Synthesis of a 3'-naphthamido-LacNAc fluorescein conjugate with high selectivity and affinity for galectin-3.
Described is the synthesis of a fluorescent LacNAc derivative appended with a 3'-deoxy-3'-naphthamido functionality, 2-(fluorescein-5/6-amido)ethyl 3-deoxy-3-(2-naphthamido)-beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranoside, which confers high affinity (Kd 170 nM) and selectivity for galectin-3 via a stacking interaction with Arg144. Its use as a selective and sensitive galectin-3 probe is demonstrated with fluorescence polarization measurements.
Aplander
Karolina
K
Organic Chemistry, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
Tejler
Johan
J
Toftered
Jörgen
J
Carlsson
Susanne
S
Kahl-Knutsson
Barbro
B
Sundin
Anders
A
Leffler
Hakon
H
Nilsson
Ulf J
UJ
D004187:Disaccharides / Q000138:chemical synthesis* / Q000378:metabolism; D005452:Fluoresceins / Q000138:chemical synthesis* / Q000378:metabolism; D005454:Fluorescence Polarization; D037502:Galectin 3 / Q000032:analysis / Q000378:metabolism*
D004187:Disaccharides; D005452:Fluoresceins; D037502:Galectin 3