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Squalene-derived flexible linkers for bioactive peptides.

Abstract：

:A regiochemical and stereochemical mixture of flexible linkers bearing terminal azide functionality was synthesized in two steps from squalene and was used to connect two high affinity NDP-alpha-MSH ligands or two low affinity MSH(4) ligands. The ligands were N-terminally acylated using N-hydroxysuccinimidoyl 5-hexynoate and were subsequently attached to the linker via copper-catalyzed 'click' 3+2 cyclization of the azide and alkyne moieties. In vitro biological evaluations showed that the binding affinity to the human melanocortin 4 receptor was not diminished for most linker-ligand combinations relative to the corresponding parental ligand. Statistical and cooperative binding effects were observed for dimeric constructs containing the low affinity ligand MSH(4), but not for dimeric NDP-alpha-MSH constructs, presumably due to slow off rates for this high affinity ligand.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Jagadish B,Sankaranarayanan R,Xu L,Richards R,Vagner J,Hruby VJ,Gillies RJ,Mash EA

doi

10.1016/j.bmcl.2007.04.001

subject

Has Abstract

pub_date

2007-06-15 00:00:00

pages

3310-3

issue

12

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(07)00425-8

journal_volume

17

pub_type

杂志文章

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