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

Oligoamines in cellular metabolism carry extremely diverse biological functions (i.e., regulating Ca<sup>2+</sup>-influx, neuronal nitric oxide synthase, membrane potential, Na<sup>+</sup>, K<sup>+</sup>-ATPase activity in synaptosomes, etc.). Furthermore, they al...

Full description

Saved in:
Bibliographic Details
Main Authors: Péter Kisfaludi, Sára Spátay, Marcell Krekó, Panna Vezse, Tünde Tóth, Péter Huszthy, Ádám Golcs
Format: Article
Language:English
Published: MDPI AG 2024-09-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/29/18/4390
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Oligoamines in cellular metabolism carry extremely diverse biological functions (i.e., regulating Ca<sup>2+</sup>-influx, neuronal nitric oxide synthase, membrane potential, Na<sup>+</sup>, K<sup>+</sup>-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.).
ISSN:1420-3049