An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
Abstract Fluorophores are essential tools for optical imaging and biomedical research. Their synthetic modification to incorporate new functions, however, remains a challenging task. Conventional strategies rely on linear synthesis in which a parent framework is gradually extended. We here designed and synthesized a versatile library of multi‐functional fluorophores via a scaffold‐based Ugi four‐component reaction (U‐4CR). The adaptability of the scaffold is achieved through modification of starting materials. This allows to use a small range of starting materials for the creation of fluorogenic probes that can detect reactive‐oxygen species and where the localization into subcellular organelles or membranes can be controlled. We present reaction yields ranging from 60 % to 90 % and discovered that some compounds can even function as imaging and therapeutic agents via Fenton chemistry inducing pyroptosis in living cancer cells. Our study underlines the potential of scaffold‐based synthesis for versatile creation of functional fluorophores and their applications.
Background: How to ingeniously design multi-effect photosensitizers (PSs), including multimodal imaging and multi-channel therapy, is of great significance for highly spatiotemporal controllable precise phototherapy of malignant tumors. Methods: Herein, a novel multifunctional zinc(II) phthalocyanine-based planar micromolecule amphiphile ( ZnPc 1 ) was successfully designed and synthesized, in which N atom with photoinduced electron transfer effect was introduced to enhance the near-infrared absorbance and nonradiative heat generation. After simple self-assembling into nanoparticles (NPs), ZnPc 1 NPs would exhibit enhanced multimodal imaging properties including fluorescence (FL) imaging (FLI) /photoacoustic (PA) imaging (PAI) /infrared (IR) thermal imaging, which was further used to guide the combined photodynamic therapy (PDT) and photothermal therapy (PTT). Results: It was that under the self-guidance of the multimodal imaging, ZnPc 1 NPs could precisely pinpoint the tumor from the vertical and horizontal boundaries achieving highly efficient and accurate treatment of cancer. Conclusion: Accordingly, the integration of FL/PA/IR multimodal imaging and PDT/PTT synergistic therapy pathway into one ZnPc 1 could provide a blueprint for the next generation of phototherapy, which offered a new paradigm for the integration of diagnosis and treatment in tumor and a promising prospect for precise cancer therapy. Keywords: multimodality imaging guided synergistic cancer phototherapy, FL/PA/IR multimodal imaging, PDT/PTT dual synergistic therapy pathway, Zn phthalocyanine derivant
Building functional fluorophores from a simple scaffold. In their Research Article (e202415627), Lei Zhang, Su Jing, Thorben Cordes, and co-workers use the Ugi-4-component reaction to assemble fluorogenic dye molecules that selectively localize to mitochondria or lysosomes. The multifunctional fluorophores are not only fluorogenic but also induce pyroptosis in living cancer cells. The study shows the potential of scaffold-based synthesis for creation of new functional fluorophores.
Silicon phthalocyanine derivatives 1a and 1b were synthesized and characterized by UV, 1H-NMR and MS. The photophysical properties of the compounds in DMSO were investigated. The maximum absorption peaks of compounds 1a and 1b at the Q-band are 681 nm. With ZnPc (ΦF = 0.20, ΦΔ = 0.67) as a reference, the fluorescence quantum yield (ΦF) of 1a and 1b are 0.20 and 0.31 respectively, and the singlet oxygen quantum yield (ΦΔ) are 0.66 and 0.59 respectively. The DNA-photocleavage activities of compounds 1a and 1b were studied by gel electrophoresis. Compounds 1a and 1b possess good photocleavage activity to pBR322 DNA. The results demonstrate that compounds 1a and 1b are potential photosensitizers for tumor therapy.
The differences in urinary proteins could provide a novel opportunity to distinguish the different types of drug-induced kidney injury (DIKI). In this research, Au nanoparticles–polyethyleneimine (AuNPs–PEI) and the three fluorophore-labeled proteins (FLPs) have been constructed as a multichannel fluorescent array sensor via electrostatic interaction, which was used to detect the subtle changes in urine collected from the pathological state of DIKI. Once the urine from different types of DIKI was introduced, the binding equilibrium between AuNPs–PEI and FLPs would be broken due to the competitive binding of urinary protein, and the corresponding fluorescence response pattern would be generated. Depending on the different fluorescence response patterns, the different types of DIKI were successfully identified by principal component analysis (PCA) and linear discriminant analysis (LDA). Accordingly, the strategy was expected to be a powerful technique for evaluating the potential unclear mechanisms of nephrotoxic drugs, which would provide a promising method for screening potential renal-protective drugs.
The construction of diaryl alkanes from aromatic aldehydes or ketones with electron-deficient arenes is achieved in the presence of trivalent phosphine under electrochemical conditions. Reductive coupling between electron-deficient arenes and the carbonyl groups of aldehydes or ketones occurs at the cathode to yield diaryl alcohols. At the anode, the trivalent phosphine reagent may undergo single-electron oxidation to generate its radical cation, which reacts with the diaryl alcohols to form dehydroxylated products.
Natural products-coordinated metal ions to form the nanomedicines are in the spotlight for cancer therapy. Some natural products could be coordinated with metal ions forming nanomedicines via simple and green environmental self-assembly, which not only improved the bioavailability of natural products, but also conferred multiple therapeutic modalities and multimodal imaging. On the one hand, in the weak acidity, glutathione (GSH) and hydrogen peroxide (H2O2) overexpression of tumor microenvironment (TME), such carrier-free nanomedicines could be further enhanced the therapeutic effect via optimizing the species of metal ions. On the other hand, nanomedicines could exert the precise treatment of tumor under the guidance of multiple imaging. Hence, this review summarized the research progress in recent years on the application of natural product-coordinated metal ions in cancer therapy. In addition, the prospects and challenges for the application of natural product-coordinated metal ions were discussed, especially how to improve targeting ability and stability and assess the safety of metal ions, so as to facilitate the clinical translation and application of natural product-coordinated metal ions nanomedicines.
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