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DNA damage by fasicularin.

Sanjay Dutta1, Hideki Abe, Sakae Aoyagi

  • 1School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi, Hachioji, Tokyo 192-0392, Japan.

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|October 27, 2005
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Fasicularin, a novel alkaloid from sea squirts, damages DNA by alkylating guanine residues. This natural compound forms an aziridinium ion, similar to certain chemotherapy drugs, offering new insights into DNA-damaging natural products.

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Area of Science:

  • Natural Product Chemistry
  • Molecular Biology
  • Biochemistry

Background:

  • Fasicularin is a novel thiocyanate-containing alkaloid isolated from the ascidian *Nephteis fasicularis*.
  • Previous studies suggested fasicularin exhibits cytotoxic properties potentially through DNA damage.

Purpose of the Study:

  • To elucidate the mechanism by which fasicularin induces DNA damage.
  • To characterize the chemical species involved in fasicularin-mediated DNA cleavage.

Main Methods:

  • Sequence gel analysis of a 5'-32P-labeled DNA duplex treated with fasicularin.
  • Biochemical assays to identify DNA lesions and reactive intermediates.

Main Results:

  • Fasicularin treatment caused selective strand cleavage at guanine residues in DNA.
  • The DNA damage mechanism involves alkylation of guanine by a fasicularin-derived aziridinium ion.
  • This aziridinium ion formation is analogous to that of clinically used anticancer alkylating agents.

Conclusions:

  • Fasicularin is the first natural product identified to generate a DNA-alkylating aziridinium ion.
  • The mechanism of action of fasicularin provides a novel natural product model for DNA alkylation relevant to anticancer drug development.