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WIREs Nanomed Nanobiotechnol

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Viral chemistry: the chemical functionalization of viral architectures to create new technology

Advanced Review

Zhuo Chen, Na Li, Shaobo Li, Madushani Dharmarwardana, Anna Schlimme, Jeremiah J Gassensmith

Published Online: Dec 10 2015

DOI: 10.1002/wnan.1379

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The modification of viruses using chemical conjugation techniques has brought the distant worlds of virology right into the center of nanotechnology. Viruses are naturally resilient biomolecules and this makes them exceptional templates for the creation of higher order polymers and as scaffolds for biological imaging and targeted drug delivery. In this review, we highlight progress in utilizing chemical strategies to interface viruses with synthetic polymers, to create bright bionanoparticles using synthetic fluorescent dyes, and how orthogonal chemical transformations allow for targeted drug delivery. WIREs Nanomed Nanobiotechnol 2016, 8:512–534. doi: 10.1002/wnan.1379 This article is categorized under: Diagnostic Tools > Diagnostic Nanodevices Diagnostic Tools > In Vivo Nanodiagnostics and Imaging Implantable Materials and Surgical Technologies > Nanomaterials and Implants Biology-Inspired Nanomaterials > Protein and Virus-Based Structures

Crystallographically obtained structures of common VLPs Qβ, MS2, Cowpea Mosaic Virus (CPMV), Cowpea Chlorotic Mottle Virus (CCMV), and Tobacco Mosaic Virus (TMV). TMV is not illustrated to scale.

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Dual‐surface modified bacteriophage MS2 capsid with photosensitizer and targeting ligands for photodynamic therapy, which significantly and specifically killed target cells. (Reprinted with permission from Ref . Copyright 2010 American Chemical Society)

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(a) Targeting strategies using electrostatic (left) or biological interaction (right). PS: photosensitizer; NP: nanoparticle; PLL: poly‐L‐lysine; Sa: S. aureus cell; SpA: protein A; Ab: anti‐SpA‐mAb‐B; B: bitotin; StAv: streptavidin. (Reprinted with permission from Ref . Copyright 2007 American Chemical Society)

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The combination of CCMV and photosensitizer for PDT. (Left) FESEM image of CCMV‐PS‐biotin conjugate covering on the cell wall through complementary biological interaction; (upper middle) CCMV; (lower middle) zoomed in micrograph of targeted cell wall; (upper right) photosensitizer (Ru(bpy2)phen‐IA); (lower right) cartoon represents the ROS generation upon illumination on the CCMV‐PS conjugate. (Reprinted with permission from Ref . Copyright 2007 American Chemical Society)

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(a) Azido‐functionalized polymer hybrid Qβ particle coupled with Doxorubicin with hydrazone linker via CuAAC reaction. (b) in vivo Doxorubicin release profile from Qβ‐polymer conjugate at pH 5.5 and 7.4; (C) MTT assay for HeLa cell viability with particle conjugates and free Doxorubicin alone. (Reprinted with permission from Ref . Copyright 2011 American Chemical Society)

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Different chemical modification approaches of M13 virus and structures of small molecules that were covalently bonding to M13. (Reprinted with permission from Ref . Copyright 2010 American Chemical Society)

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Modification of PVX with PEG linker (SM(PEG)₄), Alexa Fluor 647 NHS ester and subsequent labeled by GE11 peptide. (Reprinted with permission from Ref . Copyright 2015 American Chemical Society)

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(a) Chemical structure of the bombesin analog covalently bound with a PEG linker. (b) Sythetic processes of Dye‐labeled CPMV–PEG and CPMV–PEG–bombesin. (Reprinted with permission from Ref . Copyright 2011 John Wiley and Sons)

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Scheme of ATRP of poly(OEGMA) on outer shell of Qβ. (Reprinted with permission from Ref . Copyright 2011 American Chemical Society)

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Synthesis of Fluorescein‐F56 complex and conjugation to CPMV. (Reprinted with permission from Ref . Copyright 2010 American Chemical Society)

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Scheme of ATRP of pDMAEMA within T93 Qβ interior. (Reprinted with permission from Ref . Copyright 2014 American Chemical Society)

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Scheme of internal initiator‐attachment followed by ATRP of pAEMA and crosslinked with bisacrylamide (bis). The final step demonstrated the appended amine groups functionalized with FITC and Gd complex. (Reprinted with permission from Ref . Copyright 2012 Nature Publishing Group)

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(a) Schematic presentation of the attachment of poly(2‐oxazoline) onto azide‐functionalized Qβ exterior. PBS represents phosphate‐buffered saline. (b) Molecular composition of poly(2‐oxazoline) derivatives possessing various amounts of alkyne attachment points. (Reprinted with permission from Ref . Copyright 2011 John Wiley and Sons)

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Scheme of ATRP of neoglycopolymer (1→3), fluorescein attached to polymer termini via alkyne‐azide coupling (3→5), and fluorescein‐labeled polymer attached to CPMV exterior(6→9). (Reprinted with permission from Ref . Copyright 2005 Royal Society of Chemistry)

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Azo conjugation strategies developed on VLPs. (a) The initial strategy developed by Francis and coworkers involving hetero‐Diels‐Alder to place substituents. (b) Second generation Francis azo coupling utilizing oximes to place substituents. (c) Wang azo coupling using an alkyne‐functionalized diazonium for CuAAC chemistry to place substituents.

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