Chemo-enzymatic synthesis of LacdiNAc dimers of varying length as novel galectin ligands

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11320%2F14%3A10400183" target="_blank" >RIV/00216208:11320/14:10400183 - isvavai.cz</a>
Alternative codes found
RIV/61388971:_____/14:00428358
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=3f.6Zx2rkq" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=3f.6Zx2rkq</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.molcatb.2013.12.018" target="_blank" >10.1016/j.molcatb.2013.12.018</a>

Result language
angličtina
Original language name
Chemo-enzymatic synthesis of LacdiNAc dimers of varying length as novel galectin ligands
Original language description
A set of sixteen bivalent symmetrical and asymmetrical LacdiNAc dimers containing flexible alkyl linkers were efficiently synthesized by means of chemo-enzymatic synthesis, using the versatile potential of the Y284L mutant of human placental beta 1,4-galactosyltransferase-1. LacdiNAc was confirmed to be a specific ligand for human galectin-3 contrary to human galectin-1. The compounds were tested as ligands for human galectin-3 in competitive binding assays and compared to a monovalent LacdiNAc standard. Molecular modeling was performed to calculate approximate length of respective ligands and its relation to their inhibitory capacity. The best performance was observed in symmetrical compounds carrying two LacdiNAc units connected with a hydrophobic linker of sufficient length (alkyl chain n >= 6). Here, the IC50 value was about three times lower than that of the monovalent standard. Our results propose that hydrophobicity directed by the alkyl chain length as well as the specificity and bivalency of the LacdiNAc contribute to the inhibition potential of these ligands. Though only slightly pronounced in this case, higher multivalency is a promising feature in the design of optimized ligands for galectin-3. (C) 2014 Elsevier B.V. All rights reserved.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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