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DNA-binding studies of AV-153, an antimutagenic and DNA repair-stimulating derivative of 1,4-dihydropiridine

E Buraka1, C Yu-Chian Chen2, M Gavare3

  • 1Department of Medical Biochemistry, Faculty of Medicine, University of Latvia, No. 4 Kronvalda Boulevard, Riga LV-1010, Latvia; Latvian Institute of Organic Synthesis, No. 21 Aizkraukles Street, Riga LV-1006, Latvia.

Chemico-Biological Interactions
|July 13, 2014
PubMed
Abstract

Insights

The antimutagenic compound AV-153 intercalates into DNA strands, particularly at single-strand break sites near pyrimidines. This interaction is key to its DNA repair-stimulating and antimutagenic properties.

Area of Science:

  • Molecular Biology
  • Biochemistry
  • Pharmacology

Background:

  • DNA intercalation is crucial for anticancer drug activity.
  • Some antimutagenic compounds also exhibit DNA intercalating properties.
  • Dihydropyridine (DHP) AV-153 is known for its antimutagenic and DNA repair-stimulating effects.

Purpose of the Study:

  • To elucidate the interaction mechanism between the dihydropyridine (DHP) AV-153 and DNA.
  • To determine if AV-153 exhibits DNA intercalating activity, similar to some anticancer agents.

Main Methods:

  • UV/VIS spectroscopy
  • Fluorimetry
  • Infrared spectroscopy
  • Computer modeling
  • DNA nick induction studies

Main Results:

  • AV-153 demonstrated significant interaction with DNA, evidenced by spectral shifts (hyperchromic and bathochromic effects).
  • Binding affinity increased substantially upon induction of DNA single-strand breaks, suggesting interaction at nick sites.
  • AV-153 competed with ethidium bromide for DNA intercalation sites.
  • Spectroscopic analyses indicated AV-153 interacts with guanine, cytosine, and thymine bases, but not adenine.

Conclusions:

  • The antimutagenic substance AV-153 intercalates between DNA strands.
  • This intercalation preferentially occurs at DNA nick sites, specifically in the vicinity of two pyrimidines.
  • The findings provide insight into the molecular mechanism of AV-153's antimutagenic and DNA repair-stimulating activities.
Keywords:
1,4-DihydropyridinesAntimutagenic compoundsDNA intercalationFTIRFluorimetryUV/VIS spectroscopy

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