Inhibition of the D-fructose transporter protein GLUT5 by fused-ring glyco-1,3-oxazolidin-2-thiones and -oxazolidin-2-ones.
The glucose transporter 5 (GLUT5)-a specific D-fructose transporter-belongs to a family of facilitating sugar transporters recently enlarged by the human genome sequencing. Prompted by the need to develop specific photolabels of these isoforms, we have studied the interaction of conformationally locked D-fructose and L-sorbose derived 1,3-oxazolidin-2-thiones and 1,3-oxazolidin-2-ones to provide a rational basis for an interaction model. The inhibition properties of the D-fructose transporter GLUT5 by glyco-1,3-oxazolidin-2-thiones and glyco-1,3-oxazolidin-2-ones is now reported. In vitro, the fused-rings systems tested showed an efficient inhibition of GLUT5, thus bringing new insights on the interaction of D-fructose with GLUT5.
Girniene
Jolanta
J
ICOA, UMR 6005, Université d'Orléans, BP 6759, F-45067 Orléans, France.
Tatibouët
Arnaud
A
Sackus
Algirdas
A
Yang
Jing
J
Holman
Geoffrey D
GD
Rollin
Patrick
P
D000818:Animals; D001665:Binding Sites; D016466:CHO Cells; D002250:Carbon Radioisotopes; D006224:Cricetinae; D005632:Fructose / Q000031:analogs & derivatives / Q000378:metabolism / Q000494:pharmacology; D051296:Glucose Transporter Type 5; D007700:Kinetics; D009004:Monosaccharide Transport Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010080:Oxazoles / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*; D011485:Protein Binding; D013013:Sorbose / Q000031:analogs & derivatives / Q000378:metabolism / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013871:Thiones / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*
D002250:Carbon Radioisotopes; D051296:Glucose Transporter Type 5; D009004:Monosaccharide Transport Proteins; D010080:Oxazoles; D013871:Thiones; C064210:oxazolidine; D005632:Fructose; D013013:Sorbose