Bioorthogonal dual functionalization of self-assembling peptide fibers

Biomaterials - Tập 32 - Trang 3712-3720 - 2011
Zahra N. Mahmoud1, Smita B. Gunnoo1, Andrew R. Thomson1, Jordan M. Fletcher1, Derek N. Woolfson1,2
1School of Chemistry, University of Bristol, BS8 1TS, UK
2School of Biochemistry, University of Bristol, BS8 1TD, UK

Tài liệu tham khảo

Kopecek, 2009, Peptide-directed self-assembly of hydrogels, Acta Biomater, 5, 805, 10.1016/j.actbio.2008.10.001 Woolfson, 2010, More than just bare scaffolds: towards multi-component and decorated fibrous biomaterials, Chem Soc Rev, 39, 3464, 10.1039/c0cs00032a Wang, 2005, Facile modification of collagen directed by collagen mimetic peptides, J Am Chem Soc, 127, 4130, 10.1021/ja0431915 Mart, 2006, Peptide-based stimuli-responsive biomaterials, Soft Mater, 2, 822, 10.1039/b607706d Mahmoud, 2010, The non-covalent decoration of self-assembling protein fibers, Biomaterials, 10.1016/j.biomaterials.2010.06.041 Kolb, 2001, Click chemistry: diverse chemical function from a few good reactions, Angew Chem-Int Edit, 40, 2004, 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 Rostovtsev, 2002, A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes, Angew Chem-Int Edit, 41, 2596, 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 Tornoe, 2002, Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides, J Org Chem, 67, 3057, 10.1021/jo011148j Nandivada, 2007, Click chemistry: versatility and control in the hands of materials scientists, Adv Mater, 19, 2197, 10.1002/adma.200602739 DeForest, 2009, Sequential click reactions for synthesizing and patterning three-dimensional cell microenvironments, Nat Mater, 8, 659, 10.1038/nmat2473 Sletten, 2009, Bioorthogonal chemistry: fishing for selectivity in a Sea of Functionality, Angew Chem-Int Edit, 48, 6974, 10.1002/anie.200900942 Pandya, 2000, Sticky-end assembly of a designed peptide fiber provides insight into protein fibrillogenesis, Biochemistry, 39, 8728, 10.1021/bi000246g Smith, 2006, Engineering increased stability into self-assembled protein fibers, Adv Funct Mater, 16, 1022, 10.1002/adfm.200500568 Ryadnov, 2004, Fiber recruiting peptides: noncovalent decoration of an engineered protein scaffold, J Am Chem Soc, 126, 7454, 10.1021/ja048144r Papapostolou, 2008, Electrostatic control of thickness and stiffness in a designed protein fiber, J Am Chem Soc, 130, 5124, 10.1021/ja0778444 Wang, 2003, Bioconjugation by copper(I)-catalyzed azide-alkyne [3+2] cycloaddition, J Am Chem Soc, 125, 3192, 10.1021/ja021381e Khire, 2006, Ultrathin gradient films using thiol-ene polymerizations, J Polym Sci Part A-1 Polym Chem, 44, 7027, 10.1002/pola.21786 Goddard-Borger, 2007, An expeditious synthesis of isofagomine, Aust J Chem, 60, 211, 10.1071/CH07016 Ryadnov, 2003, Introducing branches into a self-assembling peptide fiber, Angew Chem-Int Edit, 42, 3021, 10.1002/anie.200351418 Ryadnov, 2003, Engineering the morphology of a self-assembling protein fibre, Nat Mater, 2, 329, 10.1038/nmat885 Chan, 2004, Polytriazoles as copper(I)-stabilizing ligands in catalysis, Org Lett, 6, 2853, 10.1021/ol0493094 Bromley, 2010, The assembly pathway of a designed alpha-helical protein fiber, Biophys J, 98, 1668, 10.1016/j.bpj.2009.12.4309 Papapostolou, 2007, Engineering nanoscale order into a designed protein fiber, Proc Natl Acad Sci U S A, 104, 10853, 10.1073/pnas.0700801104 Killops, 2008, Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "Click" chemistry, J Am Chem Soc, 130, 5062, 10.1021/ja8006325 Bryant, 2000, Cytocompatibility of UV and visible light photoinitiating systems on cultured NIH/3T3 fibroblasts in vitro, J Biomater Sci Polym Ed, 11, 439, 10.1163/156856200743805 Fairbanks, 2009, Thiol-Yne Photopolymerizations: novel mechanism, kinetics, and step-growth formation of highly cross-linked networks, Macromolecules, 42, 211, 10.1021/ma801903w Goddard-Borger, 2007, An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride, Org Lett, 9, 3797, 10.1021/ol701581g Isaad, 2008, N-alpha-Fmoc-protected omega-azido- and omega-alkynyl-l-amino acids as building blocks for the synthesis of clickable peptides, Eur J Org Chem, 31, 5308, 10.1002/ejoc.200800717 Punna, 2005, “Clickable” agarose for affinity chromatography, Bioconjugate Chem, 16, 1536, 10.1021/bc0501496 Seo, 2003, Click chemistry to construct fluorescent oligonucleotides for DNA sequencing, J Org Chem, 68, 609, 10.1021/jo026615r Link, 2003, Cell surface labeling of Escherichia coli via copper(I)-catalyzed [3+2] cycloaddition, J Am Chem Soc, 125, 11164, 10.1021/ja036765z Wang, 2009, Bioconjugation of biotin to the interfaces of polymeric micelles via in situ click chemistry, Langmuir, 25, 744, 10.1021/la802810w