46744-67-6Relevant academic research and scientific papers
The Cooperative Effect of Both Molecular and Supramolecular Chirality on Cell Adhesion
Liu, Jinying,Yuan, Feng,Ma, Xiaoyu,Auphedeous, Dang-i Y.,Zhao, Changli,Liu, Chuntai,Shen, Changyu,Feng, Chuanliang
, p. 6475 - 6479 (2018)
Although helical nanofibrous structures have great influence on cell adhesion, the role played by chiral molecules in these structures on cells behavior has usually been ignored. The chirality of helical nanofibers is inverted by the odd–even effect of methylene units from homochiral l-phenylalanine derivative during assembly. An increase in cell adhesion on left-handed nanofibers and weak influence of cell behaviors on right-handed nanofibers are observed, even though both were derived from l-phenylalanine derivatives. Weak and negative influences on cell behavior was also observed for left- and right-handed nanofibers derived from d-phenylalanine, respectively. The effect on cell adhesion of single chiral molecules and helical nanofibers may be mutually offset.
1,2,4-Triazole-3-thione Compounds as Inhibitors of Dizinc Metallo-β-lactamases
Sevaille, Laurent,Gavara, Laurent,Bebrone, Carine,De Luca, Filomena,Nauton, Lionel,Achard, Maud,Mercuri, Paola,Tanfoni, Silvia,Borgianni, Luisa,Guyon, Carole,Lonjon, Pauline,Turan-Zitouni, Gülhan,Dzieciolowski, Julia,Becker, Katja,Bénard, Lionel,Condon, Ciaran,Maillard, Ludovic,Martinez, Jean,Frère, Jean-Marie,Dideberg, Otto,Galleni, Moreno,Docquier, Jean-Denis,Hernandez, Jean-Fran?ois
, p. 972 - 985 (2017/06/27)
Metallo-β-lactamases (MBLs) cause resistance of Gram-negative bacteria to β-lactam antibiotics and are of serious concern, because they can inactivate the last-resort carbapenems and because MBL inhibitors of clinical value are still lacking. We previously identified the original binding mode of 4-amino-2,4-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione (compound IIIA) within the dizinc active site of the L1 MBL. Herein we present the crystallographic structure of a complex of L1 with the corresponding non-amino compound IIIB (1,2-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione). Unexpectedly, the binding mode of IIIB was similar but reverse to that of IIIA. The 3 D structures suggested that the triazole–thione scaffold was suitable to bind to the catalytic site of dizinc metalloenzymes. On the basis of these results, we synthesized 54 analogues of IIIA or IIIB. Nineteen showed IC50 values in the micromolar range toward at least one of five representative MBLs (i.e., L1, VIM-4, VIM-2, NDM-1, and IMP-1). Five of these exhibited a significant inhibition of at least four enzymes, including NDM-1, VIM-2, and IMP-1. Active compounds mainly featured either halogen or bulky bicyclic aryl substituents. Finally, some compounds were also tested on several microbial dinuclear zinc-dependent hydrolases belonging to the MBL-fold superfamily (i.e., endonucleases and glyoxalase II) to explore their activity toward structurally similar but functionally distinct enzymes. Whereas the bacterial tRNases were not inhibited, the best IC50 values toward plasmodial glyoxalase II were in the 10 μm range.
NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer. Part I. Discovering the guidelines
Cohen, Yael,Bodner, Efrat,Richman, Michal,Afri, Michal,Frimer, Aryeh A.
experimental part, p. 98 - 113 (2009/12/31)
The development of "molecular rulers" would allow one to quantitatively locate intercalants within the liposomal bilayer. To this end, we have attempted to correlate the 13C NMR chemical shift of a polarizable "reporter" carbon (e.g., carbonyl) of the intercalant-with the ET(30) polarity it experiences, and with its Angstrom distance from the interface. This requires families of molecules with the same two "reporter carbons" separated by a fixed distance, residing at various depths/polarities within the bilayer. The families studied included 4,4-dialkylcyclohexa-2,5-dienones 1, benzenediacetic esters 15, benzenedipropionic esters 17, 4-alkoxybenzaldehydes 19 and methyl 4-alkoxybenzoates 22. These compounds possessed the following characteristics: (1) a planar backbone; (2) polar/hydrophilic "head" groups; (3) modular hydrophobic tails; (4) large changes in the 13C NMR chemical shift (Δδ) of the reporter atoms with solvent polarity. These studies revealed a fifth requirement, namely: (5) the reporter carbons must not be strongly conjugated, lest it reflect the charge build-up at another site within the conjugated system.
Both-faces Hindered Porphyrins. Part 3. Synthesis and Characterization of Internally Five-co-ordinated Iron(II) Basket Handle Porphyrins derived from 5,10,15,20-Tetrakis(o-aminophenyl)porphyrin
Momenteau, Michel,Mispelter, Joel,Loock, Bernard,Lhoste, Jean-Marc
, p. 221 - 232 (2007/10/02)
The synthesis of a series of so-called amide 'hanging base' porphyrins (10), (14) and (18), derived from 5,10,15,20-tetrakis(o-aminophenyl)porphyrin (αβαβ-atropisomer) (3), in which one of the faces is hindered by an alkylene or an arylene-p-bisalkylene bridge and the other face is bridged by a pyridine-3,5-diyl-bisalkylene or an imidazolyl-alkylene chain, is described.The structural assignment of the various compounds is based on the 1H n.m.r. spectra of the free bases, and of their zinc(II) and iron(II) complexes.Unlike the ether 'hanging base' metalloporphyrins, the metallic ion of amide 'hanging base' porphyrins is actually five-co-ordinated by the proximal base.Furthermore, not only is the equilibrium pyridine plane orientation dependent on the length of its linking chain, but the bridging forces the amide protons to point toward the centre of the macrocycle core.These structural properties are potential factors which may affect the binding of dioxygen.The synthesis of a bis-pyridine 'basket handle' porphyrin is also reported.
