Improved methodology for the preparation of water-soluble maleimide-functionalized small gold nanoparticles

Langmuir

Volumn 28, Issue 33, 2012, Pages 12357-12363

  Gobbo, Pierangelo ^a   Workentin, Mark S ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BIO-CONJUGATION; DEPROTECTION; GOLD NANOPARTICLES; HYDROLYSIS PRODUCTS; MALEIMIDES; MICHAEL ADDITIONS; REACTIVE MOIETY;

ADDITION REACTIONS; HYDROLYSIS; ORGANIC SOLVENTS;

METAL NANOPARTICLES;

GOLD; MALEIC ACID; MALEIC ACID DERIVATIVE; MALEIMIDE; MALEIMIDE DERIVATIVE; METAL NANOPARTICLE; QUATERNARY AMMONIUM DERIVATIVE; WATER;

ARTICLE; CHEMISTRY; METHODOLOGY; NANOTECHNOLOGY; PARTICLE SIZE; SOLUBILITY;

GOLD; MALEATES; MALEIMIDES; METAL NANOPARTICLES; NANOTECHNOLOGY; PARTICLE SIZE; QUATERNARY AMMONIUM COMPOUNDS; SOLUBILITY; WATER;

EID: 84865491053     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la302168g     Document Type: Article

References (18)

1. Hermanson, G. T. Bioconjugate Techniques, 2 nd ed.; Academic Press: San Diego, 2008.
2. Kim, Y.; Ho, S. O.; Gassman, N. R.; Korlann, Y.; Landorf, E. V; Collart, F. R.; Weiss, S. Efficient site-specific labeling of proteins via cysteines Bioconjugate Chem. 2008, 19, 786-791 (Pubitemid 351431411)
3. Jain, S.; Hirst, D. G.; O'Sullivan, J. M. Gold nanoparticles as novel agents for cancer therapy Br. J. Radiol. 2012, 85, 101-113
4. Manju, S.; Sreenivasan, K. Gold nanoparticles generated and stabilized by water soluble curcumin-polymer conjugate: blood compatibility evaluation and targeted drug delivery onto cancer cells J. Colloid Interface Sci. 2012, 368, 144-151
5. Ba, H.; Rodriguez-Fernández, J.; Stefani, F. D.; Feldman, J. Immobilization of gold nanoparticles on living cell membranes upon controlled lipid binding Nano Lett. 2010, 10, 3006-3012
6. Oh, E.; Susumu, K.; Blanco-Canosa, J. B.; Medintz, I. L.; Dawson, P. E.; Mattoussi, H. Preparation of stable maleimide-functionalized Au nanoparticles and their use in counting surface ligands Small 2010, 6, 1273-1278
7. Gregori, L.; Hainfeld, J. F.; Simon, M. N.; Goldgaber, D. Binding of amyloid beta protein to the 20 S proteasome J. Biol. Chem. 1997, 272, 58-62 (Pubitemid 27021124)
8. Zhu, J; Waengler, C.; Lennox, R. B.; Schirrmacher, R. Preparation of water-soluble maleimide-functionalized 3 nm gold nanoparticles: a new bioconjugation template Langmuir 2012, 28, 5508-5512
9. Zhu, J.; Kell, A. J.; Workentin, M. S. A retro-Diels Alder reaction as an alternative route to uncovering maleimide-modified surfaces on monolayer protected nanoparticles Org. Lett. 2006, 8, 4993-4996
10. Yousaf, M. N.; Mrksich, M. Diels Alder reaction for the selective immobilization of protein to electroactive self-assembled monolayers J. Am. Chem. Soc. 1999, 121, 4286-4287 (Pubitemid 29220308)
11. Mantovani, G.; Lecolley, F.; Tao, L.; Haddleton, D. M.; Clerx, J.; Cornelissen, J. J. L. M.; Velonia, K. Design and synthesis of N -maleimido-functionalized hydrophilic polymers via copper-mediated living radical polymerization: A suitable alternative to PEGylation chemistry J. Am. Chem. Soc. 2005, 127, 2966-2973 (Pubitemid 40349875)
12. Toncelli, C.; De Reus, D. C.; Picchioni, F.; Broekhuis, A. A. Properties of reversible Diels-Alder furan/maleimide polymer networks as function of crosslink density Macromol. Chem. Phys. 2012, 213, 157-165
13. Gandini, A. The furan/maleimide Diels-Alder reaction: a versatile click-unclick tool in macromolecular synthesis. Prog. Polym. Sci., published online April 28, 2012, http://dx.doi.org/10.1016/j.progpolymsci.2012.04.002.
14. Zhu, J; Ganton, M. D.; Kerr, M. A.; Workentin, M. S. Chemical modification of monolayer protected gold-nanoparticels using hyperbaric conditions J. Am. Chem. Soc. 2007, 129, 4904-4905 (Pubitemid 46651365)
15. Zhu, J.; Lines, B. M.; Ganton, M. D.; Kerr, M. A.; Workentin, M. S. Efficient synthesis of isoxazolidine-tethered monolayer-protected gold nanoparticles (MPGNs) via 1,3-dipolar cycloadditions under high-pressure conditions J. Org. Chem. 2008, 73, 1099-1105 (Pubitemid 351198757)
16. Hartlen, K. D.; Ismaili, H.; Zhu, J.; Workentin, M. S. Michael addition reactions for the modification of gold nanoparticles facilitated by hyperbaric conditions Langmuir 2012, 28, 864-871
17. Zheng, M.; Li, Z.; Huang, X. Ethylene glycol monolayer protected nanoparticles: synthesis, characterization, and interactions with biological molecules Langmuir 2004, 20, 4226-4235
18. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides Anal. Biochem. 1970, 34, 595-598