Design, synthesis and analysis of antiviral nucleosides bearing pyrrolepolyamide binding to nucleic acid (II): N2-pyrrolepolyamidopropylguanosine

Yusuke Ohba; Kazuo Kamaike; Yusuke Terui; Tairo Oshima; Etsuko Kawashima

doi:10.1093/nass/3.1.29

Design, synthesis and analysis of antiviral nucleosides bearing pyrrolepolyamide binding to nucleic acid (II): N2-pyrrolepolyamidopropylguanosine

Nucleic Acids Res Suppl. 2003:(3):29-30. doi: 10.1093/nass/3.1.29.

Authors

Yusuke Ohba¹, Kazuo Kamaike, Yusuke Terui, Tairo Oshima, Etsuko Kawashima

Affiliation

¹ Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachiouji, Tokyo 192-0392, Japan.

PMID: 14510364
DOI: 10.1093/nass/3.1.29

Abstract

Synthesis of guanosine bearing pyrrolepolyamide (1) and analysis of DNA interaction with 1 were carried out. Compound 1 was synthesized by condensation of 2-N-beta-alanyl-3,5-TIPDS-guanosine with 1-methyl-4-[1-methyl-4-[1-methyl-4-(formylamino)pyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxylic acid which was prepared from N-methylpyrrole. To investigate the interaction between 1 and DNA in Circular Dichroism spectra and Tm values, we used distamycin A and adenosine bearing pyrrolepolyamide (Apy), which has the high sequence-selectivity of DNA, as a contrast.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antiviral Agents / chemical synthesis
Antiviral Agents / chemistry*
Antiviral Agents / metabolism
Base Sequence
Circular Dichroism
DNA / metabolism
Guanosine / analogs & derivatives
Guanosine / chemical synthesis
Guanosine / chemistry*
Guanosine / metabolism
Pyrroles / chemical synthesis
Pyrroles / chemistry*
Pyrroles / metabolism
Spectrophotometry, Ultraviolet

Substances

Antiviral Agents
N-(((guanosin-2'-yl)ethylaminocarbonyl)ethyl) 1-methyl-4-(1-methyl-4-(1-methyl-4-(formylamino)pyrrole-2-carboxamido)pyrrole-2-carboxamido)pyrrole-2-carboxamide
Pyrroles
Guanosine
DNA