Poly(4‐acryloylmorpholine) oligomers carrying a β‐cyclodextrin residue at one terminus |
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Authors: | Marco Bencini Elisabetta Ranucci Paolo Ferruti Amedea Manfredi Francesco Trotta Roberta Cavalli |
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Institution: | 1. Dipartimento di Chimica Organica e Industriale, Università di Milano, via Venezian 21, 20133 Milano, Italy;2. Centro Interdipartimentale Materiali e Interfacce Nanostrutturati (CIMAINA), Università di Milano, via Venezian 21, 20133 Milano, Italy;3. Dipartimento di Chimica Inorganica, Fisica e dei Materiali, Università di Torino, via P.Giuria 6, 10125 Torino, Italy;4. Dipartimento di Scienza del Farmaco, Università di Torino, via P.Giuria 6, 10125 Torino, Italy |
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Abstract: | A straightforward synthesis of amphiphilic β‐cyclodextrin‐poly(4‐acryloylmorpholine) (β‐CD‐PACM) polymers of controlled molecular weight, consisting of the radical polymerization of 4‐acryloylmorpholine in the presence of 6‐deoxy‐6‐mercapto‐β‐cyclodextrin (β‐CD‐SH) as chain‐transfer agent, has been established. These derivatives carry a single β‐cyclodextrin (β‐CD) moiety at one terminus and their average molecular weight is in the order of 104. Thus, their β‐CD content is ~ 10% by weight. No evidence of un‐functionalized PACM was found in the final products. The chain‐transfer constant (CT) of β‐CD‐SH was found to be 1.30 by independently determining the reaction constants of both chain‐transfer and propagation reactions. This ensures that the molecular weight, hence the β‐CD content of the polymers, does not significantly vary with conversion. These β‐CD‐PACM polymers are highly soluble in water as well as in several organic solvents such as chloroform and lower alcohols. They proved capable of solubilizing in water poorly soluble drugs such as 9‐(2‐hydroxyethoxy)methyl]guanine (Acyclovir) and of gradually releasing them in aqueous systems. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 1607–1617, 2008 |
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Keywords: | bioactive and biocompatible polymers biological applications of polymers drug complexation drug delivery systems drug solubilization functionalization of polymers hydrophilic polymers β ‐cyclodextrin‐poly(4‐acryloylmorpholine) |
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