The nonmetabolizable glucose analogue 3-O-methylglucose is known to protect pancreatic B-cells against streptozocin (STZ) when injected with or just before STZ. If 3-O-methyl-glucose and the sugar moiety of STZ compete for a glucose recognition site on B-cells, it seemed likely that 3-O-methyl-2-deoxy-2-{[(methylnitrosoamino) carbonyl]amino}-D-glucopyranose, an analogue of STZ with a 3-O-methyl-glucosyl residue, would cause experimental diabetes. This possibility was tested by synthesis of this analogue (α-anomer) and comparison of its diabetogenic activity in Wistar rats with that of STZ. Results showed that the compound was diabetogenic and as potent as STZ. This new analogue is the first of the various STZ derivatives reported to show diabetogenic activity. Its activity supports the idea that 3-O-methyl-glucose and STZ bind competitively with a glucose recognition site on pancreatic B-cells.
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Original contribution|
January 01 1986
New Diabetogenic Streptozocin Analogue, 3-O-Methyl-2-{[(methylnitrosoamino) carbonyl]amino}-D-glucopyranose: Evidence for a Glucose Recognition Site on Pancreatic B-Cells
Jun Kawada;
Jun Kawada
Department of Biochemistry, Faculty of Pharmaceutical Sciences, University of Tokushima
Tokushima 770
Research Laboratories, Tanabe Seiyaku Co. Ltd.
Kawagishi, Toda-shi, Saitama 335, Japan
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Kiyotaka Toide;
Kiyotaka Toide
Department of Biochemistry, Faculty of Pharmaceutical Sciences, University of Tokushima
Tokushima 770
Research Laboratories, Tanabe Seiyaku Co. Ltd.
Kawagishi, Toda-shi, Saitama 335, Japan
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Mikio Nishida;
Mikio Nishida
Department of Biochemistry, Faculty of Pharmaceutical Sciences, University of Tokushima
Tokushima 770
Research Laboratories, Tanabe Seiyaku Co. Ltd.
Kawagishi, Toda-shi, Saitama 335, Japan
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Yoshiyuki Yoshimura;
Yoshiyuki Yoshimura
Department of Biochemistry, Faculty of Pharmaceutical Sciences, University of Tokushima
Tokushima 770
Research Laboratories, Tanabe Seiyaku Co. Ltd.
Kawagishi, Toda-shi, Saitama 335, Japan
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Kenji Tsujihara
Kenji Tsujihara
Department of Biochemistry, Faculty of Pharmaceutical Sciences, University of Tokushima
Tokushima 770
Research Laboratories, Tanabe Seiyaku Co. Ltd.
Kawagishi, Toda-shi, Saitama 335, Japan
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Address reprint requests to Dr. Jun Kawada, Department of Biochemistry, Faculty of Pharmaceutical Sciences, University of Tokushima, Tokushima 770, Japan
Diabetes 1986;35(1):74–77
Article history
Received:
May 15 1985
Revision Received:
July 30 1985
PubMed:
2934286
Citation
Jun Kawada, Kiyotaka Toide, Mikio Nishida, Yoshiyuki Yoshimura, Kenji Tsujihara; New Diabetogenic Streptozocin Analogue, 3-O-Methyl-2-{[(methylnitrosoamino) carbonyl]amino}-D-glucopyranose: Evidence for a Glucose Recognition Site on Pancreatic B-Cells. Diabetes 1 January 1986; 35 (1): 74–77. https://doi.org/10.2337/diab.35.1.74
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