UNEXPECTED PRODUCTS OF THE REACTION OF PURINE NUCLEIC BASE PERCHLORATES WITH ACETYLACETONE CAUSING SINGLE-STRAND BREAKS IN THE DNA MOLECULE

Authors

  • Polina S. Zdereva Lermontov Secondary School No. 280 of Saint Petersburg, 52 Sadovaya St., Saint Petersburg 190103
  • Grigorii V. Bezhenar Lermontov Secondary School No. 280 of Saint Petersburg, 52 Sadovaya St., Saint Petersburg 190103
  • Anastasiya N. Sokolova Pavlov First Saint Petersburg State Medical University, Department of General and Bioorganic Chemistry, 6-8 L'va Tolstogo St., Saint Petersburg 197022
  • Boris V. Paponov Pavlov First Saint Petersburg State Medical University, Department of General and Bioorganic Chemistry, 6-8 L'va Tolstogo St., Saint Petersburg 197022
  • Andrey M. Rumyantsev Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034
  • Elena V. Sambuk Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg 199034
  • Dmitry N. Maistrenko Russian Research Center for Radiology and Surgical Technologies named after Academician A. M. Granov, 70 Leningradskaya St., Saint Petersburg 197758
  • Oleg E. Molchanov Russian Research Center for Radiology and Surgical Technologies named after Academician A. M. Granov, 70 Leningradskaya St., Saint Petersburg 197758

Keywords:

DNA, guanine, perchlorate, purines, ring opening, single-strand breaks, adenine

Abstract

The reactions of purine nucleic base perchlorates with the simplest 1,3-diketone – acetylacetone – were studied for the first time. It was demonstrated that adenine reacts with acetylacetone in a 1:2 molar ratio via opening of the pyrimidine fragment of the bicyclic structure, elimination of a one-carbon fragment in the form of a formic acid molecule, and recyclization into 8-(4,6-dimethylpyrimidin-2-yl)-2,4-dimethylimidazo[1,5-a]pyrimidine. Guanine, in turn, reacted with acetylacetone in a 1:1 ratio and formed 7,9-dimethyl-3H-pyrimido-[2,1-b]purin-10-ium-4-olate. In this case, the direction of heterocyclization differed from that observed in the reaction of guanine with malondialdehyde during the in vitro and in vivo formation of the minor nucleotide base M1G. The synthesized compounds were capable of causing single-strand breaks in DNA macromolecules.

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Published

2024-08-01

Issue

Vol. 60 No. 5/6 (2024)

Section

Short Communications