2-4-dinitrofluorobenzene-sulfonic-acid and 4-4-difluoro-4-bora-3a-4a-diaza-s-indacene

Herein, we developed a dual-activated prodrug, BTC, that contains three functional components: a glutathione (GSH)-responsive BODIPY-based photosensitizer with a photoinduced electron transfer (PET) effect between BODIPY and the 2,4-dinitrobenzenesulfonate (DNBS) group, and an ROS-responsive thioketal linker connecting BODIPY and the chemotherapeutic agent camptothecin (CPT). Interestingly, CPT displayed low toxicity because the active site of CPT was modified by the BODIPY-based macrocycle. Additionally, BTC was encapsulated with the amphiphilic polymer DSPE-mPEG

Topics: Animals; Breast Neoplasms; Cell Line, Tumor; Female; Humans; Mice; Nanoparticles; Photochemotherapy; Photosensitizing Agents; Prodrugs; Reactive Oxygen Species

We have synthesized a styryl boron-dipyrromethene (BODIPY)/2,4-dinitrobenzenesulfonyl (DNBS) dyad based red-emitting molecular probe for specific detection of cysteine among the biological thiols. The probe shows intensive absorption at 556 nm and the probe is non-fluorescent. The DNBS moiety can be cleaved off by thiols, the red emission of the BODIPY fluorophore at 590 nm is switched on, with an emission enhancement of 46-fold. The probe shows good specificity toward cysteine over other biological molecules, such as glutathione and amino acids. The emission of the probe is pH-independent in the physiological pH range. The probe is used for fluorescent imaging of cellular thiols. Theoretical calculations based on density functional theory (DFT) were used to elucidate the fluorescence sensing mechanism of the probe, which indicate a dark excited state (S(1)) for the probe but an emissive excited state (S(1)) for the cleaved product (i.e. the fluorophore).

Topics: Biosensing Techniques; Boron Compounds; Cysteine; Dinitrofluorobenzene; Fluorescent Dyes; Hydrogen-Ion Concentration; Molecular Probe Techniques; Molecular Probes; Spectrometry, Fluorescence; Styrenes; Sulfhydryl Compounds

Two highly selective OFF-ON green emitting fluorescent thiol probes (1 and 2) with intense absorption in the visible spectrum (molar extinction coefficient ε is up to 73 800 M(-1) cm(-1) at 509 nm) based on dyads of BODIPY (as electron donor of the photo-induced electron transfer, i.e.PET) and 2,4-dinitrobenzenesulfonyl (DNBS) (as electron acceptor of the PET process) were devised. The single crystal structures of the two probes were determined. The distance between the electron donor (BODIPY fluorophore) and the electron acceptor (DNBS) of probe 2 is larger than that of probe 1, as a result the contrast ratio (or the PET efficiency) of probe 2 is smaller than that of probe 1. However, fluorescence OFF-ON switching effects were observed for both probe 1 and probe 2 in the presence of cysteine (the emission enhancement is 300-fold for probe 1 and 54-fold for probe 2). The fluorescence OFF-ON sensing mechanism is rationalized by DFT/TDDFT calculations. We demonstrated with DFT calculations that DNBS is ca. 0.76 eV more potent to accept electrons than the maleimide moiety. The probes were used for fluorescent imaging of cellular thiols.

Topics: Boron Compounds; Cell Line; Crystallography, X-Ray; Darkness; Dinitrofluorobenzene; Electron Transport; Fluorescent Dyes; Models, Molecular; Molecular Conformation; Quantum Theory; Spectrometry, Fluorescence; Sulfhydryl Compounds; Sulfonamides