diaza crown ethers
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Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2225
Author(s):  
Stepan S. Basok ◽  
Igor A. Schepetkin ◽  
Andrei I. Khlebnikov ◽  
Anatoliy F. Lutsyuk ◽  
Tatiana I. Kirichenko ◽  
...  

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.


2019 ◽  
Vol 68 (4) ◽  
pp. 848-854 ◽  
Author(s):  
O. K. Grigorova ◽  
D. I. Gusev ◽  
A. D. Averin ◽  
O. A. Maloshitskaya ◽  
I. P. Beletskaya

2018 ◽  
Vol 857 ◽  
pp. 170-179 ◽  
Author(s):  
Benjamin W. Stein ◽  
Samantha K. Cary ◽  
John M. Berg ◽  
Eva R. Birnbaum ◽  
Stosh A. Kozimor ◽  
...  

Polyhedron ◽  
2015 ◽  
Vol 102 ◽  
pp. 677-683 ◽  
Author(s):  
Jaromir Kira ◽  
Pawel Niedzialkowski ◽  
Dorota Zarzeczanska ◽  
Grzegorz Romanowski ◽  
Tadeusz Ossowski

ChemInform ◽  
2010 ◽  
Vol 23 (24) ◽  
pp. no-no
Author(s):  
H. TSUKUBE ◽  
H. MINATOGAWA ◽  
M. MUNAKATA ◽  
M. TODA ◽  
K. MATSUMOTO

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