Regulation of telomeric i-motif stability by 5-methylcytosine and 5-hydroxymethylcytosine modification

Org Biomol Chem. 2015 May 28;13(20):5646-51. doi: 10.1039/c4ob02646b.

Abstract

The two important epigenetic markers in the human genome, 5-methylcytosine (mC) and 5-hydroxymethylcytosine (hmC), are involved in gene regulation processes. As a major epigenetic target, cytosines in a C-rich DNA sequence were substituted with mC and hmC to investigate the thermal stability and pH sensitivity of the corresponding i-motifs. Circular Dichroism (CD) studies indicate the formation of i-motifs at acidic pH (<6.5) for mC- and hmC-modified DNA sequences. Thermal denaturation results suggest that DNA i-motifs are stabilized when modified with one or two mCs. However, hypermethylation with mC and single modification with hmC cause destabilization of the structure. A biomimetic crowding agent does not alter the stability effect trends resulting from mC and hmC modifications, though the corresponding i-motifs show elevated melting temperatures without significant changes in pKa values.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 5-Methylcytosine / analogs & derivatives
  • 5-Methylcytosine / chemistry*
  • Circular Dichroism
  • Cytosine / analogs & derivatives*
  • Cytosine / chemistry
  • DNA / chemistry*
  • DNA / genetics
  • DNA Methylation*
  • Humans
  • Nucleotide Motifs / genetics*
  • Protein Structure, Tertiary
  • Telomere / chemistry
  • Telomere / genetics*
  • Temperature

Substances

  • 5-hydroxymethylcytosine
  • 5-Methylcytosine
  • Cytosine
  • DNA