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Syntheses of Chalcone-Type Chlorophyll Derivatives Possessing a Bacteriochlorin, Chlorin, or Porphyrin <i>π</i> -System and Their Optical Properties
摘要： C3-(Trans-arylethenyl)carbonylated chlorophyll derivatives possessing a bacteriochlorin or chlorin π-system were synthesized by cross-aldol (Claisen-Schmidt) condensation of methyl pyrobacteriopheophorbide-a or 3-acetyl-3-devinyl-pyropheophorbide-a bearing the C3-acetyl group with p-(un)substituted benzaldehydes under basic conditions. The corresponding porphyrin-type chlorophyll derivatives were prepared by the oxidation (17,18-didehydrogenation) of the chlorin-type. Their Qy absorption and fluorescence emission maxima in dichloromethane correlated well with Hammett substituent constants of the p-substituents. Several electron-withdrawing p-substituents suppressed the emission due to photoinduced electron transfer quenching in a molecule. The substitution sensitivities for their maxima and fluorescence quantum yields decreased in the order of bacteriochlorin-, chlorin-, and porphyrin-type derivatives.
关键词： Chlorophyll derivatives,Optical properties,Bacteriochlorin,Cross-aldol condensation,Hammett substituent constants,Porphyrin,Chlorin
更新于2025-09-23 15:21:01
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Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer
摘要： Near infrared (NIR) fluorescent probes are attractive tools for biomedical in vivo imaging due to the relatively deeper tissue penetration and lower background autofluorescence. Activatable probes are turned on only after binding to their target, further improving target to background ratios. However, the number of available activatable NIR probes is limited. In this study, we introduce two types of activatable NIR fluorophores derived from bacteriochlorin; chlorin-bacteriochlorin energy-transfer dyads and boron-dipyrromethene (BODIPY)-bacteriochlorin energy-transfer dyads. These fluorophores are characterized by multiple narrow excitation bands with relatively strong emission in the NIR. Targeted bacteriochlorin-based antibody or peptide probes have been previously limited by aggregation after conjugation. Polyethylene glycol (PEG) chains were added to improve the hydrophilicity without altering pharmacokinetics of the targeting moieties. These PEGylated bacteriochlorin-based activatable fluorophores have potential as targeted activatable, multi-color NIR fluorescent probes for in vivo applications.
关键词： Monoclonal antibody,Molecular imaging,Bacteriochlorin,Cancer
更新于2025-09-09 09:28:46