The genome factor in region-specific DNA damage: the DNA-reactive drug U-78779 prefers mixed A/T-G/C sequences at the nucleotide level but is region-specific for long pure AT islands at the genomic level

Biochemistry. 2002 Feb 5;41(5):1545-55. doi: 10.1021/bi011907s.

Abstract

Bizelesin is the first anticancer drug capable of damaging specific regions of the genome with clusters of its binding sites T(A/T)(4)A. This study characterized the sequence- and region-specificity of a bizelesin analogue, U-78779, designed to interact with mixed A/T-G/C motifs. At the nucleotide level, U-78779 was found to prefer runs of A/Ts interspersed with 1 or 2 G/C pairs, although 25% of the identified sites corresponded to pure AT motifs similar to bizelesin sites. The in silico computational analysis showed that the preferred mixed A/T-G/C motifs distribute uniformly at the genomic level. In contrast, the secondary, pure AT motifs (A/T)(6)A were found densely clustered in the same long islands of AT-rich DNA that bizelesin targets. Mapping the sites and quantitating the frequencies of U-78779 adducts in model AT island and non-AT island naked DNAs demonstrated that clusters of pure AT motifs outcompete isolated mixed A/T-G/C sites in attracting drug binding. Regional preference of U-78779 for AT island domains was verified also in DNA from drug-treated cells. Thus, while the primary sequence preference gives rise to non-region-specific scattered lesions, the clustering of the minor pure AT binding motifs seems to determine region-specificity of U-78779 in the human genome. The closely correlated cytotoxic activities of U-78779 and bizelesin in several cell lines further imply that both drugs may share common cellular targets. This study underscores the significance of the genome factor in a drug's potential for region-specific DNA damage, by showing that it can take precedence over drug binding preferences at the nucleotide level.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Adenine Nucleotides / isolation & purification
  • Adenine Nucleotides / metabolism
  • Antineoplastic Agents, Alkylating / chemistry*
  • Antineoplastic Agents, Alkylating / metabolism
  • Antineoplastic Agents, Alkylating / toxicity
  • Binding Sites / drug effects
  • Binding Sites / genetics
  • Cell Nucleus / chemistry
  • Cell Nucleus / drug effects
  • Cell Nucleus / metabolism
  • Cross-Linking Reagents / chemistry
  • Cross-Linking Reagents / metabolism
  • Cytosine Nucleotides / metabolism
  • DNA Adducts / chemistry
  • DNA Adducts / metabolism
  • DNA Damage*
  • DNA, Neoplasm / chemistry*
  • DNA, Neoplasm / metabolism
  • DNA, Superhelical / chemistry
  • DNA, Superhelical / metabolism
  • DNA, Viral / chemistry*
  • DNA, Viral / metabolism
  • Dinucleotide Repeats / drug effects*
  • Duocarmycins
  • Genome, Human*
  • Guanine Nucleotides / metabolism
  • Humans
  • Indoles / chemistry*
  • Indoles / metabolism
  • Indoles / toxicity
  • Intracellular Fluid / chemistry
  • Intracellular Fluid / metabolism
  • Reproducibility of Results
  • Sequence Analysis, DNA
  • Simian virus 40 / drug effects
  • Simian virus 40 / genetics
  • Thymine Nucleotides / isolation & purification
  • Thymine Nucleotides / metabolism
  • Tumor Cells, Cultured
  • Urea / analogs & derivatives*
  • Urea / chemistry*
  • Urea / metabolism
  • Urea / toxicity

Substances

  • Adenine Nucleotides
  • Antineoplastic Agents, Alkylating
  • Cross-Linking Reagents
  • Cytosine Nucleotides
  • DNA Adducts
  • DNA, Neoplasm
  • DNA, Superhelical
  • DNA, Viral
  • Duocarmycins
  • Guanine Nucleotides
  • Indoles
  • Thymine Nucleotides
  • Urea
  • bizelesin