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.

• Författare: Christopher T. Öberg; Ann Louise Noresson; Hakon Leffler; Ulf J. Nilsson
• Avdelning/ar: Centrum för analys och syntes; Avdelningen för mikrobiologi, immunologi och glykobiologi - MIG; BioCARE: Biomarkers in Cancer Medicine improving Health Care, Education and Innovation
• Publiceringsår: 2011
• Språk: Engelska
• Sidor: 8139-8144
• Publikation/Tidskrift/Serie: Chemistry: A European Journal
• Volym: 17
• Issue: 29
• Länkar: http://dx.doi.org/10.1002/chem.201003247
• Dokumenttyp: Artikel i tidskrift
• Förlag: Wiley-Blackwell
• Ämne: Immunology in the medical area; Microbiology in the medical area
• Nyckelord: arginine; benzamides; galectins; molecular recognition; structure-activity relationships
• Status: Published
• ISBN/ISSN/Övrigt: ISSN: 1521-3765