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Development of a platform for activatable fluorescent substrates of glucose transporters (GLUTs).

Abstract：

:We have developed a platform for activatable fluorescent substrates of glucose transporters (GLUTs). We firstly conjugated fluorescein to glucosamine via an amide or methylene linker at the C-2 position of d-glucosamine, but the resulting compounds, FLG1 and FLG2, showed no uptake into MIN6 cells. So, we changed the fluorophore moiety to a fluorescein analogue, 2-Me TokyoGreen, which is less negatively charged. TokyoGreen-conjugated glucosamines TGG1 and TGG2 were successfully taken up into cells via GLUT. We further derivatized TGG1 and TGG2, and among the synthesized compounds, 2-Me-4-OMe TGG showed weak fluorescence under the acidic conditions of the extracellular environment inside tumors and in gastric cancers, and strong fluorescence at the intracellular physiological pH, under the control of a photoinduced electron transfer (PeT) process. This fluorogenic platform should be useful for developing a range of activatable fluorescent substrates targeting GLUTs, as well as derivatives that would be fluorescently activated by various intracellular enzymes, such as esterases, β-galactosidase and bioreductases.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Takasugi T,Hanaoka K,Sasaki A,Ikeno T,Komatsu T,Ueno T,Yamada K,Urano Y

doi

10.1016/j.bmc.2019.02.055

subject

Has Abstract

pub_date

2019-05-15 00:00:00

pages

2122-2126

issue

10

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(18)32171-0

journal_volume

27

pub_type

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