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Preparation of oligodimethylsiloxanes with sugar moiety at a terminal group as a transdermal penetration enhancer
Author(s) -
Akimoto Tomoko,
Kawahara Kazunari,
Nagase Yu,
Aoyagi Takao
Publication year - 2000
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/1521-3935(20001201)201:18<2729::aid-macp2729>3.0.co;2-u
Subject(s) - transdermal , moiety , chemistry , hydrolysis , sodium methoxide , ether , materials science , polymer chemistry , nuclear chemistry , organic chemistry , medicine , pharmacology , catalysis
Oligodimethylsiloxanes (ODMSs) containing glucose or cellobiose moiety at a terminal group were prepared to develop a silicone‐based transdermal penetration enhancer. Glucopiranosyl‐terminated ODMS was prepared by the hydrosilylation of hydrosilyl‐terminated ODMS with 1‐allyl‐β‐D‐glucose tetraacetate followed by hydrolysis of the acetyl groups with sodium methoxide, to afford glucopiranosyl‐terminated ODMS with a ether linkage between glucopiranosyl and ODMS components (GlcO‐ODMS), and by the coupling reaction of iodopropyl‐terminated ODMS with 2‐(2,3,4,6‐ O ‐tetraacetyl‐β‐D‐glucopyranosyl)thiopseudourea hydrobromide followed by the similar hydrolysis to afford glucopiranosyl‐terminated ODMS with a thioether linkage (GlcS‐ODMS). Cellobiosyl‐terminated ODMS (Cell‐ODMS) was also prepared by the similar procedure as GlcO‐ODMS. The enhancing activity of GlcO‐ODMS, GluS‐ODMS and Cell‐ODMS on the drug permeation through the rabbit abdominal skin was evaluated by in vitro experiments using a two‐chamber diffusion cell and antipyrine as a model drug. The permeation of antipyrine through the skin was increased by the addition of GlcS‐ODMS and GlcO‐ODMS but not by Cell‐ODMS.