Tyrosine modified analogues of the α4β7 integrin inhibitor biotin-R(8)ERY prepared via Click Chemistry: Synthesis and biological evaluation.
Summary of "Tyrosine modified analogues of the α4β7 integrin inhibitor biotin-R(8)ERY prepared via Click Chemistry: Synthesis and biological evaluation."
Our continuing programme aiming at developing inhibitors of integrin α4β7, a key mediator of various inflammatory diseases, led us to synthesise a library of cell-permeable peptides based on the biotin-R(8)ERY(∗) template, wherein the tyrosine residue has been modified by using the CuAAC reaction. The peptidomimetics were evaluated in a cell adhesion assay and shown to inhibit Mn(2+)-activated adhesion of mouse TK-1 T cells to mouse MAdCAM-1. Two of the synthesised peptidomimetics, analogues 11 and 14, are more active than our previously reported lead compound biotin-r(9)YDRREY at concentrations of 100 and 50μM, with 14 exhibiting an IC(50) of less than 10μM.
School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland Central 1010, New Zealand.
This article was published in the following journal.
Name: Bioorganic & medicinal chemistry
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22421276
- DOI: http://dx.doi.org/10.1016/j.bmc.2012.02.035
Medical and Biotech [MESH] Definitions
An integrin alpha subunit that primarily associates with INTEGRIN BETA1 or INTEGRIN BETA4 to form laminin-binding heterodimers. Integrin alpha6 has two alternatively spliced isoforms: integrin alpha6A and integrin alpha6B, which differ in their cytoplasmic domains and are regulated in a tissue-specific and developmental stage-specific manner.
An integrin beta subunit of approximately 85-kDa in size which has been found in INTEGRIN ALPHAIIB-containing and INTEGRIN ALPHAV-containing heterodimers. Integrin beta3 occurs as three alternatively spliced isoforms, designated beta3A-C.
A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS.
An integrin alpha subunit that binds COLLAGEN and LAMININ though its I domain. It combines with INTEGRIN BETA1 to form the heterodimer INTEGRIN ALPHA1BETA1.
An integrin alpha subunit that primarily combines with INTEGRIN BETA1 to form the INTEGRIN ALPHA2BETA1 heterodimer. It contains a domain which has homology to collagen-binding domains found in von Willebrand factor.
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