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Investigation of α-thioaryl galactopyranosides to improve affinity towards Galectin-9N

Gummesson, Sofi LU (2018) KEMK01 20181
Department of Chemistry
Abstract
Galectins are a family of carbohydrate recognition proteins involved in modulation of cell signaling and cell adhesion. galectin-9 especially is involved in regulation of the immune response. In this work, galectin-9N inhibitors have been designed, synthesized and evaluated. The aim was to synthesize compounds with higher affinity than currently known compounds. Three compounds were synthesized with different substituents at the alpha position of the anomeric carbon. Substituent patterns employed in this study were phenyl, methyl phenyl and fluoro phenyl. Affinities of compounds were evaluated in a fluorescence polarization assay. The compound with best affinity was the galectin-9N inhibitor with fluoro phenyl as the substituent, with... (More)
Galectins are a family of carbohydrate recognition proteins involved in modulation of cell signaling and cell adhesion. galectin-9 especially is involved in regulation of the immune response. In this work, galectin-9N inhibitors have been designed, synthesized and evaluated. The aim was to synthesize compounds with higher affinity than currently known compounds. Three compounds were synthesized with different substituents at the alpha position of the anomeric carbon. Substituent patterns employed in this study were phenyl, methyl phenyl and fluoro phenyl. Affinities of compounds were evaluated in a fluorescence polarization assay. The compound with best affinity was the galectin-9N inhibitor with fluoro phenyl as the substituent, with affinity of 5. The polar interaction between the binding pocket and the inhibitor is believed to be the reason for the good affinity. (Less)
Popular Abstract (Swedish)
Galektiner är en proteinfamilj som har visats vara aktiv i cancerceller. Proteinet har bland annat funktioner så som utveckling och spridning av cancerceller. För att förhindra proteinets inblandning i cancercellen kan man introducera en inhibitor, som hindrar aktiviteten hos proteinet. Genom att inhibitorn placerar sig i den position där substratet naturligt skulle binda.
Inhibitorn tävlar med det naturliga substratet. För att inhibitorn ska vara så effektiv som möjligt är det viktigt att den binder så starkt som möjligt för att konkurrera ut det naturliga substratet.
I mitt projekt utvecklades tre molekyler som skulle förhindra galektin-9Ns aktivitet, ett protein ur galektin-familjen. Galektin-9N är viktig för immunförsvaret och har... (More)
Galektiner är en proteinfamilj som har visats vara aktiv i cancerceller. Proteinet har bland annat funktioner så som utveckling och spridning av cancerceller. För att förhindra proteinets inblandning i cancercellen kan man introducera en inhibitor, som hindrar aktiviteten hos proteinet. Genom att inhibitorn placerar sig i den position där substratet naturligt skulle binda.
Inhibitorn tävlar med det naturliga substratet. För att inhibitorn ska vara så effektiv som möjligt är det viktigt att den binder så starkt som möjligt för att konkurrera ut det naturliga substratet.
I mitt projekt utvecklades tre molekyler som skulle förhindra galektin-9Ns aktivitet, ett protein ur galektin-familjen. Galektin-9N är viktig för immunförsvaret och har bland annat funktioner så som programmerad celldöd (apoptos) och förflyttning av cellen mot eller ifrån en ökad koncentration av ett kemiskt ämne (kemo taxis). Syntesen utgick från galaktos-molekylen och byggdes upp till en mer avancerad struktur som var designad för att binda till galektin-9N. Målet var att se om de nya molekylerna band starkare till den avsiktliga positionen än tidigare studerade molekyler gjort. (Less)
Please use this url to cite or link to this publication:
author
Gummesson, Sofi LU
supervisor
organization
course
KEMK01 20181
year
type
M2 - Bachelor Degree
subject
keywords
organic chemistry, organisk kemi
language
English
id
8958925
date added to LUP
2019-02-26 10:28:09
date last changed
2019-02-26 10:28:09
@misc{8958925,
  abstract     = {{Galectins are a family of carbohydrate recognition proteins involved in modulation of cell signaling and cell adhesion. galectin-9 especially is involved in regulation of the immune response. In this work, galectin-9N inhibitors have been designed, synthesized and evaluated. The aim was to synthesize compounds with higher affinity than currently known compounds. Three compounds were synthesized with different substituents at the alpha position of the anomeric carbon. Substituent patterns employed in this study were phenyl, methyl phenyl and fluoro phenyl. Affinities of compounds were evaluated in a fluorescence polarization assay. The compound with best affinity was the galectin-9N inhibitor with fluoro phenyl as the substituent, with affinity of 5. The polar interaction between the binding pocket and the inhibitor is believed to be the reason for the good affinity.}},
  author       = {{Gummesson, Sofi}},
  language     = {{eng}},
  note         = {{Student Paper}},
  title        = {{Investigation of α-thioaryl galactopyranosides to improve affinity towards Galectin-9N}},
  year         = {{2018}},
}