Supramolecular fluorophores for biological studies: phenylene vinylene-amino acid amphiphiles.
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.
Harrington
Daniel A
DA
Department of Materials Science and Engineering, Northwestern University, Evanston, Illinois 60208-3108, USA.
Behanna
Heather A
HA
Tew
Gregory N
GN
Claussen
Randal C
RC
Stupp
Samuel I
SI
D000596:Amino Acids / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D000818:Animals; D002417:Cattle; D002478:Cells, Cultured; D004149:Dioxoles / Q000737:chemistry* / Q000378:metabolism; D005347:Fibroblasts / Q000187:drug effects*; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D051379:Mice; D015394:Molecular Structure; D011721:Pyrenes / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D013050:Spectrometry, Fluorescence; D013501:Surface-Active Agents / Q000737:chemistry* / Q000494:pharmacology
D000596:Amino Acids; D004149:Dioxoles; D005456:Fluorescent Dyes; D011721:Pyrenes; D013501:Surface-Active Agents; C031134:vinylene carbonate