A new bifunctional amino acid chelator targeting the glucose transporter

Sangeeta R. Banerjee; John W. Babich; Jon Zubieta

doi:10.1016/j.ica.2005.11.022

A new bifunctional amino acid chelator targeting the glucose transporter

Sangeeta R. Banerjee, John W. Babich, Jon Zubieta

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

The coupling reactions of d-glucosamine, 1,3,4,6-tetra-O-acetylglucosamine, and 4-aminophenyl-galactopyranosine with N,N-bis(quinolinoyl)aminovaleric acid (L1) provided a series of conjugates containing a potentially tridentate donor group terminus linked to a sugar moiety, L2′, L2 and L3, respectively. Reactions of the ligands with [NEt₄]₂[Re(CO) ₃Br₃] in refluxing methanol provided the rhenium complexes [Re(CO₃)(L1)]Br (ReL1), [Re(CO)₃(L2)]Br (ReL2), [Re(CO)₃(L2′)]Br (ReL2′) and [Re(CO)₃(L3)]Br (ReL3). The ligands and complexes were characterized by elemental analyses, ¹H and ¹³C NMR, mass spectroscopy and, in the case of L1 and ReL1, by X-ray crystallography. The rhenium complexes exhibit fluorescence emissions with long lifetimes, large Stokes shifts, and moderate quantum yields.

Original language	English (US)
Pages (from-to)	1603-1612
Number of pages	10
Journal	Inorganica Chimica Acta
Volume	359
Issue number	5
DOIs	https://doi.org/10.1016/j.ica.2005.11.022
State	Published - Mar 20 2006

Keywords

Bifunctional chelates
Fluorescent probes
Glucosamine derivatives
Rhenium(I)-tricarbonyl core
Single amino acid chelates

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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title = "A new bifunctional amino acid chelator targeting the glucose transporter",

abstract = "The coupling reactions of d-glucosamine, 1,3,4,6-tetra-O-acetylglucosamine, and 4-aminophenyl-galactopyranosine with N,N-bis(quinolinoyl)aminovaleric acid (L1) provided a series of conjugates containing a potentially tridentate donor group terminus linked to a sugar moiety, L2′, L2 and L3, respectively. Reactions of the ligands with [NEt4]2[Re(CO) 3Br3] in refluxing methanol provided the rhenium complexes [Re(CO3)(L1)]Br (ReL1), [Re(CO)3(L2)]Br (ReL2), [Re(CO)3(L2′)]Br (ReL2′) and [Re(CO)3(L3)]Br (ReL3). The ligands and complexes were characterized by elemental analyses, 1H and 13C NMR, mass spectroscopy and, in the case of L1 and ReL1, by X-ray crystallography. The rhenium complexes exhibit fluorescence emissions with long lifetimes, large Stokes shifts, and moderate quantum yields.",

keywords = "Bifunctional chelates, Fluorescent probes, Glucosamine derivatives, Rhenium(I)-tricarbonyl core, Single amino acid chelates",

author = "Banerjee, {Sangeeta R.} and Babich, {John W.} and Jon Zubieta",

year = "2006",

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AU - Banerjee, Sangeeta R.

AU - Babich, John W.

AU - Zubieta, Jon

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AB - The coupling reactions of d-glucosamine, 1,3,4,6-tetra-O-acetylglucosamine, and 4-aminophenyl-galactopyranosine with N,N-bis(quinolinoyl)aminovaleric acid (L1) provided a series of conjugates containing a potentially tridentate donor group terminus linked to a sugar moiety, L2′, L2 and L3, respectively. Reactions of the ligands with [NEt4]2[Re(CO) 3Br3] in refluxing methanol provided the rhenium complexes [Re(CO3)(L1)]Br (ReL1), [Re(CO)3(L2)]Br (ReL2), [Re(CO)3(L2′)]Br (ReL2′) and [Re(CO)3(L3)]Br (ReL3). The ligands and complexes were characterized by elemental analyses, 1H and 13C NMR, mass spectroscopy and, in the case of L1 and ReL1, by X-ray crystallography. The rhenium complexes exhibit fluorescence emissions with long lifetimes, large Stokes shifts, and moderate quantum yields.

KW - Bifunctional chelates

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KW - Glucosamine derivatives

KW - Rhenium(I)-tricarbonyl core

KW - Single amino acid chelates

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