Improvement in the properties of 3-phenyl-3-trifluoromethyldiazirine based photoreactive bis-glucose probes for GLUT4 following substitution on the phenyl ring

M Hashimoto, J Yang, Y Hatanaka, Y Sadakane, K Nakagomi, G D Holman

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Abstract

We have developed two novel 3-phenyl-3-trifluoromethyldiazirinyl bis-glucose derivatives to investigate the properties of the adipocyte glucose transporter GLUT4. These compounds were substituted by electron-withdrawing (iodo and nitro) groups on the aromatic ring of 3-phenyl-3-trifluoromethyldiazirine photophore and were found to be more photosensitive than compounds without such substituents. The compounds were used as inhibitors of insulin-stimulated glucose transport activity in order to assess half-maximal Inhibition or relative affinity values for GLUT4. The affinities were found to be 60-130 times higher than the parent compound D-glucose. Because of the increased photo-reactivity and high affinity these compounds will be useful in studies directed at further elucidation of GLUT4 function.
Original languageEnglish
Pages (from-to)1004-1006
Number of pages3
JournalChemical & Pharmaceutical Bulletin
Volume50
Issue number7
Publication statusPublished - 2002

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Substitution reactions
Glucose
Facilitative Glucose Transport Proteins
Adipocytes
Electrons
Insulin
Derivatives
phenyl-3-trifluoromethyldiazirine

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Improvement in the properties of 3-phenyl-3-trifluoromethyldiazirine based photoreactive bis-glucose probes for GLUT4 following substitution on the phenyl ring. / Hashimoto, M; Yang, J; Hatanaka, Y; Sadakane, Y; Nakagomi, K; Holman, G D.

In: Chemical & Pharmaceutical Bulletin, Vol. 50, No. 7, 2002, p. 1004-1006.

Research output: Contribution to journalArticle

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AU - Hatanaka, Y

AU - Sadakane, Y

AU - Nakagomi, K

AU - Holman, G D

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AB - We have developed two novel 3-phenyl-3-trifluoromethyldiazirinyl bis-glucose derivatives to investigate the properties of the adipocyte glucose transporter GLUT4. These compounds were substituted by electron-withdrawing (iodo and nitro) groups on the aromatic ring of 3-phenyl-3-trifluoromethyldiazirine photophore and were found to be more photosensitive than compounds without such substituents. The compounds were used as inhibitors of insulin-stimulated glucose transport activity in order to assess half-maximal Inhibition or relative affinity values for GLUT4. The affinities were found to be 60-130 times higher than the parent compound D-glucose. Because of the increased photo-reactivity and high affinity these compounds will be useful in studies directed at further elucidation of GLUT4 function.

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