Arene-anion based arginine-binding motif on a galactose scaffold : Structure-activity relationships of interactions with arginine-rich galectins

Summary, in English

Two series of C3-benzamido and O2-anion-substituted galactopyranosides were synthesized and studied as binders to arginine-rich proteins galectin-1, -3, -7, -8N (N-terminal domain), and -9N (N-terminal domain). The first series had a 4-methylbenzamide at C3 and the anionic O2-substituent was varied. The second series varied the 4-substituent of the C3-benzamide, whereas the anionic O2 substituent was kept as a sulfate. The influence of the O2-anion substituent correlated negatively with the oxygen charge density in case of galectin-1, -3, and -9N. In the second series, the electron-donating capacity of the 4-substituent of the C3-benzamides correlated positively with the magnitude of the affinity enhancement by the 2O-sulfate.

• Author: Christopher T. Öberg; Ann Louise Noresson; Hakon Leffler; Ulf J. Nilsson
• Department/s: Centre for Analysis and Synthesis; Division of Microbiology, Immunology and Glycobiology - MIG; BioCARE: Biomarkers in Cancer Medicine improving Health Care, Education and Innovation
• Publishing year: 2011
• Language: English
• Pages: 8139-8144
• Publication/Series: Chemistry: A European Journal
• Volume: 17
• Issue: 29
• Links: http://dx.doi.org/10.1002/chem.201003247
• Document type: Journal article
• Publisher: Wiley-Blackwell
• Topic: Immunology in the medical area; Microbiology in the medical area
• Keywords: arginine; benzamides; galectins; molecular recognition; structure-activity relationships
• Status: Published
• ISBN/ISSN/Other: ISSN: 1521-3765