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

Masahiko Oshige; Koki Kano; Shunsuke Shinada; Akifumi Kawaguchi; Takato Uchida; Nozomi Ishii; Hiroaki Horiuchi; Fumio Sugawara; Kengo Sakaguchi; Ichiro Matsuo; Shinji Katsura

doi:10.1016/j.bmcl.2021.128391

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

Bioorg Med Chem Lett. 2021 Nov 15:52:128391. doi: 10.1016/j.bmcl.2021.128391. Epub 2021 Sep 30.

Authors

Affiliations

¹ Department of Environmental Engineering Science, Graduate School of Science and Technology, Gunma University, Kiryu, Gunma 376-8515, Japan; Gunma University Center for Food Science and Wellness (GUCFW), Maebashi, Gunma 371-8510, Japan. Electronic address: oshige@gunma-u.ac.jp.
² Department of Molecular Science, Graduate School of Science and Technology, Gunma University, Kiryu, Gunma 376-8515, Japan.
³ Department of Environmental Engineering Science, Graduate School of Science and Technology, Gunma University, Kiryu, Gunma 376-8515, Japan.
⁴ Department of Applied Biological Science, Faculty of Science and Technology, Tokyo University of Science, Noda, Chiba 278-8510, Japan.
⁵ Department of Environmental Engineering Science, Graduate School of Science and Technology, Gunma University, Kiryu, Gunma 376-8515, Japan; Gunma University Center for Food Science and Wellness (GUCFW), Maebashi, Gunma 371-8510, Japan.

PMID: 34601028
DOI: 10.1016/j.bmcl.2021.128391

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).

Keywords: Cytotoxicity; Lipase; Structural modification; Sulfur including glycolipid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

A549 Cells
Cell Survival / drug effects
Dose-Response Relationship, Drug
Humans
Lipase / metabolism*
Molecular Structure
Radiation-Sensitizing Agents / chemistry
Radiation-Sensitizing Agents / metabolism
Radiation-Sensitizing Agents / pharmacology*
Structure-Activity Relationship

Substances

Radiation-Sensitizing Agents
Lipase