94605-71-7Relevant academic research and scientific papers
A light-regulated synthetic ion channel constructed by an azobenzene modified hydraphile
Yang, Rong-Yan,Bao, Chun-Yan,Lin, Qiu-Ning,Zhu, Lin-Yong
, p. 851 - 856 (2015)
Biological ion channels are key molecules for cellular regulation and communication. To mimic the structure and functions of nature ion channels, a new class of light-regulated transmembrane ion channels was reported based on tri(macrocycle) hydraphile an
Improved Syntheses of Benzyl Hydraphile Synthetic Cation-Conducting Channels
Curvey, Nichole S.,Luderer, Sarah E.,Walker, John K.,Gokel, George W.
, p. 2771 - 2779 (2015/02/19)
The tris(macrocycle)s that function in bilayer membranes as ion channels have recently shown versatile new applications such as antibiotic synergists and as agents for direct injection chemotherapy. This report records the development of new and versatile approaches to these molecules that produce significantly better overall yields for a group of previously reported hydraphiles having spacer chains ranging from octylene to hexadecylene.
Synthetic ion channel activity documented by electrophysiological methods in living cells
Leevy, W. Matthew,Huettner, James E.,Pajewski, Robert,Schlesinger, Paul H.,Gokel, George W.
, p. 15747 - 15753 (2007/10/03)
Hydraphiles are synthetic ion channels that use crown ethers as entry portals and that span phospholipid bilayer membranes. Proton and sodium cation transport by these compounds has been demonstrated in liposomes and planar bilayers. In the present work, whole cell patch clamp experiments show that hydraphiles integrate into the membranes of human embryonic kidney (HEK 293) cells and significantly increase membrane conductance. The altered membrane permeability is reversible, and the cells under study remain vital during the experiment. Control compounds that are too short (C8-benzyl channel) to span the bilayer or are inactive owing to a deficiency in the central relay do not induce similar conductance increases. Control experiments confirm that the inactive channel analogues do not show nonspecific effects such as activation of native channels. These studies show that the combination of structural features that have been designed into the hydraphiles afford true, albeit simple, channel function in live cells.
Synthesis and Molecular Recognition of Pyrenophanes with Polycationic or Amphiphilic Functionalities: Artificial Plate-Shaped Cavitant Incorporating Arenes and Nucleotides in Water
Abe, Hajime,Mawatari, Yosuke,Teraoka, Haruna,Fujimoto, Kazuhisa,Inouye, Masahiko
, p. 495 - 504 (2007/10/03)
Water-soluble pyrenophanes possessing polycationic or amphiphilic side chains have been developed as synthetic host molecules to investigate hydrophobic and/or π-stacking interactions. By utilizing ω-acetalic alkyl side chains to retain solubility and ver
Ditopic receptors capable of hydrogen bonding: Synthesis and complexation behaviour of diaza crown-ethers having melamine sidearms
Quici, Silvio,Manfredi, Amedea,Pozzi, Gianluca,Cavazzini, Marco,Rozzoni, Angela
, p. 10487 - 10496 (2007/10/03)
The new ditopic receptors 1-3 (Figure 1) have been synthesized and their binding ability for alkaline and transition metal cations has ben investigated by halide and UV-Vis titrations. The recognition of complementary molecules through hydrogen bonding has been studied by 1H- NMR. The simultaneous recognition of these two guests is an anti-cooperative event.
Steric and stereoelectronic effects in aza crown ether complexes
Solov'ev, Vitally P.,Strakhova, Nadezhda N.,Kazachenko, Vladimir P.,Solotnov, Alexandr F.,Baulin, Vladimir E.,Raevsky, Oleg A.,Ruediger, Volker,Eblinger, Frank,Schneider, Hans-Joerg
, p. 1379 - 1389 (2007/10/03)
Stability constants and enthalpy changes determined by calorimetric titrations and supported by selected NMR titrations are reported for the complexation of sodium and potassium cations with 18 different crown ethers containing nitrogen atoms with different number, location and substitution pattern. The data, measured in methanol mostly with potassium salts, are compared to literature data; they show striking differences between all-oxygen analogs and the macrocycles with NH groups. In contrast, affinities with aza crown ethers bearing alkyl groups at the nitrogen as well as with the cryptand [2.2.2] come closer to the complexation free energies predicted from the number and electron donating capacity of the ligand heteroatoms. This is rationalised on the basis of molecular mechanics calculations, showing that a NH-containing crown predominates in conformations with axial N lone pairs, due to their repulsive electrostatic interactions with the ring oxygen atoms. Replacement of the hydrogen by alkyl groups forces the lone pairs to an equatorial position, thus enabling better complex formation, as borne out by experiment. In line with these arguments the IgK differences are with some exceptions more due to ΔH than to TΔS differences. The calorimetric data show linear isoequilibrium correlations between TΔS and ΔH, with slopes between those observed with other crown ether and cryptand complexes. Preliminary investigations of some synthetic macrocyclic amide precursors yield appreciable complexation only, if the two carbonyl oxygens can come in close contact with the guest cation. Computer aided molecular modelling shows that this is possible in a small 15C5-derivative, in which the polyethylenglycol cycle only serves as ring template without binding contributions from the ether oxygen atoms.
Synthetic models for transmembrane channels: Structural variations that alter cation flux
Murillo, Oscar,Watanabe, Shigeru,Nakano, Akio,Gokel, George W.
, p. 7665 - 7679 (2007/10/03)
Twelve novel bis- or tris(macrocyclic) compounds have been designed as models for cation-conducting channels that function in phospholipid bilayer vesicle membranes. In general, the channel model systems have the structure "sidearm-crown-spacer-crown-spac
Syntheses of unsymmetrically N,N′-bis (substituted)-4,13-diaza-18-crown-6-ether derivatives as a new electron donor-spacer-acceptor triad
Morimoto, Minoru,Fukui, Keijiro,Kawasaki, Norioki,Iyoda, Tomokazu,Shimidzu, Takeo
, p. 95 - 98 (2007/10/02)
A simple and general synthetic strategy potentially applicable for the preparation of a wide variety of unsymmetrically N,N′-bis(substituted)-4, 13-diaza-18-crown-6-ether derivatives was reported.
