A Bis(Acridino)-Crown Ether for Recognizing Oligoamines in Spermine Biosynthesis

被引:0
|
作者
Kisfaludi, Peter [1 ]
Spatay, Sara [1 ,2 ]
Kreko, Marcell [2 ,3 ]
Vezse, Panna [1 ]
Toth, Tunde [1 ,4 ]
Huszthy, Peter [1 ]
Golcs, Adam [1 ,2 ,3 ]
机构
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, Szent Gellert Sq 4, H-1111 Budapest, Hungary
[2] Semmelweis Univ, Dept Pharmaceut Chem, Hogyes Endre St 9, H-1092 Budapest, Hungary
[3] Semmelweis Univ, Dept Pharmaceut Chem, Ctr Pharmacol & Drug Res & Dev, Ulloi St 26, H-1092 Budapest, Hungary
[4] HUN REN Ctr Energy Res, Konkoly Thege Miklos St 29 33, H-1121 Budapest, Hungary
来源
MOLECULES | 2024年 / 29卷 / 18期
关键词
biogenic oligoamines; spermine; spermidine; fluorescence; chemosensor; crown ether; BIOGENIC-AMINES; AGGREGATION; POLYAMINES; ACRIDONO-18-CROWN-6; COMPLEXATION; PRODUCTS; BINDING; ACIDS;
D O I
10.3390/molecules29184390
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Oligoamines in cellular metabolism carry extremely diverse biological functions (i.e., regulating Ca2+-influx, neuronal nitric oxide synthase, membrane potential, Na+, K+-ATPase activity in synaptosomes, etc.). Furthermore, they also act as longevity agents and have a determinative role in autophagy, cell growth, proliferation, and death, while oligoamines dysregulation is a key in a variety of cancers. However, many of their mechanisms of actions have just begun to be understood. In addition to the numerous biosensing methods, only a very few simple small molecule-based tests are available for their selective but reversible tracking or fluorescent labeling. Motivated by this, we present herein a new fluorescent bis(acridino)-crown ether as a sensor molecule for biogenic oligoamines. The sensor molecule can selectively distinguish oligoamines from aliphatic mono- and diamino-analogues, while showing a reversible 1:2 (host:guest) complexation with a stepwise binding process accompanied by a turn-on fluorescence response. Both computational simulations on molecular docking and regression methods on titration experiments were carried out to reveal the oligoamine-recognition properties of the sensor molecule. The new fluorescent chemosensor molecule has a high potential for molecular-level functional studies on the oligoamine systems in cell processes (cellular uptake, transport, progression in cancers, etc.).
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页数:22
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