激基复合物和锥形交叉导致 2-氨基嘌呤与天然嘌呤碱基形成的π堆积二聚体中的荧光猝灭。
Exciplexes and conical intersections lead to fluorescence quenching in π-stacked dimers of 2-aminopurine with natural purine nucleobases.
机构信息
Department of Chemistry, Temple University, Philadelphia, PA 19122, USA.
出版信息
Photochem Photobiol Sci. 2013 Aug;12(8):1387-400. doi: 10.1039/c3pp25449f.
Abstract
Fluorescent analogues of the natural DNA bases are useful in the study of nucleic acids' structure and dynamics. 2-Aminopurine (2AP) is a widely used analogue with environmentally sensitive fluorescence behavior. The quantum yield of 2AP has been found to be significantly decreased when engaged in π-stacking interactions with the native bases. We present a theoretical study on fluorescence quenching mechanisms in dimers of 2AP π-stacked with adenine or guanine as in natural DNA. Relaxation pathways on the potential energy surfaces of the first excited states have been computed and reveal the importance of exciplexes and conical intersections in the fluorescence quenching process.
摘要
荧光类似物是研究核酸结构和动力学的有用工具。2-氨基嘌呤（2AP）是一种广泛使用的类似物，具有环境敏感的荧光行为。当与天然碱基发生π-堆积相互作用时，2AP 的量子产率已被发现显著降低。我们提出了一个关于在与天然 DNA 中腺嘌呤或鸟嘌呤π-堆积的 2AP 二聚体中荧光猝灭机制的理论研究。已计算了第一激发态势能表面上的弛豫途径，并揭示了激基复合物和锥形交叉在荧光猝灭过程中的重要性。
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本文引用的文献
1
Bonded excimer formation in π-stacked 9-methyladenine dimers.
J Phys Chem A. 2013 Sep 12;117(36):8718-28. doi: 10.1021/jp4033194. Epub 2013 Jun 18.
2
Correction to Pathways for Fluorescence Quenching in 2-Aminopurine π-Stacked with Pyrimidine Nucleobases.
J Am Chem Soc. 2012 Jun 27;134(25):10713-4. doi: 10.1021/ja303361z. Epub 2012 Jun 14.
3
Communication: Adjusting charge transfer state energies for configuration interaction singles: without any parameterization and with minimal cost.
J Chem Phys. 2012 Apr 28;136(16):161101. doi: 10.1063/1.4705757.
4
Monomeric adenine decay dynamics influenced by the DNA environment.
J Comput Chem. 2012 May 15;33(13):1225-35. doi: 10.1002/jcc.22952. Epub 2012 Mar 13.
5
Interplay between "neutral" and "charge-transfer" excimers rules the excited state decay in adenine-rich polynucleotides.
Angew Chem Int Ed Engl. 2011 Dec 9;50(50):12016-9. doi: 10.1002/anie.201104382. Epub 2011 Oct 19.
6
Communication: configuration interaction singles has a large systematic bias against charge-transfer states.
J Chem Phys. 2011 Aug 21;135(7):071104. doi: 10.1063/1.3627152.
7
Pathways for fluorescence quenching in 2-aminopurine π-stacked with pyrimidine nucleobases.
J Am Chem Soc. 2011 May 4;133(17):6799-808. doi: 10.1021/ja2007998. Epub 2011 Apr 12.
8
Low-lying excited states and nonradiative processes of the adenine analogues 7H- and 9H-2-aminopurine.
J Chem Phys. 2011 Mar 21;134(11):114307. doi: 10.1063/1.3567090.
9
Base pairing enhances fluorescence and favors cyclobutane dimer formation induced upon absorption of UVA radiation by DNA.
J Am Chem Soc. 2011 Apr 13;133(14):5163-5. doi: 10.1021/ja110879m. Epub 2011 Mar 18.
10
Photoinduced electron transfer occurs between 2-aminopurine and the DNA nucleic acid monophosphates: results from cyclic voltammetry and fluorescence quenching.
J Phys Chem B. 2010 Aug 19;114(32):10573-80. doi: 10.1021/jp102355v.
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