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A versatile approach towards regioselective platinated DNA sequences.

Robert J Heetebrij1, Martin de Kort, Nico J Meeuwenoord

  • 1Leiden Institute of Chemistry Gorlaeus Laboratories, Leiden University, P.O. Box 9502, The Netherlands.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 17, 2003
PubMed
Summary

A new method uses diphenylcarbamoyl (DPC) protection to prevent unwanted platinum binding to DNA. This allows precise platinum adducts to be introduced at specific guanine sites in oligodeoxynucleotides (ODNs).

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Area of Science:

  • Chemical Synthesis
  • Oligonucleotide Chemistry
  • Medicinal Chemistry

Background:

  • Platinum-based drugs are crucial in cancer therapy.
  • Site-specific modification of DNA is essential for understanding drug-DNA interactions.
  • Uncontrolled N(7) guanine platination can lead to undesired side reactions.

Purpose of the Study:

  • To develop a method for site-specific N(7) guanine platination in oligodeoxynucleotides (ODNs).
  • To utilize a sterically demanding protecting group to control platination sites.
  • To synthesize and characterize ODNs with defined platinum adducts for further studies.

Main Methods:

  • Employing diphenylcarbamoyl (DPC) as an O(6)-protecting group for guanine residues.
  • Utilizing a base-labile oxalyl linker for controlled cleavage from solid support (CPG).

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  • Synthesizing hexanucleotides with specific guanine sequences (5'-GGBGGT-3') and introducing platinum GG adducts at G4,G5.

    • Main Results:

    • Achieved site-specific N(7) platination by preventing undesired reactions.
    • Successfully synthesized and isolated site-specific platinated hexamers with a 65% yield.
    • Comprehensive characterization using HPLC, LCMS, MALDI-TOF MS, PAGE, and Maxam-Gilbert sequencing.

    Conclusions:

    • The DPC protection strategy effectively directs platination to specific guanine sites.
    • This method enables the preparation of well-defined, site-specific platinum-DNA adducts.
    • The synthesized platinated ODNs are suitable for detailed structural and functional analysis.