- Topology-Selective, Fluorescent “Light-Up” Probes for G-Quadruplex DNA Based on Photoinduced Electron Transfer
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Six novel probes were prepared by covalent attachment of a G4-DNA ligand (bis(quinolinium) pyridodicarboxamide; PDC) to various coumarin or pyrene fluorophores. In the absence of DNA, the fluorescence of all probes is quenched due to intramolecular photoinduced electron transfer (PET), as evidenced by photophysical and electrochemical studies, molecular modeling, and DFT calculations. All probes demonstrate similarly high thermal stabilization of various G4-DNA substrates belonging to different folding topologies, as assessed by fluorescence melting experiments; however, their fluorimetric response is strongly heterogeneous with respect to the structures of the probes and G4-DNA targets. Thus, the probes containing the 7-diethylaminocoumarin fluorophore demonstrate significant fluorescence enhancement in the presence of G4-DNA, with the strongest “light-up” response (20- to 180-fold) observed for antiparallel G4 structures as well as for hybrid G4 structures, formed by the variants of human telomeric sequence and capable of a conformation change to the antiparallel isoform. These results shed light on the influence of the linker and electronic properties of fluorophores on the efficiency of G4-DNA “light-up” probes operating via PET.
- Xie, Xiao,Reznichenko, Oksana,Chaput, Ludovic,Martin, Pascal,Teulade-Fichou, Marie-Paule,Granzhan, Anton
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- Enzyme-Instructed Self-Assembly Enabled Monomer–Excimer Transition to Construct Higher Ordered Luminescent Supramolecular Assembly for Activity-based Bioimaging
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It is challenging to construct high-performing excimer-based luminescent analytic tools at low molecular concentrations. We report that enzyme-instructed self-assembly (EISA) enables the monomer–excimer transition of a coumarin dye (Cou) at low molecular concentrations, and the resulting higher ordered luminescent supramolecular assemblies (i.e., nanofibers) efficiently record the spatiotemporal details of alkaline phosphatase (ALP) activity in vitro and in vivo. Cou was conjugated to short self-assembly peptides with a hydrophilic ALP-responsive group. By ALP triggering, EISA actuated a nanoparticles–nanofibers transition at low peptide concentrations followed by monomer–excimer transition of Cou. Analysis of structure–property relationships revealed that the self-assembly motif was a prerequisite for peptides to induce the monomer–excimer transition of Cou. Luminescent supramolecular nanofibers of pYD (LSN-pYD) illuminated the intercellular bridge of cancer cells and distinguished cancer cells (tissues) from normal cells (tissues) efficiently and rapidly, promising potential use for the early diagnosis of cancer. This work extends the functions of EISA and provides a new application of supramolecular chemistry.
- Zhong, Yuanzhi,Zhan, Jie,Xu, Guanghui,Chen, Yumiao,Qin, Qin,Liao, Xu,Ma, Shaodan,Yang, Zhimou,Cai, Yanbin
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- Design of irreversible optical nanothermometers for thermal ablations
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Nanothermometers composed from a gold nanorod core, temperature sensitive linker and fluorescent dye are reported. The nanothermometers have low fluorescence due to a self-quenching mechanism at temperatures below 50 °C and become highly fluorescence above 70 °C.
- Gustafson, Tiffany P.,Cao, Qian,Wang, Steven T.,Berezin, Mikhail Y.
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- A Photocaged, Water-Oxidizing, and Nucleolus-Targeted Pt(IV) Complex with a Distinct Anticancer Mechanism
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Targeted anticancer prodrugs that can be controllably activated are highly desired for personalized precision medicine in cancer therapy. Such prodrugs with unique action modes are also promising to overcome drug resistance. Herein, we report coumaplatin,
- Deng, Zhiqin,Lau, Tai-Chu,Liu, Yingying,Wang, Na,Wang, Zhigang,Xu, Zoufeng,Zhu, Guangyu
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- A FRET-based approach to ratiometric fluorescence detection of hydrogen peroxide
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We report the synthesis, properties, and biological applications of Ratio-Peroxyfluor-1 (RPF1), a new ratiometric fluorescent reporter for hydrogen peroxide. RPF1 is comprised of a two-fluorophore cassette, where the spectral overlap between coumarin dono
- Albers, Aaron E.,Okreglak, Voytek S.,Chang, Christopher J.
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- Photochemically amplified detection of molecular recognition events: An ultra-sensitive fluorescence turn-off binding assay
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Amplified fluorescence quenching methodology based on massive autocatalytic photo-unmasking of a dual function sensitizer-quencher is developed and adopted for photoassisted ultra-sensitive detection of molecular recognition events. The resulting binding
- Gustafson, Tiffany P.,Metzel, Greg A.,Kutateladze, Andrei G.
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- Intracellular delivery of chemical probes using a glutathione-responsive traceless tag
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A new glutathione (GSH)-responsive traceless tag that facilitates intracellular delivery of small molecule chemical probes has been developed.
- Aoyama, Eriko,Fuchida, Hirokazu,Oshikawa, Yuji,Uchinomiya, Shohei,Ojida, Akio
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- Fluorescent probe for detecting hypochlorous acid, and synthesis method and application thereof
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The invention provides a fluorescent probe for detecting hypochlorous acid, and belongs to the field of organic small molecular fluorescent probe, wherein the fluorescent probe has the structural formula defined in the specification. The fluorescent probe is obtained by reaction of reaction products of rhodamine B and hydroxylamine hydrochloride with reaction products of 7-diethylaminocoumarin-3-carboxylic acid and N-hydroxysuccinimide at room temperature. The fluorescent probe for detecting hypochlorous acid has the advantages of fast detection speed, good selectivity and strong anti-interference ability to other molecules. The synthesis of the fluorescent probe can be completed in only a few steps, and the post-processing process is relatively simple. The fluorescent probe can be used asa specific indicator for displaying hypochlorous acid molecules in aqueous solutions and biological cells, can be used for real-time qualitative visual colorimetric detection and has broad application prospects in the field of biomolecular detection.
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Paragraph 0017
(2019/02/13)
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- Synthesis, Biological Evaluation of Fluorescent 23-Hydroxybetulinic Acid Probes, and Their Cellular Localization Studies
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23-Hydroxybetulinic acid (23-HBA) is a complex lupane triterpenoid, which has attracted increasing attention as an anticancer agent. However, its detailed mechanism of anticancer action remains elusive so far. To reveal its anticancer mode of action, a series of fluorescent 23-HBA derivatives conjugated with coumarin dyes were designed, synthesized, and evaluated for their antiproliferative activities. Subcellular localization and uptake profile studies of representative fluorescent 23-HBA probe 26c were performed in B16F10 cells, and the results suggested that probe 26c was rapidly taken up into B10F10 cells in a dose-dependent manner and mitochondrion was the main site of its accumulation. Further mode of action studies implied that the mitochondrial pathway was involved in 23-HBA-mediated apoptosis. Together, our results provided new clues for revealing the molecular mechanism of natural product 23-HBA for its further development into an antitumor agent.
- Yao, Hong,Wei, Guoxiang,Liu, Yanpeng,Yao, Hequan,Zhu, Zheying,Ye, Wencai,Wu, Xiaoming,Xu, Jinyi,Xu, Shengtao
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p. 1030 - 1034
(2018/10/15)
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- Responsive hetero-organelle partition conferred fluorogenic sensing of mitochondrial depolarization
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Malfunctioning organelles are often difficult to probe with classical organelle-homing sensors owing to disruption of physiological organelle-probe affinity. We herein report the use of a responsive hetero-organelle partition and signal activable probe (RC-TPP) for detecting mitochondrial depolarization, a pathologically relevant event featuring loss of the electrical potentials across the mitochondrial membrane (ΔΨm). Partitioned in mitochondria to give blue fluorescence, RC-TPP relocates into lysosomes upon mitochondrial depolarization and exhibits red fluorescence triggered by lysosomal acidity, enabling determination of autophagy relevant mitochondrial depolarization and the chronological sequence of mitochondrial depolarization and lysosomal neutralization in distinct cell death signalling pathways. As an alternative to classic homo-organelle specific molecular systems, this hetero-organelle responsive approach provides a new perspective from which to study dysfunctional organelles.
- Xue, Zhongwei,Zhao, Hu,Liu, Jian,Han, Jiahuai,Han, Shoufa
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p. 1915 - 1921
(2017/03/09)
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- Fluorescently Labeled Amino Acids as Building Blocks for Bioactive Molecules
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A series of twelve fluorescently labeled amino acids were designed by assembling different coumarin, fluorescein, or nitrobenzo-furazan fluorophores with N-protected lysine or 2-aminopropionic acid. The synthesized amino acids were evaluated with regard to their spectroscopic properties. The easy introduction of the amino acids into peptides and peptidomimetics was exemplarily shown for one coumarin-labeled- amino acid.
- H?u?ler, Daniela,Gütschow, Michael
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p. 245 - 255
(2016/01/15)
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- 23-hydroxybetulinic acid fluorescent probe and its preparation method and use in cellular localization and uptake
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The invention relates to the field of novel 23-hydroxybetulinic acid fluorescent derivative organic synthesis and pharmaceutical chemistry and concretely relates to a 23-hydroxybetulinic acid fluorescent probe obtained through connection of a coumarin flu
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Paragraph 0016; 0040; 0042
(2016/10/10)
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- A FRET-based ratiometric redox probe for detecting oxidative stress by confocal microscopy, FLIM and flow cytometry
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Understanding the role of oxidative stress in disease requires real time monitoring of redox status within a cell. We report a FRET-based, ratiometric redox probe which can be applied to monitor cellular oxidative capacity using three different modalities
- Kaur, Amandeep,Haghighatbin, Mohammad A.,Hogan, Conor F.,New, Elizabeth J.
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supporting information
p. 10510 - 10513
(2015/06/25)
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- Fluorescent peptides labeled with environment-sensitive 7-aminocoumarins and their interactions with lipid bilayer membranes and living cells
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The photophysical properties of protected nonnatural amino acids BocL- Dap(7DEAC)OMe (7DEAC: 7-diethylaminocoumarin) and BocL- Dap(C343)OMe (C343: coumarin 343) were investigated to evaluate the suitability of these amino acids as fluorescent units in peptide-based fluorescent biosensors. The absorption and fluorescence spectra of BocL- Dap(7DEAC)OMe and BocL- Dap(C343)OMe exhibited significant red shifts with increasing solvent polarity. The fluorescence quantum yield and lifetime of BocL- Dap(7DEAC)OMe solutions decreased remarkably with increasing solvent polarity, whereas those of BocL- Dap(C343)OMe were slightly affected by the solvent polarity. Fluorescent peptides HDap( 7DEAC)LLAOMe (1), HDap( 7DEAC)KLAOMe (2), and HDap( 7DEAC)ELAOMe (3) labeled with environment-sensitive 7DEAC were synthesized to examine the interactions of these labeled peptides with lipid membranes and living cells. Neutral 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and anionic 1,2-dimyristoyl-sn-glycero-3-[phospho-rac-(1-glycerol)] (DMPG) liposomes were used to investigate peptidemembrane interactions. Hydrophobic peptide 1 exhibited high affinities to both DMPC and DMPC/DMPG mixed membranes. Of the three peptides, cationic peptide 2 exhibited the strongest affinity to DMPC/DMPG membranes, whereas anionic peptide 3 showed a much lower affinity to DMPC/DMPG membranes. These results could be interpreted based on hydrophobic and electrostatic interactions between the peptides and membranes. Peptide 1 was efficiently internalized into HeLa cells, whereas peptides 2 and 3 showed a much lower intracellular delivery.
- Murase, Tokiko,Yoshihara, Toshitada,Yamada, Keiichi,Tobita, Seiji
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supporting information
p. 510 - 519
(2013/06/04)
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- MCM-enzyme-supramolecular hydrogel hybrid as a fluorescence sensing material for polyanions of biological significance.
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Polyanions are important sensing targets because of their wide variety of biological activities. We report a novel polyanion-selective fluorescence sensing system composed of a hybrid material of supramolecular hydrogel, enzymes, and aminoethyl-modified M
- Wada, Atsuhiko,Tamaru, Shun-ichi,Ikeda, Masato,Hamachi, Itaru
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supporting information; experimental part
p. 5321 - 5330
(2009/09/30)
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