Peptide-derivatized shell-cross-linked nanoparticles. 1. Synthesis and characterization

Bioconjugate Chemistry

Volumn 15, Issue 4, 2004, Pages 699-709

  Becker, Matthew L ^a,b   Remsen, Edward E ^a,c   Pan, Dipanjan ^a   Wooley, Karen L ^a  

^a WASHINGTON UNIVERSITY   (United States)

^b NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

^c CABOT MICROELECTRONICS CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIOPHAGES; BIOSYNTHESIS; BLOCK COPOLYMERS; CELL MEMBRANES; EFFICIENCY; GOLD NANOPARTICLES; HYDROGELS; ULTRAVIOLET VISIBLE SPECTROSCOPY;

CELL SURFACES; FUNCTIONALIZATIONS; GLOBAL SOLUTIONS; HIV-1 TAT; PEPTIDE SEQUENCES; PROTEIN TRANSDUCTION DOMAINS; SHELL CROSS-LINKED NANOPARTICLES; SURFACE BINDING; SYNTHESIS AND CHARACTERIZATIONS; TAT PROTEIN;

PEPTIDES;

ACRYLIC ACID DERIVATIVE; BLOCK COPOLYMER; COPOLYMER; NANOPARTICLE; PEPTIDE; PHENYLGLYOXAL; PROTEIN TRANSDUCTION DOMAIN; TRANSACTIVATOR PROTEIN; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL CELL; ARTICLE; ATOMIC FORCE MICROSCOPY; CARBON NUCLEAR MAGNETIC RESONANCE; CELL SURFACE; CHO CELL; CONJUGATION; CONTROLLED STUDY; CROSS LINKING; DERIVATIZATION; DIFFERENTIAL SCANNING CALORIMETRY; GEL PERMEATION CHROMATOGRAPHY; INTERNALIZATION; METHODOLOGY; NONHUMAN; PEPTIDE DERIVATIZATION; PROTEIN ANALYSIS; PROTEIN BINDING; PROTEIN DOMAIN; PROTON NUCLEAR MAGNETIC RESONANCE; SEDIMENTATION; SEDIMENTATION EQUILIBRIUM; SHELL CROSS LINKED NANOPARTICLE; SIGNAL TRANSDUCTION; STOICHIOMETRY; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY; ZETA POTENTIAL;

ANIMALIA; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 3242755083     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc049946e     Document Type: Article

References (39)

1. Mammen, M., Choi, S. K., and Whitesides, G. M. (1998) Polyvalent Interactions in Biological Systems. Angew. Chem., Int. Ed. 37, 2754-2794.
2. Wadia, J. S., and Dowdy, S. F. (2002) Protein Transduction Technology. Curr. Opin. Biotechnol. 13, 52.
3. Green, M., and Loewenstein, P. (1988) Autonomous Functional Domains of Chemically Synthesized Human Immunodeficiency Virus tat Trans-activator Protein. Cell 55, 1179-1188.
4. Frankel, A., and Pabo, C. (1988) Cellular Uptake of the tat Protein from Human Immunodeficiency Virus. Cell 55, 1189-1193.
5. Schwarze, S. R., Ho, A., Vorcero-Akbani, A., and Dowdy, S. F. (1999) In vivo Protein Transduction: Delivery of a Biologically Active Protein into the Mouse. Science 285, 1569-72.
6. Wender, P. A., Mitchell, D. J., Pattabiraman, K., Pelkey, E. T., Steinman, L., and Rothbard, J. B. (2000). The Design, Synthesis, and Evaluation of Molecules that Enable or Enhance Cellular Uptake: Peptoid Molecular Transporters. Proc. Natl. Acad. Sci. U.S.A. 97, 13003.
7. Futaki, S., Nakase, I., Suzuki, T., Youjun, Z., and Sugiura, Y. (2002) Translocation of Branched Chain Arginine Peptides through Cell Membranes: Flexibility in the Spatial Disposition of Positive Charges in the Membrane-Permeable Peptides. Biochemistry 41, 7925.
8. Gammon, S. T., Villalobos, V. M., Prior, J. L., Sharma, V., and Piwnica-Worms, D. (2003) Quantitative Analysis of Permeatation Peptide Complexes Labeled with Technetium-99m: Chiral and Sequence-Specific Effects on Net Cell Uptake. Bioconjugate Chem. 14, 368-376.
9. Nagahara, H., Vocero-Akbani, H. M., Snyder, E. L., Ho, A., Latham, D. G., Lissy, N. A., Becker-Hapak, M., Ezhevsky, S. A., and Dowdy, S. F. (1998) Transduction of Full length TAT Fusion Proteins into Mammalian Cells: TAT-p27 induces Cell Migration. Nat. Med. 4, 1449.
10. Niesner, U., Halin, C., Lozzi, L., Gunthert, M., Neri, P., Wunderli-Allenspach, H., Zardi, L., and Neri, D. (2002) Quantitation of the Tumor-Targeting Properties of Antibody Fragments Conjugated to Cell-Permeating HIV-1 Tat Peptides. Bioconjugate Chem. 13, 729.
11. Jensen, K. D., Nori, A., Tijerina, M., Kopeckova, P., and Kopecek, J. (2003) Cytoplasmic Delivery and Nuclear Targeting of Synthetic Macromolecules. J. Controlled Release 87, 89-105.
12. Nori, A., Jensen, K. D., Tijerina, M., Kopeckova, P., and Kopecek, J. (2003) Tat-Conjugated Synthetic Macromolecules Facilitate Cytoplasmic Drug Delivery To Human Ovarian Carcinoma Cells. Bioconjugate Chem. 14, 44-50.
13. Sandhu, K. K., McIntosh, C. M., Simard, J. M., Smith, S. W., and Rotello, V. M. (2002) Gold Nanoparticle-Mediated Transfection of Mammalian Cells. Bioconjugate Chem. 13, 3.
14. Zhao, M., Kircher, M. F., Josephson, L., and Weissleder, R. (2002) Differntial Conjugation of Tat Peptide to Super-paramagnetic Nanoparticles and its Effects on Cellular Uptake. Bioconjugate Chem. 13, 840-844.
15. Torchilin, V., Rammohan, R., Weissig, V., and Levchenko, T. S. (2001) Tat Peptide on the Surface of Liposomes Affords their Efficient Intracellular Delivery Even at Low Temperature and in the Presence of Metabolic Inhibitors. Proc. Natl. Acad. Sci. U.S.A. 98, 8786.
16. Klok, H.-A., and Lecommandoux, S. (2001) Supramolecular Materials via Block Copolymer Self-Assemble. Adv. Mater. 34, 1217-1229.
17. Matyjaszewski, K., and Xia, J. (2001) Atom Transfer Radical Polymerization. Chem. Rev. 101, 2921-2990.
18. Hawker, C. J., Bosman, A. W., and Harth, E. (2001) New Polymer Synthesis by Nitroxide Mediated Living Radical Polymerizations. Chem. Rev. 101, 3661-3688.
19. Thurmond, K. B., II, Kowalewski, T., and Wooley, K. L. (1996) Water-Soluble Knedel-like Structures: The Preparation of Shell-Cross-Linked Small Particles. J. Am. Chem. Soc. 118, 7239-7240.
20. Liu, S., Weaver, J. V. M., Save, M., and Armes, S. P. (2002) Synthesis of pH-Responsive Shell Cross-Linked Micelles and Their Use as Nanoreactors for the Preparation of Gold Nanoparticles. Langmuir 18, 8350-8357.
21. Buetuen, V., Lowe, A. B., Billingham, N. C., and Armes, S. P. (1999) Synthesis of Zwitterionic Shell Cross-Linked Micelles. J. Am. Chem. Soc. 121, 4288-4289.
22. Wooley, K. L. (2000) Shell Cross-linked Polymer Assemblies: Nanoscale Constructs Inspired from Biological Systems. J. Polym. Sci., Part A: Polym. Chem. 38, 1397-1407.
23. Huang, H., Kowalewski, T., Remsen, E. E., Gertzmann, R., and Wooley, K. L. (1997) Hydrogel-Coated Glassy Nanospheres: A Novel Method for the Synthesis of Shell Cross-Linked Knedels. J. Am. Chem. Soc. 119, 11653-11659.
24. Remsen, E. E., Thurmond, K. B., II, and Wooley, K. L. (1999) Solution and Surface Charge Properties of Shell Cross-Linked Knedel Nanoparticles. Macromolecules 32, 3685-3689.
25. Huang, H., Wooley, K. L., and Schaefer, J. (2001) REDOR Determination of the Composition of Shell Cross-Linked Amphiphilic Core-Shell Nanoparticles and the partitioning of Sequestered Fluorinated Guests. Macromolecules 34, 547-551.
26. Kao, H.-M., O'Connor, R. D., Mehta, A. K., Huang, H., Poliks, B., Wooley, K. L., and Schaefer, J. (2001) Location of Cholic Acid Sequestered by Core-Shell Nanoparticles Using REDOR NMR. Macromolecules 34, 544-546.
27. Liu, J., Zhang, Q., Remsen, E. E., and Wooley, K. L. (2001) Bioconjugates of Protein Transduction Domain(PTD) and Shell Cross-Linked Nanoparticles: Nanostructured Materials Designed for Delivery into Cells. Biomacromolecules 2, 362-368.
28. Jairajpuri, M. A., Azam, N., Baburaj, K., Bulliraju, E., and Durani, S. (1998) Charge and Solvation Effects in Anion Reactive Centers: an Inquiry Exploiting Reactive Arginines. Biochemistry 37, 10780-10791.
29. Takahashi, K. (1968) The Reaction of Phenylglyoxal with Arginine Residues in Proteins. J. Biol. Chem. 243, 6171-6179.
30. Miller, J. F., Schatzel, F., and Vincent, B. (1991). The Determination of very Small Electrophoretic Mobilities in Polar and Nonpolar Colloidal Dispersions Using Phase-Analysis Light-Scattering J. Colloid Interface Sci. 143, 532.
31. Wang, J.-S., and Matyjaszewski, K. (1995) Controlled/Living Radical Polymerization. Atom Transfer Radical Polymerization in the Presence of Transition Metal Complexes. J. Am. Chem. Soc. 117, 5614-15.
32. Ma, Q., and Wooley, K. L. (2000) The Preparation of tert-Butyl Acrylate, Methyl Acrylate, and Styrene Block Copolymers by Atom Transfer Radical Polymerization: Precursors to Amphiphilic and Hydrophilic Block Copolymers and Conversion to Complex Nanostructured Materials. J. Polym. Sci., Part A: Polym. Chem. 38, 4805-4820.
33. Becker, M. L., Remsen, E. E., and Wooley, K. L. (2001) Diblock Copolymers, Micelles, and Shell Cross-linked Nanoparticles Containing Poly(4-fluorostyrene): Tools for Detailed Analysis of Nanostructured Materials. J. Polym. Sci.: Polym. Chem. 39, 4215.
34. Murthy, K. S., Ma, Q., Clark, C. G., Jr., Remsen, E. E., and Wooley, K. L. (2001) Fundamental Design Aspects of Amphiphilic Shell-Cross-linked Nanoparticles for Controlled Release Applications. Chem. Commun., 773-774.
35. Suzuki, T., Futaki, S., Niwa, M., Tanaka, S., Ueda, K., and Sugiura, Y. (2002) Possible Existence of Common Internalization Mechanisms among Arginine Rich Peptides. J. Biol. Chem. 277, 2437-43.
36. Mai, J., C., Shen, H., Watkins, S., C., Cheng, T., and Robbins, P. D. (2002) Efficiency of Protein Transduction is Cell Type Dependent and is Enhanced by Dextran Sulfate. J. Biol. Chem. 277, 30208-30218.
37. Vives, E., Richard J. P., Rispal, C., Lebleu, B. (2003) TAT Peptide Internalization: Seeking the Mechanism of Entry. Curr. Protein Pept. Sci. 4, 125-132.
38. Vives, E. (2003) Cellular Uptake of the Tat Peptide: An Endocytosis Mechanism Following Ionic Interactions. J. Mol. Recognit. 16, 265-272.
39. Wadia, J. S., Stan, R. V., Dowdy, S. F. (2004) Transducible TAT-HA Fusogenic Peptide Enhances Escape of TAT-fusion Proteins After Lipid Raft Macropinocytosis. Nat. Med. 10 (3), 310-315.