34995-01-2Relevant academic research and scientific papers
Solid-phase synthesis of polyfunctional polylysine dendrons using aldehyde linkers
Svenssen, Daniel K.,Mirsharghi, Sahar,Boas, Ulrik
, p. 3942 - 3945 (2014)
A straightforward method for the solid-phase synthesis of C-terminally modified polylysine dendrons has been developed by applying bisalkoxybenzaldehyde and trisalkoxybenzaldehyde linkers. The method has been used for the synthesis of polylysine dendrons with a variety of C-terminal 'tail groups' such as alkyl, propargyl, and dansyl to give dendrons in high crude purity. Furthermore, the method was successful for the synthesis of dendrons with multiple N-terminal pentapeptide groups together with C-terminal alkyl and propargyl tail groups. Finally, the method was shown to be well-suited for automated synthesis.
Aggregation and host-guest interactions in dansyl-substituted poly(acrylate)s in the presence of β-cyclodextrin and a β-cyclodextrin dimer in aqueous solution: A UV-vis, fluorescence, 1H NMR, and rheological study
Wang, Jie,Pham, Duc-Truc,Kee, Tak W.,Clafton, Scott N.,Guo, Xuhong,Clements, Philip,Lincoln, Stephen F.,Prud'homme, Robert K.,Easton, Christopher J.
, p. 9782 - 9791 (2011)
A UV-vis, steady-state, and time-resolved fluorescence 2D 1H NOESY NMR spectroscopic and rheological study of new poly(acrylate)s 3% randomly substituted with either N-(2-aminoethyl)-, N-(6-aminohexyl)-, or N-(12-aminododecyl)-5-dansyl-sulfonamide to give the substituted polymers PAADSen, PAADShn, and PAADSddn, respectively, is reported. Their dansyl substituent aggregation and complexation by β-cyclodextrin, βCD, and its covalently linked dimer N,N′-bis(6A-deoxy-6 A-β-cyclodextrin)urea, 66βCD2ur, is also reported. The βCD complexation of the dansyl substituents is characterized by apparent complexation constants, K = 89, 105, and 55 dm3 mol -1 for PAADSen, PAADShn, and PAADSddn, respectively, and the analogous complexations by 66βCD2ur are characterized by K = 3.04 × 103, 3.42 × 104, and 2.42 × 105 dm3 mol-1 at pH 7.0 in aqueous 0.10 mol dm-3 NaCl at 298.2 K. Under the same conditions the dansyl substituent shows three fluorescence decay constants assigned to the aggregated (τ1 = 2.2, 2.5, and 3.2 ns), single (τ2 = 5.0, 5.3, and 9.5 ns), βCD (τ3 = 13.2, 11.7 ns, and undetected), and 66βCD2ur complexed dansyl substituent states (τ3 = 13.9, 20.8, and 19.3 ns) where the values in each data set correspond to PAADSen, PAADShn, and PAAddn solutions, respectively. 2D 1H NOESY NMR spectroscopy provides additional insight into dansyl substituent complexation by βCD and 66βCD2ur, as do rheological studies. These data are interpreted in terms of the factors affecting dansyl substituent fluorescence quenching and the impact of tether length on dansyl substituent aggregation, complexation, and network formation.
Fluorescent probes for adenosine receptors: Synthesis and biology of N6-dansylaminoalkyl-substituted NECA derivatives
Macchia, Marco,Salvetti, Francesca,Barontini, Silvia,Calvani, Federico,Gesi, Marco,Hamdan, Mahmoud,Lucacchini, Antonio,Pellegrini, Antonio,Soldani, Paola,Martini, Claudia
, p. 3223 - 3228 (1998)
New fluorescent ligands for adenosine receptors are described; these compounds were obtained by the insertion, in the N6 position of NECA (a potent adenosine agonist), of dansylaminoalkyl moieties with alkyl spacers of increasing carbon chain length (from 3 to 12). Among them, the compound with a C6 alkyl spacer proved to be the most interesting one, showing a marked selectivity for the A1 receptor subtype; furthermore, in fluorescence microscopy assays it proved to be able to visualize and localize this receptor subtype at the level of the molecular layer of the rat cerebellar cortex.
Solvatochromic characteristics of dansyl molecular probes bearing alkyl diamine chains
Ionita, Gabriela,Matei, Iulia,Mocanu, Sorin
, (2020/05/05)
A series of dansyl-based fluorescent probes bearing linear alkyl-1,n-diamine chains of different length (DA1.n, n = 2–8, 10, 12) was characterized in terms of the absorptive and emissive features in solvents of different polarity and hydrogen bond donor/hydrogen bond acceptor character. The probes show solvent-dependent absorption, a feature that is uncommon among dansyl derivatives. The dual emission of DA1.n probes is strong in non-aqueous solvents and is influenced by the chain length and interactions with the solvent. Solvent effects on the spectral parameters were rationalized on the basis of the Kamlet-Taft and Catalán solvatochromic models, in order to quantify the degree of polarity-driven and hydrogen bonding interactions. A comparative discussion of the results predicted by the two models was made. In ground state, the DA1.n probes act as hydrogen bond acceptors. In excited state, hydrogen bonding is less favoured, the solute-solvent interactions being governed by the increasing polarity of the solvent that results in a large bathochromic shift of the emission. A comparison was made with the spectral features previously reported for the corresponding series of bis-dansyl fluorescent probes (2DA1.n).
1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines
Froehlich, Richard F. G.,Furneaux, Richard H.,Mahuran, Don J.,Rigat, Brigitte A.,Stuetz, Arnold E.,Tropak, Michael B.,Wicki, Jacqueline,Withers, Stephen G.,Wrodnigg, Tanja M.
experimental part, p. 1371 - 1376 (2010/10/02)
Cyclization by double reductive amination of D-xylo-hexos-5-ulose with methyl 6-aminohexanoate gave (methoxycarbonyl)pentyl-1-deoxynojirimycin. Reaction of the terminal carboxylic acid with N-dansyl- 1,6-diaminohexane provided the corresponding chain-extended fluorescent derivative. By reaction with bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Both compounds are strong inhibitors of D-glucosidases and could also be shown to distinctly improve, at subinhibitory concentrations, the activity of β-glucocerebrosidase in a Gaucher fibroblast (N370S) cell-line through chaperoning of the enzyme to the lysosome.
A probe for detection of G-rich target strands through fluorescence quenching
Misra, Arvind,Dwivedi, Pratibha,Shahid, Mohammad
experimental part, p. 62 - 67 (2009/07/25)
A modified fluorescent probe UFAA AAT CTC CGC CGC was synthesized using the nucleoside analogue 3-O-(N,N-diisopropylamino-2- cyanoethoxyphosphinyl)-5-O-(4,4-dimethoxytrityl)-2-O-(dansyl-1- sulfonamidohexylaminocarbonyl)uridine for hybridization studies with perfectly matched (U/A) complementary DNA and with a DNA strand having similar G-rich telomeric units at their 3-ends. Data on the thermal stability and decrease in fluorescence intensity due to the presence of dG units clearly demonstrated the potential application of this approach in DNA diagnostics in homogeneous hybridization assays.
Synthesis and pharmacological evaluation of fluorescent and photoactivatable analogues of antiplasmodial naphthylisoquinolines
Bringmann, Gerhard,Gampe, Christian M.,Reichert, Yanina,Bruhn, Torsten,Faber, Johan H.,Mikyna, Martin,Reichert, Matthias,Leippe, Matthias,Brun, Reto,Gelhaus, Christoph
, p. 6104 - 6115 (2008/09/16)
The naphthylisoquinoline (NIQ) alkaloids from tropical Ancistrocladaceae and Dioncophyllaceae plants show high antiplasmodial activities in vitro and in vivo, even against chloroquine-resistant strains of the malaria pathogen. For the directed optimization of these activities, an investigation of the mode of action seems most rewarding. We have therefore embarked on the identification of the respective target protein in Plasmodium falciparum. For this purpose, we have developed a flexible pathway for the synthesis of a chemically divergent series of photoactive and fluorescent derivatives of such alkaloids and succeeded in preparing the first functionalized NIQ derivatives, 10, 12, and 35, suited for fluorescence and photoaffinity labeling experiments. Pharmacological investigations ensured that the modified alkaloid derivatives retained their antiplasmodial activity. The work may pave the way for a further improvement of the activity of these natural products and will thus increase their pharmacological potential as a valuable lead structure against the widespread tropical disease malaria.
Immobilization of glycoconjugate polymers on cellulose membrane for affinity separation
Miyagawa, Atsushi,Kasuya, Maria Carmelita Z.,Hatanaka, Kenichi
, p. 348 - 356 (2007/10/03)
Membranes with immobilized glycoconjugate polymers were prepared and lectin adsorption was evaluated. Glycoconjugate polymers having the carbohydrates, lactose, and mannose, the amino groups of the reaction point, and a fluorescence label were synthesized, while cellulose membranes were carboxymethylated. The content of the carboxyl group was evaluated by titration. Subsequently, the glycoconjugate polymers were immobilized on the cellulose membranes by amide linkages formed by condensation reaction. Analysis of the luminescence of the fluorescence labels revealed that the glycoconjugate polymers had been immobilized on the cellulose membranes. Examination of lectin adsorption by the glycoconjugate polymer on the membrane revealed that the membrane with the immobilized mannose-having polymer adsorbed 53% of the applied ConA and the membrane with the immobilized lactose-having polymer adsorbed 83% of the applied RCA120. The membrane with immobilized glycoconjugate polymers selectively adsorbed each lectin. In addition, membranes with different types of immobilized glycoconjugate polymers were used in stacks, and in this case, the membranes selectively adsorbed lectin. Thus, membranes with immobilized glycoconjugate polymers efficiently and easily purify lectin.
Design, synthesis, and biological evaluation of potent discodermolide fluorescent and photoaffinity molecular probes
Smith III, Amos B.,Rucker, Paul V.,Brouard, Ignacio,Freeze, B. Scott,Xia, Shujun,Horwitz, Susan Band
, p. 5199 - 5202 (2007/10/03)
(Chemical Equation Presented) The design, synthesis, and biological evaluation of a series of (+)-discodermolide molecular probes possessing photoaffinity and fluorescent appendages has been achieved. Stereoselective olefin cross-metathesis comprised a ke
Hapten-phosphoramidites based on 6-[(2E)-N-(hexyl)prop-2-enamidyl]-2′-deoxyuridine
Adamczyk, Maciej,Akireddy, Srinivasa Rao,Mattingly, Phillip G,Reddy, Rajarathnam E
, p. 5621 - 5623 (2007/10/03)
Novel hapten-phosphoramidites 11a-c were prepared from 2′-deoxyuridine (2) by functionalization at the 6-position and subsequent conjugation with adamantane, carbazole and dansyl reporter groups in good overall yield.
