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Non-covalent binding interaction between phthalic acid esters and DNA.

Hao Cheng1, Chao Qin2, Bing Yang1

  • 1Institute of Organic Contaminant Control and Soil Remediation, College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, PR China.

Environment International
|January 22, 2022
PubMed
Summary

Phthalic acid esters (PAEs) bind to DNA, primarily interacting with thymines in the minor groove through hydrogen bonding and van der Waals forces. This binding does not alter DNA structure, but electrostatic potential plays a role.

Keywords:
Binding interactionDNAMechanismsPAEsQuantum chemical calculations

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Area of Science:

  • Environmental Chemistry
  • Molecular Biology
  • Toxicology

Background:

  • Phthalic acid esters (PAEs) are known endocrine disruptors with teratogenic and carcinogenic effects.
  • The precise binding mechanisms and strengths of PAEs with DNA have been underexplored.
  • Understanding PAE-DNA interactions is crucial for assessing their health risks.

Purpose of the Study:

  • To investigate and confirm the binding interaction between various PAEs and DNA.
  • To elucidate the binding strength, mechanism, and location of PAE-DNA interactions.
  • To determine if PAE binding induces conformational changes in DNA.

Main Methods:

  • Fluorescence titration quenching experiments to confirm binding and determine binding constants (KA).
  • DNA melting point, UV-vis spectroscopy, and Fourier transform infrared spectroscopy (FTIR) to identify interaction sites.
  • Quantum chemical calculations to analyze binding forces.
  • Circular dichroism (CD) and FTIR to assess DNA conformational changes.

Main Results:

  • Fluorescence titration confirmed PAE-DNA binding with varying binding constants for different PAEs (e.g., DEP: 4.11 × 105 L/mol).
  • Analyses indicated PAEs predominantly bind to thymines within the DNA minor groove.
  • Hydrogen bonding and van der Waals forces were identified as the primary binding interactions.
  • No significant DNA conformational changes were observed via CD and FTIR spectra.

Conclusions:

  • PAEs exhibit distinct binding affinities to DNA, with interactions primarily occurring in the minor groove.
  • The binding mechanism involves hydrogen bonding and van der Waals forces, without inducing DNA structural alterations.
  • Electrostatic surface potential may significantly influence PAE-DNA binding, warranting further investigation.