A fluorescent 3,7-bis-(naphthalen-1-ylethynylated)-2'-deoxyadenosine analogue reports thymidine in complementary DNA by a large emission Stokes shift
A fluorescent 3,7-bis-(naphthalen-1-ylethynylated)-2'-deoxyadenosine analogue reports thymidine in complementary DNA by a large emission Stokes shift
复制标题
荧光 3,7-双-(萘-1-乙炔化)-2-脱氧腺苷类似物通过大发射斯托克斯位移报告互补 DNA 中的胸苷
DOI：
10.1039/c8ob00062j
复制
发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Y. Saito
中科院分区：
文献类型：
--
作者：
M. Yanagi;A. Suzuki;R. H. E. Hudson;Y. Saito
合成了新的环境响应荧光核苷3,7-二-（萘-1-乙炔基）-8-氮杂-3,7-双氧杂-2 ' -脱氧腺苷（3n7nzA, 1）和7-（萘-1-乙炔基）-8-氮杂-3,7-双氧杂-2 ' -脱氧腺苷（37nzA, 2）。3n7nzA(1)和37nzA(2)均具有较大的π共轭体系，其π共轭体系分别延伸到小槽和主槽中或仅延伸到主槽中。这些核苷表现出较大的溶剂变色位移（3n7nzA： Δλ = 45 nm, 37nzA： Δλ = 78 nm），并对其荧光报告杂交事件的能力进行了检测。当加入到ODN探针中时，双取代的3n7nzA(1)选择性地识别目标链上的胸苷，其发射波长在长波长区域发生明显变化，而37nzA(2)则倾向于与胞苷配对，波长位移较小。因此，3n7nzA(1)有潜力作为一种荧光探针用于DNA / rna的结构研究，包括检测靶DNA序列的单碱基改变。
The new environmentally responsive fluorescent nucleosides, 3,7-bis-(naphthalen-1-ylethynyl)-8-aza-3,7-dideaza-2′-deoxyadenosine (3n7nzA, 1) and 7-(naphthalen-1-ylethynyl)-8-aza-3,7-dideaza-2′-deoxyadenosine (37nzA, 2), have been synthesized. Both 3n7nzA (1) and 37nzA (2) possess large π-conjugated systems which extend into both the minor and major grooves or the major groove alone, respectively. The nucleosides exhibited large solvatochromic shifts (3n7nzA: Δλ = 45 nm, 37nzA: Δλ = 78 nm) and were examined for their ability to fluorimetrically report hybridization events. When incorporated into ODN probes, the bis-substituted 3n7nzA (1) selectively recognized thymidine on target strands which was reported by a distinct change in its emission wavelength in the long wavelength region, whereas 37nzA (2) showed a preference for pairing to cytidine and a smaller wavelength shift. Thus, 3n7nzA (1) has the potential for use as a fluorescent probe for structural studies of DNAs/RNAs including the detection of single-base alterations in target DNA sequences.