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Supramolecular structures formed by phospholiponucleosides: Aggregational properties and molecular recognition

  • Debora Berti
  • Uwe Keiderling
  • Piero Baglioni
Conference paper
Part of the Progress in Colloid and Polymer Science book series (PROGCOLLOID, volume 120)

Abstract

We report an investigation of the aggregation and molecular recognition properties of phospholi-pid derivatives containing a nucleosidic unit on the phospholipid polar head. Long chain 5′-(1,2-dioleoyl-sn-glycero(3)phospho)-adenosine, 5′-(1,2-dioleoyl-sn-glycero(3)phospho)-uridine, 5′-(1,2-dioleoyl-sn-glycero(3)phospho)-cytidine, and 5′-(1,2-dioleoyl-sn-glycero(3)phospho)-ethenoadenosine phospholipid derivatives form vesicles, while short-chain 5′-(1,2-dioctanoyl-sn-glycero(3)phospho)-adenosine and 5′-(1,2-dioctyl-sn-glycero(3)phospho)-uridine form ellipsoidal micelles. We demonstrated that the arrangement of these novel surfactants in supramolecular devices, driven by hydrophobic interactions, provides the cooperative effect necessary to promote recognition between the complementary bases, though bases are exposed to an aqueous environment. In particular, despite the presence of the aqueous environment, molecular recognition occurs between the phospholiponu-cleoside complementary bases via stacking and hydrogen bonding in a way that strictly resembles the Watson-Crick recognition pattern of DNA and RNA. Generally, hydrogen-bond-mediated interactions are not effective in aqueous systems, since water forms strong hydrogen-bond interactions with host molecules. These findings highlight the importance of phospholipid nucleosidic derivatives as model devices for molecular recognition in biological systems and for biotechnological applications.

Key words

Phospholiponucleosides Molecular recognition Micelles Vesicles Liposomes 

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Copyright information

© Springer-Verlag 2002

Authors and Affiliations

  • Debora Berti
    • 1
  • Uwe Keiderling
    • 1
    • 2
  • Piero Baglioni
    • 1
  1. 1.Department of Chemistry and CSGIUniversity of FlorenceFlorenceItaly
  2. 2.Hahn-Meitner-Institut BerlinBerlinGermany

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