Synthesis of 3-octadecanoxypropyl 6-deoxy-6-sulfo-α-d-glucopyranoside (ODSG) as a lipase-resistant SQAP derivative. (15th November 2021)

• Record Type: Journal Article
• Authors: Oshige, Masahiko; Kano, Koki; Shinada, Shunsuke; Kawaguchi, Akifumi; Uchida, Takato; Ishii, Nozomi; Horiuchi, Hiroaki; Sugawara, Fumio; Sakaguchi, Kengo; Matsuo, Ichiro; Katsura, Shinji
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 52(2021)
• Publication Date: 2021-11-15
• Subjects: Sulfur including glycolipid -- Structural modification -- Lipase -- Cytotoxicity; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2021.128391
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: Sulfoquynovosylacyl propanediol (SQAP; 1 ) has been developed as a radiosensitizer (anti-cancer agent) for solid tumors, but it was easily cleaved in vivo and had a problem of short residence time. We synthesized a novel compound of a SQAP derivative (3-octadecanoxypropyl 6-deoxy-6-sulfo-α-d -glucopyranoside: ODSG; 2 ) to solve these problems not easily cleaved by lipase. ODSG (2 ) cytotoxicity was investigated in vitro, resulting in low toxicity like SQAP (1 ).