Chinese Science Bulletin

, Volume 58, Issue 21, pp 2570–2575 | Cite as

Star-shaped conjugated oligoelectrolyte for bioimaging in living cells

Open Access
Article Special Issue: Nono-Biomedical Optoelectronic Materials and Devices

Abstract

A new star-shaped oligoelectrolyte (TEFCOONa) with triphenylamine as the core, acetylene as linkage and anionic fluorenes as arms was obtained and used for direct imaging in living PANC-1 cells. Because of the hydrophobic conjugated groups of the oligoelectrolyte, TEFCOONa can form nanospheres with an average diameter of ∼75 nm in 10 mmol/L PBS. These nanospheres possess a relatively high absolute quantum yield (16.5% in PBS), low cytotoxicity and can penetrate into the nucleus through the cytoplasm, which is essential for living cellular imaging. Collectively, these results validate our rational design of conjugated oligoelectrolyte and even hyper branched polymers-copolyelectrolyte as effective nanovectors for bioimaging and other clinical applications.

Keywords

star-shaped oligoelectrolyte absolute quantum yield nanospheres bioimaging 

References

  1. 1.
    Xia F, Heeger A J, Plaxco K W, et al. On the binding of cationic, water-soluble conjugated polymers to DNA: Electrostatic and hydrophobic interactions. J Am Chem Soc, 2010, 132: 1252–1254CrossRefGoogle Scholar
  2. 2.
    Satrijo A, Swager T M. Anthryl-doped conjugated polyelectrolytes as aggregation-based sensors for nonquenching multicationic. J Am Chem Soc, 2007, 129: 16020–16028CrossRefGoogle Scholar
  3. 3.
    McQuade D T, Hegedus A H, Swager T M. Signal amplification of a “turn-on” sensor: Harvesting the light captured by a conjugated polymer. J Am Chem Soc, 2000, 122: 12389–12390CrossRefGoogle Scholar
  4. 4.
    Ho H A, Leclerc M. Optical sensors based on hybrid aptamer/conjugated polymer complexes. J Am Chem Soc, 2004, 126: 1384–1387CrossRefGoogle Scholar
  5. 5.
    Ho H A, Leclerc M. New colorimetric and fluorometric chemosensor based on a cationic polythiophene derivative for iodide-specific detection. J Am Chem Soc, 2003, 125: 4412–4413CrossRefGoogle Scholar
  6. 6.
    Dore K, Boudreau D, Leclerc M. Fluorescent polymeric transducer for the rapid, simple, and specific detection of nucleic acids at the zeptomole level. J Am Chem Soc, 2004, 126: 4240–4244CrossRefGoogle Scholar
  7. 7.
    Zhang Z Y, Fan Q L, Huang W, et al. Highly selective anionic counterion-based fluorescent sensor for Hg2+ by grafted conjugated polyelectrolytes. Macromol Rapid Commun, 2010, 31: 2160–2165CrossRefGoogle Scholar
  8. 8.
    Xue W X, Zhang D Q, Zhu D B, et al. Colorimetric detection of glucose and an assay for acetylcholinesterase with amine-terminated polydiacetylene vesicles. Chin Sci Bull, 2011, 56: 1877–1883CrossRefGoogle Scholar
  9. 9.
    Fan Q L, Huang W, Zhou Y, et al. Water-soluble cationic poly(p-phenyleneethynylene)s (PPEs): Effects of acidity and ionic strength on optical behavior. Macromolecules, 2005, 38: 2927–2936CrossRefGoogle Scholar
  10. 10.
    Kim I K, Shin H, Bunz U H F, et al. Use of a folate-PPE conjugate to image cancer cells in vitro. Bio Chem, 2007, 18: 815–820Google Scholar
  11. 11.
    Pu K Y, Li K, Liu B, et al. Fluorescent single-molecular core-shell nanospheres of hyperbranched conjugated polyelectrolyte for live-cell imaging. Chem Mater, 2009, 21: 3816–3822CrossRefGoogle Scholar
  12. 12.
    Wang G, Lai Y H, Liu B, et al. Star-shaped glycosylated conjugated oligomer for two-photon fluorescence imaging of live cells. Chem Mater, 2011, 23: 4428–4434CrossRefGoogle Scholar
  13. 13.
    Schacher F, Walther A, Muller A H E, et al. Multicompartment core micelles of triblock terpolymers in organic media. Macromolecules, 2009, 42: 3540–3548CrossRefGoogle Scholar
  14. 14.
    Lai W Y, Huang W, Zhou R, et al. Monodisperse six-armed triazatruxenes: Microwave-enhanced synthesis and highly efficient pure-deep-blue electroluminescence. Macromolecules, 2006, 39: 3707–3709CrossRefGoogle Scholar
  15. 15.
    Lai W Y, Huang W, He Q Y, et al. Kinked Star-shaped fluorene/triazatruxene co-oligomer hybrids with enhanced functional froperties for high-performance, solution-processed, blue organic light-emitting diodes. Adv Funct Mater, 2008, 18: 265–276CrossRefGoogle Scholar
  16. 16.
    Lo S C, Burn P L. Development of hyperbranched polymers polymers: Macromolecules for use in organic light-emitting diodes and solar cells. Chem Rev, 2007, 107: 1097–1166CrossRefGoogle Scholar
  17. 17.
    Li K, Pu K Y, Liu B. Phalloidin-functionalized hyperbranched conjugated polyelectrolyte for filamentous actin imaging in living Hela cells. Chem Mater, 2011, 23: 2113–2119CrossRefGoogle Scholar
  18. 18.
    Gaylord B S, Heeger A J, Bazan G C. DNA detection using water-soluble conjugated polymers and peptide nucleic acid probes. Proc Natl Acad Sci USA, 2002, 99: 10954–10957CrossRefGoogle Scholar
  19. 19.
    Pawlicki M, Collins H A, Anderson H L, et al. Two-photon absorption and the design of two-photon dyes. Angew Chem Int Ed, 2009, 48: 3244–3266CrossRefGoogle Scholar
  20. 20.
    Terenziani F, Katan C, Badaeva E, et al. Enhanced two-photon absorption of organic chromophores: Theoretical and experimental assessments. Adv Mater, 2008, 20: 4641–4678CrossRefGoogle Scholar
  21. 21.
    He G S, Tan L S, Zheng Q, et al. Multiphoton absorbing materials: Molecular designs, characterizations, and applications. Chem Rev, 2008, 108: 1245–1330CrossRefGoogle Scholar

Copyright information

© The Author(s) 2013

Authors and Affiliations

  1. 1.Key Laboratory for Organic Electronics & Information Displays (KLOEID) and Institute of Advanced Materials (IAM)Nanjing University of Posts & Telecommunications (NJUPT)NanjingChina

Personalised recommendations