Citation: Yu Fei SONG, Pin YANG. Synthesis and DNA Cleavage Studies of 2,6-Dimethoxyhydroquinone-3-Mercaptoacetic Acid Conjugates[J]. Chinese Chemical Letters, ;2001, 12(8): 697-700. shu

Synthesis and DNA Cleavage Studies of 2,6-Dimethoxyhydroquinone-3-Mercaptoacetic Acid Conjugates

Yu Fei SONG ,
Pin YANG

Institute of Molecular Science, Shanxi University, Taiyuan 030006

Received Date: 16 January 2001

Fund Project: The authors sincerely thank Dr L.Sheh at Tunghai University, Taiwan for experimental assistance and valuable discussions. The authors acknowledge the support of the National Natural Science Foundation of China and Provincial Natural Foundation of Shanxi.

In an effort to investigate the use of short peptide chains as carriers of new anti-tumor agents, we synthesized four tripeptide-cytotoxic agent conjugates:DMQ-MA-Lys(DMQ-MA)-Phe-Arg-Ome, DMQ-MA-Lys(DMQ-MA)-Ile-Arg-Ome, DMQ-MA-Lys(DMQ-MA)-Val-Arg-Ome, DMQ-MA-Lys(DMQ-MA)-Lys(Cbz)-Arg-Ome. The cytotoxic agent conjugated to the N-terminal and the ξ-amino group of Lysine of the tripeptide is 2,6-dimethoxyhydroquinone-3-mercaptoacetic acid (DMQ-MA). The tripeptides were synthesized by coupling protected amino acid residues according to Pfp/DCC methods (Pfp:pentafluorophenol, DCC:N,N'-dicyclohexyl-carbodiimide) in solution. Agarose gel electrophoresis showed that these compounds can cleave supercoiled DNA into open-circular form in drug concentration as low as 4-50 μM without H₂O₂ and UV irradiation. Further studies on their cytotoxicity for these conjugates are ongoing.
- 2,6-Dimethoxyhydroquinone-3-mercaptoacetic acid,
- tripeptide,
- cleavage,
- pBR322 DNA.
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