Assembly of Poly[N-(2-hydroxypropyl)methacrylamide] Having Long Alkyl Moieties as Terminal Groups

• SUGIYAMA Kazuo

  Program in Material Technology, Graduate School of Industrial Technology, Kinki University; 1 Umenobe, Takaya, Higashihiroshima-shi 739-2116 Japan

• HANAMURA Ryo

  Program in Material Technology, Graduate School of Industrial Technology, Kinki University; 1 Umenobe, Takaya, Higashihiroshima-shi 739-2116 Japan

Bibliographic Information

Other Title

• 末端に長鎖アルキル基を有するポリ[N-(2-ヒドロキシプロピル)メタクリルアミド]の分子集合性
• マッタン ニ チョウサ アルキルキ オ ユウスル ポリ N 2 ヒドロキシプロピル メタクリルアミド ノ ブンシ シュウゴウセイ

Abstract

Amphiphilic poly[N-(2-hydroxypropyl)methacrylamide]s (PHPMA) having long alkyl moieties as terminal groups, PHPMA-C₁₂, PHPMA-DC₁₂ and PHPMA-C₁₈, were prepared by radical polymerization of N-(2-hydroxypropyl) methacrylamide (HPMA) initiated with lipophilic azo-initiators such as 4, 4′-azobis(dodecyl 4-cyanopentanoate) (VA-C₁₂), 4, 4′-azobis[(2-dodecyloxy-1-dodecyloxymethylethyl) 4-cyanopentanoate] (VA-DC₁₂) and 4, 4′-azobis(octadecyl 4-cyanopentanoate) (VA-C₁₈) in the presence of 2-mercaptoethanol as a chain transfer reagent. An amphiphilic polymer having octadecyl moieties as both terminal groups, PHPMA-2C₁₈, was also prepared by radical polymerization of HPMA initiated with VA-C₁₈ in the presence of 1-octadecanethiol(ODT) as a chain transfer reagent. From the fluorescence measurements of aqueous polymer solution using 1-(6-dimethylamino-2-naphthyl)-1-dodecanone (DMAND) as a fluorescent probe, the critical micelle concentrations (CMC) of PHPMAs were found to be PHPMA-C₁₂>>PHPMA-DC₁₂>PHPMA-C₁₈>>PHPMA-2C₁₈ in order. From SAX measurements of a drug model consisting of PHPMA-C₁₈ and cholesterol, it was suggested that cholesterol molecules are incorporated in a hydrophobic domain formed by the terminal octadecyl groups. It was also found that no acceleration in the enzymatic reaction of thrombin and a synthetic substrate S-2238 occurred in the presence of PHPMA-C₁₂, PHPMA-C₁₈, or PHPMA-2C₁₈. These PHPMAs are thus expected as carrier molecules of drug delivery system.

Journal

• NIPPON KAGAKU KAISHI

  NIPPON KAGAKU KAISHI 2000 (8), 577-583, 2000

  The Chemical Society of Japan

Keywords

• General Chemistry

Details

• CRID: 1390001204388677632
• NII Article ID: 10004688884
• NII Book ID: AN00186595
• DOI: 10.1246/nikkashi.2000.577
• COI: 1:CAS:528:DC%2BD3cXmt1Wltrc%3D
• ISSN: 21850925
• ISSN: 03694577
• NDL BIB ID: 5436814
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I5436814
• Web Site: https://www.jstage.jst.go.jp/article/nikkashi/2000/8/2000_8_577/_pdf
• Text Lang: ja
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed