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C 2 ‐Symmetrical Thiodigalactoside Bis‐Benzamido Derivatives as High‐Affinity Inhibitors of Galectin‐3: Efficient Lectin Inhibition through Double Arginine–Arene Interactions
Author(s) -
Cumpstey Ian,
Sundin Anders,
Leffler Hakon,
Nilsson Ulf J.
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200500627
Subject(s) - galectin , dissociation constant , amide , chemistry , arginine , stacking , stereochemistry , lectin , dissociation (chemistry) , combinatorial chemistry , biochemistry , amino acid , receptor , organic chemistry
Inhibitors of galectin‐3 , which has been implicated in cancer‐ and immunity‐related processes, can be synthesized from thiodigalactoside derivatives with aromatic amide substituents at both C3 positions (see structure). Dissociation constant ( K d ) values as low as 33 n M have been obtained. Computer modeling suggests that such high affinity stems from double arginine–arene stacking interactions.