Studies toward the synthesis of potencial artificial nucleases derived from trypargine

Studies toward the synthesis of potencial artificial nucleases derived from trypargine

Pirovani, Rodrigo V.; Pilli, Ronaldo A.

Abstract:

The ability to efficiently hydrolyze nucleic acids in a biomimetic non-destructive process with high selectivity has become important because one can find many applications in structural design of new probes and drug development. This molecular recognition is a common feature in biological systems, where some functional groups form supramolecular systems by non-covalent interactions. For example, the guanidinium group present in the active site of the Staphylococcus nuclease is used to recognize the phosphodiester group, accelerating its hydrolysis. Recently, our group has synthesized the alkaloid tetrahydro-_-carboline (S)-(-)-trypargine (1) that presents a side chain at C1 with a terminal guanidine residue. Therefore, we decided to synthesize new derivatives of trypargine (2 and 3) in order to investigate their ability to recognize and trigger hydrolysis of phosphodiesters, such as DNA and RNA.

The ability to efficiently hydrolyze nucleic acids in a biomimetic non-destructive process with high selectivity has become important because one can find many applications in structural design of new probes and drug development. This molecular recognition is a common feature in biological systems, where some functional groups form supramolecular systems by non-covalent interactions. For example, the guanidinium group present in the active site of the Staphylococcus nuclease is used to recognize the phosphodiester group, accelerating its hydrolysis. Recently, our group has synthesized the alkaloid tetrahydro-_-carboline (S)-(-)-trypargine (1) that presents a side chain at C1 with a terminal guanidine residue. Therefore, we decided to synthesize new derivatives of trypargine (2 and 3) in order to investigate their ability to recognize and trigger hydrolysis of phosphodiesters, such as DNA and RNA.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0341-1

Referências bibliográficas

• [1] 1 a) Cowan, J. A. Curr. Opin. Chem. Biol. 2001, 5, 634; b) Schug, K. A.; Lindner, W. Chem. Rev. 2005, 105, 67.
• [2] 2 Pilli, R. A.; Rodrigues Jr., M. T. J. Braz. Chem. Soc. 2009, 20, 1434.

Como citar:

Pirovani, Rodrigo V.; Pilli, Ronaldo A.; "Studies toward the synthesis of potencial artificial nucleases derived from trypargine", p-341-341. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0341-1