Synthesis, Fluorescence Spectra, Redox Property and the DNA Binding Studies of 7-phenylacenaphtho[1,2-b]quinoxalin-7-ium chloride: Evidences of the Formation of Neutral Radical Analogue

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• 作者：Suman Kundu ; Ananya Banerjee ; Arpan De ; Asma Yasmeen Khan…
• 关键词：7 ; phenylacenaphtho[1 ; 2 ; b]quinoxalin ; 7 ; ium chloride ; 7 ; phenylacenaphtho[1 ; 2 ; b]quinoxalin radical ; DNA intercalator ; Biophysical studies
• 刊名：Journal of Fluorescence
• 出版年：2015
• 出版时间：November 2015
• 年：2015
• 卷：25
• 期：6
• 页码：1645-1654
• 全文大小：1,585 KB
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• 作者单位：Suman Kundu (1)
  Ananya Banerjee (2)
  Arpan De (2)
  Asma Yasmeen Khan (3)
  Gopinatha Suresh Kumar (3)
  Ranjan Bhadra (1)
  Prasanta Ghosh (1)
  
  1. Department of Chemistry, R. K. M. Residential College, Narendrapur, Kolkata, 700103, India
  2. VJRC R&D Center, Vijaygarh Jyotish Ray College, Bijoygarh, Kolkata, 700 032, India
  3. Biophysical Chemistry Laboratory, Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, Kolkata, 700032, India
  
• 刊物类别：Biomedical and Life Sciences
• 刊物主题：Biomedicine
  Biomedicine
  Biophysics and Biomedical Physics
  Biotechnology
  Biochemistry
  Analytical Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1573-4994

文摘

Reaction of acenaphthoquinone with N-phenyl-o-phenylenediamine in methanol in presence of HCl yielded 7-phenylacenaphtho[1,2-b]quinoxalin-7-ium chloride, [1][Cl]. [1][Cl] is brightly fluorescencent in dichloromethane (λ_ex--03 nm and λ_em--42, 464, 488 nm) and water (λ_ex--08 nm and λ_em--45 nm). Density functional theory (DFT) and time dependent (TD) DFT calculations on [1]+ at the B3LYP level of the theory elucidated that the origin of the lower energy excitation at around 400 nm is due to π?→?π* transition. [1]+ is redox active and exhibits a reversible cathodic wave at ?.66 V referenced to Fc+/Fc couple due to [1]+/[1]-/sup> redox couple. Electrogenerated neutral radical analogue [1]-/sup> was characterized by electron paramagnetic resonance (EPR), UV–vis spectra and DFT calculations. DNA binding studies using the techniques of UV–vis absorption, fluorescence, circular dichroism (CD) spectra, viscosity, gel electrophoresis, hydrodynamic, isothermal titration calorimetry (ITC) and UV optical melting studies of [1][Cl] revealed that [1]+ is a strong DNA intercalator obeying neighbor exclusion principle. ITC experiment authenticated that the binding of [1]+ to DNA is entropy driven. Keywords 7-phenylacenaphtho[1,2-b]quinoxalin-7-ium chloride 7-phenylacenaphtho[1,2-b]quinoxalin radical DNA intercalator Biophysical studies