Direct surface PEGylation of nanodiamond via RAFT polymerization

Applied Surface Science

Volumn 357, Issue , 2015, Pages 2147-2153

  Shi, Yingge ^a,c   Liu, Meiying ^a   Wang, Ke ^b   Huang, Hongye ^a   Wan, Qing ^a   Tao, Lei ^b   Fu, Lihua ^c   Zhang, Xiaoyong ^a   Wei, Yen ^b  

^a NANCHANG UNIVERSITY   (China)

^b TSINGHUA UNIVERSITY   (China)

^c GUANGXI UNIVERSITY   (China)

Author keywords

Biocompatibility; Nanodiamond; Raft polymerization; Surface initiated pegylation; Water dispersibility

Indexed keywords

BIOCOMPATIBILITY; CHAINS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; FREE RADICAL POLYMERIZATION; GRAVIMETRIC ANALYSIS; LIVING POLYMERIZATION; MEDICAL APPLICATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SURFACE TREATMENT; THERMOGRAVIMETRIC ANALYSIS; X RAY PHOTOELECTRON SPECTROSCOPY;

BIOMEDICAL APPLICATIONS; CARBON NANO-MATERIALS; CHAIN TRANSFER AGENTS; PEGYLATION; RAFT POLYMERIZATION; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER POLYMERIZATION; THERMAL GRAVIMETRIC ANALYSIS; WATER DISPERSIBILITY;

NANODIAMONDS;

EID: 84960399130     PISSN: 01694332     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apsusc.2015.09.200     Document Type: Article

References (49)

1. A. Krueger, New carbon materials: biological applications of functionalized nanodiamond materials, Chem. Eur. J. 14 (2008) 1382-1390.
2. X. Zhang, S. Wang, M. Liu, B. Yang, L. Feng, Y. Ji, L. Tao, Y. Wei, Size tunable fluorescent nano-graphite oxides: preparation and cell imaging applications, Phys. Chem. Chem. Phys. 15 (2013) 19013-19018.
3. S. Stehlik, T. Petit, H.A. Girard, J.-C. Arnault, A. Kromka, B. Rezek, Nanoparticles assume electrical potential according to substrate, size, and surface termination, Langmuir 29 (2013) 1634-1641.
4. Y.-R. Chang, H.-Y. Lee, K. Chen, C.-C. Chang, D.S. Tsai, C.-C. Fu, T.-S. Lim, Y.-K. Tzeng, C.-Y. Fang, C.-C. Han, Mass production and dynamic imaging of fluorescent nanodiamonds, Nat. Nanotechnol. 3 (2008) 284-288.
5. Y. Zhu, J. Li, W. Li, Y. Zhang, X. Yang, N. Chen, Y. Sun, Y. Zhao, C. Fan, Q. Huang, The biocompatibility of nanodiamonds and their application in drug delivery systems, Theranostics 2 (2012) 302.
6. X. Zhang, J. Yin, C. Kang, J. Li, Y. Zhu, W. Li, Q. Huang, Z. Zhu, Biodistribution and toxicity of nanodiamonds in mice after intratracheal instillation, Toxicol. Lett. 198 (2010) 237-243.
7. X. Zhang, W. Hu, J. Li, L. Tao, Y. Wei, A comparative study of cellular uptake and cytotoxicity of multi-walled carbon nanotubes, graphene oxide, and nanodiamond, Toxicol. Res. 1 (2012)62-68.
8. X. Zhang, J. Yin, C. Peng, W. Hu, Z. Zhu, W. Li, C. Fan, Q. Huang, Distribution and biocompatibility studies of graphene oxide in mice after intravenous administration, Carbon 49 (2011) 986-995.
9. T. Huang, Y. Tzeng, Y. Liu, Y. Chen, K. Walker, R. Guntupalli, C. Liu, Immobilization of antibodies and bacterial binding on nanodiamond and carbon nanotubes for biosensor applications, Diam. Relat. Mater. 13 (2004) 1098-1102.
10. W. Zhang, K. Patel, A. Schexnider, S. Banu, A.D. Radadia, Nanostructuring of biosensing electrodes with nanodiamonds for antibody immobilization, ACS Nano 8 (2014) 1419-1428.
11. X. Zhang, S. Wang, C. Zhu, M. Liu, Y. Ji, L. Feng, L. Tao, Y. Wei, Carbon-dots derived from nanodiamond: photoluminescence tunable nanoparticles for cell imaging, J. Colloid Interface Sci. 397 (2011) 39-44.
12. N. Mohan, C.-S. Chen, H.H. Hsieh, Y.-C. Wu, H.-C. Chang, In vivo imaging and toxicity assessments of fluorescent nanodiamonds in Caenorhabditis elegans, Nano Lett. 10 (2010) 3692-3699.
13. C.-C. Fu, H.-Y. Lee, K. Chen, T.-S. Lim, H.-Y. Wu, P.-K. Lin, P.-K. Wei, P.-H. Tsao, H.-C. Chang, W. Fann, Characterization and application of single fluorescent nanodiamonds as cellular biomarkers, Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 727-732.
14. M. Liu, J. Ji, X. Zhang, X. Zhang, B. Yang, F. Deng, Z. Li, K. Wang, Y. Yang, Y. Wei, Self-polymerization of dopamine and polyethyleneimine: novel fluorescent organic nanoprobes for biological imaging applications, J. Mater. Chem. B3 (2015)3476-3482.
15. J. Li, Y. Zhu, W. Li, X. Zhang, Y. Peng, Q. Huang, Nanodiamonds as intracellular transporters of chemotherapeutic drug, Biomaterials 31 (2010) 8410-8418.
16. X. Zhang, S. Wang, C. Fu, L. Feng, Y. Ji, L. Tao, S. Li, Y. Wei, PolyPEGylated nanodiamond for intracellular delivery of a chemotherapeutic drug, Polym. Chem. 3 (2012) 2716.
17. X.-Q. Zhang, R. Lam, X. Xu, E.K. Chow, H.-J. Kim, D. Ho, Multimodal nanodiamond drug delivery carriers for selective targeting, imaging, and enhanced chemotherapeutic efficacy, Adv. Mater. 23 (2012) 4770-4775.
18. Y. Li, X. Zhou, D. Wang, B. Yang, P. Yang, Nanodiamond mediated delivery of chemotherapeutic drugs, J. Mater. Chem. 21 (2011) 16406-16412.
19. E.K. Chow, X.-Q. Zhang, M. Chen, R. Lam, E. Robinson, H. Huang, D. Schaffer, E. Osawa, A. Goga, D. Ho, Nanodiamond therapeutic delivery agents mediate enhanced chemoresistant tumor treatment, Sci. Transl. Med. 3 (2011) 73ra21.
20. E.V. Basiuk, V.A. Basiuk, V. Meza-Laguna, F.F. Contreras-Torres, M. Martínez, A. Rojas-Aguilar, M. Salerno, G. Zavala, A. Falqui, R. Brescia, Solvent-free covalent functionalization of multi-walled carbon nanotubes and nanodiamond with diamines: looking for cross-linking effects, Appl. Surf. Sci. 259 (2012) 465-476.
21. E.V. Basiuk, A. Santamaria-Bonfil, V. Meza-Laguna, T.Y. Gromovoy, E. Alvares-Zauco, F.F. Contreras-Torres, J. Rizo, G. Zavala, V.A. Basiuk, Solvent-free covalent functionalization of nanodiamond with amines, Appl. Surf. Sci. 275 (2013) 324-334.
22. H. Huang, Y. Wang, J. Zang, L. Bian, Improvement of suspension stability and electrophoresis of nanodiamond powder by fluorination, Appl. Surf. Sci. 258 (2013)4079-4084.
23. K. Huang, X. Hu, H. Xu, Y. Shen, A. Khomich, The oxidization behavior and mechanical properties of ultrananocrystalline diamond films at high temperature annealing, Appl. Surf. Sci. 317 (2014) 11-18.
24. B.J.M. Etzold, I. Neitzel, M. Kett, F. Strobl, V.N. Mochalin, Y. Gogotsi, Layer-by-layer oxidation for decreasing the size of detonation nanodiamond, Chem. Mater. 26 (2014) 3479-3484.
25. B.T. Branson, P.S. Beauchamp, J.C. Beam, C.M. Lukehart, J.L. Davidson, Nanodiamond nanofluids for enhanced thermal conductivity, ACS Nano 7 (2013)3183-3189.
26. S. Torrengo, R. Canteri, R. Dell'Anna, L. Minati, A. Pasquarelli, G.X.P.S. Speranza, ToF-SIMS investigation of nanocrystalline diamond oxidized surfaces, Appl. Surf. Sci. 276 (2013) 101-111.
27. E.L. Thomas, D.B. Alward, D.J. Kinning, D.C. Martin, D.L. Handlin Jr., L.J. Fetters, Ordered bicontinuous double-diamond structure of star block copolymers: a new equilibrium microdomain morphology, Macromolecules 19 (1986) 2197-2202.
28. G. Jarre, S. Heyer, E. Memmel, T. Meinhardt, A. Krueger, Synthesis of nanodiamond derivatives carrying amino functions and quantification by a modified Kaisertest, Beilstein J. Org. Chem. 10 (2014) 2729-2737.
29. Y. Liu, Z. Gu, J.L. Margrave, V.N. Khabashesku, Functionalization of nanoscale diamond powder: fluoro-, alkyl-, amino-, and amino acid-nanodiamond derivatives, Chem. Mater. 16 (2004) 3924-3930.
30. Z. Yao, N. Braidy, G.A. Botton, A. Adronov, Polymerization from the surface of single-walled carbon nanotubes-preparation and characterization of nanocomposites, J. Am. Chem. Soc. 125 (2003) 16015-16024.
31. Q. Wan, M. Liu, J. Tian, F. Deng, G. Zeng, Z. Li, K. Wang, Q. Zhang, X. Zhang, Y. Wei, Surface modification of carbon nanotubes via combination of mussel inspired chemistry and SET-LRP, Polym. Chem. 6 (2015) 1786-1792.
32. Y. Shi, M. Liu, K. Wang, F. Deng, Q. Wan, Q. Huang, L. Fu, X. Zhang, Y. Wei, Bioinspired preparation of thermo-responsive graphene oxide nanocomposites in an aqueous solution, Polym. Chem. (2015), http://dx.doi.org/10.1039/C1035PY00844A.
33. Q. Wan, M. Liu, J. Tian, F. Deng, Y. Dai, K. Wang, Z. Li, Q. Zhang, X. Zhang, Y. Wei, Toward the development of versatile functionalized carbon nanotubes, RSC Adv. 5 (2015) 38316-38323.
34. X. Zhang, J. Ji, X. Zhang, B. Yang, M. Liu, W. Liu, L. Tao, Y. Chen, Y. Wei, Mussel inspired modification of carbon nanotubes using RAFT derived stimuli-responsive polymers, RSC Adv. 3 (2013) 21817-21823.
35. H. Kong, C. Gao, D. Yan, Functionalization of multiwalled carbon nanotubes by atom transfer radical polymerization and defunctionalization of the products, Macromolecules 37 (2004) 4022-4030.
36. V.T. Huynh, S. Pearson, J.-M. Noy, A. Abboud, R.H. Utama, H. Lu, M.H. Stenzel, Nanodiamonds with surface grafted polymer chains as vehicles for cell imaging and cisplatin delivery: enhancement of cell toxicity by POEGMEMA coating, ACS Macro Lett. 2 (2013) 246-250.
37. X. Zhang, K. Wang, M. Liu, X. Zhang, L. Tao, Y. Chen, Y. Wei, Polymeric AIE-based nanoprobes for biomedical applications: recent advances and perspectives, Nanoscale 7 (2015) 11486-11508.
38. Q. Wan, L. Mao, M. Liu, K. Wang, G. Zeng, D. Xu, H. Huang, X. Zhang, Y. Wei, Towards development of a versatile and efficient strategy for fabrication of GO based polymer nanocomposites, Polym. Chem. (2015), http://dx.doi.org/10.1039/C1035PY01238D.
39. L. Li, J. Davidson, C.M. Lukehart, Surface functionalization of nanodiamond particles via atom transfer radical polymerization, Carbon 44 (2006) 2308-2315.
40. S. Zhu, J. Zhang, X. Liu, B. Li, X. Wang, S. Tang, Q. Meng, Y. Li, C. Shi, R. Hu, Graphene quantum dots with controllable surface oxidation, tunable fluorescence and up-conversion emission, RSC Adv. 2 (2012) 2717-2720.
41. X. Zhang, X. Zhang, B. Yang, M. Liu, W. Liu, Y. Chen, Y. Wei, Polymerizable aggregation induced emission dye based fluorescent nanoparticles for cell imaging applications, Polym. Chem. 5 (2014) 356-360.
42. X. Zhang, X. Zhang, B. Yang, J. Hui, M. Liu, W. Liu, Y. Chen, Y. Wei, PEGylation, Cell imaging applications of AIE based fluorescent organic nanoparticles via ring-opening reaction, Polym. Chem. 5 (2014) 689-693.
43. X. Zhang, H. Qi, S. Wang, L. Feng, Y. Ji, L. Tao, S. Li, Y. Wei, Cellular responses of aniline oligomers: a preliminary study, Toxicol. Res. 1 (2012) 201-205.
44. H. Qi, M. Liu, L. Xu, L. Feng, Y. Ji Tao, X. Zhang, Y. Wei, Biocompatibility evaluation of aniline oligomers with different end-functional groups, Toxicol. Res. 2 (2013) 427-433.
45. H. Willcock, A. Lu, C.F. Hansell, E. Chapman, I.R. Collins, R.K. O'Reilly, One-pot synthesis of responsive sulfobetaine nanoparticles by RAFT polymerisation: the effect of branching on the UCST cloud point, Polym. Chem. 5 (2013) 1023-1030.
46. M. Bagheri, E. Bigdeli, Z. Pourmoazzen, Self-assembled micellar nanoparticles of a novel amphiphilic cholesteryl-poly (l-lactic acid)-b-poly (poly (ethylene glycol) methacrylate) block-brush copolymer, Iran. Polym. J. 22 (2013) 293-302.
47. Y. Li, R. Liu, W. Liu, H. Kang, M. Wu, Y. Huang, Synthesis, self-assembly, and thermosensitive properties of ethyl cellulose-g-P (PEGMA) amphiphilic copolymers, J. Polym. Sci. Polym. Chem. 46 (2008) 6907-6915.
48. L.-P. Zhu, Y.-Y. Xu, H.-B. Dong, Z. Yi, B.-K. Zhu, Amphiphilic PPESK-graft-P(PEGMA) copolymer for surface modification of PPESK membranes, Mater. Chem. Phys. 115 (2009) 223-228.
49. X. Zhang, J. Hui, B. Yang, Y. Yang, D. Fan, M. Liu, L. Tao, Y. Wei, PEGylation of fluoridated HAp: Ln3 + nanorods for cell imaging, Polym. Chem. 4 (2013) 4120-4125.