35060-08-3Relevant articles and documents
Transmission of binding information across lipid bilayers
Dijkstra, Harmen P.,Hutchinson, Jordan J.,Hunter, Christopher A.,Qin, Haiyuan,Tomas, Salvador,Webb, Simon J.,Williams, Nicholas H.
, p. 7215 - 7222 (2007)
A synthetic transmembrane receptor that is capable of transmitting binding information across a lipid bilayer membrane is reported. The binding event is based on aggregation of the receptor triggered by copper(II) complexation to ethylenediamine functionalities. By labelling the receptor with fluorescent dansyl groups, the copper(II) binding event could be monitored by measuring the extent of fluorescence quenching. Comparing the receptor with a control receptor lacking the transmembrane linkage revealed that the transmembrane receptor binds copper(II) ions more tightly than the non-spanning control receptor at low copper(II) concentrations. Since the intrinsic binding to copper(II) is the same for both receptors, this effect was attributed to synergy between the connected interior and exterior binding sides of the transmembrane receptor. Thus, this is the first reported artificial signalling event in which binding of a messenger on one side of the membrane leads to a cooperative binding event on the opposite side of the membrane, resembling biological signalling systems and helping us to get a better understanding of the requirements for more effective artificial signalling systems.
Homogeneous competitive assay of ligand affinities based on quenching fluorescence of tyrosine/tryptophan residues in a protein via Frster-resonance-energy-transfer
Xie, Yanling,Yang, Xiaolan,Pu, Jun,Zhao, Yunsheng,Zhang, Ying,Xie, Guoming,Zheng, Jun,Yuan, Huidong,Liao, Fei
, p. 869 - 876 (2010)
A new homogeneous competitive assay of ligand affinities was proposed based on quenching the fluorescence of tryptophan/tyrosine residues in a protein via Frster-resonance-energy-transfer using a fluorescent reference ligand as the acceptor. Under excitation around 280 nm, the fluorescence of a protein or a bound acceptor was monitored upon competitive binding against a nonfluorescent candidate ligand. Chemometrics for deriving the binding ratio of the acceptor with either fluorescence signal was discussed; the dissociation constant (K d) of a nonfluorescent candidate ligand was calculated from its concentration to displace 50% binding of the acceptor. N-biotinyl-N′-(1- naphthyl)-ethylenediamine (BNEDA) and N-biotinyl-N′-dansyl-ethylenediamine (BDEDA) were used as the reference ligands and acceptors to streptavidin to test this new homogeneous competitive assay. Upon binding of an acceptor to streptavidin, there were the quench of streptavidin fluorescence at 340 nm and the characteristic fluorescence at 430 nm for BNEDA or at 525 nm for BDEDA. Kd of BNEDA and BDEDA was obtained via competitive binding against biotin. By quantifying BNEDA fluorescence, Kd of each tested nonfluorescent biotin derivative was consistent with that by quantifying streptavidin fluorescence using BNEDA or BDEDA as the acceptor. The overall coefficients of variation were about 10%. Therefore, this homogeneous competitive assay was effective and promising to high-throughput-screening.
Synthesis of monoconjugated and multiply conjugated oligonucleotides by "click thiol" thiol-Michael-type additions and by combination with CuAAC "click huisgen"
Meyer, Albert,Vasseur, Jean-Jacques,Morvan, Francois
, p. 465 - 473 (2013)
Monoconjugated and multiply conjugated oligonucleotides were efficiently synthesized by starting from mono-thiohexyl- or tetra-thiohexyl-oligonucleotides and treatment with acrylamide derivatives (carbohydrates, ferrocene, biotin, fluorescent dyes, deoxyc
Polyamine metabolism I: synthesis of dansyl derivatives of N (monoaminoalkyl) and N (polyaminoalkyl)acetamides and elucidation in urine of a cancer patient
Abdel Monem,Ohno
, p. 1089 - 1094 (1977)
The dansyl derivatives of N-(monoaminoalkyl)- and N-(polyaminoalkyl)acetamides were synthesized and unequivocally characterized. TLC of the dansyl derivatives obtained from human urine indicated the presence of N-[3-[(4-aminobutyl)amino]propyl]acetamide (N1-acetylspermidine), N-[4-[(3-aminopropyl)amino]butyl]acetamide (N8-acetylspermidine), and N-(4-aminobutyl)acetamide (N-acetylputrescine) in appreciable amounts. The dansyl derivatives of N1-acetylspermidine, N8-acetylspermidine, and N-acetylputrescine were isolated and purified using various chromatographic methods. The mass spectra of these compounds were similar to those of authentic samples, which confirmed the identity of these compounds and established the presence of N8-acetylspermidine as well as N1-acetylspermidine and N-acetylputrescine in human urine.
Deuterium Isotope Effect on Volume Phase Transition of Polymer Gel: Temperature Dependence
Shirota, Hideaki,Kuwabara, Nozomi,Ohkawa, Kazuya,Horie, Kazuyuki
, p. 10400 - 10408 (1999)
The deuterium isotope effects on the volume phase transition of a typical temperature-sensitive polymer gel (poly(N-isopropylacrylamide) (PNIPAM) gel) and the phase separation of the linear polymer (PNIPAM) have been investigated. For the comparison between the bulk change and the microenvironment change, the deuterium isotope effects of PNIPAM gel and linear PNIPAM solution have also been investigated by using a fluorescence probe. Both the transition temperature of the polymer gel and the phase separation temperature of the linear polymer in heavy water are about 0.7 ?°C higher than those in water. However, the deuterium isotope effects on the difference of the transition temperatures in the heating process and the cooling process in the microenvironments of PNIPAM gel and linear PNIPAM solution are not observed.
General Method for Post-Synthetic Modification of Oligonucleotides Based on Oxidative Amination of 4-Thio-2′-deoxyuridine
Wang, Jingyi,Shang, Jiachen,Xiang, Yu,Tong, Aijun
, p. 721 - 728 (2021)
Functionalized oligonucleotides (ONs) are widely applied as target binding molecules for biosensing and regulators for gene expression. Numerous efforts have been focused on developing facile methods for preparing these useful ONs carrying diverse modifications. Herein, we present a general method for postsynthetic modification of ONs via oxidative amination of 4-thio-2′-deoxyuridine (4SdU). 4SdU-containing ON can be derived by both alkyl and aromatic amines. Using this approach, ONs are successfully attached with alkyne/azide, biotin and dansylamide moieties, and these as-prepared ONs possess the expected biorthogonal reactivity, streptavidin affinity and fluorescent property, respectively. Furthermore, we also directly install fluorophores to the ON nucleobase based on oxidative amination of 4SdU, and these fluorophores exhibit distinct luminescence behaviors before and after conjugation. We believe our method will be a versatile strategy for constructing various functionalized ONs used in a wide range of nucleic acid applications.
Design of Environmentally Responsive Fluorescent Polymer Probes for Cellular Imaging
Yamada, Arisa,Hiruta, Yuki,Wang, Jian,Ayano, Eri,Kanazawa, Hideko
, p. 2356 - 2362 (2015)
We report the development of environmentally responsive fluorescent polymers. The reversible temperature-induced phase transition of copolymers composed of N-isopropylacrylamide and a fluorescent monomer based on the fluorescein (FL), coumarin (CO), rhodamine (RH), or dansyl (DA) skeleton was used as a molecular switch to control the fluorescence intensity. The poly(N-isopropylacrylamide) (PNIPAAm) chain showed an expanded coil conformation below the lower critical solution temperature (LCST) due to hydration, but it changed to a globular form above the LCST due to dehydration. Through the combination of a polarity-sensitive fluorophore with PNIPAAm, the synthetic fluorescent polymer displayed a response to external temperature, with the fluorescence strength dramatically changing close to the LCST. Additionally, the P(NIPAAm-co-FL) and P(NIPAAm-co-CO) polymers, containing fluorescein and coumarin groups, respectively, exhibited pH responsiveness. The environmental responsiveness of the reported polymers is derived directly from the PNIPAAm and fluorophore structures, thus allowing for the cellular uptake of the fluorescence copolymer by RAW264.7 cells to be temperature-controlled. Cellular uptake was suppressed below the LCST but enhanced above the LCST. Furthermore, the cellular uptake of both P(NIPAAm-co-CO) and P(NIPAAm-co-RH) conjugated with a fusogenic lipid, namely, L-α-phosphatidylethanolamine, dioleoyl (DOPE), was enhanced. Such lipid-conjugated fluorescence probes are expected to be useful as physiological indicators for intracellular imaging. (Chemical Equation Presented).
Development of a Fluorescent-Labeled Trapping Reagent to Detect Reactive Acyl Glucuronides
Shibazaki, Chikako,Mashita, Okishi,Takahashi, Kyoko,Nakamura, Shigeo,Mashino, Tadahiko,Ohe, Tomoyuki
, p. 2343 - 2352 (2021/11/16)
Acyl glucuronides are common metabolites of carboxylic acid-containing compounds. Since acyl glucuronides sometimes show high reactivity, they are considered to be involved in drug toxicity. Therefore, it is important to evaluate the risk posed by acyl glucuronides in the development of safe drugs; however, there are no suitable evaluation methods for the early stages of drug discovery. We aimed to develop a trapping reagent that detects reactive acyl glucuronides to assess their risk. We designed a diamine-structured trapping reagent, Dap-Dan, and compared its trapping ability with the reported one that has an amino group, and results showed that Dap-Dan showed higher accuracy. In the trapping assay with 17 medicines containing a carboxylic acid, Dap-Dan trapped acyl glucuronides that had a higher risk of toxicity. In conclusion, Dap-Dan can be useful for evaluating the risk of reactive acyl glucuronides.
