Synthetic nucleosides and nucleotides. 40. Selective inhibition of eukaryotic DNA polymerase alpha by 9-(beta-D-arabinofuranosyl)-2-(p-n-butylanilino) adenine 5'-triphosphate (BuAaraATP) and its 2'-up azido analog: synthesis and enzymatic evaluations

A Tomikawa; M Seno; K Sato-Kiyotaki; C Ohtsuki; T Hirai; T Yamaguchi; T Kawaguchi; S Yoshida; M Saneyoshi

doi:10.1080/07328319808005193

Synthetic nucleosides and nucleotides. 40. Selective inhibition of eukaryotic DNA polymerase alpha by 9-(beta-D-arabinofuranosyl)-2-(p-n-butylanilino) adenine 5'-triphosphate (BuAaraATP) and its 2'-up azido analog: synthesis and enzymatic evaluations

Nucleosides Nucleotides. 1998 Jan-Mar;17(1-3):487-501. doi: 10.1080/07328319808005193.

Authors

A Tomikawa¹, M Seno, K Sato-Kiyotaki, C Ohtsuki, T Hirai, T Yamaguchi, T Kawaguchi, S Yoshida, M Saneyoshi

Affiliation

¹ Department of Biological Sciences, Teikyo University of Science and Technology, Yamanashi, Japan.

PMID: 9708358
DOI: 10.1080/07328319808005193

Abstract

Starting from 2',3',5'-tri-O-acetyl-2-iodoadenosine, 9-(beta-D-arabinofuranosyl)-2-(p-n-butylanilino)adenine and its 2'(S)-azido counterparts were synthesized in seven steps. These exhibited only moderate growth-inhibitory effects against mouse leukemic P388 cells (IC50 = 13-24 microM), although 5'-triphosphate derivatives showed strong and selective inhibitory action on calf thymus DNA polymerase alpha, but not on beta- and epsilon-polymerases from eukaryotes.

MeSH terms

Adenine / analogs & derivatives
Adenosine / analogs & derivatives
Adenosine Triphosphate / analogs & derivatives*
Animals
Azo Compounds / chemical synthesis*
Cell Division / drug effects
Enzyme Inhibitors / chemical synthesis*
Kinetics
Magnetic Resonance Spectroscopy
Mice
Nucleic Acid Synthesis Inhibitors*
Nucleosides / chemical synthesis*
Nucleotides / chemical synthesis*
Tumor Cells, Cultured

Substances

Azo Compounds
Enzyme Inhibitors
Nucleic Acid Synthesis Inhibitors
Nucleosides
Nucleotides
Adenosine Triphosphate
Adenine
Adenosine