Modification on the O-glucoside of Sergliflozin-A: A new strategy for SGLT2 inhibitor design

Bioorg Med Chem Lett. 2016 May 1;26(9):2170-3. doi: 10.1016/j.bmcl.2016.03.065. Epub 2016 Mar 16.

Abstract

Poor pharmacokinetic stability is one of the issues of O-glucoside SGLT2 inhibitors in clinical trials, hence C-glucoside inhibitors have been developed and extensively applied. Herein, we provided an alternative approach to improve the pharmacokinetic stability of such inhibitors. Nine derivatives of Sergliflozin-A with modifications on the O-glucoside fragment were prepared, among which the 4-O-methyl derivative exhibited similar pharmacodynamics potency in excreted glucose urine test. Most attractively, significantly increased pharmacokinetic stability was observed for 4-O-methyl derivative of O-glucosides. This work proved that modification on the O-glucoside fragment could be a promising approach to the future SGLT2 inhibitor design.

Keywords: O-Glucoside; Pharmacokinetic stability; SGLT2 inhibitor; Sergliflozin-A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzhydryl Compounds / chemical synthesis
  • Benzhydryl Compounds / pharmacokinetics*
  • Benzhydryl Compounds / urine
  • Hypoglycemic Agents / chemical synthesis
  • Hypoglycemic Agents / pharmacokinetics*
  • Hypoglycemic Agents / urine
  • In Vitro Techniques
  • Monosaccharides / chemical synthesis
  • Monosaccharides / pharmacokinetics*
  • Monosaccharides / urine
  • Rats
  • Sodium-Glucose Transporter 2
  • Sodium-Glucose Transporter 2 Inhibitors*

Substances

  • 2-((4-methoxyphenyl)methyl)phenyl-4-O-methyl-beta-D-glucopyranoside
  • Benzhydryl Compounds
  • Hypoglycemic Agents
  • Monosaccharides
  • Slc5a2 protein, rat
  • Sodium-Glucose Transporter 2
  • Sodium-Glucose Transporter 2 Inhibitors
  • sergliflozin-A