Synthesis of terminally modified oligonucleotides and their hybridization dependence on the size of the target RNAs

Org Biomol Chem. 2009 Jun 7;7(11):2440-51. doi: 10.1039/b900301k. Epub 2009 Apr 17.

Abstract

We have developed new artificial oligonucleotide probes that show selective recognition for short RNA targets over long RNA targets. Our results suggested that modification of the termini of the oligonucleotide probes by bulky substituents such as cyclohexyl and 4-(3,6,9-trioxaundecylenedioxy)phenyl (Bzcr) groups significantly improved the selectivity of the probes toward the short RNA targets. The selectivity was further improved by the addition of a phosphate group on the cyclohexane ring. Although much improved selectivity toward short RNA targets is desirable in a general sense, it is particularly applicable to the selective detection of matured-miRNA over pre-miRNAs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cytidine / analogs & derivatives*
  • Cytidine / chemical synthesis
  • Cytidine / chemistry
  • Deoxyadenosines / chemical synthesis*
  • Deoxyadenosines / chemistry
  • MicroRNAs / metabolism
  • Models, Molecular
  • Nucleic Acid Conformation
  • Nucleic Acid Hybridization
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / chemistry
  • Oligonucleotides / metabolism*
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry
  • RNA / metabolism*
  • Structure-Activity Relationship
  • Thermodynamics

Substances

  • Deoxyadenosines
  • MicroRNAs
  • Oligonucleotides
  • Organophosphorus Compounds
  • Cytidine
  • RNA