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Studies of Arginine–Arene Interactions through Synthesis and Evaluation of a Series of Galectin-Binding Aromatic Lactose Esters by Ian Cumpstey; Emma Salomonsson; Anders Sundin; Hakon Leffler; Ulf J. Nilsson is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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## Abstract Aromatic lactose 2‐__O__‐esters were synthesized and used to probe arene–arginine interactions with the galectin family of proteins. They were found to be low μM inhibitors of galectin‐1, ‐3, and ‐9N‐terminal domain and moderate inhibitors of galectin‐7, but not inhibitors of galectin‐8N‐terminal, which lacks an arginine residue close to the critical, esterified lactose 2‐__O__‐position. Molecular modeling of galectins in complex with aromatic lactose 2‐__O__‐esters, as well as binding studies with a galectin‐3 R186S mutant, confirmed that the inhibitory efficiency of the lactose 2‐__O__‐esters was due to the formation of strong interactions between the aromatic ester moieties and the arginine guanidinium groups of galectin‐1 and ‐3. An important common feature shared by galectin‐1 and ‐3 was that the arginines formed in‐plane ion pairs with two side‐chain carboxylates, which resulted in extended planar π‐electron surfaces that did not require solvation by water; these surfaces were ideal for stacking with aromatic moieties of the ligands. The results provide a basis for the design of lectin inhibitors and drugs that exploit interactions with arginine side‐chains via ar

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Author

Ian Cumpstey; Emma Salomonsson; Anders Sundin; Hakon Leffler; Ulf J. Nilsson

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 1439-4227)

Published

2007

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)