DNA-binding and DNA-photocleavaging properties of 12a,14a- diazoniapentaphene

The association of 12a,14a-diazoniapentaphene dibromide (5) with DNA and its ability to photoinduce DNA damage was studied. Spectrophotometric and fluorimetric titrations show that the title compound (5) binds to DNA (K ≈ 5·10 5 M -1 ) with the highest affinity towards GC-rich regions. The highest affinity was observed for GC base pairs. Compound 5 binds to DNA primarily by intercalation as shown by LD spectroscopy and energy-transfer experiments. Moreover, efficient DNA damage was observed on UVA irradiation in the presence of 5. Preliminary experiments suggest that singlet oxygen may be involved in the photoinduced DNA damage.

• Publication year

  2004

• Venue

  Arkivoc

• Publication date

  2004-03-19

• Fields of study

  Chemistry

• Identifiers
  DOI 10.3998/ARK.5550190.0005.520
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• Principles of fluorescence spectroscopy

  1983cited by this paper

• Synthesis, structure, and optical properties of 3-(1H-1,2,3-triazol-1-yl)-substituted 4H-pyrido[1,2–a]pyrimidin-4-ones and 4H-quinolizin-4-ones

  2026cites this paper
• New Insights into the Phototoxicity of Anthracene-Based Chromophores: The Chloride Salt Effect

  2023cites this paper
• Electrochemical studies on the binding of the sulfonated reactive dye Levafix Royal Blue E-FR with DNA

  2022cites this paper
• Binding of new cationic porphyrin-tetrapeptide conjugates to nucleoprotein complexes.

  2013cites this paper
• Voltammetric and ultraviolet–visible spectroscopic studies on the interaction of etoposide with deoxyribonucleic acid

  2013cites this paper
• Thermodynamic analysis of complex formation of ethidium bromide with DNA in water solutions

  2011cites this paper
• Using Photoactive Vitamin Nanoparticles as Photodynamic Antimicrobial Chemotherapeutic (PACT) Agents to Treat Chronic Wounds

  2010cites this paper
• Bicyclic 6-6 Systems with One Bridgehead (Ring Junction) Nitrogen Atom: No Extra Heteroatom

  2008cites this paper
• One‐Pot Solvent Free Synthesis and DNA Binding Studies of Thieno[2,3‐b]‐1,8‐Naphthyridines

  2007cites this paper
• Intercalation of Organic Dye Molecules into Double-stranded DNA. Part 2: The Annelated Quinolizinium Ion as a Structural Motif in DNA Intercalators†

  2005cites this paper