Ligand compatibility of salacinol-type α-glucosidase inhibitors toward the GH31 family

Fumihiro Ishikawa; Aiko Hirano; Yuuto Yoshimori; Kana Nishida; Shinya Nakamura; Katsuki Takashima; Shinsuke Marumoto; Kiyofumi Ninomiya; Isao Nakanishi; Weijia Xie; Toshio Morikawa; Osamu Muraoka; Genzoh Tanabe

doi:10.1039/D0RA10038B

Ligand compatibility of salacinol-type α-glucosidase inhibitors toward the GH31 family†

Fumihiro Ishikawa,

^a Aiko Hirano,^a Yuuto Yoshimori,^a Kana Nishida,^a Shinya Nakamura,^b Katsuki Takashima,^a Shinsuke Marumoto,^c Kiyofumi Ninomiya,^d Isao Nakanishi,^b Weijia Xie,^e Toshio Morikawa,

^d Osamu Muraoka^d and Genzoh Tanabe

*^ad

Author affiliations

* Corresponding authors

^a Pharmaceutical Organic Chemistry Lab, Faculty of Pharmacy, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan

^b Computational Drug Design and Discovery Lab, Faculty of Pharmacy, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan

^c Joint Research Center, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan

^d Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan

^e State Key Laboratory of Natural Medicines, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 2100009, P. R. China
E-mail: g-tanabe@phar.kindai.ac.jp

Abstract

We show that salacinol-type α-glucosidase inhibitors are ligand-compatible with the GH 31 family. Salacinol and its 3′-O-benzylated analogs inhibit human lysosomal α-glucosidase at submicromolar levels. Simple structure-activity relationship studies reveal that the salacinol side-chain stereochemistry significantly influences binding to GH31 α-glucosidases.

This article is part of the themed collection: 2021 RSC Advances HOT Article Collection

RSC Advances

Ligand compatibility of salacinol-type α-glucosidase inhibitors toward the GH31 family†

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Ligand compatibility of salacinol-type α-glucosidase inhibitors toward the GH31 family

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