Direct, Controlled Synthesis of the Nonimmunogenic Hydrophilic Polymer, Poly(N-(2-Hydroxypropyl)methacrylamide) Via RAFT in Aqueous Media

Abstract

Poly(N-(2-hydroxypropyl)methacrylamide) (PHPMA) is a nonimmunogenic, neutral-hydrophilic polymer currently employed in the delivery of anticancer drugs. Herein, we report conditions that facilitate the direct, controlled RAFT polymerization of HPMA in aqueous media. We demonstrate that the use of 4-cyanopentanoic acid dithiobenzoate and 4,4′-azobis(4-cyanopentanoic acid) as the chain transfer agent (CTA) and initiating species, respectively, in the presence of an acetic acid buffer solution at 70 °C is a suitable condition leading to controlled polymerization. The "living" nature of these polymerizations is demonstrated via chain-extension of an HPMA macroCTA to yield the corresponding poly(HPMA-b-HPMA) "homopolymer".

Department(s)

Materials Science and Engineering

Keywords and Phrases

Acetic acid; Drug products; Free radical polymerization; Hydrophilicity; Solutions; Synthesis (chemical), Anticancer drugs; Chain transfer agents (CTA); Hydrophilic polymers; Poly(N-(2-hydroxypropyl)methacrylamide) (PHPMA), Organic polymers, acetic acid; antineoplastic agent; benzoic acid derivative; buffer; poly[n (2 hydroxypropyl)methacrylamide]; valeric acid derivative, aqueous solution; article; controlled study; drug delivery system; hydrophilicity; immunogenicity; polymerization; priority journal; synthesis; temperature, Magnetic Resonance Spectroscopy; Polymers; Polymethacrylic Acids; Scattering, Radiation; Water

International Standard Serial Number (ISSN)

1525-7797

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2005 American Chemical Society (ACS), All rights reserved.

Publication Date

01 Jul 2005

PubMed ID

16004419

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