Document Detail

Synthesis of O-methylsulfonyl derivatives of D-glucose as potential alkylating agents for targeted drug delivery to the brain. Evaluation of their interaction with the human erythrocyte GLUT1 hexose transporter.
MedLine Citation:
PMID:  9129293     Owner:  NLM     Status:  MEDLINE    
In order to obtain hydrophilic analogues of 1,4-dimethylsulfonyloxybutane (busulfan) with enhanced selectivity and improved brain penetration, we have synthesized 6-O-methylsulfonyl-D-glucose, 3-O-methylsulfonyl-D-glucose, 3,6-di-O-methylsulfonyl-D-glucose, 4-O-methylsulfonyl-D-glucose, and 4,6-di-O-methylsulfonyl-D-glucose, and we have studied their interactions with the human erythrocyte GLUT1 hexose transport system. Mesylation of OH-4 and OH-6 of glucose resulted in a slightly diminished affinity for the GLUT1 glucose transporter, whereas mesylation of OH-3 led to complete loss of affinity.
T Halmos; M Santarromana; K Antonakis; D Scherman
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Carbohydrate research     Volume:  299     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  1997 Mar 
Date Detail:
Created Date:  1997-06-02     Completed Date:  1997-06-02     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  15-21     Citation Subset:  IM    
UMR 133 CNRS/Rhône-Poulenc Rorer, Laboratoire de Chimie Organique Biologique, Villejuif, France.
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MeSH Terms
Antineoplastic Agents, Alkylating / chemical synthesis*,  pharmacology
Blood-Brain Barrier
Busulfan / analogs & derivatives*,  chemical synthesis*,  pharmacology
Erythrocytes / metabolism*
Glucose / metabolism
Glucose Transporter Type 1
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Structure
Monosaccharide Transport Proteins / blood*,  drug effects
Sulfonic Acids
Reg. No./Substance:
0/Antineoplastic Agents, Alkylating; 0/Glucose Transporter Type 1; 0/Indicators and Reagents; 0/Monosaccharide Transport Proteins; 0/SLC2A1 protein, human; 0/Sulfonic Acids; 50-99-7/Glucose; 55-98-1/Busulfan

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