Synthesis of adamantyl naphthalene diimide and its interaction with double stranded DNA

Nucleic Acids Res Suppl. 2002:(2):213-4. doi: 10.1093/nass/2.1.213.


An adamantyl naphthalene diimide derivative (AND) was synthesized as a highly selective double stranded DNA binding reagent. The binding studies with sonicated calf thymus DNA revealed that AND can bind to double stranded DNA by the threading mode, where the two adamantyl moieties are located in the major and minor grooves of DNA duplex separately. In the presence of beta-cyclodextrin (beta-CD), the complex of AND with DNA duplex was stabilized by capping of the adamantyl moieties of AND by beta-CD. In other words, beta-CD serves as a stabilizer for the complex of AND with DNA duplex to result in an enhanced selectivity of AND for double stranded DNA over single stranded DNA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adamantane / analogs & derivatives
  • Adamantane / chemical synthesis*
  • Adamantane / chemistry
  • Cyclodextrins / chemistry
  • DNA / chemistry*
  • Kinetics
  • Phenanthrolines / chemical synthesis*
  • Phenanthrolines / chemistry
  • beta-Cyclodextrins*


  • 2,7-((methyl)(3-(adamantylacetamido)propyl)amino)propylbenzo(lmn)(3,8)phenanthroline-1,3,6,8(24H,7H)-tetrone
  • Cyclodextrins
  • Phenanthrolines
  • beta-Cyclodextrins
  • DNA
  • betadex
  • Adamantane