N. N. Vorozhtsov Institute of Organic Chemistry SB RAS, 9th Lavrentiev Avenue, 630090 Novosibirsk, Russia.
Institute of Chemistry, Technische Universität Chemnitz, 09107 Chemnitz, Germany.
Molecules. 2021 Feb 12;26(4):980. doi: 10.3390/molecules26040980.
Selective recognition of nucleotides with synthetic receptors is an emerging direction to solve a series of nucleic acid-related challenges in biochemistry. Towards this goal, a new aza-cyclophane with two different dyes, naphthalimide and pyrene, connected through a triamine linker has been synthesized and studied for the ability to bind and detect nucleoside triphosphates in an aqueous solution. The receptor shows Foerster resonance energy transfer (FRET) in fluorescence spectra upon excitation in DMSO, which is diminished dramatically in the presence of water. According to binding studies, the receptor has a preference to bind ATP (adenosine triphosphate) and CTP (cytidine triphosphate) with a "turn-on" fluorescence response. Two separate emission bands of dyes allow one to detect nucleotides in a ratiometric manner in a broad concentration range of 10-10 M. Spectroscopic measurements and quantum chemical calculations suggest the formation of receptor-nucleotide complexes, which are stabilized by dispersion interactions between a nucleobase and dyes, while hydrogen bonding interactions of nucleobases with the amine linkers are responsible for selectivity.
选择性识别核苷酸的合成受体是解决生物化学中一系列与核酸相关挑战的新兴方向。为此，我们合成了一种带有两个不同染料（萘酰亚胺和芘）的新型氮杂环笼，通过三胺连接子连接，并研究了其在水溶液中结合和检测核苷三磷酸的能力。该受体在 DMSO 中激发时在荧光光谱中表现出Förster 共振能量转移（FRET），而在存在水的情况下则急剧减少。根据结合研究，该受体优先与 ATP（三磷酸腺苷）和 CTP（三磷酸胞苷）结合，具有“开启”荧光响应。染料的两个单独发射带允许以比率方式在 10-10 M 的宽浓度范围内检测核苷酸。光谱测量和量子化学计算表明形成了受体-核苷酸复合物，这些复合物通过碱基和染料之间的色散相互作用稳定，而碱基与胺连接子的氢键相互作用则负责选择性。
