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On-chip synthesis and screening of a sialoside library yields a high affinity ligand for Siglec-7

Academic Article
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Overview

related to degree

  • Rillahan, Cory, Ph.D. in Biology, Scripps Research 2007 - 2012

authors

  • Rillahan, Cory
  • Schwartz, E.
  • Rademacher, C.
  • McBride, R.
  • Rangarajan, J.
  • Fokin, Valery
  • Paulson, James

publication date

  • July 2013

journal

  • ACS Chemical Biology  Journal

abstract

  • The Siglec family of sialic acid-binding proteins are differentially expressed on white blood cells of the immune system and represent an attractive class of targets for cell-directed therapy. Nanoparticles decorated with high-affinity Siglec ligands show promise for delivering cargo to Siglec-bearing cells, but this approach has been limited by a lack of ligands with suitable affinity and selectivity. Building on previous work employing solution-phase sialoside library synthesis and subsequent microarray screening, we herein report a more streamlined 'on-chip' synthetic approach. By printing a small library of alkyne sialosides and subjecting these to 'on-chip' click reactions, the largest sialoside analogue library to date was generated. Siglec-screening identified a selective Siglec-7 ligand, which when displayed on liposomal nanoparticles, allows for targeting of Siglec-7(+) cells in peripheral human blood. In silico docking to the crystal structure of Siglec-7 provides a rationale for the affinity gains observed for this novel sialic acid analogue.

subject areas

  • Antigens, Differentiation, Myelomonocytic
  • Binding Sites
  • Crystallography, X-Ray
  • Drug Delivery Systems
  • Drug Evaluation, Preclinical
  • Fluoresceins
  • Humans
  • Jurkat Cells
  • Lectins
  • Ligands
  • Liposomes
  • Microarray Analysis
  • Molecular Structure
  • Sialic Acids
  • Small Molecule Libraries
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Identity

PubMed Central ID

  • PMC3751994

International Standard Serial Number (ISSN)

  • 1554-8937 (Electronic) 1554-8929 (Linking)

Digital Object Identifier (DOI)

  • 10.1021/cb400125w

PubMed ID

  • 23597400
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Additional Document Info

start page

  • 1417

end page

  • 1422

volume

  • 8

issue

  • 7

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