67000-89-9Relevant articles and documents
Broad-spectrum antibacterial amphiphilic aminoglycosides: A new focus on the structure of the lipophilic groups extends the series of active dialkyl neamines
Zimmermann, Louis,Kempf, Julie,Briée, Florian,Swain, Jitendriya,Mingeot-Leclercq, Marie-Paule,Décout, Jean-Luc
, p. 1512 - 1525 (2018)
Amphiphilic aminoglycosides (AAGs) constitute a new class of antibacterial compounds targeting the bacterial membranes. We have identified the 3′,6-dinonyl neamine 9 as a broad spectrum antibacterial AAG. Here, we report on the synthesis, antibacterial activity and eukaryotic cytotoxicity of new 3′,6-dialkyl neamines designed in order to finely delineate the structure-activity relationships relating their activity to a lipophilicity window. New broad-spectrum antibacterial derivatives were obtained carrying two identical linear or branched alkyl groups or two different linear alkyl groups. Two fluorescent antibacterial 3′,6-heterodialkyl neamines carrying a pyrenylbutyl fluorophore were also identified as potential tools for mechanistic study. Homodialkyl and heterodialkyl neamines appeared to be more active on Gram-negative bacteria than dinaphthylalkyl neamines. However, branched dialkyl neamines or heterodialkyl derivatives were found to be more cytotoxic on mammalian cells than 9. The exposure of P. aeruginosa over one month to half-MIC of one of the most active derivatives 9 demonstrated the high difficulty of resistance emergence to AAGs.
Single-molecule-magnet carbon-nanotube hybrids
Bogani, Lapo,Danieli, Chiara,Biavardi, Elisa,Bendiab, Nedjma,Barra, Anne-Laure,Dalcanale, Enrico,Wernsdorfer, Wolfgang,Cornia, Andrea
, p. 746 - 750 (2009)
(Figure Presented) Devices and desires: The self-assembly of single-molecule-magnet (SMM) carbon-nanotube (CNT) hybrids (see picture) in conditions compatible to the creation of electronic devices is described. The process is controlled at the single-mole
Highly Selective Fluorimetric Turn-Off Detection of Copper(II) by Two Different Mechanisms in Calix[4]arene-Based Chemosensors and Chemodosimeters
O'Sullivan, Justine,Colleran, John,Twamley, Brendan,Heaney, Frances
, p. 1610 - 1622 (2019)
Isoxazolo-pyrene tethered calix[4]arenes selectively detect copper(II) ions without interference from related perchlorate ions. The fluorescence emission of the probes, synthesised by nitrile oxide alkyne cycloaddition, and characterised by spectroscopic and crystallographic data, is rapidly reduced by Cu(II) ions. Detection limits are in the micromolar or sub-micromolar range (0.3–3.6 μM) based on a 1 : 1 sensor:analyte interaction. Voltammetric behaviour and 1H NMR data provide new insights into the sensing mechanism which is dependent on the calixarene substitution pattern. When the calixarene lower rim is fully substituted, Cu(II) detection occurs through a traditional chelation mechanism. In contrast, for calixarenes 1,3-disubstituted on the lower rim, detection takes place through a chemodosimetric redox reaction. The isolation of a calix[4]diquinone from the reaction with excess Cu(ClO4)2 provides confirmation that the sensor–analyte interaction culminates in irreversible sensor oxidation.
Versatile small molecule kinase assay through real-time, ratiometric fluorescence changes based on a pyrene-DPA-Zn2+complex
Kim, Jihoon,Oh, Jinyoung,Han, Min Su
, p. 10375 - 10380 (2021/03/23)
A real-time kinase assay method based on a ratiometric fluorescence probe that can be applied to various small-molecule kinases is described herein. The probe can trace the reversible interchange of ATP and ADP, which is a common phenomenon in most small-molecule kinase reactions, by a ratiometric fluorescence change. This property facilitates the monitoring of phosphorylation and dephosphorylation in small-molecule kinases, whereas most of the existing methods focus on one of these reactions. To prove the applicability of this method for small-molecule kinase assays, hexokinase and creatine kinase, which phosphorylate and dephosphorylate substrates, respectively, were analyzed. The ratiometric fluorescence change was correlated with the enzyme activity, and the inhibition efficiencies of the well-known inhibitors,N-benzoyl-d-glucosamine and iodoacetamide, were also monitored. Notably, the change in fluorescence can be observed with a simple light source by the naked eye.
Chromophore-modified deoxynucleoside phosphoramidite monomer compound, preparation method therefor and application thereof
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Paragraph 0043; 0057; 0058, (2016/10/09)
The invention discloses a chromophore-modified deoxynucleoside phosphoramidite monomer compound, a preparation method therefor and an application thereof. The preparation method comprises the steps of: connecting chromophores such as pyrene, perylene or naphthalene carboxamide with bis(diisopropylamino) chlorophosphine to obtain a phosphorous intermediate; and reacting the phosphorous intermediate with DMT-protected deoxynucleoside to obtain a chromophore-modified deoxynucleoside phosphoramidite monomer compound. By virtue of solid-phase synthesis of DNA, the compound is inserted into oligonucleotide at a fixed point to obtain a chromophore-modified fluorescent oligonucleotide probe with a stable double-chain structure. The fluorescent oligonucleotide probe is free of fluorescence-emission, and only being combined with a perfectly matching target chain, the fluorescence can be enhanced by 23.5 times, and the response speed is fast. Mismatched bases are obviously identified with nearly no fluorescence-emission, so that single base mismatch can be obviously identified. The compound can be applied to single base mutation analysis of a gene and detection of a PCR reaction process and the like, and is wide in application prospect in aspects of single base polymorphism detection and nucleic acid detection in a biochemical sample and the like.
Reaction-based Hg2+ signaling by excimer-monomer switching of a bis-pyrene dithioacetal
Cho, Yoonha,Lee, Seul Ki,Lee, Jung Woo,Ahn, Sangdoo,Chang, Suk-Kyu
, p. 5341 - 5344 (2013/09/12)
A novel reaction-based probe for fluorescence signaling of Hg2+ ions was developed. Selective Hg2+-induced cleavage of a dithioacetal resulting in switching from pyrene excimer to monomer emission was used for the signaling. Changes in excimer and monomer emissions of pyrene were readily employed for ratiometric signaling of Hg2+ ions in aqueous acetonitrile. Selective signaling of Hg2+ ions over other common metal ions was observed with a detection limit of 9.8 × 10-7 M.
Transition-metal-catalyzed immobilization of organic functional groups onto solid supports through vinylsilane coupling reactions
Park, Jung-Woo,Jun, Chul-Ho
supporting information; experimental part, p. 7268 - 7269 (2010/08/05)
A novel and efficient grafting method for covalent bonding of functional organic molecules to silica or glass surfaces has been developed. The protocol employs transition-metal-catalyzed reactions of vinylsilanes with surface hydroxyl groups. Dimethyldivinylsilane can be used in this procedure as a linker in which one vinyl group is used for direct C-C bond formation with a functional organic molecule and the other is employed to immobilize the alkylsilyl group onto the hydroxyl surface of the solid support.
Anchoring of rare-earth-based single-molecule magnets on single-walled carbon nanotubes
Kyatskaya, Svetlana,Mascaros, Jose Ramon Galan,Bogani, Lapo,Hennrich, Frank,Kappes, Manfred,Wernsdorfer, Wolfgang,Ruben, Mario
scheme or table, p. 15143 - 15151 (2010/01/30)
A new heteroleptic bis(phthalocyaninato) terbium(III) complex 1, bearing a pyrenyl group, exhibits temperature and frequency dependence of ac magnetic susceptibility, typical of single-molecule magnets. The complex was successfully attached to single-wall
Synthesis of mono- and bibrachial naphthalene-based macrocycles with pyrene or ferrocene units for anion detection
Granzhan, Anton,Teulade-Fichou, Marie-Paule
experimental part, p. 1349 - 1360 (2009/04/18)
Three bibrachial cyclobisintercaland-type macrocycles with a 2,6-naphthylene scaffold and pyrene, ferrocene, or primary amino groups in side chains were synthesized by a [2+2]-cyclocondensation of functionalized diethylenetriamine derivatives with naphthalene-2,6-dialdehyde, whereas their monobrachial counterparts were prepared by a [1+1]-cyclocondensation of polyamines with a corresponding dialdehyde building block. The pyrene-functionalized macrocycles are able to bind orthophthalate and terephthalate anions in aqueous medium, as monitored by the changes in their fluorescence (excimer or monomer) properties.
Bio-orthogonal phosphatidylserine conjugates for delivery and imaging applications
Lampkins, Andrew J.,O'Neil, Edward J.,Smith, Bradley D.
, p. 6053 - 6058 (2008/12/22)
(Chemical Equation Presented) The syntheses of phosphatidylserine (PS) conjugates are described, including fluorescent derivatives for potential cellular delivery and bioimaging applications. Installation of terminal functional groups (amine, thiol, or alkyne) onto the sn-2 chain provides reactive sites for bio-orthogonal conjugation of cargo with suitably protected PS derivatives. An amine-containing PS forms amide bonds with peptidic cargo, a thiol derivative is designed for conjugation to cargo that contain α-halo carbonyls or Michael acceptors, and the terminal alkyne PS analogue permits "click" conjugation with any azide-tagged molecule. This latter conjugation method is quite versatile as it can be performed without PS headgroup protection, in aqueous media, and with acid-labile cargo.
