Amino acids bridged to quinones and to bisquinonyl isocyanurates

ORGN 505

Julia Ditkovich1, Galina Temtsin-Krayz1, Eli Har-Lev2, and Shmuel Bittner3. (1) Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva, Israel, (2) Institute For Applied Biosciences, Ben-Gurion University of the Negev, Beer-Sheva, Israel, (3) Department of Chemistry, Ben-Gurion University of Negev, Beer-Sheva, 84105, Israel

Many natural & synthetic quinones are used as drugs for treatment of human cancer. Their antitumour activity stems from their participation in key cellular redox mechanisms with consequent generation of highly reactive oxygen species. To avoid toxic side effects, the quinonic compound should be delivered directly to tumour area. With potential clinical significance, cytotoxic quinone-bearing peptides, it is important to increase the arsenal of related quinonyl amino acids; study their chemical, spectral & structural properties.

Recent work on the syntheses of ureido- and carbamatoquinones, a prepared novel consisting of two amino acids– naphthoquinonic moieties bonded to an isocyanuratic ring. Increasing number of donor-acceptor units in these molecules and their rigidity enhance the potentiality of those molecules as anti-cancer drugs:

We also developed a new route for the synthesis of modified alanines, a quinone is attached to the methyl side chain. The amino and carboxylic groups are available for peptide attachment.