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

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.

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

scholarly journals Dansyl - Substituted Aza Crown Ethers: Complexation with Alkali, Alkaline Earth Metal Ions and Ammonium

2011 ◽  
Vol 3 (1) ◽  
Author(s):  
Nelly Mateeva ◽  
Shihab Deiab ◽  
Edikan Archibong ◽  
Donka Tasheva ◽  
Bereket Mochona ◽  
...  
Keyword(s):  
Metal Ions ◽  
Crown Ethers ◽  
Alkaline Earth ◽  
Earth Metal ◽  
Alkaline Earth Metal ◽  
Alkaline Earth Metal Ions ◽  
Aza Crown Ethers

scholarly journals Complex Uranyl Dichromates Templated by Aza-Crowns

Crystals ◽  
2018 ◽  
Vol 8 (12) ◽  
pp. 462 ◽  
Author(s):  
Oleg Siidra ◽  
Evgeny Nazarchuk ◽  
Dmitry Charkin ◽  
Stepan Kalmykov ◽  
Anastasiya Zadoya
Keyword(s):  
Aqueous Solutions ◽  
Crown Ethers ◽  
Room Temperature ◽  
Organic Molecules ◽  
Negative Charge ◽  
Uranyl Compounds ◽  
One Dimensional ◽  
Chain Complexes ◽  
Aza Crown Ethers

Three new uranyl dichromate compounds templated by aza-crown templates were obtained at room temperature by evaporation from aqueous solutions: (H2diaza-18-crown-6)2[(UO2)2(Cr2O7)4(H2O)2](H2O)3 (1), (H4[15]aneN4)[(UO2)2(CrO4)2(Cr2O7)2(H2O)] (H2O)3.5 (2) and (H4Cyclam)(H4[15]aneN4)2[(UO2)6(CrO4)8(Cr2O7)4](H2O)4 (3). The use of aza-crown templates made it possible to isolate unprecedented and complex one-dimensional units in 2 and 3, whereas the structure of 1 is based on simple uranyl-dichromate chains. It is very likely that the presence of relatively large organic molecules of aza-crown ethers does not allow uranyl chromate chain complexes to condense into the units of higher dimensionality (layers or frameworks). In general, the formation of 1, 2, and 3 is in agreement with the general principles elaborated for organically templated uranyl compounds. The negative charge of the [(UO2)(Cr2O7)2(H2O)]2−, [(UO2)2(CrO4)2(Cr2O7)2(H2O)]4− and [(UO2)3(CrO4)4(Cr2O7)2]6− one-dimensional inorganic motifs is compensated by the protonation of all nitrogen atoms in the molecules of aza-crowns.

ChemInform Abstract: Synthesis and Cation-Binding Abilities of Novel Polyquinane Crown Ethers (III) Containing a Bis-Acetal Ether Functionality.

ChemInform ◽  
1989 ◽  
Vol 20 (34) ◽  
Author(s):  
G. MEHTA ◽  
K. S. RAO ◽  
N. KRISHNAMURTHY ◽  
V. SRINIVAS ◽  
D. BALASUBRAMANIAN
Keyword(s):  
Crown Ethers ◽  
Cation Binding
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