Ion-responsive fluorescent compounds. 4. Effect of cation binding on the photophysical properties of a coumarin linked to monoaza- and diaza-crown ethers

1993 ◽  
Vol 97 (17) ◽  
pp. 4552-4557 ◽  
Author(s):  
Jean Bourson ◽  
Jacques Pouget ◽  
Bernard Valeur
Keyword(s):  
Crown Ethers ◽  
Photophysical Properties ◽  
Cation Binding ◽  
Diaza Crown Ethers ◽  
Fluorescent Compounds

scholarly journals Synthesis, Biological Evaluation, and Molecular Modeling of Aza-Crown Ethers

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2225
Author(s):  
Stepan S. Basok ◽  
Igor A. Schepetkin ◽  
Andrei I. Khlebnikov ◽  
Anatoliy F. Lutsyuk ◽  
Tatiana I. Kirichenko ◽  
...  
Keyword(s):  
Crown Ethers ◽  
Density Functional ◽  
Biological Effects ◽  
Biological Evaluation ◽  
Cation Binding ◽  
Formyl Peptide Receptor ◽  
Human Neutrophils ◽  
Formyl Peptide ◽  
Diaza Crown Ethers ◽  
Aza Crown Ethers

Synthetic and natural ionophores have been developed to catalyze ion transport and have been shown to exhibit a variety of biological effects. We synthesized 24 aza- and diaza-crown ethers containing adamantyl, adamantylalkyl, aminomethylbenzoyl, and ε-aminocaproyl substituents and analyzed their biological effects in vitro. Ten of the compounds (8, 10–17, and 21) increased intracellular calcium ([Ca2+]i) in human neutrophils, with the most potent being compound 15 (N,N’-bis[2-(1-adamantyl)acetyl]-4,10-diaza-15-crown-5), suggesting that these compounds could alter normal neutrophil [Ca2+]i flux. Indeed, a number of these compounds (i.e., 8, 10–17, and 21) inhibited [Ca2+]i flux in human neutrophils activated by N-formyl peptide (fMLF). Some of these compounds also inhibited chemotactic peptide-induced [Ca2+]i flux in HL60 cells transfected with N-formyl peptide receptor 1 or 2 (FPR1 or FPR2). In addition, several of the active compounds inhibited neutrophil reactive oxygen species production induced by phorbol 12-myristate 13-acetate (PMA) and neutrophil chemotaxis toward fMLF, as both of these processes are highly dependent on regulated [Ca2+]i flux. Quantum chemical calculations were performed on five structure-related diaza-crown ethers and their complexes with Ca2+, Na+, and K+ to obtain a set of molecular electronic properties and to correlate these properties with biological activity. According to density-functional theory (DFT) modeling, Ca2+ ions were more effectively bound by these compounds versus Na+ and K+. The DFT-optimized structures of the ligand-Ca2+ complexes and quantitative structure-activity relationship (QSAR) analysis showed that the carbonyl oxygen atoms of the N,N’-diacylated diaza-crown ethers participated in cation binding and could play an important role in Ca2+ transfer. Thus, our modeling experiments provide a molecular basis to explain at least part of the ionophore mechanism of biological action of aza-crown ethers.

Synthesis of new dibenzo-diaza-crown ethers

1996 ◽  
Vol 37 (13) ◽  
pp. 2213-2216 ◽  
Author(s):  
Bernd Gersch ◽  
Jean-Marie Lehn ◽  
Ernst Grell
Keyword(s):  
Crown Ethers ◽  
Diaza Crown Ethers

Synthesis of chiral diaza-crown ethers incorporating carbohydrate units

Tetrahedron ◽  
1984 ◽  
Vol 40 (15) ◽  
pp. 2967-2970 ◽  
Author(s):  
M. Pietraszkiewicz ◽  
J. Jurczak
Keyword(s):  
Crown Ethers ◽  
Diaza Crown Ethers

Side arm effects on cation binding, extraction, and transport functions of oligopyridine-functionalized aza-crown ethers

1993 ◽  
Vol 58 (16) ◽  
pp. 4389-4397 ◽  
Author(s):  
Hiroshi Tsukube ◽  
Junichi Uenishi ◽  
Hiromi Higaki ◽  
Kenichi Kikkawa ◽  
Takakazu Tanaka ◽  
...  
Keyword(s):  
Crown Ethers ◽  
Cation Binding ◽  
Aza Crown Ethers

Molecular design of crown ethers. 4. Syntheses and selective cation binding of 16-crown-5 and 19-crown-6 lariats

1987 ◽  
Vol 52 (12) ◽  
pp. 2420-2427 ◽  
Author(s):  
Mikio Ouchi ◽  
Yoshihisa Inoue ◽  
Kazuhito Wada ◽  
Shinichi Iketani ◽  
Tadao Hakushi ◽  
...  
Keyword(s):  
Crown Ethers ◽  
Molecular Design ◽  
Cation Binding
Sign in / Sign up

Export Citation Format

Share Document