Studies of arginine-arene interactions through synthesis and evaluation of a series of galectin-binding aromatic lactose esters.

Studies of arginine-arene interactions through synthesis and evaluation of a series of galectin-binding aromatic lactose esters. Research Abstract Details 

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Studies of arginine-arene interactions through synthesis and evaluation of a series of galectin-binding aromatic lactose esters. Abstract Text:

Ian Cumpstey,Emma Salomonsson,Anders Sundin,Hakon Leffler,Ulf J Nilsson,

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 microM 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 pi-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 aromatic moieties, which are involved in intramolecular protein salt bridges.

Studies of arginine-arene interactions through synthesis and evaluation of a series of galectin-binding aromatic lactose esters. Publishing Authors By Initials

I Cumpstey,E Salomonsson,A Sundin,H Leffler,UJ Nilsson,

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Studies of arginine-arene interactions through synthesis and evaluation of a series of galectin-binding aromatic lactose esters. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Chembiochem : a European journal of chemical biolo

VOLUME: 8

Page Numbers: 1389-98

Journal Abbreviation: Chembiochem

ISSN: 1439-4227

DAY: 13

MONTH: Aug

YEAR: 2007

Studies of arginine-arene interactions through synthesis and evaluation of a series of galectin-binding aromatic lactose esters. Information

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LANGUAGE: eng

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Grant and Affiliation Information for Studies of arginine-arene interactions through synthesis and evaluation of a series of galectin-binding aromatic lactose esters.

AFFILIATION: Organic Chemistry, Lund University, P.O. Box 124, Lund, Sweden.

Country: Germany

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MEDLINETA: Chembiochem

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