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A G4·K(+) hydrogel that self-destructs.

Taylor N Plank1, Jeffery T Davis

  • 1Department of Chemistry & Biochemistry, University of Maryland, College Park, MD 20742, USA. jdavis@umd.edu.

Chemical Communications (Cambridge, England)
|March 18, 2016
PubMed
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A novel hydrogel self-assembles from modified guanosine. Upon cyclization, the gel self-destructs, enabling the release of incorporated nucleoside analogs for potential therapeutic applications.

Area of Science:

  • Biomaterials Science
  • Supramolecular Chemistry
  • Nucleoside Chemistry

Background:

  • Guanine-rich sequences can form G4-quartet structures.
  • Self-assembling hydrogels offer tunable properties for drug delivery.
  • Borate ester linkages can be designed for controlled hydrolysis or cyclization.

Purpose of the Study:

  • To develop a G4-quartet based hydrogel with a self-destruct mechanism.
  • To investigate the in situ cyclization of borate esters of 5'-deoxy-5'-iodoguanosine (5'-IG 2).
  • To demonstrate the utility of this hydrogel for releasing pre-incorporated nucleoside analogs.

Main Methods:

  • Self-assembly of borate esters of 5'-deoxy-5'-iodoguanosine (5'-IG 2) into a hydrogel.
  • Monitoring the in situ cyclization reaction to form 5'-deoxy-N3,5'-cycloguanosine (5'-cG 3).

Related Experiment Videos

  • Observing the hydrogel's self-destruction triggered by 5'-cG 3 formation.
  • Evaluating the release of incorporated nucleoside analogs.

    • Main Results:

    • Successful formation of a G4-quartet based hydrogel via self-assembly.
    • Demonstration of in situ intramolecular cyclization of 5'-IG 2 to 5'-cG 3.
    • Confirmation that 5'-cG 3 formation leads to hydrogel self-destruction.
    • Evidence of controlled release of nucleoside analogs from the degrading gel.

    Conclusions:

    • A novel self-destructing hydrogel system based on G4-quartets and borate ester chemistry has been developed.
    • The intramolecular cyclization mechanism provides a trigger for controlled hydrogel degradation.
    • This approach is a promising strategy for the release of therapeutic nucleoside analogs.