title: Syntheses of 2-NBDG analogues for monitoring stereoselective uptake of D-glucose.
abstract: 2-NBDG is a widely used fluorescent tracer for monitoring d-glucose uptake into single living cells. However, 2-NBDG alone is not sufficient for monitoring the net stereoselective uptake of d-glucose, unless its possible non-stereoselective uptake is properly evaluated. l-Glucose derivatives, which emit fluorescence distinct from that of 2-NBDG, should provide valuable information on the stereoselective uptake, when used with 2-NBDG in combination. In the present study, we synthesized Texas Red (sulforhodamine 101 acid)-coupled and [2-(benz-2-oxa-1,3-diazol-4-yl)amino]-coupled 2-deoxy-D-glucose, referred to as [2-TRG] and [2-BDG], respectively. These derivatives showed emission wavelength longer and shorter than that of 2-NBDG, respectively. 2-TRLG, an antipode of 2-TRG, proved to be an effective tracer for evaluating the extent of non-stereoselective uptake of 2-NBDG when used simultaneously with 2-NBDG. On the other hand, 2-BDG exhibited very weak fluorescence, but the application of a novel cross coupling in the presence of a benzoxadiazole group may be useful for the future development of effective glucose tracers.
authors.affiliation: Peptide Institute, Inc., Saito Research Center, Ibaraki, Osaka 567-0085, Japan. yamamoto@peptide.co.jp
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Yamamoto
authors.forename: Shin-ichi
authors.initials: S
authors.lastname: Tanaka
authors.forename: Sechiko
authors.initials: S
authors.lastname: Suga
authors.forename: Seiji
authors.initials: S
authors.lastname: Watanabe
authors.forename: Katsuhiro
authors.initials: K
authors.lastname: Nagatomo
authors.forename: Ayako
authors.initials: A
authors.lastname: Sasaki
authors.forename: Yuji
authors.initials: Y
authors.lastname: Nishiuchi
authors.forename: Tadashi
authors.initials: T
authors.lastname: Teshima
authors.forename: Katsuya
authors.initials: K
authors.lastname: Yamada
mesh_terms: D009327:4-Chloro-7-nitrobenzofurazan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D001921:Brain / Q000378:metabolism; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D005947:Glucose / Q000737:chemistry / Q000378:metabolism*; D051379:Mice; D018613:Microscopy, Confocal; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003847:Deoxyglucose; D009327:4-Chloro-7-nitrobenzofurazan; D005947:Glucose; C098340:2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose