title: Chemoselective modification of turnip yellow mosaic virus by Cu(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction and its application in cell binding.
abstract: Turnip yellow mosaic virus (TYMV) is an icosahedral plant virus with a diameter of 28-30 nm that can be isolated in gram quantities from turnip or Chinese cabbage inexpensively. In this study, TYMV combined with spatially addressable surface chemistries was selected as a prototype bionanoparticle for modulating patterns of cell adhesion, morphology, and proliferation. We exploited the chemical reactivity of TYMV using the mild conditions of Cu(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction, the best example of "click" chemistry. Oligo-ethylene glycol (OEG) short chain, coumarintriazole, and RGD-containing peptide were grafted on the surface of TYMV via carbodiimide activation and CuAAC reaction. The bioconjugation to intact viral particles was confirmed by MS, TEM, FPLC, and SDS-PAGE with fluorescence visualization analysis. Therefore, this method is a generally useful means of incorporating various types of functionalities onto the TYMV surface. Further studies were done to learn the behavior of NIH-3T3 fibroblast cells on the modified or unmodified TYMV surfaces. OEG-modified TYMV surfaces retarded cell attachment and growth, while cell adhesion, spreading, and proliferation were dramatically enhanced on RGD-modified TYMV surfaces. Compared with RGD immobilized 3-aminopropyltriethoxysilane-coated glass surface, the cells are more ready to spread fully and proliferate on TYMV-RGD coated surface, which thus provides a more cell-friendly environment with nanometer-scale surface features. This illustrates the potential application of plant virus based materials in tissue engineering, drug delivery, and biosensing.
authors.affiliation: Biomaterial Research Center, School of Pharmaceutical Sciences, Southern Medical University, 1023 Southern Shatai Road, Guangdong, GD, 510515, China. qing_zeng@hotmail.com
authors.forename: Qingbing
authors.initials: Q
authors.lastname: Zeng
authors.forename: Sharmistha
authors.initials: S
authors.lastname: Saha
authors.forename: L Andrew
authors.initials: LA
authors.lastname: Lee
authors.forename: Hannah
authors.initials: H
authors.lastname: Barnhill
authors.forename: Jerry
authors.initials: J
authors.lastname: Oxsher
authors.forename: Theo
authors.initials: T
authors.lastname: Dreher
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D020816:Amino Acid Motifs; D000818:Animals; D001386:Azides / Q000737:chemistry*; D002213:Capsid / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D002448:Cell Adhesion; D049109:Cell Proliferation; D003300:Copper / Q000737:chemistry*; D005898:Glass / Q000737:chemistry; D051379:Mice; D008958:Models, Molecular; D041681:NIH 3T3 Cells; D053758:Nanoparticles / Q000737:chemistry* / Q000821:virology*; D009842:Oligopeptides / Q000378:metabolism; D011092:Polyethylene Glycols / Q000737:chemistry; D011437:Propylamines; D011487:Protein Conformation; D012821:Silanes / Q000737:chemistry; D013379:Substrate Specificity; D017806:Tymovirus / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D000480:Alkynes; D001386:Azides; D009842:Oligopeptides; D011437:Propylamines; D012821:Silanes; D011092:Polyethylene Glycols; D003300:Copper; C047981:arginyl-glycyl-aspartic acid; C477625:amino-propyl-triethoxysilane