Synthesis 2013; 45(17): 2426-2430
DOI: 10.1055/s-0033-1339340
paper
© Georg Thieme Verlag Stuttgart · New York

A Bis(phosphine)-Modified Peptide Ligand for Stable and Luminescent Quantum Dots in Aqueous Media

Michael E. Jung*
Department of Chemistry and Biochemistry, California NanoSystems Institute, and Department of Physiology, University of California at Los Angeles, Los Angeles, CA 90095-1569, USA   Fax: +1(310)2063722   Email: jung@chem.ucla.edu
,
Michael Trzoss
Department of Chemistry and Biochemistry, California NanoSystems Institute, and Department of Physiology, University of California at Los Angeles, Los Angeles, CA 90095-1569, USA   Fax: +1(310)2063722   Email: jung@chem.ucla.edu
,
James M. Tsay
Department of Chemistry and Biochemistry, California NanoSystems Institute, and Department of Physiology, University of California at Los Angeles, Los Angeles, CA 90095-1569, USA   Fax: +1(310)2063722   Email: jung@chem.ucla.edu
,
Shimon Weiss
Department of Chemistry and Biochemistry, California NanoSystems Institute, and Department of Physiology, University of California at Los Angeles, Los Angeles, CA 90095-1569, USA   Fax: +1(310)2063722   Email: jung@chem.ucla.edu
› Author Affiliations
Further Information

Publication History

Received: 01 May 2013

Accepted after revision: 06 June 2013

Publication Date:
17 July 2013 (online)


Abstract

We describe a new class of ligands for semiconductor nanoparticles (quantum dots = QDs), which bind well and allow for their facile dissolution in aqueous solution. As a proof of principle, we have designed and synthesized a novel bis(phosphine)-modified peptide (BPMP) and shown that it has the ability to solubilize quantum dots in aqueous media. We further showed that the corresponding phosphine oxide derivatives of these new ligands are less good at solubilizing the quantum dots. These new bis(phosphine)-modified peptide ligands are easy to prepare and may well replace thiol-containing binding sequences in functionalized peptides for quantum dot coating, potentially resulting in quantum dots with higher quantum yields.

Supporting Information

 
  • References

    • 1a Michalet X, Pinaud FF, Bentolila LA, Tsay JM, Doose S, Li JJ, Sundaresan G, Wu AM, Gambhir SS, Weiss S. Science 2005; 307: 538
    • 1b Bruchez Jr M, Moronne M, Gin P, Weiss S, Alivisatos AP. Science 1998; 281: 2013
    • 2a Dickerson BD, Irving DM, Herz E, Claus RO, Spillman Jr WB, Meissner KE. Appl. Phys. Lett. 2005; 86: 171915
    • 2b Young AG, Al-Salim N, Green DP, McQuillan AJ. Langmuir 2008; 24: 3841
    • 2c Gattas-Asfura KM, Constantine CA, Lynn MJ, Thimann DA, Ji X, Leblanc RM. J. Am. Chem. Soc. 2005; 127: 14640
    • 3a Yu WW, Chang E, Drezek R, Colvin VL. Biochem. Biophys. Res. Commun. 2006; 348: 781
    • 3b Li H, Wang X, Gao Z, He Z. Nanotechnology 2007; 18: 205603
    • 4a Moghimi SM, Hunter AC, Murray JC. FASEB J. 2005; 19: 311
    • 4b Zhou M, Ghosh I. Pept. Sci. 2006; 88: 325
    • 5a Iyer G, Pinaud F, Tsay J, Weiss S. Small 2007; 3: 793
    • 5b Pinaud F, King D, Moore HP, Weiss S. J. Am. Chem. Soc. 2004; 126: 6115
  • 6 Tsay JM, Trzoss M, Shi L, Kong X, Selke M, Jung ME, Weiss S. J. Am. Chem. Soc. 2007; 129: 6865
  • 7 Huang B, Tomalia DA. J. Lumin. 2005; 111: 215
  • 8 Kim S, Bawendi MG. J. Am. Chem. Soc. 2003; 125: 14652
    • 9a Gilbertson SR, Wang X. Tetrahedron 1999; 55: 11609
    • 9b Gilbertson SR, Chen G, Kao J, Beatty A, Campana CF. J. Org. Chem. 1997; 62: 5557
    • 9c Gilbertson SR, Starkey GW. J. Org. Chem. 1996; 61: 2922
    • 9d Gilbertson SR, Wang X. J. Org. Chem. 1996; 61: 434
    • 9e Gilbertson SR, Pawlick RV. Angew. Chem. Int. Ed. 1996; 35: 902
    • 9f Gilbertson SR, Chen G, Kao J, Beatty A, Campana CF. J. Am. Chem. Soc. 1994; 116: 4481
    • 10a Wilson ME, Nuzzo RG, Whitesides GM. J. Am. Chem. Soc. 1978; 100: 2269
    • 10b Bergbreiter DE, Liu Y.-S. Tetrahedron Lett. 1997; 38: 3703
    • 11a Boger DL, Zhou J, Winter B, Kitos PA. Bioorg. Med. Chem. 1995; 3: 1579
    • 11b Bavikar SN, Salunke DB, Hazra BG, Pore VS, Dodd RH, Thierry J, Shirazi F, Deshpande MV, Kadreppa S, Chattopadhyay S. Bioorg. Med. Chem. Lett. 2008; 18: 5512
  • 12 Although compound 9 is unknown, the corresponding dibenzyl ethyl triester is known: Moore AT, Rydon HN, Smithers MJ. J. Chem. Soc. C 1966; 2349
  • 13 Chan WC. W, Nie SM. Science 1998; 281: 2016
  • 14 Doose S, Tsay JM, Pinaud F, Weiss S. Anal. Chem. 2005; 77: 2235
  • 15 No numerical values for solubility were experimentally obtained. The solubility was judged by the cloudiness of the solution and presence of precipitate.
  • 16 Wu X, Liu H, Liu J, Haley KN, Treadway JA, Larson JP, Ge N, Peale F, Bruchez MP. Nat. Biotechnol. 2003; 21: 41