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WIREs Nanomed Nanobiotechnol
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Synthesis of poly(alkyl cyanoacrylate)‐based colloidal nanomedicines

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Abstract Nanoparticles developed from poly(alkyl cyanoacrylate) (PACA) biodegradable polymers have opened new and exciting perspectives in the field of drug delivery due to their nearly ideal characteristics as drug carriers in connection with biomedical applications. Thanks to the direct implication of organic chemistry, polymer science and physicochemistry, multiple PACA nanoparticles with different features can be obtained: nanospheres and nanocapsules (either oil‐ or water‐containing) as well as long‐circulating and ligand‐decorated nanoparticles. This review aims at emphasizing the synthetic standpoint of all these nanoparticles by describing the important aspects of alkyl cyanoacrylate chemistry as well as the experimental procedures and the different techniques involved for the preparation of the corresponding colloidal devices. Copyright © 2008 John Wiley & Sons, Inc. This article is categorized under: Therapeutic Approaches and Drug Discovery > Emerging Technologies

Structure of alkyl cyanoacrylates described in the literature: methyl cyanoacrylate (MCA), ethyl cyanoacrylate (ECA), n‐butyl cyanoacrylate (nBCA), isobutyl cyanoacrylate (IBCA), isohexyl cyanoacrylate (IHCA), octyl cyanoacrylate (OCA), isostearyl cyanoacrylate (ISCA), hexadecyl cyanoacrylate (HDCA), and methoxypoly(ethylene glycol) cyanoacrylate (MePEGCA).

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Possible degradation pathways for poly(alkyl cyanoacrylate) (PACA) polymers: hydrolysis of ester functions (a), 'unzipping' depolymerization reaction (b), the inverse Knoevenagel condensation reaction (c), and release of formaldehyde from hydrolysis of the α‐hydroxyl functions (d).

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Synthesis of folate‐decorated poly[(hexadecyl cyanoacrylate)‐co‐aminopoly(ethylene glycol) cyanoacrylate] [P(HDCA‐co‐H2 NPEGCA)] nanospheres. The moiety anchored at the surface of the nanoparticles is marked by single asterisk.

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Concentration of radioactivity in right hemisphere (a), left hemisphere (b), and cerebellum (c), after intravenous administration of 60 mg kg−1 of [14C]‐P(HDCA‐co‐MePEGCA) nanoparticles, poloxamine 908‐coated [14C]‐PHDCA nanoparticles, polysorbate 80‐coated [14C]‐PHDCA nanoparticles, and uncoated [14C]‐PHDCA nanoparticles (mice at 1 h postinjection).

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Anionic emulsion polymerization of alkyl cyanoacrylates initiated by hydroxyl groups of dextran (a) and redox radical emulsion polymerization (RREP) of alkyl cyanoacrylates initiated by dextran/cerium IV (Ce4+) ions redox couple (b).

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Schematic representation of poly(alkyl cyanoacrylate)‐based nanospheres with controlled surface properties using poly(ethylene glycol) monomethyl ether (a), poly(ethylene glycol) (b), poly[(hexadecyl cyanoacrylate)‐co‐methoxypoly(ethylene glycol) cyanoacrylate] copolymer (c), polysaccharide chains under anionic initiation (d), polysaccharide chains under redox initiation (e), and amino acids (f). The moiety anchored at the surface of the nanoparticles is marked by single asterisk.

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Schematic representation of poly(alkyl cyanoacrylate) formation via the stepwise anionic polymerization mechanism in emulsion/dispersion. Initiation step (a), reversible propagation step (b), and reversible termination step (c).

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Schematic representation of nanospheres (NS), water‐containing nanocapsules (w‐NC), and oil‐containing nanocapsules (o‐NC).

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Synthesis of random, comb‐like poly[(hexadecyl cyanoacrylate)‐co‐methoxypoly(ethylene glycol) cyanoacrylate] [P(HDCA‐co‐MePEGCA)] copolymer via Knoevenagel condensation reaction.

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Initiation and propagation steps involved during anionic (a), zwitterionic (b), and radical (c) polymerizations of alkyl cyanoacrylate monomer initiated by a base (B), a nucleophile (Nu), and a radical (P), respectively.

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Synthesis of alkyl cyanoacrylate monomer via Knoevenagel condensation reaction (a) and subsequent thermal depolymerization (b).

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