low laser energy (0.5 W/cm2). Overall, this work offers a proper methodology to fabricate tumor-targeted multi-modal nanotheranostic agents, providing great opportunity for precision imaging and cancer therapy.
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Project description:Herein, we report water-soluble mitochondria-selective molecules that consist of a target-specific moiety conjugated with a near-infrared (NIR) imaging agent through variable spacer length. The presented NIR fluorescent cyanine-5 (Cy-5) chromophore exhibits excellent photostability, narrow NIR absorption and emission bands, high molar extinction coefficient, high fluorescence quantum yield, and long fluorescence lifetime. The biological compatibility and negligible cytotoxicity further make the dye an attractive choice for biological applications. Confocal fluorescence microscopic studies in the fixed human lung carcinoma cell line (A549) stained with the targeting NIR Cy-5 dyes (Cy-5a and Cy-5b) at 700 nM concentration show their cellular uptake and localization, which is compared with the nontargeting Cy-5c. Mitochondrial target specificity is demonstrated by colocalization experiments using the mitochondrion-tracking probe, MitoTracker Red and lysosome-tracking probe, LysoTracker Green. Multicolor imaging of cellular organelles in A549 cells is achieved in combination with suitable target-specific dyes with distinct excitation and emission, such as green emitting FM 1-43FX to selectively image the plasma membrane, blue-fluorescent DAPI to stain the nucleus, and the synthesized NIR Cy-5 to image the mitochondria. Higher accumulation of the dye inside the cancer cell mitochondria compared to the noncancerous cell is also demonstrated.
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Project description:BackgroundThe construction of a nanoimmune controlled-release system that spatiotemporally recognizes tumor lesions and stimulates the immune system response step by step is one of the most potent cancer treatment strategies for improving the sensitivity of immunotherapy response.ResultsHere, a composite nanostimulator (CNS) was constructed for the release of second near-infrared (NIR-II) photothermal-mediated immune agents, thereby achieving spatiotemporally controllable photothermal-synergized immunotherapy. CNS nanoparticles comprise thermosensitive liposomes as an outer shell and are internally loaded with a NIR-II photothermal agent, copper sulfide (CuS), toll-like receptor-9 (TLR-9) agonist, cytosine-phospho-guanine oligodeoxynucleotides, and programmed death-ligand 1 (PD-L1) inhibitors (JQ1). Following NIR-II photoirradiation, CuS enabled the rapid elevation of localized temperature, achieving tumor ablation and induction of immunogenic cell death (ICD) as well as disruption of the lipid shell, enabling the precise release of two immune-therapeutical drugs in the tumor region. Combining ICD, TLR-9 stimulation, and inhibited expression of PD-L1 allows the subsequent enhancement of dendritic cell maturation and increases infiltration of cytotoxic T lymphocytes, facilitating regional antitumor immune responses.ConclusionCNS nanoparticle-mediated photothermal-synergized immunotherapy efficiently suppressed the growth of primary and distant tumors in two mouse models and prevented pulmonary metastasis. This study thus provides a novel sight into photo-controllably safe and efficient immunotherapy.
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