Advances in Click Chemistry for Single-Chain Nanoparticle Construction
Abstract
:1. Introduction
1.1. Controlled Polymerization
Polymerization Technique | Abbreviation | Nature of the SCNP Polymeric Precursors * |
---|---|---|
Reversible addition fragmentation chain transfer polymerization | RAFT | Poly(alkyl methacrylates) [5,6,7,10,15,21,22,23,24,25,26,27], poly(alkyl acrylates) [7,22,28,29], poly(styrene) [3,22,23,30,31,32], poly(haloalkyl styrene) [3,33], poly(4-N-Boc-vinylaniline) [33], poly(sodium 4-styrenesulfonate) [22], poly(N-alkyl acrylamide) [22,34,35] |
Atom transfer radical polymerization | ATRP | Poly(alkyl methacrylates) [14], poly(alkyl acrylates) [11,12], poly(styrene) [36], poly(N-hydroxyethyl acrylamide) [37] |
Nitroxide mediated radical polymerization | NMP | Poly(alkyl methacrylates) [9,38,39,40], poly(alkyl acrylates) [40], poly(styrene) [2,38,40], poly(haloalkyl styrene) [40], poly(fluorene) [41] |
Ring opening metathesis polymerization | ROMP | Poly(ε-caprolactone) [38], poly(carbonates) [42] poly(norbornenes) [13,43,44] |
1.2. Polymer Functionalization
Polymer Functionalization Technique | Functional Groups Involved | Functionalizable Polymers |
---|---|---|
Thiol-ene / thiol-yne additions * | Thiol/alkene, alkyne | Polymers bearing alkene-, alkyne- or thiol-groups |
Modification of epoxides, anhydrides, oxazolines and isocyanates by reaction with amines / alcohols / thiols * | Epoxide, anhydride, oxazoline, isocyanate/ amine, alcohol, thiol | Polymers containing epoxide-, anhydride-, oxazoline-, isocyanate-, amine-, alcohol- or thiol-groups [23] |
Modification of active esters by reaction with amines | N-Hydroxysuccinimide, pentafluorophenyl ester/ amine | Polymers bearing N-hydroxy-succinimide-, pentafluorophenyl ester- or amine-groups |
Thiol-disulfide exchange | Pyridyl disulfide/thiol | Polymers containing pyridyl disulfide- or thiol-groups [6] |
Diels-Alder reaction * | Diene/alkene | Diene- or alkene-bearing polymers [28,40,53] |
Michael-type addition | Acrylate, N-substituted-maleimide, vinyl sulfone/ thiols | Polymers bearing acrylate-, N-substituted-maleimide-, vinyl sulfone- or thiol-groups |
Copper-catalyzed azide alkyne cycloaddition (CuAAC) * | Azide / alkyne | Azide- or alkyne-bearing polymers [3,10,21,22,30,34] |
Modification of ketones and aldehydes with amines/ alkoxyamines/hydrazines | Ketone, aldehyde / amine, alkoxyamine, hydrazine | Polymers containing ketone-, aldehyde-, amine-, alkoxyamine- or hydrazine- groups |
1.3. Intrachain Folding / Collapse
Reactive functional groups | Covalent bonding interactions |
---|---|
Vinyl [33,38,39,42] | Radical coupling & Cross-Metathesis |
Benzocyclobutene [40,53] | Diels-Alder reaction * |
Benzosulfone [9,28,41] | Diels-Alder reaction * |
Azide + Protected alkyne [3,10,21,22,30,34] | Copper-catalyzed [3+2] cycloaddition ** |
Carboxilic acid [54] | Amide formation |
Isocyanate [23] | Urea formation ** |
Enediyne [11,12,24,29] | Bergman & Photo-Bergman cyclization |
Sulfonyl azide [31] | Nitrene-mediated cross-linking |
Benzoxazine [36] | Ring opening polymerization |
Alkyne [25] | Glaser-Hay coupling * |
Reactive functional groups | NC/DC bonding interactions |
---|---|
Benzamide [26] | Benzamide hydrogen bonding * |
2-Ureido-Pyrimidone (UPy) [43] | UPy dimerization * |
Coumarin [35] | Coumarin photo-dimerization ** |
Benzaldehyde [32] | Acylhydrazone formation ** |
β-Ketoester [27] | Enamine formation ** |
Methyl viologen + Naphtyl [37] | Cucurbit[n]uril complexation * |
L-Phenylalanine (Phe) [55] | Hydrophobic Phe-Phe interactions * |
Aminophenyl disulfide [44] | Disulfide formation ** |
2. Single-Chain Nanoparticle Construction via Click Chemistry
2.1. Intrachain Homocoupling via Click Chemistry
2.2. Intrachain Heterocoupling via Click Chemistry
2.3. Crosslinker-Induced Collapse via Click Chemistry
3. Applications of Single-Chain Nanoparticles
3.1. Nanomedicine
3.1.1. Peptide/Drug/siRNA Controlled Delivery
3.1.2. Image Contrast Agents
3.2. Catalysis
3.3. Other Uses
4. Conclusions
Acknowledgments
Conflict of Interest
References
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Sanchez-Sanchez, A.; Pérez-Baena, I.; Pomposo, J.A. Advances in Click Chemistry for Single-Chain Nanoparticle Construction. Molecules 2013, 18, 3339-3355. https://doi.org/10.3390/molecules18033339
Sanchez-Sanchez A, Pérez-Baena I, Pomposo JA. Advances in Click Chemistry for Single-Chain Nanoparticle Construction. Molecules. 2013; 18(3):3339-3355. https://doi.org/10.3390/molecules18033339
Chicago/Turabian StyleSanchez-Sanchez, Ana, Irma Pérez-Baena, and José A. Pomposo. 2013. "Advances in Click Chemistry for Single-Chain Nanoparticle Construction" Molecules 18, no. 3: 3339-3355. https://doi.org/10.3390/molecules18033339