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.
Fluorogenic dansyl-ligated gold nanoparticles for the detection of sulfur mustard by displacement assay
Knighton, Richard C.,Sambrook, Mark R.,Vincent, Jack C.,Smith, Simon A.,Serpell, Christopher J.,Cookson, James,Vickers, Matthew S.,Beer, Paul D.
, p. 2293 - 2295 (2013)
The dansyl fluorophore ligated to gold nanoparticles via imidazole and amine groups affords conjugates capable of detecting micromolar concentrations of the chemical warfare agent sulfur mustard by a fluorescence switching 'ON' displacement assay. The Royal Society of Chemistry.
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.
Solvent polarity scale on the fluorescence spectra of a dansyl monomer copolymerizable in aqueous media
Ren, Biye,Gao, Feng,Tong, Zhen,Yan, Yu
, p. 55 - 61 (1999)
A copolymerizable fluorescent monomer N-[2-[[[5-(N,N-dimethylamino)-1-naphthalenyl]sulfonyl]-amino]ethyl]-2- propenamide (DANSAEP) was synthesized, which exhibits dual fluorescence due to the twisted intramolecular charge transfer in the excited state. The emission maximum λem shifts from 463.3 nm in n-hexane to 530.0 nm in water, showing solvent polarity dependence. The relations between λem and the conventional solvent polarity parameters ET(30) or Z are linear, dividing solvents into protic and aprotic groups. Kamlet's linear solvation energy relationship gives a good description for λem as a solvent polarity scale. The increment of dipole moment Δμ at the excited state was estimated as 5.09 D with the solvatochromic analysis.
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
Controlling fluorescence resonance energy transfer of donor-acceptor dyes by Diels-Alder dynamic covalent bonds
Cui, Yanhui,Li, Fen,Zhang, Xin
, p. 3275 - 3278 (2021)
Two new dyes consisting of an aromatic amine donor and dansyl acceptor were synthesized, where the intramolecular donor and acceptor are connected by Diels-Alder dynamic covalent bonds. These new dyes display a switchable fluorescence resonance energy transfer through reversible formation and cleavage of Diels-Alder bonds. Single crystal X-ray diffraction revealed that Diels-Alder bonds are longer and weaker than normal single bonds. Dynamic covalent properties enable the mutual conversion of the two dyes by maleimide exchanges, where a new higher energy transfer efficiency system can be constructed.
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.
Affinity purification of multifunctional polymer nanoparticles
Hoshino,Haberaecker III, Walter W.,Kodama, Takashi,Zeng, Zhiyang,Okahata, Yoshio,Shea, Kenneth J.
, p. 13648 - 13650 (2010)
We report that multifunctional polymer nanoparticles approximately the size of a large protein can be 'purified', on the basis of peptide affinity just as antibodies, using an affinity chromatography strategy. The selection process takes advantage of the thermoresponsiveness of the nanoparticles allowing 'catch and release' of the target peptide by adjusting the temperature. Purified particles show much stronger affinity (Kdapp ≈ nM) and a narrower affinity distribution than the average of particles before purification (Kdapp > μM) at room temperature but can release the peptide just by changing the temperature. We anticipate this affinity selection will be general and become an integral step for the preparation of "plastic antibodies" with near-homogeneous and tailored affinity for target biomacromolecules.
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.
Cooperative binding at lipid bilayer membrane surfaces
Doyle, Emma L.,Hunter, Christopher A.,Phillips, Helen C.,Webb, Simon J.,Williams, Nicholas H.
, p. 4593 - 4599 (2003)
The binding of copper(II) ions to membrane-bound synthetic receptors has been investigated. Complexation fitted a 4:1 receptor: copper(II) model, and the observed binding constants are significantly enhanced at the membrane relative to solution; these effects can be explained by the lower polarity of the membrane-water interface and the concentrating effect of the membrane, with no observed contribution from receptor preorganization. The stoichiometry of the complex formed is very sensitive to the concentration of the receptor in the membrane, and at low concentrations, binding is reduced relative to solution controls. This implies that by increasing or decreasing the number of receptors in their membranes, cells can finely tune biological responses such as chemotaxis that depend on the size of the receptor-ligand clusters formed.
