Supramolecular fluorophores for biological studies: Phenylene vinylene-amino acid amphiphiles

Daniel A. Harrington, Heather A. Behanna, Gregory N. Tew, Randal C. Claussen, Samuel I. Stupp

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)


We report here on a family of self-assembling fluorescent organic amphiphiles with a biomolecular L-lysine hydrophile and a photonically active phenylene vinylene hydrophobe. Unlike conventional amphiphiles, these segmented dendrimers feature a rigid, branched hydrophobe, and have packing characteristics controlled by the ratio of cross-sectional areas of the hydrophobe and hydrophile. In dilute solution, the amphiphiles form supramolecular aggregates, which are easily taken in by cells through an endocytic pathway, and have no discernible effect on cell proliferation or morphology. An analogous pyrene-based amphiphile was cytotoxic, suggesting that cell survival may be linked either to the self-assembling nature of the amphiphiles, or to the specific properties of the phenylene vinylene segment. The combination of photonic and biological components in these amphiphiles provides great potential for applications in sensing or delivery of molecules to intracellular targets.

Original languageEnglish
Pages (from-to)1085-1091
Number of pages7
JournalChemistry and Biology
Issue number10
Publication statusPublished - Oct 2005

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmacology
  • Drug Discovery
  • Clinical Biochemistry

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